Fare Guide
Estimated lowest fares found within 7 days
The cheapest airline(s) flying from San Juan to Chicago is Delta Air Lines.
Travel Period: June 2024 - May 2025
The cheapest month(s) to fly from San Juan to Chicago is July.
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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
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May 2025
The cheapest day(s) of the week to fly from San Juan to Chicago is Tuesday.
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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
The cheapest time of the day to fly from San Juan to Chicago is in the morning.
Flight Schedules
Last Updated: Thu, 2 May, 2024
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Depart
Earliest
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- Latest
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Arrive
- Earliest
- Latest
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Airline
Filter by Airline
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Total Duration
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Stopover
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Availability
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07:01 - 11:10SJU - ORD
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07:01 (SJU)San Juan Luis Munoz Marin Intl Airport
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11:10 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1165)Boeing 737 800 - 5h 09m
- Direct
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- M
- T
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- T
- F
- S
- S
- Boeing 737 800
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13:20 - 17:25SJU - MDW
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13:20 (SJU)San Juan Luis Munoz Marin Intl Airport
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17:25 (MDW)Chicago Midway Airport
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(WN 1839)Boeing 737 Max 8 Passenger - 5h 05m
- Direct
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- -
- -
- -
- -
- -
- S
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- Boeing 737 Max 8 Passenger
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14:10 - 18:15SJU - MDW
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14:10 (SJU)San Juan Luis Munoz Marin Intl Airport
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18:15 (MDW)Chicago Midway Airport
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(WN 1839)Boeing 737 Max 8 Passenger - 5h 05m
- Direct
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- S
- Boeing 737 Max 8 Passenger
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14:20 - 18:30SJU - ORD
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14:20 (SJU)San Juan Luis Munoz Marin Intl Airport
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18:30 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 2088)Boeing 737 800 - 5h 10m
- Direct
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- M
- T
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- S
- S
- Boeing 737 800
Connecting Flights
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05:10 - 08:25SJU - MCO09:45 - 11:30MCO - MDW
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05:10 (SJU)San Juan Luis Munoz Marin Intl Airport09:45 (MCO)Orlando International Airport
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08:25 (MCO)Orlando International Airport11:30 (MDW)Chicago Midway Airport
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(WN 6145)Boeing 737 800 (WN 3156)Boeing 737 800 - 7h 20m (1h 20m)
- MCO Orlando 1h 20m
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- -
- T
- W
- -
- -
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- -
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05:10 - 08:25SJU - MCO09:30 - 11:30MCO - ORD
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05:10 (SJU)San Juan Luis Munoz Marin Intl Airport09:30 (MCO)Orlando International Airport
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08:25 (MCO)Orlando International Airport11:30 (ORD)Chicago O'Hare International Airport
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(WN 6145)Boeing 737 800 (WN 934)Boeing 737 800 - 7h 20m (1h 05m)
- MCO Orlando 1h 05m
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- -
- T
- W
- -
- -
- -
- -
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05:10 - 08:25SJU - MCO11:15 - 13:00MCO - MDW
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05:10 (SJU)San Juan Luis Munoz Marin Intl Airport11:15 (MCO)Orlando International Airport
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08:25 (MCO)Orlando International Airport13:00 (MDW)Chicago Midway Airport
