Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from Boston to Chicago is Frontier Airlines.
Cheapest Month
May
Travel Period: May 2024 - April 2025
The cheapest month(s) to fly from Boston to Chicago is May.
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May 2024
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Jun 2024
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Jul 2024
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Aug 2024
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Sep 2024
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Oct 2024
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Nov 2024
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Dec 2024
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Jan 2025
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Feb 2025
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Mar 2025
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Apr 2025
Cheapest Day of the Week
Wednesday
The cheapest day(s) of the week to fly from Boston to Chicago is Wednesday.
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Sun Sunday
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Mon Monday
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Tue Tuesday
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Wed Wednesday
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Thu Thursday
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Fri Friday
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Sat Saturday
Cheapest Time
8am
The cheapest time of the day to fly from Boston to Chicago is in the morning.
Early Morning 12:01am - 06:00am
Morning 6:01am - 12:00pm
Afternoon 12:01pm - 6:00pm
Evening 6:01pm to 12:00am
12am
6am
12pm
6pm
Flight Schedules
Last Updated: Tue, 2 Apr, 2024
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Total Duration
- Shortest
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All
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Availability
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20:55 - 22:52BOS - ORD
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20:55 (BOS)Boston Logan International Airport
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22:52 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 5603)Embraer Emb 175 - 02h 57m
- Direct
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- -
- -
- -
- -
- F
- -
- S
- Embraer Emb 175
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21:55 - 23:30BOS - MDW
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21:55 (BOS)Boston Logan International Airport
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23:30 (MDW)Chicago Midway Airport
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(WN 5774)Boeing 737 800 - 02h 35m
- Direct
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- -
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- -
- -
- -
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- S
- Boeing 737 800
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06:01 - 07:54BOS - ORD
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06:01 (BOS)Boston Logan International Airport
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07:54 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 567)Boeing 737 700 - 02h 53m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
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06:01 - 07:54BOS - ORD
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06:01 (BOS)Boston Logan International Airport
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07:54 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 567)Boeing 737 900 - 02h 53m
- Direct
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- -
- -
- -
- -
- F
- S
- -
- Boeing 737 900
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06:25 - 08:21BOS - ORD
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06:25 (BOS)Boston Logan International Airport
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08:21 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 1417)Airbus A220 100 Passenger - 02h 56m
- Direct
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- -
- -
- -
- -
- F
- -
- -
- Airbus A220 100 Passenger
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06:40 - 08:15BOS - MDW
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06:40 (BOS)Boston Logan International Airport
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08:15 (MDW)Chicago Midway Airport
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(WN 3047)Boeing 737 Max 8 Passenger - 02h 35m
- Direct
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- -
- -
- -
- -
- -
- S
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- Boeing 737 Max 8 Passenger
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07:00 - 09:08BOS - ORD
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07:00 (BOS)Boston Logan International Airport
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09:08 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1509)Airbus - 03h 08m
- Direct
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- -
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- -
- -
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- S
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- Airbus
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07:00 - 08:40BOS - MDW
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07:00 (BOS)Boston Logan International Airport
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08:40 (MDW)Chicago Midway Airport
