Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from San Juan to Chicago is Delta Air Lines.
Cheapest Month
July
Travel Period: May 2024 - April 2025
The cheapest month(s) to fly from San Juan to Chicago is July.
-
May 2024
-
Jun 2024
-
Jul 2024
-
Aug 2024
-
Sep 2024
-
Oct 2024
-
Nov 2024
-
Dec 2024
-
Jan 2025
-
Feb 2025
-
Mar 2025
-
Apr 2025
Cheapest Day of the Week
Tuesday
The cheapest day(s) of the week to fly from San Juan to Chicago is Tuesday.
-
Sun Sunday
-
Mon Monday
-
Tue Tuesday
-
Wed Wednesday
-
Thu Thursday
-
Fri Friday
-
Sat Saturday
Cheapest Time
12pm
The cheapest time of the day to fly from San Juan 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
-
Depart
Earliest
- Earliest
- Latest
-
Arrive
- Earliest
- Latest
-
Airline
Filter by Airline
All
-
Total Duration
- Shortest
- Longest
-
Stopover
All
-
Availability
- M
- T
- W
- T
- F
- S
- S
-
07:01 - 11:10SJU - ORD
-
07:01 (SJU)San Juan Luis Munoz Marin Intl Airport
-
11:10 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 1165)Boeing 737 800 - 5h 09m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
07:50 - 12:00SJU - ORD
-
07:50 (SJU)San Juan Luis Munoz Marin Intl Airport
-
12:00 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 2089)Boeing 737 800 - 5h 10m
- Direct
-
- -
- -
- -
- -
- -
- S
- S
- Boeing 737 800
-
13:20 - 17:25SJU - MDW
-
13:20 (SJU)San Juan Luis Munoz Marin Intl Airport
-
17:25 (MDW)Chicago Midway Airport
-
(WN 1839)Boeing 737 Max 8 Passenger - 5h 05m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 Max 8 Passenger
-
14:10 - 18:15SJU - MDW
-
14:10 (SJU)San Juan Luis Munoz Marin Intl Airport
-
18:15 (MDW)Chicago Midway Airport
-
(WN 1839)Boeing 737 Max 8 Passenger - 5h 05m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
-
14:20 - 18:30SJU - ORD
-
14:20 (SJU)San Juan Luis Munoz Marin Intl Airport
-
18:30 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 2088)Boeing 737 800 - 5h 10m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
Connecting Flights
-
05:10 - 08:25SJU - MCO09:45 - 11:30MCO - MDW
-
05:10 (SJU)San Juan Luis Munoz Marin Intl Airport09:45 (MCO)Orlando International Airport
-
08:25 (MCO)Orlando International Airport11:30 (MDW)Chicago Midway Airport
-
(WN 6145)Boeing 737 800 (WN 3156)Boeing 737 800 - 7h 20m (1h 20m)
- MCO Orlando 1h 20m
-
- -
- T
- W
- -
- -
- -
- -
-
05:10 - 08:25SJU - MCO09:30 - 11:30MCO - ORD
-
05:10 (SJU)San Juan Luis Munoz Marin Intl Airport09:30 (MCO)Orlando International Airport
-
08:25 (MCO)Orlando International Airport11:30 (ORD)Chicago O'Hare International Airport
-
(WN 6145)Boeing 737 800 (WN 934)Boeing 737 800 - 7h 20m (1h 05m)