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(WN 6145)Boeing 737 800 (WN 6125)Boeing 737 Max 8 Passenger - 8h 50m (2h 50m)
- MCO Orlando 2h 50m
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- -
- T
- W
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- -
- -
- -
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05:15 - 08:30SJU - MCO09:40 - 11:25MCO - MDW
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05:15 (SJU)San Juan Luis Munoz Marin Intl Airport09:40 (MCO)Orlando International Airport
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08:30 (MCO)Orlando International Airport11:25 (MDW)Chicago Midway Airport
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(WN 6145)Boeing 737 Max 8 Passenger (WN 3156)Boeing 737 800 - 7h 10m (1h 10m)
- MCO Orlando 1h 10m
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- M
- -
- -
- T
- F
- -
- -
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05:15 - 08:30SJU - MCO11:00 - 13:00MCO - ORD
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05:15 (SJU)San Juan Luis Munoz Marin Intl Airport11:00 (MCO)Orlando International Airport
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08:30 (MCO)Orlando International Airport13:00 (ORD)Chicago O'Hare International Airport
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(WN 6145)Boeing 737 Max 8 Passenger (WN 934)Boeing 737 800 - 8h 45m (2h 30m)
- MCO Orlando 2h 30m
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- M
- -
- -
- T
- F
- -
- -
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05:15 - 08:30SJU - MCO12:50 - 14:35MCO - MDW
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05:15 (SJU)San Juan Luis Munoz Marin Intl Airport12:50 (MCO)Orlando International Airport
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08:30 (MCO)Orlando International Airport14:35 (MDW)Chicago Midway Airport
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(WN 6145)Boeing 737 Max 8 Passenger (WN 3157)Boeing 737 800 - 10h 20m (4h 20m)
- MCO Orlando 4h 20m
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- M
- -
- -
- T
- F
- -
- -
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13:25 - 13:40CLE - MDW05:45 - 10:00SJU - BWI
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13:25 (CLE)Cleveland Hopkins International Airport05:45 (SJU)San Juan Luis Munoz Marin Intl Airport
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13:40 (MDW)Chicago Midway Airport10:00 (BWI)Baltimore Washington International Airport
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(WN 2969)Boeing 737 Max 8 Passenger (WN 1118)Boeing 737 800 - 8h 55m (2h)
- MDW Chicago 2h
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- -
- -
- -
- -
- -
- -
- S
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05:45 - 10:00SJU - BWI12:45 - 13:40BWI - MDW
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05:45 (SJU)San Juan Luis Munoz Marin Intl Airport12:45 (BWI)Baltimore Washington International Airport
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10:00 (BWI)Baltimore Washington International Airport13:40 (MDW)Chicago Midway Airport
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(WN 1118)Boeing 737 Max 8 Passenger (WN 5950)Boeing 737 800 - 8h 55m (2h 45m)
- BWI Baltimore 2h 45m
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- -
- -
- -
- -
- -
- S
- -
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05:45 - 10:00SJU - BWI13:15 - 14:15BWI - MDW
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05:45 (SJU)San Juan Luis Munoz Marin Intl Airport13:15 (BWI)Baltimore Washington International Airport
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10:00 (BWI)Baltimore Washington International Airport14:15 (MDW)Chicago Midway Airport
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(WN 1118)Boeing 737 800 (WN 5950)Boeing 737 Max 8 Passenger - 9h 30m (3h 15m)
- BWI Baltimore 3h 15m
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- -
- -
- -
- -
- -
- -
- S
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05:55 - 10:10SJU - BWI11:55 - 13:05BWI - ORD
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05:55 (SJU)San Juan Luis Munoz Marin Intl Airport11:55 (BWI)Baltimore Washington International Airport
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10:10 (BWI)Baltimore Washington International Airport13:05 (ORD)Chicago O'Hare International Airport
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(WN 1118)Boeing 737 Max 8 Passenger (WN 1090)Boeing 737 700 - 8h 10m (1h 45m)
- BWI Baltimore 1h 45m
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- M
- -
- -
- T
- F
- -
- -
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05:55 - 10:10SJU - BWI13:45 - 14:45BWI - MDW
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05:55 (SJU)San Juan Luis Munoz Marin Intl Airport13:45 (BWI)Baltimore Washington International Airport