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(WN 3047)Boeing 737 Max 8 Passenger - 02h 40m
- Direct
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- -
- -
- -
- -
- F
- -
- -
- Boeing 737 Max 8 Passenger
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07:00 - 09:11BOS - ORD
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07:00 (BOS)Boston Logan International Airport
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09:11 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1509)Boeing 737 800 - 03h 11m
- Direct
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- -
- -
- -
- -
- F
- -
- S
- Boeing 737 800
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07:10 - 08:50BOS - MDW
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07:10 (BOS)Boston Logan International Airport
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08:50 (MDW)Chicago Midway Airport
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(WN 3047)Boeing 737 Max 8 Passenger - 02h 40m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
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08:00 - 09:52BOS - ORD
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08:00 (BOS)Boston Logan International Airport
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09:52 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1944)Boeing 737 800 - 02h 52m
- Direct
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- -
- -
- -
- -
- F
- S
- S
- Boeing 737 800
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08:05 - 10:00BOS - ORD
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08:05 (BOS)Boston Logan International Airport
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10:00 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 1715)Airbus A220 100 Passenger - 02h 55m
- Direct
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- -
- -
- -
- -
- -
- S
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- Airbus A220 100 Passenger
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08:10 - 10:08BOS - ORD
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08:10 (BOS)Boston Logan International Airport
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10:08 (ORD)Chicago O'Hare International Airport
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JetBlue Airways (B6 311)Airbus A220 300 - 02h 58m
- Direct
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- -
- -
- -
- -
- F
- -
- S
- Airbus A220 300
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08:30 - 10:21BOS - ORD
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08:30 (BOS)Boston Logan International Airport
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10:21 (ORD)Chicago O'Hare International Airport
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JetBlue Airways (B6 311)Embraer Emb E90 - 02h 51m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Embraer Emb E90
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08:30 - 10:21BOS - ORD
-
08:30 (BOS)Boston Logan International Airport
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10:21 (ORD)Chicago O'Hare International Airport
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JetBlue Airways (B6 311)Airbus A220 300 - 02h 51m
- Direct
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- -
- -
- W
- -
- -
- -
- -
- Airbus A220 300
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08:30 - 10:28BOS - ORD
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08:30 (BOS)Boston Logan International Airport
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10:28 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1502)Boeing 737 800 - 02h 58m
- Direct
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- -
- -
- -
- -
- F
- S
- S
- Boeing 737 800
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09:40 - 11:28BOS - ORD
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09:40 (BOS)Boston Logan International Airport
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11:28 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1306)Boeing 737 800 - 02h 48m
- Direct
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- -
- -
- -
- -
- F
- S
- S
- Boeing 737 800
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10:15 - 12:09BOS - ORD
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10:15 (BOS)Boston Logan International Airport
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12:09 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 5617)Embraer Emb 175 - 02h 54m
- Direct
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- -
- -
- -
- -
- F
- -
- S
- Embraer Emb 175
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10:45 - 12:20BOS - MDW
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10:45 (BOS)Boston Logan International Airport
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12:20 (MDW)Chicago Midway Airport
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(WN 3048)Boeing 737 800 - 02h 35m
- Direct
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- -
- -
- -
- -
- F
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- Boeing 737 800
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10:50 - 12:20BOS - MDW
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10:50 (BOS)Boston Logan International Airport
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12:20 (MDW)Chicago Midway Airport
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(WN 3048)Boeing 737 700 - 02h 30m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