- MCO Orlando 1h 05m
-
- -
- T
- W
- -
- -
- -
- -
-
05:10 - 08:25SJU - MCO11:15 - 13:00MCO - MDW
-
05:10 (SJU)San Juan Luis Munoz Marin Intl Airport11:15 (MCO)Orlando International Airport
-
08:25 (MCO)Orlando International Airport13:00 (MDW)Chicago Midway Airport
-
(WN 6145)Boeing 737 800 (WN 6125)Boeing 737 Max 8 Passenger - 8h 50m (2h 50m)
- MCO Orlando 2h 50m
-
- -
- T
- W
- -
- -
- -
- -
-
05:15 - 08:30SJU - MCO09:40 - 11:25MCO - MDW
-
05:15 (SJU)San Juan Luis Munoz Marin Intl Airport09:40 (MCO)Orlando International Airport
-
08:30 (MCO)Orlando International Airport11:25 (MDW)Chicago Midway Airport
-
(WN 6145)Boeing 737 Max 8 Passenger (WN 3156)Boeing 737 800 - 7h 10m (1h 10m)
- MCO Orlando 1h 10m
-
- M
- -
- -
- T
- F
- -
- -
-
05:15 - 08:30SJU - MCO11:00 - 13:00MCO - ORD
-
05:15 (SJU)San Juan Luis Munoz Marin Intl Airport11:00 (MCO)Orlando International Airport
-
08:30 (MCO)Orlando International Airport13:00 (ORD)Chicago O'Hare International Airport
-
(WN 6145)Boeing 737 Max 8 Passenger (WN 934)Boeing 737 800 - 8h 45m (2h 30m)
- MCO Orlando 2h 30m
-
- M
- -
- -
- T
- F
- -
- -
-
05:15 - 08:30SJU - MCO12:50 - 14:35MCO - MDW
-
05:15 (SJU)San Juan Luis Munoz Marin Intl Airport12:50 (MCO)Orlando International Airport
-
08:30 (MCO)Orlando International Airport14:35 (MDW)Chicago Midway Airport
-
(WN 6145)Boeing 737 Max 8 Passenger (WN 3157)Boeing 737 800 - 10h 20m (4h 20m)
- MCO Orlando 4h 20m
-
- M
- -
- -
- T
- F
- -
- -
-
13:25 - 13:40CLE - MDW05:45 - 10:00SJU - BWI
-
13:25 (CLE)Cleveland Hopkins International Airport05:45 (SJU)San Juan Luis Munoz Marin Intl Airport
-
13:40 (MDW)Chicago Midway Airport10:00 (BWI)Baltimore Washington International Airport
-
(WN 2969)Boeing 737 Max 8 Passenger (WN 1118)Boeing 737 800 - 8h 55m (2h)
- MDW Chicago 2h
-
- -
- -
- -
- -
- -
- -
- S
-
05:45 - 10:00SJU - BWI12:45 - 13:40BWI - MDW
-
05:45 (SJU)San Juan Luis Munoz Marin Intl Airport12:45 (BWI)Baltimore Washington International Airport
-
10:00 (BWI)Baltimore Washington International Airport13:40 (MDW)Chicago Midway Airport
-
(WN 1118)Boeing 737 Max 8 Passenger (WN 5950)Boeing 737 800 - 8h 55m (2h 45m)
- BWI Baltimore 2h 45m
-
- -
- -
- -
- -
- -
- S
- -
-
05:45 - 10:00SJU - BWI13:15 - 14:15BWI - MDW
-
05:45 (SJU)San Juan Luis Munoz Marin Intl Airport13:15 (BWI)Baltimore Washington International Airport
-
10:00 (BWI)Baltimore Washington International Airport14:15 (MDW)Chicago Midway Airport
-
(WN 1118)Boeing 737 800 (WN 5950)Boeing 737 Max 8 Passenger - 9h 30m (3h 15m)
- BWI Baltimore 3h 15m
-
- -
- -
- -
- -
- -
- -
- S
-