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10:10 (BWI)Baltimore Washington International Airport14:45 (MDW)Chicago Midway Airport
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(WN 1118)Boeing 737 Max 8 Passenger (WN 5950)Boeing 737 800 - 9h 50m (3h 35m)
- BWI Baltimore 3h 35m
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- M
- -
- -
- T
- F
- -
- -
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06:00 - 10:20SJU - BWI13:05 - 14:15BWI - ORD
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06:00 (SJU)San Juan Luis Munoz Marin Intl Airport13:05 (BWI)Baltimore Washington International Airport
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10:20 (BWI)Baltimore Washington International Airport14:15 (ORD)Chicago O'Hare International Airport
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(WN 1118)Boeing 737 Max 8 Passenger (WN 3191)Boeing 737 700 - 9h 15m (2h 45m)
- BWI Baltimore 2h 45m
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- -
- T
- W
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- -
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06:00 - 10:20SJU - BWI13:05 - 14:05BWI - MDW
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06:00 (SJU)San Juan Luis Munoz Marin Intl Airport13:05 (BWI)Baltimore Washington International Airport
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10:20 (BWI)Baltimore Washington International Airport14:05 (MDW)Chicago Midway Airport
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(WN 1118)Boeing 737 Max 8 Passenger (WN 5950)Boeing 737 800 - 9h 05m (2h 45m)
- BWI Baltimore 2h 45m
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- -
- T
- W
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- -
- -
- -
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06:15 - 09:35SJU - MCO11:05 - 14:05MCO - MDW
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06:15 (SJU)San Juan Luis Munoz Marin Intl Airport11:05 (MCO)Orlando International Airport
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09:35 (MCO)Orlando International Airport14:05 (MDW)Chicago Midway Airport
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(WN 6145)Boeing 737 Max 8 Passenger (WN 6025)Boeing 737 700 - 8h 50m (1h 30m)
- MCO Orlando 1h 30m
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- -
- -
- -
- -
- -
- S
- -
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06:15 - 09:35SJU - MCO12:40 - 14:25MCO - MDW
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06:15 (SJU)San Juan Luis Munoz Marin Intl Airport12:40 (MCO)Orlando International Airport
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09:35 (MCO)Orlando International Airport14:25 (MDW)Chicago Midway Airport
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(WN 6145)Boeing 737 Max 8 Passenger (WN 3157)Boeing 737 Max 8 Passenger - 9h 10m (3h 05m)
- MCO Orlando 3h 05m
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- -
- -
- -
- -
- -
- S
- -
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06:15 - 09:35SJU - MCO12:20 - 14:25MCO - ORD
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06:15 (SJU)San Juan Luis Munoz Marin Intl Airport12:20 (MCO)Orlando International Airport
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09:35 (MCO)Orlando International Airport14:25 (ORD)Chicago O'Hare International Airport
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(WN 6145)Boeing 737 Max 8 Passenger (WN 934)Boeing 737 800 - 9h 10m (2h 45m)
- MCO Orlando 2h 45m
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- -
- -
- -
- -
- -
- S
- -
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13:00 - 13:55ATL - MDW06:15 - 09:30SJU - TPA
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13:00 (ATL)Atlanta Hartsfield-Jackson Intl Airport06:15 (SJU)San Juan Luis Munoz Marin Intl Airport
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13:55 (MDW)Chicago Midway Airport09:30 (TPA)Tampa International Airport
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(WN 1751)Boeing 737 Max 8 Passenger (WN 4795)Boeing 737 Max 8 Passenger - 8h 40m (2h)
- MDW Chicago 2h
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- -
- -
- -
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- -
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- S
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06:45 - 10:05SJU - MCO13:25 - 15:15MCO - MDW
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06:45 (SJU)San Juan Luis Munoz Marin Intl Airport13:25 (MCO)Orlando International Airport
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10:05 (MCO)Orlando International Airport15:15 (MDW)Chicago Midway Airport
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(WN 3011)Boeing 737 800 (WN 3157)Boeing 737 800 - 9h 30m (3h 20m)
- MCO Orlando 3h 20m