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11:20 - 12:50BOS - MDW
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11:20 (BOS)Boston Logan International Airport
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12:50 (MDW)Chicago Midway Airport
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(WN 3048)Boeing 737 Max 8 Passenger - 02h 30m
- Direct
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- -
- T
- W
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- Boeing 737 Max 8 Passenger
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12:05 - 14:10BOS - ORD
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12:05 (BOS)Boston Logan International Airport
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14:10 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 4262)Embraer Emb 175 - 03h 05m
- Direct
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- -
- -
- -
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- F
- S
- S
- Embraer Emb 175
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12:20 - 13:55BOS - MDW
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12:20 (BOS)Boston Logan International Airport
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13:55 (MDW)Chicago Midway Airport
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(WN 3048)Boeing 737 Max 8 Passenger - 02h 35m
- Direct
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- -
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- S
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- Boeing 737 Max 8 Passenger
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12:42 - 14:36BOS - ORD
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12:42 (BOS)Boston Logan International Airport
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14:36 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1732)Airbus - 02h 54m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Airbus
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12:42 - 14:36BOS - ORD
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12:42 (BOS)Boston Logan International Airport
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14:36 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1732)Airbus - 02h 54m
- Direct
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- -
- -
- -
- -
- F
- -
- S
- Airbus
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13:20 - 15:09BOS - ORD
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13:20 (BOS)Boston Logan International Airport
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15:09 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 2631)Airbus A220 100 Passenger - 02h 49m
- Direct
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- -
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- -
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- S
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- Airbus A220 100 Passenger
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14:05 - 16:11BOS - ORD
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14:05 (BOS)Boston Logan International Airport
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16:11 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 4357)Embraer Emb 175 - 03h 06m
- Direct
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- -
- -
- -
- -
- F
- S
- S
- Embraer Emb 175
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14:15 - 16:04BOS - ORD
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14:15 (BOS)Boston Logan International Airport
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16:04 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 2631)Airbus A220 100 Passenger - 02h 49m
- Direct
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- -
- -
- -
- -
- F
- -
- S
- Airbus A220 100 Passenger
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15:20 - 17:14BOS - ORD
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15:20 (BOS)Boston Logan International Airport
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17:14 (ORD)Chicago O'Hare International Airport
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JetBlue Airways (B6 1225)Embraer Emb E90 - 02h 54m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Embraer Emb E90
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15:20 - 17:14BOS - ORD
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15:20 (BOS)Boston Logan International Airport
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17:14 (ORD)Chicago O'Hare International Airport
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JetBlue Airways (B6 1225)Airbus A220 300 - 02h 54m
- Direct
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- -
- -
- -
- -
- F
- -
- S
- Airbus A220 300
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15:30 - 17:35BOS - ORD
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15:30 (BOS)Boston Logan International Airport
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17:35 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 4363)Embraer Emb 175 - 03h 05m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Embraer Emb 175
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15:30 - 17:35BOS - ORD
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15:30 (BOS)Boston Logan International Airport
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17:35 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 4434)Embraer Emb 175 - 03h 05m
- Direct
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- -
