Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Spirit Airlines

The cheapest airline(s) flying from San Juan to Chicago is Spirit Airlines.

  • Spirit Airlines Spirit Airlines
  • American Airlines American Airlines
  • United Airlines United Airlines
  • JetBlue Airways JetBlue Airways
  • Frontier Airlines Frontier Airlines
Cheapest Month May

Travel Period: January 2025 - December 2025

The cheapest month(s) to fly from San Juan to Chicago is May.

  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
  • Dec 2025
Cheapest Day of the Week Thursday

The cheapest day(s) of the week to fly from San Juan to Chicago is Thursday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday

Flight Schedules

Last Updated: Mon, 2 Dec, 2024

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      • Availability
        • M
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        • S
      • 20:31 SJU
        23:58 ORD
        5Hrs, 27m Direct
      • SJUSan Juan Luis Munoz Marin Intl Airport 20:31 - ORD 23:58 5h 27m Direct
      • SJUSan Juan Luis Munoz Marin Intl Airport 20:31
      • ORDChicago O'Hare International Airport 23:58
      • 5h 27m
      • Direct
      • Spirit Airlines (NK 492)Airbus A320 Neo
      • Spirit Airlines (NK 492)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Airbus A320 Neo
      • 08:35 SJU
        11:54 ORD
        5Hrs, 19m Direct
      • SJUSan Juan Luis Munoz Marin Intl Airport 08:35 - ORD 11:54 5h 19m Direct
      • SJUSan Juan Luis Munoz Marin Intl Airport 08:35
      • ORDChicago O'Hare International Airport 11:54
      • 5h 19m
      • Direct
      • United Airlines (UA 2089)Boeing 737 Max 9 Passenger
      • United Airlines (UA 2089)
        • M
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        • T
        • F
        • S
        • S
      • Boeing 737 Max 9 Passenger
      • 15:45 SJU
        19:00 MDW
        5Hrs, 15m Direct
      • SJUSan Juan Luis Munoz Marin Intl Airport 15:45 - MDW 19:00 5h 15m Direct
      • SJUSan Juan Luis Munoz Marin Intl Airport 15:45
      • MDWChicago Midway Airport 19:00
      • 5h 15m
      • Direct
      • Southwest Airlines (WN 5192)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 5192)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 16:00 SJU
        19:25 ORD
        5Hrs, 25m Direct
      • SJUSan Juan Luis Munoz Marin Intl Airport 16:00 - ORD 19:25 5h 25m Direct
      • SJUSan Juan Luis Munoz Marin Intl Airport 16:00
      • ORDChicago O'Hare International Airport 19:25
      • 5h 25m
      • Direct
      • American Airlines (AA 2268)Boeing 737 800
      • American Airlines (AA 2268)
        • M
        • -
        • -
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        • S
        • S
      • Boeing 737 800
      • 16:43 SJU
        20:13 ORD
        5Hrs, 30m Direct
      • SJUSan Juan Luis Munoz Marin Intl Airport 16:43 - ORD 20:13 5h 30m Direct
      • SJUSan Juan Luis Munoz Marin Intl Airport 16:43
      • ORDChicago O'Hare International Airport 20:13
      • 5h 30m
      • Direct
      • Spirit Airlines (NK 851)Airbus A320 Neo
      • Spirit Airlines (NK 851)
        • M
        • T
        • -
        • -
        • -
        • -
        • -
      • Airbus A320 Neo
      • 16:52 SJU
        20:11 ORD
        5Hrs, 19m Direct
      • SJUSan Juan Luis Munoz Marin Intl Airport 16:52 - ORD 20:11 5h 19m Direct
      • SJUSan Juan Luis Munoz Marin Intl Airport 16:52
      • ORDChicago O'Hare International Airport 20:11
      • 5h 19m
      • Direct
      • United Airlines (UA 2088)Boeing 737 Max 9 Passenger
      • United Airlines (UA 2088)
        • M
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        • W
        • T
        • F
        • S
        • S
      • Boeing 737 Max 9 Passenger
      • 17:10 SJU
        20:40 ORD
        5Hrs, 30m Direct