05:55 - 10:10SJU - BWI11:55 - 13:05BWI - ORD
-
05:55 (SJU)San Juan Luis Munoz Marin Intl Airport11:55 (BWI)Baltimore Washington International Airport
-
10:10 (BWI)Baltimore Washington International Airport13:05 (ORD)Chicago O'Hare International Airport
-
(WN 1118)Boeing 737 Max 8 Passenger (WN 1090)Boeing 737 700 - 8h 10m (1h 45m)
- BWI Baltimore 1h 45m
-
- M
- -
- -
- T
- F
- -
- -
-
05:55 - 10:10SJU - BWI13:45 - 14:45BWI - MDW
-
05:55 (SJU)San Juan Luis Munoz Marin Intl Airport13:45 (BWI)Baltimore Washington International Airport
-
10:10 (BWI)Baltimore Washington International Airport14:45 (MDW)Chicago Midway Airport
-
(WN 1118)Boeing 737 Max 8 Passenger (WN 5950)Boeing 737 800 - 9h 50m (3h 35m)
- BWI Baltimore 3h 35m
-
- M
- -
- -
- T
- F
- -
- -
-
06:00 - 10:20SJU - BWI13:05 - 14:15BWI - ORD
-
06:00 (SJU)San Juan Luis Munoz Marin Intl Airport13:05 (BWI)Baltimore Washington International Airport
-
10:20 (BWI)Baltimore Washington International Airport14:15 (ORD)Chicago O'Hare International Airport
-
(WN 1118)Boeing 737 Max 8 Passenger (WN 3191)Boeing 737 700 - 9h 15m (2h 45m)
- BWI Baltimore 2h 45m
-
- -
- T
- W
- -
- -
- -
- -
-
06:00 - 10:20SJU - BWI13:05 - 14:05BWI - MDW
-
06:00 (SJU)San Juan Luis Munoz Marin Intl Airport13:05 (BWI)Baltimore Washington International Airport
-
10:20 (BWI)Baltimore Washington International Airport14:05 (MDW)Chicago Midway Airport
-
(WN 1118)Boeing 737 Max 8 Passenger (WN 5950)Boeing 737 800 - 9h 05m (2h 45m)
- BWI Baltimore 2h 45m
-
- -
- T
- W
- -
- -
- -
- -
-
06:15 - 09:35SJU - MCO11:05 - 14:05MCO - MDW
-
06:15 (SJU)San Juan Luis Munoz Marin Intl Airport11:05 (MCO)Orlando International Airport
-
09:35 (MCO)Orlando International Airport14:05 (MDW)Chicago Midway Airport
-
(WN 6145)Boeing 737 Max 8 Passenger (WN 6025)Boeing 737 700 - 8h 50m (1h 30m)
- MCO Orlando 1h 30m
-
- -
- -
- -
- -
- -
- S
- -
-
06:15 - 09:35SJU - MCO12:40 - 14:25MCO - MDW
-
06:15 (SJU)San Juan Luis Munoz Marin Intl Airport12:40 (MCO)Orlando International Airport
-
09:35 (MCO)Orlando International Airport14:25 (MDW)Chicago Midway Airport
-
(WN 6145)Boeing 737 Max 8 Passenger (WN 3157)Boeing 737 Max 8 Passenger - 9h 10m (3h 05m)
- MCO Orlando 3h 05m
-
- -
- -
- -
- -
- -
- S
- -
-
06:15 - 09:35SJU - MCO12:20 - 14:25MCO - ORD
-
06:15 (SJU)San Juan Luis Munoz Marin Intl Airport12:20 (MCO)Orlando International Airport
-
09:35 (MCO)Orlando International Airport14:25 (ORD)Chicago O'Hare International Airport
-
(WN 6145)Boeing 737 Max 8 Passenger (WN 934)Boeing 737 800 - 9h 10m (2h 45m)
- MCO Orlando 2h 45m
-
- -
- -
- -
- -
- -
- S
- -
-
13:00 - 13:55ATL - MDW06:15 - 09:30SJU - TPA