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- F
- -
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- Embraer Emb 175
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16:20 - 18:21BOS - ORD
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16:20 (BOS)Boston Logan International Airport
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18:21 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 5603)Embraer Emb 175 - 03h 01m
- Direct
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- -
- -
- -
- -
- -
- S
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- Embraer Emb 175
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16:20 - 17:55BOS - MDW
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16:20 (BOS)Boston Logan International Airport
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17:55 (MDW)Chicago Midway Airport
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(WN 3049)Boeing 737 800 - 02h 35m
- Direct
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- -
- -
- -
- -
- F
- -
- -
- Boeing 737 800
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16:47 - 18:40BOS - ORD
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16:47 (BOS)Boston Logan International Airport
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18:40 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1298)Boeing 737 900 - 02h 53m
- Direct
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- -
- -
- W
- -
- -
- -
- -
- Boeing 737 900
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16:47 - 18:40BOS - ORD
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16:47 (BOS)Boston Logan International Airport
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18:40 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1298)Boeing 737 800 - 02h 53m
- Direct
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- -
- -
- -
- -
- F
- S
- S
- Boeing 737 800
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16:50 - 18:30BOS - MDW
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16:50 (BOS)Boston Logan International Airport
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18:30 (MDW)Chicago Midway Airport
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(WN 3049)Boeing 737 Max 8 Passenger - 02h 40m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Boeing 737 Max 8 Passenger
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16:55 - 18:35BOS - MDW
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16:55 (BOS)Boston Logan International Airport
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18:35 (MDW)Chicago Midway Airport
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(WN 3049)Boeing 737 Max 8 Passenger - 02h 40m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
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17:05 - 19:00BOS - ORD
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17:05 (BOS)Boston Logan International Airport
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19:00 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 2933)Airbus A220 100 Passenger - 02h 55m
- Direct
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- -
- -
- -
- -
- F
- -
- S
- Airbus A220 100 Passenger
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17:29 - 19:33BOS - ORD
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17:29 (BOS)Boston Logan International Airport
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19:33 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 3972)Embraer Emb 175 - 03h 04m
- Direct
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- -
- T
- -
- -
- -
- -
- -
- Embraer Emb 175
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17:30 - 19:26BOS - ORD
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17:30 (BOS)Boston Logan International Airport
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19:26 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1434)Airbus - 02h 56m
- Direct
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- -
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- -
- -
- F
- S
- S
- Airbus
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18:31 - 20:25BOS - ORD
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18:31 (BOS)Boston Logan International Airport
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20:25 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 2609)Boeing 737 900 - 02h 54m
- Direct
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- -
- -
- -
- -
- F
- -
- -
- Boeing 737 900
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18:31 - 20:25BOS - ORD
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18:31 (BOS)Boston Logan International Airport
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20:25 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 2609)Airbus - 02h 54m
- Direct
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- -
- -
- -
- -
- -
- S
- S
- Airbus
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19:10 - 20:45BOS - MDW
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19:10 (BOS)Boston Logan International Airport
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20:45 (MDW)Chicago Midway Airport
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(WN 5774)Boeing 737 800 - 02h 35m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
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19:20 - 21:00BOS - MDW
-
19:20 (BOS)Boston Logan International Airport
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21:00 (MDW)Chicago Midway Airport