      • SJUSan Juan Luis Munoz Marin Intl Airport 17:10 - ORD 20:40 5h 30m Direct
      • SJUSan Juan Luis Munoz Marin Intl Airport 17:10
      • ORDChicago O'Hare International Airport 20:40
      • 5h 30m
      • Direct
      • Spirit Airlines (NK 851)Airbus A320 Neo
      • Spirit Airlines (NK 851)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Airbus A320 Neo
      • 00:55 SJU
        06:39 MDW
        7Hrs, 44m 1 Stop (PHL)
      • SJUSan Juan Luis Munoz Marin Intl Airport 00:55 - MDW 06:39 7h 44m 1 Stop (PHL) Philadelphia
      • SJUSan Juan Luis Munoz Marin Intl Airport 00:55
        PHLPhiladelphia International Airport 05:15
      • PHLPhiladelphia International Airport 03:59
        MDWChicago Midway Airport 06:39
      • 7h 44m (1h 16m)
      • 1 Stop PHL · Philadelphia 1h 16m
      • Frontier Airlines (F9 4461)Airbus A320 Neo
        Frontier Airlines (F9 1617)Airbus A320 Neo
      • Frontier Airlines (F9 4461)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 00:59 SJU
        06:39 MDW
        7Hrs, 40m 1 Stop (PHL)
      • SJUSan Juan Luis Munoz Marin Intl Airport 00:59 - MDW 06:39 7h 40m 1 Stop (PHL) Philadelphia
      • SJUSan Juan Luis Munoz Marin Intl Airport 00:59
        PHLPhiladelphia International Airport 05:15
      • PHLPhiladelphia International Airport 04:03
        MDWChicago Midway Airport 06:39
      • 7h 40m (1h 12m)
      • 1 Stop PHL · Philadelphia 1h 12m
      • Frontier Airlines (F9 4461)Airbus A321 Neo
        Frontier Airlines (F9 1617)Airbus A320 Neo
      • Frontier Airlines (F9 4461)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 01:30 SJU
        08:25 ORD
        8Hrs, 55m 1 Stop (DFW)
      • SJUSan Juan Luis Munoz Marin Intl Airport 01:30 - ORD 08:25 8h 55m 1 Stop (DFW) Dallas
      • SJUSan Juan Luis Munoz Marin Intl Airport 01:30
        DFWDallas/Fort Worth Intl Airport 06:00
      • DFWDallas/Fort Worth Intl Airport 05:05
        ORDChicago O'Hare International Airport 08:25
      • 8h 55m (55m)
      • 1 Stop DFW · Dallas 55m
      • American Airlines (AA 1759)Boeing 737 800
        American Airlines (AA 3076)Boeing 737 800
      • American Airlines (AA 1759)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • 01:30 SJU
        08:25 ORD
        8Hrs, 55m 1 Stop (DFW)
      • SJUSan Juan Luis Munoz Marin Intl Airport 01:30 - ORD 08:25 8h 55m 1 Stop (DFW) Dallas
      • SJUSan Juan Luis Munoz Marin Intl Airport 01:30
        DFWDallas/Fort Worth Intl Airport 06:00
      • DFWDallas/Fort Worth Intl Airport 05:05
        ORDChicago O'Hare International Airport 08:25
      • 8h 55m (55m)
      • 1 Stop DFW · Dallas 55m
      • American Airlines (AA 1759)Boeing 737 800
        American Airlines (AA 3012)Boeing 737 800
      • American Airlines (AA 1759)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 01:30 SJU
        09:25 ORD
        9Hrs, 55m 1 Stop (DFW)
      • SJUSan Juan Luis Munoz Marin Intl Airport 01:30 - ORD 09:25 9h 55m 1 Stop (DFW) Dallas
      • SJUSan Juan Luis Munoz Marin Intl Airport 01:30
        DFWDallas/Fort Worth Intl Airport 07:00
      • DFWDallas/Fort Worth Intl Airport 05:05
        ORDChicago O'Hare International Airport 09:25
      • 9h 55m (1h 55m)
      • 1 Stop DFW · Dallas 1h 55m
      • American Airlines (AA 1759)Boeing 737 800
        American Airlines (AA 1106)Boeing 737 800
      • American Airlines (AA 1759)
        • -
        • -
        • -
        • T
        • F
        • S
        • -
      • 02:05 SJU
        08:49 ORD
        8Hrs, 44m 1 Stop (EWR)
      • SJUSan Juan Luis Munoz Marin Intl Airport 02:05 - ORD 08:49 8h 44m 1 Stop (EWR) New York City
      • SJUSan Juan Luis Munoz Marin Intl Airport 02:05
        EWRNewark Liberty International Airport 07:05
      • EWRNewark Liberty International Airport 05:22
        ORDChicago O'Hare International Airport 08:49
      • 8h 44m (1h 43m)