-
13:00 (ATL)Atlanta Hartsfield-Jackson Intl Airport06:15 (SJU)San Juan Luis Munoz Marin Intl Airport
-
13:55 (MDW)Chicago Midway Airport09:30 (TPA)Tampa International Airport
-
(WN 1751)Boeing 737 Max 8 Passenger (WN 4795)Boeing 737 Max 8 Passenger - 8h 40m (2h)
- MDW Chicago 2h
-
- -
- -
- -
- -
- -
- -
- S
-
06:45 - 10:05SJU - MCO13:25 - 15:15MCO - MDW
-
06:45 (SJU)San Juan Luis Munoz Marin Intl Airport13:25 (MCO)Orlando International Airport
-
10:05 (MCO)Orlando International Airport15:15 (MDW)Chicago Midway Airport
-
(WN 3011)Boeing 737 800 (WN 3157)Boeing 737 800 - 9h 30m (3h 20m)
- MCO Orlando 3h 20m
-
- -
- -
- -
- -
- -
- -
- S
-
06:45 - 10:05SJU - MCO11:55 - 14:00MCO - ORD
-
06:45 (SJU)San Juan Luis Munoz Marin Intl Airport11:55 (MCO)Orlando International Airport
-
10:05 (MCO)Orlando International Airport14:00 (ORD)Chicago O'Hare International Airport
-
(WN 3011)Boeing 737 800 (WN 3648)Boeing 737 800 - 8h 15m (1h 50m)
- MCO Orlando 1h 50m
-
- -
- -
- -
- -
- -
- -
- S
-
06:45 - 10:00SJU - TPA14:40 - 16:20TPA - MDW
-
06:45 (SJU)San Juan Luis Munoz Marin Intl Airport14:40 (TPA)Tampa International Airport
-
10:00 (TPA)Tampa International Airport16:20 (MDW)Chicago Midway Airport
-
(WN 4795)Boeing 737 800 (WN 5891)Boeing 737 Max 8 Passenger - 10h 35m (4h 40m)
- TPA Tampa 4h 40m
-
- M
- -
- -
- T
- F
- -
- -
-
06:45 - 10:00SJU - TPA12:30 - 14:25TPA - ORD
-
06:45 (SJU)San Juan Luis Munoz Marin Intl Airport12:30 (TPA)Tampa International Airport
-
10:00 (TPA)Tampa International Airport14:25 (ORD)Chicago O'Hare International Airport
-
(WN 4795)Boeing 737 800 (WN 2163)Boeing 737 700 - 8h 40m (2h 30m)
- TPA Tampa 2h 30m
-
- M
- -
- -
- T
- F
- -
- -
-
07:00 - 10:15SJU - TPA11:05 - 12:40TPA - MDW
-
07:00 (SJU)San Juan Luis Munoz Marin Intl Airport11:05 (TPA)Tampa International Airport
-
10:15 (TPA)Tampa International Airport12:40 (MDW)Chicago Midway Airport
-
(WN 4795)Boeing 737 800 (WN 3248)Boeing 737 800 - 6h 40m (50m)
- TPA Tampa 50m
-
- -
- -
- -
- -
- -
- S
- -
-
12:35 - 14:50MSY - MDW07:00 - 10:15SJU - TPA
-
12:35 (MSY)New Orleans Louis Armstrong Intl Airport07:00 (SJU)San Juan Luis Munoz Marin Intl Airport
-
14:50 (MDW)Chicago Midway Airport10:15 (TPA)Tampa International Airport
-
(WN 2055)Boeing 737 Max 8 Passenger (WN 4795)Boeing 737 800 - 8h 50m (1h 45m)
- MDW Chicago 1h 45m
-
- -
- -
- -
- -
- -
- S
- -
-
12:55 - 14:30BNA - MDW07:00 - 10:15SJU - TPA
-
12:55 (BNA)Nashville Airport07:00 (SJU)San Juan Luis Munoz Marin Intl Airport
-
14:30 (MDW)Chicago Midway Airport10:15 (TPA)Tampa International Airport
-
(WN 5597)Boeing 737 800 (WN 4795)Boeing 737 800 - 8h 30m (1h 45m)