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(WN 5774)Boeing 737 800 - 02h 40m
- Direct
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- -
- -
- -
- -
- F
- -
- -
- Boeing 737 800
Connecting Flights
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20:15 - 22:00+ 1BOS - BNA22:40 - 00:10+ 1BNA - MDW
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20:15 (BOS)Boston Logan International Airport22:40 (BNA)Nashville Airport
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22:00 (BNA)Nashville Airport + 100:10 (MDW)Chicago Midway Airport
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(WN 794)Boeing 737 Max 8 Passenger (WN 5212)Boeing 737 700 - 04h 55m (00h 40m)
- BNA Nashville 00h 40m
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- -
- -
- -
- -
- -
- -
- S
-
05:00 - 07:28BOS - CLT09:08 - 10:15CLT - ORD
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05:00 (BOS)Boston Logan International Airport09:08 (CLT)Charlotte Airport
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07:28 (CLT)Charlotte Airport10:15 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 418)Boeing 737 800 American Airlines (AA 1038)Airbus - 06h 15m (01h 40m)
- CLT Charlotte 01h 40m
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- -
- -
- W
- -
- -
- -
- -
-
05:14 - 06:30BOS - JFK07:35 - 09:25JFK - ORD
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05:14 (BOS)Boston Logan International Airport07:35 (JFK)New York John F. Kennedy International Airport
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06:30 (JFK)New York John F. Kennedy International Airport09:25 (ORD)Chicago O'Hare International Airport
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JetBlue Airways (B6 217)Airbus JetBlue Airways (B6 605)Embraer Emb E90 - 05h 11m (01h 05m)
- JFK New York City 01h 05m
-
- -
- -
- W
- -
- -
- -
- -
-
05:14 - 06:30BOS - JFK07:05 - 08:55JFK - ORD
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05:14 (BOS)Boston Logan International Airport07:05 (JFK)New York John F. Kennedy International Airport
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06:30 (JFK)New York John F. Kennedy International Airport08:55 (ORD)Chicago O'Hare International Airport
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JetBlue Airways (B6 217)Embraer Emb E90 JetBlue Airways (B6 605)Embraer Emb E90 - 04h 41m (00h 35m)
- JFK New York City 00h 35m
-
- -
- -
- -
- -
- -
- -
- S
-
05:14 - 06:30BOS - JFK07:05 - 08:51JFK - ORD
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05:14 (BOS)Boston Logan International Airport07:05 (JFK)New York John F. Kennedy International Airport
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06:30 (JFK)New York John F. Kennedy International Airport08:51 (ORD)Chicago O'Hare International Airport
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JetBlue Airways (B6 217)Embraer Emb E90 JetBlue Airways (B6 605)Embraer Emb E90 - 04h 37m (00h 35m)
- JFK New York City 00h 35m
-
- -
- -
- -
- -
- -
- S
- -
-
05:20 - 07:00BOS - BNA08:15 - 10:00BNA - ORD
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05:20 (BOS)Boston Logan International Airport08:15 (BNA)Nashville Airport
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07:00 (BNA)Nashville Airport10:00 (ORD)Chicago O'Hare International Airport
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(WN 528)Boeing 737 800 (WN 3623)Boeing 737 700 - 05h 40m (01h 15m)
- BNA Nashville 01h 15m
-
- -
- -
- -
- -
- -
- -
- S
-
05:30 - 07:58BOS - CLT09:08 - 10:15CLT - ORD
-
05:30 (BOS)Boston Logan International Airport09:08 (CLT)Charlotte Airport
-
07:58 (CLT)Charlotte Airport10:15 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 418)Airbus American Airlines (AA 1038)Airbus - 05h 45m (01h 10m)
- CLT Charlotte 01h 10m
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- -
- -
- -
- -
- -
- S
- S
-
05:30 - 07:12BOS - IAD08:28 - 09:37IAD - ORD
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05:30 (BOS)Boston Logan International Airport08:28 (IAD)Washington Dulles International Airport
-
07:12 (IAD)Washington Dulles International Airport09:37 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 248)Boeing 737 800 United Airlines (UA 2440)Boeing 737 800 - 05h 07m (01h 16m)
- IAD Washington 01h 16m
-
- -
- -
- -
- T
- -
- -
- -
-
05:35 - 07:49BOS - DTW09:00 - 09:25DTW - ORD
-
05:35 (BOS)Boston Logan International Airport09:00 (DTW)Detroit Wayne County
-
07:49 (DTW)Detroit Wayne County09:25 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 1659)Boeing 737 900 Delta Air Lines (DL 5809)Embraer Emb 175 - 04h 50m (01h 11m)
- DTW Detroit 01h 11m
-
- -
- -
- -
- -
- -
- -
- S
-
05:35 - 07:49BOS - DTW08:30 - 08:50DTW - MDW
-
05:35 (BOS)Boston Logan International Airport08:30 (DTW)Detroit Wayne County
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07:49 (DTW)Detroit Wayne County08:50 (MDW)Chicago Midway Airport
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Delta Air Lines (DL 1659)Boeing 737 900 Delta Air Lines (DL 3822)Embraer 175 - 04h 15m (00h 41m)
- DTW Detroit 00h 41m
-
- -
- -
- -
- -
- -
- S
- S
-
05:35 - 07:50BOS - DTW09:00 - 09:25DTW - ORD
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05:35 (BOS)Boston Logan International Airport09:00 (DTW)Detroit Wayne County
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07:50 (DTW)Detroit Wayne County09:25 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 1659)Airbus Delta Air Lines (DL 5809)Embraer Emb 175 - 04h 50m (01h 10m)
- DTW Detroit 01h 10m
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- -