      • 1 Stop EWR · New York City 1h 43m
      • United Airlines (UA 2219)Boeing 737 Max 9 Passenger
        United Airlines (UA 1994)Boeing 737 900
      • United Airlines (UA 2219)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 02:05 SJU
        09:42 ORD
        9Hrs, 37m 1 Stop (EWR)
      • SJUSan Juan Luis Munoz Marin Intl Airport 02:05 - ORD 09:42 9h 37m 1 Stop (EWR) New York City
      • SJUSan Juan Luis Munoz Marin Intl Airport 02:05
        EWRNewark Liberty International Airport 08:00
      • EWRNewark Liberty International Airport 05:22
        ORDChicago O'Hare International Airport 09:42
      • 9h 37m (2h 38m)
      • 1 Stop EWR · New York City 2h 38m
      • United Airlines (UA 2219)Boeing 737 Max 9 Passenger
        United Airlines (UA 2100)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2219)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 02:05 SJU
        09:44 ORD
        9Hrs, 39m 1 Stop (EWR)
      • SJUSan Juan Luis Munoz Marin Intl Airport 02:05 - ORD 09:44 9h 39m 1 Stop (EWR) New York City
      • SJUSan Juan Luis Munoz Marin Intl Airport 02:05
        EWRNewark Liberty International Airport 08:00
      • EWRNewark Liberty International Airport 05:22
        ORDChicago O'Hare International Airport 09:44
      • 9h 39m (2h 38m)
      • 1 Stop EWR · New York City 2h 38m
      • United Airlines (UA 2219)Boeing 737 Max 9 Passenger
        United Airlines (UA 2100)Boeing 737 900
      • United Airlines (UA 2219)
        • M
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        • -
        • T
        • F
        • S
        • S
      • 03:54 SJU
        09:24 ORD
        7Hrs, 30m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:54 - ORD 09:24 7h 30m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:54
        MCOOrlando International Airport 07:00
      • MCOOrlando International Airport 06:09
        ORDChicago O'Hare International Airport 09:24
      • 7h 30m (51m)
      • 1 Stop MCO · Orlando 51m
      • Frontier Airlines (F9 1823)Airbus A320 Neo
        Frontier Airlines (F9 3043)Airbus A321 Neo
      • Frontier Airlines (F9 1823)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 03:54 SJU
        09:31 MDW
        7Hrs, 37m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:54 - MDW 09:31 7h 37m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:54
        MCOOrlando International Airport 07:35
      • MCOOrlando International Airport 06:09
        MDWChicago Midway Airport 09:31
      • 7h 37m (1h 26m)
      • 1 Stop MCO · Orlando 1h 26m
      • Frontier Airlines (F9 1823)Airbus A321 Neo
        Frontier Airlines (F9 1457)Airbus A320 Neo
      • Frontier Airlines (F9 1823)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 03:54 SJU
        09:54 ORD
        8Hrs, 00m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:54 - ORD 09:54 8h 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:54
        MCOOrlando International Airport 07:30
      • MCOOrlando International Airport 06:09
        ORDChicago O'Hare International Airport 09:54
      • 8h (1h 21m)
      • 1 Stop MCO · Orlando 1h 21m
      • Frontier Airlines (F9 1823)Airbus A321 Neo
        Frontier Airlines (F9 3043)Airbus A321 Neo
      • Frontier Airlines (F9 1823)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 03:54 SJU
        09:54 ORD
        8Hrs, 00m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:54 - ORD 09:54 8h 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:54
        MCOOrlando International Airport 07:30
      • MCOOrlando International Airport 06:09
        ORDChicago O'Hare International Airport 09:54
      • 8h (1h 21m)
      • 1 Stop MCO · Orlando 1h 21m
      • Frontier Airlines (F9 1823)Airbus A321 Neo
        Frontier Airlines (F9 3043)Airbus A320 Neo
      • Frontier Airlines (F9 1823)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 03:54 SJU