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- -
- -
- -
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- S
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06:45 - 10:05SJU - MCO11:55 - 14:00MCO - ORD
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06:45 (SJU)San Juan Luis Munoz Marin Intl Airport11:55 (MCO)Orlando International Airport
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10:05 (MCO)Orlando International Airport14:00 (ORD)Chicago O'Hare International Airport
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(WN 3011)Boeing 737 800 (WN 3648)Boeing 737 800 - 8h 15m (1h 50m)
- MCO Orlando 1h 50m
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- -
- -
- -
- -
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- -
- S
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06:45 - 10:00SJU - TPA14:40 - 16:20TPA - MDW
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06:45 (SJU)San Juan Luis Munoz Marin Intl Airport14:40 (TPA)Tampa International Airport
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10:00 (TPA)Tampa International Airport16:20 (MDW)Chicago Midway Airport
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(WN 4795)Boeing 737 800 (WN 5891)Boeing 737 Max 8 Passenger - 10h 35m (4h 40m)
- TPA Tampa 4h 40m
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- M
- -
- -
- T
- F
- -
- -
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06:45 - 10:00SJU - TPA12:30 - 14:25TPA - ORD
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06:45 (SJU)San Juan Luis Munoz Marin Intl Airport12:30 (TPA)Tampa International Airport
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10:00 (TPA)Tampa International Airport14:25 (ORD)Chicago O'Hare International Airport
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(WN 4795)Boeing 737 800 (WN 2163)Boeing 737 700 - 8h 40m (2h 30m)
- TPA Tampa 2h 30m
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- M
- -
- -
- T
- F
- -
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07:00 - 10:15SJU - TPA11:05 - 12:40TPA - MDW
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07:00 (SJU)San Juan Luis Munoz Marin Intl Airport11:05 (TPA)Tampa International Airport
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10:15 (TPA)Tampa International Airport12:40 (MDW)Chicago Midway Airport
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(WN 4795)Boeing 737 800 (WN 3248)Boeing 737 800 - 6h 40m (50m)
- TPA Tampa 50m
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- -
- -
- -
- -
- -
- S
- -
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12:35 - 14:50MSY - MDW07:00 - 10:15SJU - TPA
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12:35 (MSY)New Orleans Louis Armstrong Intl Airport07:00 (SJU)San Juan Luis Munoz Marin Intl Airport
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14:50 (MDW)Chicago Midway Airport10:15 (TPA)Tampa International Airport
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(WN 2055)Boeing 737 Max 8 Passenger (WN 4795)Boeing 737 800 - 8h 50m (1h 45m)
- MDW Chicago 1h 45m
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- -
- -
- -
- -
- -
- S
- -
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12:55 - 14:30BNA - MDW07:00 - 10:15SJU - TPA
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12:55 (BNA)Nashville Airport07:00 (SJU)San Juan Luis Munoz Marin Intl Airport
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14:30 (MDW)Chicago Midway Airport10:15 (TPA)Tampa International Airport
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(WN 5597)Boeing 737 800 (WN 4795)Boeing 737 800 - 8h 30m (1h 45m)
- MDW Chicago 1h 45m
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- -
- -
- -
- -
- -
- S
- -
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07:15 - 10:35SJU - MCO12:50 - 14:35MCO - MDW
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07:15 (SJU)San Juan Luis Munoz Marin Intl Airport12:50 (MCO)Orlando International Airport
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10:35 (MCO)Orlando International Airport14:35 (MDW)Chicago Midway Airport
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(WN 3011)Boeing 737 800 (WN 3157)Boeing 737 800 - 8h 20m (2h 15m)
- MCO Orlando 2h 15m
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- M
- -
- -
- T
- F
- -
- -
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07:15 - 10:35SJU - MCO14:40 - 16:45MCO - ORD
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07:15 (SJU)San Juan Luis Munoz Marin Intl Airport14:40 (MCO)Orlando International Airport
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10:35 (MCO)Orlando International Airport16:45 (ORD)Chicago O'Hare International Airport
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(WN 3011)Boeing 737 800 (WN 3650)Boeing 737 Max 8 Passenger - 10h 30m (4h 05m)