- -
- -
- -
- -
- -
- S
-
05:35 - 07:49BOS - DTW08:25 - 08:49DTW - ORD
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05:35 (BOS)Boston Logan International Airport08:25 (DTW)Detroit Wayne County
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07:49 (DTW)Detroit Wayne County08:49 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 1659)Boeing 737 900 Delta Air Lines (DL 2575)Boeing 717 - 04h 14m (00h 36m)
- DTW Detroit 00h 36m
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- -
- -
- -
- -
- -
- S
- -
-
05:35 - 07:50BOS - DTW08:30 - 08:50DTW - MDW
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05:35 (BOS)Boston Logan International Airport08:30 (DTW)Detroit Wayne County
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07:50 (DTW)Detroit Wayne County08:50 (MDW)Chicago Midway Airport
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Delta Air Lines (DL 1659)Airbus Delta Air Lines (DL 3822)Embraer 175 - 04h 15m (00h 40m)
- DTW Detroit 00h 40m
-
- -
- -
- -
- -
- -
- -
- S
-
05:40 - 07:20BOS - BNA09:00 - 10:45BNA - ORD
-
05:40 (BOS)Boston Logan International Airport09:00 (BNA)Nashville Airport
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07:20 (BNA)Nashville Airport10:45 (ORD)Chicago O'Hare International Airport
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(WN 528)Boeing 737 800 (WN 510)Boeing 737 700 - 06h 05m (01h 40m)
- BNA Nashville 01h 40m
-
- M
- -
- -
- T
- F
- -
- -
-
05:45 - 07:25BOS - BNA09:45 - 11:15BNA - MDW
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05:45 (BOS)Boston Logan International Airport09:45 (BNA)Nashville Airport
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07:25 (BNA)Nashville Airport11:15 (MDW)Chicago Midway Airport
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(WN 528)Boeing 737 800 (WN 2119)Boeing 737 700 - 06h 30m (02h 20m)
- BNA Nashville 02h 20m
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- -
- T
- W
- -
- -
- -
- -
-
05:45 - 07:25BOS - BNA09:00 - 10:45BNA - ORD
-
05:45 (BOS)Boston Logan International Airport09:00 (BNA)Nashville Airport
-
07:25 (BNA)Nashville Airport10:45 (ORD)Chicago O'Hare International Airport
-
(WN 528)Boeing 737 800 (WN 510)Boeing 737 700 - 06h 00m (01h 35m)
- BNA Nashville 01h 35m
-
- -
- T
- W
- -
- -
- -
- -
-
05:45 - 08:40BOS - ATL10:20 - 11:22ATL - ORD
-
05:45 (BOS)Boston Logan International Airport10:20 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
08:40 (ATL)Atlanta Hartsfield-Jackson Intl Airport11:22 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 695)Airbus A321 Neo Delta Air Lines (DL 1147)Boeing 757 200 Series - 06h 37m (01h 40m)
- ATL Atlanta 01h 40m
-
- -
- -
- -
- -
- -
- S
- S
-
05:45 - 08:40BOS - ATL09:15 - 10:10ATL - MDW
-
05:45 (BOS)Boston Logan International Airport09:15 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
08:40 (ATL)Atlanta Hartsfield-Jackson Intl Airport10:10 (MDW)Chicago Midway Airport
-
Delta Air Lines (DL 695)Airbus A321 Neo Delta Air Lines (DL 2417)Boeing 717 - 05h 25m (00h 35m)
- ATL Atlanta 00h 35m
-
- -
- -
- -
- -
- -
- S
- -
-
05:45 - 07:27BOS - IAD08:28 - 09:37IAD - ORD
-
05:45 (BOS)Boston Logan International Airport08:28 (IAD)Washington Dulles International Airport
-
07:27 (IAD)Washington Dulles International Airport09:37 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 248)Boeing 737 800 United Airlines (UA 2440)Boeing 737 800 - 04h 52m (01h 01m)
- IAD Washington 01h 01m
-
- -
- -
- -
- -
- -
- S
- -
-
05:45 - 07:27BOS - IAD08:26 - 09:35IAD - ORD
-
05:45 (BOS)Boston Logan International Airport08:26 (IAD)Washington Dulles International Airport
-
07:27 (IAD)Washington Dulles International Airport09:35 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 248)Boeing 737 800 United Airlines (UA 2440)Boeing 737 800 - 04h 50m (00h 59m)
- IAD Washington 00h 59m
-
- -
- -
- -
- -
- -
- -
- S
-
05:50 - 08:20BOS - CVG10:51 - 11:14CVG - ORD
-
05:50 (BOS)Boston Logan International Airport10:51 (CVG)Cincinnati Northern Kentucky Intl Airport
-
08:20 (CVG)Cincinnati Northern Kentucky Intl Airport11:14 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 4703)Embraer Emb 175 American Airlines (AA 3752)Embraer Emb 175 - 06h 24m (02h 31m)
- CVG Cincinnati 02h 31m
-
- M
- T
- W
- T
- F
- -
- -
-
05:50 - 08:20BOS - CVG10:52 - 11:15CVG - ORD
-
05:50 (BOS)Boston Logan International Airport10:52 (CVG)Cincinnati Northern Kentucky Intl Airport
-
08:20 (CVG)Cincinnati Northern Kentucky Intl Airport11:15 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 4703)Embraer Emb 175 American Airlines (AA 3752)Embraer Emb 175 - 06h 25m (02h 32m)
- CVG Cincinnati 02h 32m
-
- -
- -
- -
- -
- -
- S
- -
-
05:59 - 07:41BOS - DCA09:45 - 10:59DCA - ORD
-
05:59 (BOS)Boston Logan International Airport09:45 (DCA)Washington Ronald Reagan National Airport
-
07:41 (DCA)Washington Ronald Reagan National Airport10:59 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 2159)Airbus American Airlines (AA 978)Airbus - 06h 00m (02h 04m)
- DCA Washington 02h 04m
-
- -
- -
- -
- -
- -
- -
- S
-
06:00 - 07:24BOS - LGA09:15 - 11:02LGA - ORD
-
06:00 (BOS)Boston Logan International Airport09:15 (LGA)New York La Guardia Airport
-
07:24 (LGA)New York La Guardia Airport11:02 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 2245)Airbus A220 100 Passenger Delta Air Lines (DL 2954)Airbus - 06h 02m (01h 51m)
- LGA New York City 01h 51m
-
- -
- -
- -
- -
- -
- -
- S
-
06:00 - 07:32BOS - LGA09:50 - 11:28LGA - ORD
-
06:00 (BOS)Boston Logan International Airport09:50 (LGA)New York La Guardia Airport