        09:55 MDW
        8Hrs, 01m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:54 - MDW 09:55 8h 01m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:54
        MCOOrlando International Airport 08:00
      • MCOOrlando International Airport 06:09
        MDWChicago Midway Airport 09:55
      • 8h 01m (1h 51m)
      • 1 Stop MCO · Orlando 1h 51m
      • Frontier Airlines (F9 1823)Airbus A320 Neo
        Frontier Airlines (F9 1457)Airbus A320 Neo
      • Frontier Airlines (F9 1823)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 03:54 SJU
        10:04 ORD
        8Hrs, 10m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:54 - ORD 10:04 8h 10m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:54
        MCOOrlando International Airport 07:40
      • MCOOrlando International Airport 06:09
        ORDChicago O'Hare International Airport 10:04
      • 8h 10m (1h 31m)
      • 1 Stop MCO · Orlando 1h 31m
      • Frontier Airlines (F9 1823)Airbus A321 Neo
        Frontier Airlines (F9 3043)Airbus A320 Neo
      • Frontier Airlines (F9 1823)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 03:54 SJU
        10:19 ORD
        8Hrs, 25m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:54 - ORD 10:19 8h 25m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:54
        MCOOrlando International Airport 07:55
      • MCOOrlando International Airport 06:09
        ORDChicago O'Hare International Airport 10:19
      • 8h 25m (1h 46m)
      • 1 Stop MCO · Orlando 1h 46m
      • Frontier Airlines (F9 1823)Airbus A320 Neo
        Frontier Airlines (F9 3043)Airbus A321 Neo
      • Frontier Airlines (F9 1823)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 03:54 SJU
        10:28 ORD
        8Hrs, 34m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:54 - ORD 10:28 8h 34m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:54
        MCOOrlando International Airport 08:10
      • MCOOrlando International Airport 06:09
        ORDChicago O'Hare International Airport 10:28
      • 8h 34m (2h 01m)
      • 1 Stop MCO · Orlando 2h 01m
      • Frontier Airlines (F9 1823)Airbus A320 Neo
        Frontier Airlines (F9 3043)Airbus A320 Neo
      • Frontier Airlines (F9 1823)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 03:59 SJU
        09:31 MDW
        7Hrs, 32m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:59 - MDW 09:31 7h 32m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:59
        MCOOrlando International Airport 07:35
      • MCOOrlando International Airport 06:14
        MDWChicago Midway Airport 09:31
      • 7h 32m (1h 21m)
      • 1 Stop MCO · Orlando 1h 21m
      • Frontier Airlines (F9 1823)Airbus A320 Neo
        Frontier Airlines (F9 1457)Airbus A320 Neo
      • Frontier Airlines (F9 1823)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 03:59 SJU
        09:54 ORD
        7Hrs, 55m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:59 - ORD 09:54 7h 55m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 03:59
        MCOOrlando International Airport 07:30
      • MCOOrlando International Airport 06:14
        ORDChicago O'Hare International Airport 09:54
      • 7h 55m (1h 16m)
      • 1 Stop MCO · Orlando 1h 16m
      • Frontier Airlines (F9 1823)Airbus A320 Neo
        Frontier Airlines (F9 3043)Airbus A321 Neo
      • Frontier Airlines (F9 1823)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 05:18 SJU
        10:46 ORD
        7Hrs, 28m 1 Stop (MIA)
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:18 - ORD 10:46 7h 28m 1 Stop (MIA) Miami
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:18
        MIAMiami International Airport 08:20
      • MIAMiami International Airport 07:18
        ORDChicago O'Hare International Airport 10:46
      • 7h 28m (1h 02m)
      • 1 Stop MIA · Miami 1h 02m