- MDW Chicago 1h 45m
-
- -
- -
- -
- -
- -
- S
- -
-
07:15 - 10:35SJU - MCO12:50 - 14:35MCO - MDW
-
07:15 (SJU)San Juan Luis Munoz Marin Intl Airport12:50 (MCO)Orlando International Airport
-
10:35 (MCO)Orlando International Airport14:35 (MDW)Chicago Midway Airport
-
(WN 3011)Boeing 737 800 (WN 3157)Boeing 737 800 - 8h 20m (2h 15m)
- MCO Orlando 2h 15m
-
- M
- -
- -
- T
- F
- -
- -
-
07:15 - 10:35SJU - MCO14:40 - 16:45MCO - ORD
-
07:15 (SJU)San Juan Luis Munoz Marin Intl Airport14:40 (MCO)Orlando International Airport
-
10:35 (MCO)Orlando International Airport16:45 (ORD)Chicago O'Hare International Airport
-
(WN 3011)Boeing 737 800 (WN 3650)Boeing 737 Max 8 Passenger - 10h 30m (4h 05m)
- MCO Orlando 4h 05m
-
- M
- -
- -
- T
- F
- -
- -
-
07:30 - 10:50SJU - MCO13:05 - 14:50MCO - MDW
-
07:30 (SJU)San Juan Luis Munoz Marin Intl Airport13:05 (MCO)Orlando International Airport
-
10:50 (MCO)Orlando International Airport14:50 (MDW)Chicago Midway Airport
-
(WN 3011)Boeing 737 Max 8 Passenger (WN 3157)Boeing 737 Max 8 Passenger - 8h 20m (2h 15m)
- MCO Orlando 2h 15m
-
- -
- T
- W
- -
- -
- -
- -
-
07:30 - 10:50SJU - MCO14:40 - 16:45MCO - ORD
-
07:30 (SJU)San Juan Luis Munoz Marin Intl Airport14:40 (MCO)Orlando International Airport
-
10:50 (MCO)Orlando International Airport16:45 (ORD)Chicago O'Hare International Airport
-
(WN 3011)Boeing 737 Max 8 Passenger (WN 3650)Boeing 737 700 - 10h 15m (3h 50m)
- MCO Orlando 3h 50m
-
- -
- T
- W
- -
- -
- -
- -
-
08:10 - 11:05SJU - FLL14:20 - 16:30FLL - MDW
-
08:10 (SJU)San Juan Luis Munoz Marin Intl Airport14:20 (FLL)Fort Lauderdale/Hollywood Intl Airport
-
11:05 (FLL)Fort Lauderdale/Hollywood Intl Airport16:30 (MDW)Chicago Midway Airport
-
(WN 3826)Boeing 737 800 (WN 2771)Boeing 737 700 - 9h 20m (3h 15m)
- FLL Miami 3h 15m
-
- -
- -
- -
- -
- -
- S
- -
-
08:30 - 11:40SJU - TPA15:45 - 17:25TPA - MDW
-
08:30 (SJU)San Juan Luis Munoz Marin Intl Airport15:45 (TPA)Tampa International Airport
-
11:40 (TPA)Tampa International Airport17:25 (MDW)Chicago Midway Airport
-
(WN 4795)Boeing 737 800 (WN 5891)Boeing 737 Max 8 Passenger - 9h 55m (4h 05m)
- TPA Tampa 4h 05m
-
- -
- T
- W
- -
- -
- -
- -
-
08:30 - 11:40SJU - TPA12:30 - 14:25TPA - ORD
-
08:30 (SJU)San Juan Luis Munoz Marin Intl Airport12:30 (TPA)Tampa International Airport
-
11:40 (TPA)Tampa International Airport14:25 (ORD)Chicago O'Hare International Airport
-
(WN 4795)Boeing 737 800 (WN 2163)Boeing 737 800 - 6h 55m (50m)
- TPA Tampa 50m
-
- -
- T
- W
- -
- -
- -
- -
-
14:40 - 15:45STL - MDW08:30 - 11:40SJU - TPA
-
14:40 (STL)St Louis Lambert Intl Airport08:30 (SJU)San Juan Luis Munoz Marin Intl Airport