- MCO Orlando 4h 05m
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- M
- -
- -
- T
- F
- -
- -
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07:30 - 10:50SJU - MCO13:05 - 14:50MCO - MDW
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07:30 (SJU)San Juan Luis Munoz Marin Intl Airport13:05 (MCO)Orlando International Airport
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10:50 (MCO)Orlando International Airport14:50 (MDW)Chicago Midway Airport
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(WN 3011)Boeing 737 Max 8 Passenger (WN 3157)Boeing 737 Max 8 Passenger - 8h 20m (2h 15m)
- MCO Orlando 2h 15m
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- -
- T
- W
- -
- -
- -
- -
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07:30 - 10:50SJU - MCO14:40 - 16:45MCO - ORD
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07:30 (SJU)San Juan Luis Munoz Marin Intl Airport14:40 (MCO)Orlando International Airport
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10:50 (MCO)Orlando International Airport16:45 (ORD)Chicago O'Hare International Airport
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(WN 3011)Boeing 737 Max 8 Passenger (WN 3650)Boeing 737 700 - 10h 15m (3h 50m)
- MCO Orlando 3h 50m
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- -
- T
- W
- -
- -
- -
- -
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08:10 - 11:05SJU - FLL14:20 - 16:30FLL - MDW
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08:10 (SJU)San Juan Luis Munoz Marin Intl Airport14:20 (FLL)Fort Lauderdale/Hollywood Intl Airport
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11:05 (FLL)Fort Lauderdale/Hollywood Intl Airport16:30 (MDW)Chicago Midway Airport
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(WN 3826)Boeing 737 800 (WN 2771)Boeing 737 700 - 9h 20m (3h 15m)
- FLL Miami 3h 15m
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- -
- -
- -
- -
- -
- S
- -
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08:30 - 11:40SJU - TPA15:45 - 17:25TPA - MDW
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08:30 (SJU)San Juan Luis Munoz Marin Intl Airport15:45 (TPA)Tampa International Airport
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11:40 (TPA)Tampa International Airport17:25 (MDW)Chicago Midway Airport
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(WN 4795)Boeing 737 800 (WN 5891)Boeing 737 Max 8 Passenger - 9h 55m (4h 05m)
- TPA Tampa 4h 05m
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- -
- T
- W
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- -
- -
- -
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08:30 - 11:40SJU - TPA12:30 - 14:25TPA - ORD
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08:30 (SJU)San Juan Luis Munoz Marin Intl Airport12:30 (TPA)Tampa International Airport
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11:40 (TPA)Tampa International Airport14:25 (ORD)Chicago O'Hare International Airport
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(WN 4795)Boeing 737 800 (WN 2163)Boeing 737 800 - 6h 55m (50m)
- TPA Tampa 50m
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- -
- T
- W
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- -
- -
- -
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14:40 - 15:45STL - MDW08:30 - 11:40SJU - TPA
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14:40 (STL)St Louis Lambert Intl Airport08:30 (SJU)San Juan Luis Munoz Marin Intl Airport
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15:45 (MDW)Chicago Midway Airport11:40 (TPA)Tampa International Airport
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(WN 3242)Boeing 737 Max 8 Passenger (WN 4795)Boeing 737 800 - 8h 15m (1h 35m)
- MDW Chicago 1h 35m
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- -
- T
- W
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- -
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09:40 - 12:55SJU - MCO17:00 - 18:55MCO - MDW
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09:40 (SJU)San Juan Luis Munoz Marin Intl Airport17:00 (MCO)Orlando International Airport
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12:55 (MCO)Orlando International Airport18:55 (MDW)Chicago Midway Airport
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(WN 3012)Boeing 737 800 (WN 998)Boeing 737 800 - 10h 15m (4h 05m)
- MCO Orlando 4h 05m
-
- -
- -
- -
- -
- -
- S
- -
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09:40 - 12:55SJU - MCO14:45 - 16:30MCO - MDW
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09:40 (SJU)San Juan Luis Munoz Marin Intl Airport14:45 (MCO)Orlando International Airport
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12:55 (MCO)Orlando International Airport16:30 (MDW)Chicago Midway Airport