-
07:32 (LGA)New York La Guardia Airport11:28 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 1326)Airbus American Airlines (AA 327)Airbus - 06h 28m (02h 18m)
- LGA New York City 02h 18m
-
- M
- T
- W
- T
- F
- -
- -
-
06:00 - 07:24BOS - LGA09:07 - 10:54LGA - ORD
-
06:00 (BOS)Boston Logan International Airport09:07 (LGA)New York La Guardia Airport
-
07:24 (LGA)New York La Guardia Airport10:54 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 2245)Airbus A220 100 Passenger Delta Air Lines (DL 2954)Airbus A220 100 Passenger - 05h 54m (01h 43m)
- LGA New York City 01h 43m
-
- M
- T
- W
- T
- F
- -
- -
-
06:00 - 07:24BOS - EWR09:00 - 10:40EWR - ORD
-
06:00 (BOS)Boston Logan International Airport09:00 (EWR)Newark Liberty International Airport
-
07:24 (EWR)Newark Liberty International Airport10:40 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 601)Boeing 737 Max 9 Passenger United Airlines (UA 2290)Boeing 737 900 - 05h 40m (01h 36m)
- EWR New York City 01h 36m
-
- M
- T
- W
- T
- F
- -
- -
-
06:00 - 07:25BOS - JFK08:30 - 10:19JFK - ORD
-
06:00 (BOS)Boston Logan International Airport08:30 (JFK)New York John F. Kennedy International Airport
-
07:25 (JFK)New York John F. Kennedy International Airport10:19 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 2611)Airbus Delta Air Lines (DL 5728)Embraer Emb 175 - 05h 19m (01h 05m)
- JFK New York City 01h 05m
-
- -
- -
- -
- -
- -
- S
- S
-
06:00 - 07:24BOS - EWR09:00 - 10:40EWR - ORD
-
06:00 (BOS)Boston Logan International Airport09:00 (EWR)Newark Liberty International Airport
-
07:24 (EWR)Newark Liberty International Airport10:40 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 601)Boeing 737 900 United Airlines (UA 2290)Airbus - 05h 40m (01h 36m)
- EWR New York City 01h 36m
-
- -
- -
- -
- -
- -
- S
- -
-
06:00 - 07:24BOS - EWR09:00 - 10:40EWR - ORD
-
06:00 (BOS)Boston Logan International Airport09:00 (EWR)Newark Liberty International Airport
-
07:24 (EWR)Newark Liberty International Airport10:40 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 601)Boeing 737 Max 9 Passenger United Airlines (UA 2290)Airbus - 05h 40m (01h 36m)
- EWR New York City 01h 36m
-
- -
- -
- -
- -
- -
- -
- S
-
06:05 - 07:40BOS - BWI10:10 - 11:10BWI - MDW
-
06:05 (BOS)Boston Logan International Airport10:10 (BWI)Baltimore Washington International Airport
-
07:40 (BWI)Baltimore Washington International Airport11:10 (MDW)Chicago Midway Airport
-
(WN 489)Boeing 737 Max 8 Passenger (WN 1930)Boeing 737 Max 8 Passenger - 06h 05m (02h 30m)
- BWI Baltimore 02h 30m
-
- -
- T
- W
- -
- -
- -
- -
-
06:05 - 08:20BOS - MSP08:55 - 10:25MSP - ORD
-
06:05 (BOS)Boston Logan International Airport08:55 (MSP)Minneapolis International Airport
-
08:20 (MSP)Minneapolis International Airport10:25 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 735)Airbus Delta Air Lines (DL 308)Boeing 717 - 05h 20m (00h 35m)
- MSP Minneapolis 00h 35m
-
- -
- -
- -
- -
- -
- S
- -
-
06:05 - 07:40BOS - BWI08:40 - 10:00BWI - ORD
-
06:05 (BOS)Boston Logan International Airport08:40 (BWI)Baltimore Washington International Airport
-
07:40 (BWI)Baltimore Washington International Airport10:00 (ORD)Chicago O'Hare International Airport
-
(WN 489)Boeing 737 Max 8 Passenger (WN 3626)Boeing 737 700 - 04h 55m (01h 00m)
- BWI Baltimore 01h 00m
-
- -
- T
- W
- -
- -
- -
- -
-
06:05 - 08:20BOS - MSP10:00 - 11:25MSP - ORD
-
06:05 (BOS)Boston Logan International Airport10:00 (MSP)Minneapolis International Airport
-
08:20 (MSP)Minneapolis International Airport11:25 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 735)Airbus Delta Air Lines (DL 1367)Boeing 717 - 06h 20m (01h 40m)
- MSP Minneapolis 01h 40m
-
- -
- -
- -
- -
- -
- -
- S
-
06:05 - 07:40BOS - BWI08:40 - 10:00BWI - ORD
-
06:05 (BOS)Boston Logan International Airport08:40 (BWI)Baltimore Washington International Airport
-
07:40 (BWI)Baltimore Washington International Airport10:00 (ORD)Chicago O'Hare International Airport
-
(WN 489)Boeing 737 Max 8 Passenger (WN 3626)Boeing 737 800 - 04h 55m (01h 00m)
- BWI Baltimore 01h 00m
-
- M
- -
- -
- T
- F
- -
- -
-
06:05 - 08:20BOS - MSP09:00 - 10:37MSP - MDW
-
06:05 (BOS)Boston Logan International Airport09:00 (MSP)Minneapolis International Airport
-
08:20 (MSP)Minneapolis International Airport10:37 (MDW)Chicago Midway Airport
-
Delta Air Lines (DL 735)Airbus Delta Air Lines (DL 4070)Embraer 175 - 05h 32m (00h 40m)
- MSP Minneapolis 00h 40m
-
- -
- -
- -
- -
- -
- S
- S
-
06:20 - 08:04BOS - DCA09:56 - 11:09DCA - ORD
-
06:20 (BOS)Boston Logan International Airport09:56 (DCA)Washington Ronald Reagan National Airport
-
08:04 (DCA)Washington Ronald Reagan National Airport11:09 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 2159)Airbus American Airlines (AA 978)Airbus - 05h 49m (01h 52m)
- DCA Washington 01h 52m
-
- -
- -
- -
- -
- -
- S
- -
-
06:30 - 08:48BOS - CMH10:54 - 11:23CMH - ORD
-
06:30 (BOS)Boston Logan International Airport10:54 (CMH)Columbus Port Columbus Intl Airport
-
08:48 (CMH)Columbus Port Columbus Intl Airport11:23 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 4334)Embraer Emb 175 American Airlines (AA 4849)Crj 700 Canadair Regional - 05h 53m (02h 06m)
- CMH Columbus 02h 06m
-
- -
- -
- -
- -
- -
- -
- S
-
06:30 - 08:07BOS - PHL10:00 - 11:25PHL - ORD
-
06:30 (BOS)Boston Logan International Airport10:00 (PHL)Philadelphia International Airport
-
08:07 (PHL)Philadelphia International Airport11:25 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 2096)Boeing 737 800 American Airlines (AA 2098)Boeing 737 800 - 05h 55m (01h 53m)