-
15:45 (MDW)Chicago Midway Airport11:40 (TPA)Tampa International Airport
-
(WN 3242)Boeing 737 Max 8 Passenger (WN 4795)Boeing 737 800 - 8h 15m (1h 35m)
- MDW Chicago 1h 35m
-
- -
- T
- W
- -
- -
- -
- -
-
09:40 - 12:55SJU - MCO17:00 - 18:55MCO - MDW
-
09:40 (SJU)San Juan Luis Munoz Marin Intl Airport17:00 (MCO)Orlando International Airport
-
12:55 (MCO)Orlando International Airport18:55 (MDW)Chicago Midway Airport
-
(WN 3012)Boeing 737 800 (WN 998)Boeing 737 800 - 10h 15m (4h 05m)
- MCO Orlando 4h 05m
-
- -
- -
- -
- -
- -
- S
- -
-
09:40 - 12:55SJU - MCO14:45 - 16:30MCO - MDW
-
09:40 (SJU)San Juan Luis Munoz Marin Intl Airport14:45 (MCO)Orlando International Airport
-
12:55 (MCO)Orlando International Airport16:30 (MDW)Chicago Midway Airport
-
(WN 3012)Boeing 737 800 (WN 3313)Boeing 737 700 - 7h 50m (1h 50m)
- MCO Orlando 1h 50m
-
- -
- -
- -
- -
- -
- S
- -
-
09:55 - 14:00SJU - STL17:10 - 18:15STL - MDW
-
09:55 (SJU)San Juan Luis Munoz Marin Intl Airport17:10 (STL)St Louis Lambert Intl Airport
-
14:00 (STL)St Louis Lambert Intl Airport18:15 (MDW)Chicago Midway Airport
-
(WN 1473)Boeing 737 800 (WN 3244)Boeing 737 800 - 9h 20m (3h 10m)
- STL Saint Louis 3h 10m
-
- -
- -
- -
- -
- -
- S
- -
-
10:45 - 14:00SJU - MCO15:35 - 17:25MCO - MDW
-
10:45 (SJU)San Juan Luis Munoz Marin Intl Airport15:35 (MCO)Orlando International Airport
-
14:00 (MCO)Orlando International Airport17:25 (MDW)Chicago Midway Airport
-
(WN 3012)Boeing 737 800 (WN 3313)Boeing 737 800 - 7h 40m (1h 35m)
- MCO Orlando 1h 35m
-
- -
- -
- -
- -
- -
- -
- S
-
10:50 - 15:05SJU - BWI16:00 - 17:00BWI - MDW
-
10:50 (SJU)San Juan Luis Munoz Marin Intl Airport16:00 (BWI)Baltimore Washington International Airport
-
15:05 (BWI)Baltimore Washington International Airport17:00 (MDW)Chicago Midway Airport
-
(WN 4130)Boeing 737 Max 8 Passenger (WN 2136)Boeing 737 800 - 7h 10m (55m)
- BWI Baltimore 55m
-
- -
- -
- -
- -
- -
- S
- -
-
10:50 - 15:05SJU - BWI18:45 - 19:45BWI - MDW
-
10:50 (SJU)San Juan Luis Munoz Marin Intl Airport18:45 (BWI)Baltimore Washington International Airport
-
15:05 (BWI)Baltimore Washington International Airport19:45 (MDW)Chicago Midway Airport
-
(WN 4130)Boeing 737 Max 8 Passenger (WN 1789)Boeing 737 Max 8 Passenger - 9h 55m (3h 40m)
- BWI Baltimore 3h 40m
-
- -
- -
- -
- -
- -
- S
- -
-
12:00 - 15:15SJU - MCO18:00 - 19:50MCO - MDW
-
12:00 (SJU)San Juan Luis Munoz Marin Intl Airport18:00 (MCO)Orlando International Airport
-
15:15 (MCO)Orlando International Airport19:50 (MDW)Chicago Midway Airport
-
(WN 3012)Boeing 737 Max 8 Passenger (WN 3158)Boeing 737 Max 8 Passenger - 8h 50m (2h 45m)