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(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
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09:55 (SJU)San Juan Luis Munoz Marin Intl Airport17:10 (STL)St Louis Lambert Intl Airport
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14:00 (STL)St Louis Lambert Intl Airport18:15 (MDW)Chicago Midway Airport
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(WN 1473)Boeing 737 800 (WN 3244)Boeing 737 800 - 9h 20m (3h 10m)
- STL Saint Louis 3h 10m
-
- -
- -
- -
- -
- -
- S
- -
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10:45 - 14:00SJU - MCO15:35 - 17:25MCO - MDW
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10:45 (SJU)San Juan Luis Munoz Marin Intl Airport15:35 (MCO)Orlando International Airport
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14:00 (MCO)Orlando International Airport17:25 (MDW)Chicago Midway Airport
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(WN 3012)Boeing 737 800 (WN 3313)Boeing 737 800 - 7h 40m (1h 35m)
- MCO Orlando 1h 35m
-
- -
- -
- -
- -
- -
- -
- S
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10:50 - 15:05SJU - BWI16:00 - 17:00BWI - MDW
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10:50 (SJU)San Juan Luis Munoz Marin Intl Airport16:00 (BWI)Baltimore Washington International Airport
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15:05 (BWI)Baltimore Washington International Airport17:00 (MDW)Chicago Midway Airport
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(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
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10:50 (SJU)San Juan Luis Munoz Marin Intl Airport18:45 (BWI)Baltimore Washington International Airport
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15:05 (BWI)Baltimore Washington International Airport19:45 (MDW)Chicago Midway Airport
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(WN 4130)Boeing 737 Max 8 Passenger (WN 1789)Boeing 737 Max 8 Passenger - 9h 55m (3h 40m)
- BWI Baltimore 3h 40m
-
- -
- -
- -
- -
- -
- S
- -
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12:00 - 15:15SJU - MCO18:00 - 19:50MCO - MDW
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12:00 (SJU)San Juan Luis Munoz Marin Intl Airport18:00 (MCO)Orlando International Airport
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15:15 (MCO)Orlando International Airport19:50 (MDW)Chicago Midway Airport
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(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
- -
- -
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12:45 - 16:00SJU - MCO17:00 - 18:55MCO - MDW
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12:45 (SJU)San Juan Luis Munoz Marin Intl Airport17:00 (MCO)Orlando International Airport
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16:00 (MCO)Orlando International Airport18:55 (MDW)Chicago Midway Airport
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(WN 1119)Boeing 737 800 (WN 998)Boeing 737 800 - 7h 10m (1h)
- MCO Orlando 1h
-
- -
- -
- -
- -
- -
- S
- -
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12:55 - 17:10SJU - BWI21:10 - 22:20BWI - ORD
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12:55 (SJU)San Juan Luis Munoz Marin Intl Airport21:10 (BWI)Baltimore Washington International Airport
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17:10 (BWI)Baltimore Washington International Airport22:20 (ORD)Chicago O'Hare International Airport
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(WN 4130)Boeing 737 Max 8 Passenger (WN 5289)Boeing 737 800 - 10h 25m (4h)
- BWI Baltimore 4h
-
- -
- -
- -
- -
- -
- -
- S
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12:55 - 17:10SJU - BWI18:55 - 20:00BWI - MDW
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12:55 (SJU)San Juan Luis Munoz Marin Intl Airport18:55 (BWI)Baltimore Washington International Airport
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17:10 (BWI)Baltimore Washington International Airport20:00 (MDW)Chicago Midway Airport
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(WN 4130)Boeing 737 Max 8 Passenger (WN 1789)Boeing 737 800 - 8h 05m (1h 45m)
- BWI Baltimore 1h 45m
-
- -
- -
- -
- -
- -
- -
- S
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13:35 - 16:30SJU - FLL19:10 - 21:20FLL - MDW
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13:35 (SJU)San Juan Luis Munoz Marin Intl Airport19:10 (FLL)Fort Lauderdale/Hollywood Intl Airport
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16:30 (FLL)Fort Lauderdale/Hollywood Intl Airport21:20 (MDW)Chicago Midway Airport
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(WN 1992)Boeing 737 Max 8 Passenger (WN 3107)Boeing 737 Max 8 Passenger - 8h 45m (2h 40m)
- FLL Miami 2h 40m