      • American Airlines (AA 3064)Boeing 737 800
        American Airlines (AA 1431)Boeing 737 800
      • American Airlines (AA 3064)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:18 SJU
        11:44 ORD
        8Hrs, 26m 1 Stop (MIA)
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:18 - ORD 11:44 8h 26m 1 Stop (MIA) Miami
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:18
        MIAMiami International Airport 09:12
      • MIAMiami International Airport 07:18
        ORDChicago O'Hare International Airport 11:44
      • 8h 26m (1h 54m)
      • 1 Stop MIA · Miami 1h 54m
      • American Airlines (AA 3064)Boeing 737 800
        American Airlines (AA 2174)Boeing 737 800
      • American Airlines (AA 3064)
        • M
        • T
        • -
        • T
        • F
        • S
        • S
      • 10:59 CLT
        07:18 MIA
        8Hrs, 49m 1 Stop (ORD)
      • CLTCharlotte Airport 10:59 - MIA 07:18 8h 49m 1 Stop (ORD) Chicago
      • CLTCharlotte Airport 10:59
        SJUSan Juan Luis Munoz Marin Intl Airport 05:18
      • ORDChicago O'Hare International Airport 12:07
        MIAMiami International Airport 07:18
      • 8h 49m (1h 31m)
      • 1 Stop ORD · Chicago 1h 31m
      • American Airlines (AA 2279)Boeing 737 800
        American Airlines (AA 3064)Boeing 737 800
      • American Airlines (AA 2279)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:18 SJU
        14:00 ORD
        10Hrs, 42m 1 Stop (MIA)
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:18 - ORD 14:00 10h 42m 1 Stop (MIA) Miami
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:18
        MIAMiami International Airport 11:30
      • MIAMiami International Airport 07:18
        ORDChicago O'Hare International Airport 14:00
      • 10h 42m (4h 12m)
      • 1 Stop MIA · Miami 4h 12m
      • American Airlines (AA 3064)Boeing 737 800
        American Airlines (AA 1763)Boeing 737 800
      • American Airlines (AA 3064)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • 05:35 SJU
        10:35 MDW
        7Hrs, 00m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:35 - MDW 10:35 7h 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:35
        MCOOrlando International Airport 08:45
      • MCOOrlando International Airport 07:50
        MDWChicago Midway Airport 10:35
      • 7h (55m)
      • 1 Stop MCO · Orlando 55m
      • Southwest Airlines (WN 365)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 858)Boeing 737 800
      • Southwest Airlines (WN 365)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:35 SJU
        10:45 ORD
        7Hrs, 10m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:35 - ORD 10:45 7h 10m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:35
        MCOOrlando International Airport 08:40
      • MCOOrlando International Airport 07:50
        ORDChicago O'Hare International Airport 10:45
      • 7h 10m (50m)
      • 1 Stop MCO · Orlando 50m
      • Southwest Airlines (WN 365)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 4080)Boeing 737 700
      • Southwest Airlines (WN 365)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:35 SJU
        11:15 MDW
        7Hrs, 40m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:35 - MDW 11:15 7h 40m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:35
        MCOOrlando International Airport 09:25
      • MCOOrlando International Airport 07:50
        MDWChicago Midway Airport 11:15
      • 7h 40m (1h 35m)
      • 1 Stop MCO · Orlando 1h 35m
      • Southwest Airlines (WN 365)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 546)Boeing 737 700
      • Southwest Airlines (WN 365)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:35 SJU
        12:10 MDW
        8Hrs, 35m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:35 - MDW 12:10 8h 35m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:35