- MCO Orlando 2h 45m
-
- M
- -
- -
- T
- F
- -
- -
-
12:45 - 16:00SJU - MCO17:00 - 18:55MCO - MDW
-
12:45 (SJU)San Juan Luis Munoz Marin Intl Airport17:00 (MCO)Orlando International Airport
-
16:00 (MCO)Orlando International Airport18:55 (MDW)Chicago Midway Airport
-
(WN 1119)Boeing 737 800 (WN 998)Boeing 737 800 - 7h 10m (1h)
- MCO Orlando 1h
-
- -
- -
- -
- -
- -
- S
- -
-
12:55 - 17:10SJU - BWI21:10 - 22:20BWI - ORD
-
12:55 (SJU)San Juan Luis Munoz Marin Intl Airport21:10 (BWI)Baltimore Washington International Airport
-
17:10 (BWI)Baltimore Washington International Airport22:20 (ORD)Chicago O'Hare International Airport
-
(WN 4130)Boeing 737 Max 8 Passenger (WN 5289)Boeing 737 800 - 10h 25m (4h)
- BWI Baltimore 4h
-
- -
- -
- -
- -
- -
- -
- S
-
12:55 - 17:10SJU - BWI18:55 - 20:00BWI - MDW
-
12:55 (SJU)San Juan Luis Munoz Marin Intl Airport18:55 (BWI)Baltimore Washington International Airport
-
17:10 (BWI)Baltimore Washington International Airport20:00 (MDW)Chicago Midway Airport
-
(WN 4130)Boeing 737 Max 8 Passenger (WN 1789)Boeing 737 800 - 8h 05m (1h 45m)
- BWI Baltimore 1h 45m
-
- -
- -
- -
- -
- -
- -
- S
-
13:35 - 16:30SJU - FLL19:10 - 21:20FLL - MDW
-
13:35 (SJU)San Juan Luis Munoz Marin Intl Airport19:10 (FLL)Fort Lauderdale/Hollywood Intl Airport
-
16:30 (FLL)Fort Lauderdale/Hollywood Intl Airport21:20 (MDW)Chicago Midway Airport
-
(WN 1992)Boeing 737 Max 8 Passenger (WN 3107)Boeing 737 Max 8 Passenger - 8h 45m (2h 40m)
- FLL Miami 2h 40m
-
- -
- T
- W
- -
- -
- -
- -
-
13:40 - 17:00SJU - MCO21:30 - 23:20MCO - MDW
-
13:40 (SJU)San Juan Luis Munoz Marin Intl Airport21:30 (MCO)Orlando International Airport
-
17:00 (MCO)Orlando International Airport23:20 (MDW)Chicago Midway Airport
-
(WN 1119)Boeing 737 Max 8 Passenger (WN 1328)Boeing 737 Max 8 Passenger - 10h 40m (4h 30m)
- MCO Orlando 4h 30m
-
- -
- -
- -
- -
- -
- -
- S
-
13:40 - 17:00SJU - MCO18:55 - 20:50MCO - MDW
-
13:40 (SJU)San Juan Luis Munoz Marin Intl Airport18:55 (MCO)Orlando International Airport
-
17:00 (MCO)Orlando International Airport20:50 (MDW)Chicago Midway Airport
-
(WN 1119)Boeing 737 Max 8 Passenger (WN 3159)Boeing 737 700 - 8h 10m (1h 55m)
- MCO Orlando 1h 55m
-
- -
- -
- -
- -
- -
- -
- S
-
13:40 - 17:00SJU - MCO18:50 - 20:55MCO - ORD
-
13:40 (SJU)San Juan Luis Munoz Marin Intl Airport18:50 (MCO)Orlando International Airport
-
17:00 (MCO)Orlando International Airport20:55 (ORD)Chicago O'Hare International Airport
-
(WN 1119)Boeing 737 Max 8 Passenger (WN 3650)Boeing 737 Max 8 Passenger - 8h 15m (1h 50m)
- MCO Orlando 1h 50m
-
- -
- -
- -