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- -
- T
- W
- -
- -
- -
- -
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13:40 - 17:00SJU - MCO21:30 - 23:20MCO - MDW
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13:40 (SJU)San Juan Luis Munoz Marin Intl Airport21:30 (MCO)Orlando International Airport
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17:00 (MCO)Orlando International Airport23:20 (MDW)Chicago Midway Airport
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(WN 1119)Boeing 737 Max 8 Passenger (WN 1328)Boeing 737 Max 8 Passenger - 10h 40m (4h 30m)
- MCO Orlando 4h 30m
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- -
- -
- -
- -
- -
- -
- S
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13:40 - 17:00SJU - MCO18:55 - 20:50MCO - MDW
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13:40 (SJU)San Juan Luis Munoz Marin Intl Airport18:55 (MCO)Orlando International Airport
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17:00 (MCO)Orlando International Airport20:50 (MDW)Chicago Midway Airport
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(WN 1119)Boeing 737 Max 8 Passenger (WN 3159)Boeing 737 700 - 8h 10m (1h 55m)
- MCO Orlando 1h 55m
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- -
- -
- -
- -
- -
- -
- S
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13:40 - 17:00SJU - MCO18:50 - 20:55MCO - ORD
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13:40 (SJU)San Juan Luis Munoz Marin Intl Airport18:50 (MCO)Orlando International Airport
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17:00 (MCO)Orlando International Airport20:55 (ORD)Chicago O'Hare International Airport
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(WN 1119)Boeing 737 Max 8 Passenger (WN 3650)Boeing 737 Max 8 Passenger - 8h 15m (1h 50m)
- MCO Orlando 1h 50m
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- -
- -
- -
- -
- -
- -
- S
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14:10 - 17:10SJU - FLL19:10 - 21:25FLL - MDW
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14:10 (SJU)San Juan Luis Munoz Marin Intl Airport19:10 (FLL)Fort Lauderdale/Hollywood Intl Airport
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17:10 (FLL)Fort Lauderdale/Hollywood Intl Airport21:25 (MDW)Chicago Midway Airport
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(WN 1992)Boeing 737 800 (WN 3107)Boeing 737 800 - 8h 15m (2h)
- FLL Miami 2h
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- M
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- -
- T
- F
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14:35 - 17:50SJU - MCO20:40 - 22:25MCO - MDW
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14:35 (SJU)San Juan Luis Munoz Marin Intl Airport20:40 (MCO)Orlando International Airport
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17:50 (MCO)Orlando International Airport22:25 (MDW)Chicago Midway Airport
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(WN 3014)Boeing 737 800 (WN 1328)Boeing 737 700 - 8h 50m (2h 50m)
- MCO Orlando 2h 50m
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- -
- -
- -
- -
- -
- S
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14:45 - 18:10SJU - MCO21:20 - 23:10MCO - MDW
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14:45 (SJU)San Juan Luis Munoz Marin Intl Airport21:20 (MCO)Orlando International Airport
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18:10 (MCO)Orlando International Airport23:10 (MDW)Chicago Midway Airport
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(WN 3014)Boeing 737 800 (WN 1328)Boeing 737 800 - 9h 25m (3h 10m)
- MCO Orlando 3h 10m
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- -
- T
- W
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21:30 - 22:35STL - MDW14:45 - 18:10SJU - MCO
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21:30 (STL)St Louis Lambert Intl Airport14:45 (SJU)San Juan Luis Munoz Marin Intl Airport
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22:35 (MDW)Chicago Midway Airport18:10 (MCO)Orlando International Airport
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(WN 3244)Boeing 737 Max 8 Passenger (WN 3014)Boeing 737 800 - 8h 50m (1h 45m)
- MDW Chicago 1h 45m
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- -
- T
- W
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The fastest flight time for direct flights from San Juan to Chicago is 5 hours 5 minutes. Check latest flight schedules & prices on Wego.
The flight distance between San Juan and Chicago is 3305km. Check all available flights on Wego.
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.
There are 3 airlines that offer direct flights from San Juan to Chicago. Find out the list of airlines on Wego.
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