        MCOOrlando International Airport 10:20
      • MCOOrlando International Airport 07:50
        MDWChicago Midway Airport 12:10
      • 8h 35m (2h 30m)
      • 1 Stop MCO · Orlando 2h 30m
      • Southwest Airlines (WN 365)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 546)Boeing 737 800
      • Southwest Airlines (WN 365)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 10:35 BNA
        07:50 MCO
        8Hrs, 40m 1 Stop (MDW)
      • BNANashville Airport 10:35 - MCO 07:50 8h 40m 1 Stop (MDW) Chicago
      • BNANashville Airport 10:35
        SJUSan Juan Luis Munoz Marin Intl Airport 05:35
      • MDWChicago Midway Airport 12:15
        MCOOrlando International Airport 07:50
      • 8h 40m (1h 40m)
      • 1 Stop MDW · Chicago 1h 40m
      • Southwest Airlines (WN 4877)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 365)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4877)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:35 SJU
        12:15 MDW
        8Hrs, 40m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:35 - MDW 12:15 8h 40m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:35
        MCOOrlando International Airport 10:25
      • MCOOrlando International Airport 07:50
        MDWChicago Midway Airport 12:15
      • 8h 40m (2h 35m)
      • 1 Stop MCO · Orlando 2h 35m
      • Southwest Airlines (WN 365)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 546)Boeing 737 800
      • Southwest Airlines (WN 365)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:35 SJU
        13:00 MDW
        9Hrs, 25m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:35 - MDW 13:00 9h 25m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 05:35
        MCOOrlando International Airport 11:05
      • MCOOrlando International Airport 07:50
        MDWChicago Midway Airport 13:00
      • 9h 25m (3h 15m)
      • 1 Stop MCO · Orlando 3h 15m
      • Southwest Airlines (WN 365)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 3764)Boeing 737 800
      • Southwest Airlines (WN 365)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:00 SJU
        11:11 MDW
        7Hrs, 11m 1 Stop (BWI)
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:00 - MDW 11:11 7h 11m 1 Stop (BWI) Baltimore
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:00
        BWIBaltimore Washington International Airport 10:07
      • BWIBaltimore Washington International Airport 09:07
        MDWChicago Midway Airport 11:11
      • 7h 11m (1h)
      • 1 Stop BWI · Baltimore 1h
      • Frontier Airlines (F9 2265)Airbus A321 Neo
        Frontier Airlines (F9 3087)Airbus A320 Neo
      • Frontier Airlines (F9 2265)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 06:00 SJU
        12:03 MDW
        8Hrs, 03m 1 Stop (BWI)
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:00 - MDW 12:03 8h 03m 1 Stop (BWI) Baltimore
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:00
        BWIBaltimore Washington International Airport 10:59
      • BWIBaltimore Washington International Airport 09:07
        MDWChicago Midway Airport 12:03
      • 8h 03m (1h 52m)
      • 1 Stop BWI · Baltimore 1h 52m
      • Frontier Airlines (F9 2265)Airbus A321 Neo
        Frontier Airlines (F9 3087)Airbus A320 Neo
      • Frontier Airlines (F9 2265)
        • -
        • -
        • -
        • T
        • -
        • -
        • S
      • 06:00 SJU
        13:06 MDW
        9Hrs, 06m 1 Stop (BWI)
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:00 - MDW 13:06 9h 06m 1 Stop (BWI) Baltimore
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:00
        BWIBaltimore Washington International Airport 12:02
      • BWIBaltimore Washington International Airport 09:07
        MDWChicago Midway Airport 13:06
      • 9h 06m (2h 55m)
      • 1 Stop BWI · Baltimore 2h 55m