- -
- -
- -
- S
-
14:10 - 17:10SJU - FLL19:10 - 21:25FLL - MDW
-
14:10 (SJU)San Juan Luis Munoz Marin Intl Airport19:10 (FLL)Fort Lauderdale/Hollywood Intl Airport
-
17:10 (FLL)Fort Lauderdale/Hollywood Intl Airport21:25 (MDW)Chicago Midway Airport
-
(WN 1992)Boeing 737 800 (WN 3107)Boeing 737 800 - 8h 15m (2h)
- FLL Miami 2h
-
- M
- -
- -
- T
- F
- -
- -
-
14:35 - 17:50SJU - MCO20:40 - 22:25MCO - MDW
-
14:35 (SJU)San Juan Luis Munoz Marin Intl Airport20:40 (MCO)Orlando International Airport
-
17:50 (MCO)Orlando International Airport22:25 (MDW)Chicago Midway Airport
-
(WN 3014)Boeing 737 800 (WN 1328)Boeing 737 700 - 8h 50m (2h 50m)
- MCO Orlando 2h 50m
-
- -
- -
- -
- -
- -
- S
- -
-
14:45 - 18:10SJU - MCO21:20 - 23:10MCO - MDW
-
14:45 (SJU)San Juan Luis Munoz Marin Intl Airport21:20 (MCO)Orlando International Airport
-
18:10 (MCO)Orlando International Airport23:10 (MDW)Chicago Midway Airport
-
(WN 3014)Boeing 737 800 (WN 1328)Boeing 737 800 - 9h 25m (3h 10m)
- MCO Orlando 3h 10m
-
- -
- T
- W
- -
- -
- -
- -
-
21:30 - 22:35STL - MDW14:45 - 18:10SJU - MCO
-
21:30 (STL)St Louis Lambert Intl Airport14:45 (SJU)San Juan Luis Munoz Marin Intl Airport
-
22:35 (MDW)Chicago Midway Airport18:10 (MCO)Orlando International Airport
-
(WN 3244)Boeing 737 Max 8 Passenger (WN 3014)Boeing 737 800 - 8h 50m (1h 45m)
- MDW Chicago 1h 45m
-
- -
- T
- W
- -
- -
- -
- -
No Schedules
Sorry, there are no schedules matching your filters. Try removing one.
reset
What’s the fastest flight time from San Juan to Chicago?
The fastest flight time for direct flights from San Juan to Chicago is 5 hours 5 minutes. Check latest flight schedules & prices on Wego.
How far is Chicago from San Juan?
The flight distance between San Juan and Chicago is 3305km. Check all available flights on Wego.
When is the earliest and latest flight of the day?
The earliest flight of the day departs at 05:10. The last flight of the day departs at 05:10. See the full list of flight times on Wego.
How many airlines offer direct flights from San Juan to Chicago?
There are 3 airlines that offer direct flights from San Juan to Chicago. Find out the list of airlines on Wego.
All Airports in Chicago
Popular destinations from Chicago
Popular destinations from San Juan
Popular Hotels in Chicago
- Clarion Inn Elmhurst - Oak Brook near I-88, I-290, I-294
- The Royal Sonesta Chicago Downtown
- Club Quarters Hotel, Central Loop, Chicago
- The Ritz-Carlton, Chicago
- Fairmont Chicago at Millennium Park Gold Experience
- Swissôtel Chicago
- Pendry Chicago
- Hotel Felix Chicago
- Hotel Saint Clair
- Best Western River North Hotel