- PHL Philadelphia 01h 53m
-
- -
- -
- -
- -
- -
- S
- S
-
06:37 - 07:59BOS - EWR09:00 - 10:40EWR - ORD
-
06:37 (BOS)Boston Logan International Airport09:00 (EWR)Newark Liberty International Airport
-
07:59 (EWR)Newark Liberty International Airport10:40 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1936)Boeing 737 Max 9 Passenger United Airlines (UA 2290)Airbus - 05h 03m (01h 01m)
- EWR New York City 01h 01m
-
- -
- -
- -
- -
- -
- -
- S
-
06:45 - 09:39BOS - ATL10:20 - 11:22ATL - ORD
-
06:45 (BOS)Boston Logan International Airport10:20 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
09:39 (ATL)Atlanta Hartsfield-Jackson Intl Airport11:22 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 923)Airbus Delta Air Lines (DL 1147)Boeing 757 200 Series - 05h 37m (00h 41m)
- ATL Atlanta 00h 41m
-
- -
- -
- -
- -
- -
- -
- S
-
06:45 - 09:39BOS - ATL11:00 - 11:55ATL - MDW
-
06:45 (BOS)Boston Logan International Airport11:00 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
09:39 (ATL)Atlanta Hartsfield-Jackson Intl Airport11:55 (MDW)Chicago Midway Airport
-
Delta Air Lines (DL 923)Airbus Delta Air Lines (DL 2417)Boeing 717 - 06h 10m (01h 21m)
- ATL Atlanta 01h 21m
-
- -
- -
- -
- -
- -
- -
- S
-
06:45 - 09:34BOS - ATL10:20 - 11:22ATL - ORD
-
06:45 (BOS)Boston Logan International Airport10:20 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
09:34 (ATL)Atlanta Hartsfield-Jackson Intl Airport11:22 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 923)Boeing 757 200 Winglets Delta Air Lines (DL 1147)Boeing 757 200 Series - 05h 37m (00h 46m)
- ATL Atlanta 00h 46m
-
- M
- T
- W
- T
- F
- -
- -
-
06:45 - 09:34BOS - ATL11:00 - 11:55ATL - MDW
-
06:45 (BOS)Boston Logan International Airport11:00 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
09:34 (ATL)Atlanta Hartsfield-Jackson Intl Airport11:55 (MDW)Chicago Midway Airport
-
Delta Air Lines (DL 923)Boeing 757 200 Winglets Delta Air Lines (DL 2417)Boeing 717 - 06h 10m (01h 26m)
- ATL Atlanta 01h 26m
-
- M
- T
- W
- T
- F
- -
- -
-
06:47 - 09:15BOS - CLT11:05 - 12:24CLT - ORD
-
06:47 (BOS)Boston Logan International Airport11:05 (CLT)Charlotte Airport
-
09:15 (CLT)Charlotte Airport12:24 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 1699)Airbus American Airlines (AA 2052)Airbus - 06h 37m (01h 50m)
- CLT Charlotte 01h 50m
-
- -
- -
- -
- -
- -
- S
- S
-
07:00 - 09:28BOS - CMH10:54 - 11:23CMH - ORD
-
07:00 (BOS)Boston Logan International Airport10:54 (CMH)Columbus Port Columbus Intl Airport
-
09:28 (CMH)Columbus Port Columbus Intl Airport11:23 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 4334)Embraer Emb 175 American Airlines (AA 4849)Crj 700 Canadair Regional - 05h 23m (01h 26m)
- CMH Columbus 01h 26m
-
- -
- -
- -
- -
- -
- S
- -
-
07:00 - 09:24BOS - STL10:09 - 11:29STL - ORD
-
07:00 (BOS)Boston Logan International Airport10:09 (STL)St Louis Lambert Intl Airport
-
09:24 (STL)St Louis Lambert Intl Airport11:29 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 4344)Embraer Emb 175 American Airlines (AA 3564)Embraer 170 - 05h 29m (00h 45m)
- STL Saint Louis 00h 45m
-
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- -
- -
- -
- -
- -
- S
-
07:00 - 08:29BOS - LGA09:07 - 10:54LGA - ORD
-
07:00 (BOS)Boston Logan International Airport09:07 (LGA)New York La Guardia Airport
-
08:29 (LGA)New York La Guardia Airport10:54 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 5843)Embraer Emb 175 Delta Air Lines (DL 2954)Airbus A220 100 Passenger - 04h 54m (00h 38m)
- LGA New York City 00h 38m
-
- M
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- W
- T
- F
- -
- -
-
07:30 - 09:17BOS - PHL10:00 - 11:25PHL - ORD
-
07:30 (BOS)Boston Logan International Airport10:00 (PHL)Philadelphia International Airport
-
09:17 (PHL)Philadelphia International Airport11:25 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 2764)Airbus A321 Neo American Airlines (AA 2098)Boeing 737 800 - 04h 55m (00h 43m)
- PHL Philadelphia 00h 43m
-
- -
- -
- -
- -
- -
- S
- S
-
07:30 - 09:17BOS - PHL11:00 - 12:29PHL - ORD
-
07:30 (BOS)Boston Logan International Airport11:00 (PHL)Philadelphia International Airport
-
09:17 (PHL)Philadelphia International Airport12:29 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 2764)Airbus A321 Neo American Airlines (AA 1959)Airbus - 05h 59m (01h 43m)
- PHL Philadelphia 01h 43m
-
- -
- -
- -
- -
- -
- S
- S
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What’s the fastest flight time from Boston to Chicago?
The fastest flight time for direct flights from Boston to Chicago is 2 hours 30 minutes. Check latest flight schedules & prices on Wego.
What’s the most popular airline flying from Boston to Chicago?
The most popular airline flying from Boston to Chicago is American Airlines. Find the latest flight deals on Wego.
How far is Chicago from Boston?
The flight distance between Boston and Chicago is 1366km. Check all available flights on Wego.
When is the earliest and latest flight of the day?
The earliest flight of the day departs at 00:15. The last flight of the day departs at 23:50. See the full list of flight times on Wego.
How many airlines offer direct flights from Boston to Chicago?
There are 5 airlines that offer direct flights from Boston to Chicago. Find out the list of airlines on Wego.
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Popular Airlines flying from Boston to Chicago
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Popular destinations from Boston
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