      • Frontier Airlines (F9 2265)Airbus A321 Neo
        Frontier Airlines (F9 3087)Airbus A320 Neo
      • Frontier Airlines (F9 2265)
        • M
        • -
        • -
        • -
        • F
        • -
        • -
      • 06:05 SJU
        13:30 MDW
        9Hrs, 25m 1 Stop (BWI)
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:05 - MDW 13:30 9h 25m 1 Stop (BWI) Baltimore
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:05
        BWIBaltimore Washington International Airport 12:25
      • BWIBaltimore Washington International Airport 09:25
        MDWChicago Midway Airport 13:30
      • 9h 25m (3h)
      • 1 Stop BWI · Baltimore 3h
      • Southwest Airlines (WN 424)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2833)Boeing 737 800
      • Southwest Airlines (WN 424)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:05 SJU
        14:00 ORD
        9Hrs, 55m 1 Stop (BWI)
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:05 - ORD 14:00 9h 55m 1 Stop (BWI) Baltimore
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:05
        BWIBaltimore Washington International Airport 12:40
      • BWIBaltimore Washington International Airport 09:25
        ORDChicago O'Hare International Airport 14:00
      • 9h 55m (3h 15m)
      • 1 Stop BWI · Baltimore 3h 15m
      • Southwest Airlines (WN 424)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1727)Boeing 737 800
      • Southwest Airlines (WN 424)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:10 SJU
        14:15 MDW
        10Hrs, 05m 1 Stop (BWI)
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:10 - MDW 14:15 10h 05m 1 Stop (BWI) Baltimore
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:10
        BWIBaltimore Washington International Airport 13:10
      • BWIBaltimore Washington International Airport 09:30
        MDWChicago Midway Airport 14:15
      • 10h 05m (3h 40m)
      • 1 Stop BWI · Baltimore 3h 40m
      • Southwest Airlines (WN 424)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2833)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 424)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:10 SJU
        14:50 MDW
        10Hrs, 40m 1 Stop (BWI)
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:10 - MDW 14:50 10h 40m 1 Stop (BWI) Baltimore
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:10
        BWIBaltimore Washington International Airport 13:45
      • BWIBaltimore Washington International Airport 09:30
        MDWChicago Midway Airport 14:50
      • 10h 40m (4h 15m)
      • 1 Stop BWI · Baltimore 4h 15m
      • Southwest Airlines (WN 424)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1689)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 424)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:10 SJU
        14:00 ORD
        9Hrs, 50m 1 Stop (BWI)
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:10 - ORD 14:00 9h 50m 1 Stop (BWI) Baltimore
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:10
        BWIBaltimore Washington International Airport 12:40
      • BWIBaltimore Washington International Airport 09:30
        ORDChicago O'Hare International Airport 14:00
      • 9h 50m (3h 10m)
      • 1 Stop BWI · Baltimore 3h 10m
      • Southwest Airlines (WN 424)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1727)Boeing 737 800
      • Southwest Airlines (WN 424)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:10 SJU
        14:00 ORD
        9Hrs, 50m 1 Stop (BWI)
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:10 - ORD 14:00 9h 50m 1 Stop (BWI) Baltimore
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:10
        BWIBaltimore Washington International Airport 12:40
      • BWIBaltimore Washington International Airport 09:30
        ORDChicago O'Hare International Airport 14:00
      • 9h 50m (3h 10m)
      • 1 Stop BWI · Baltimore 3h 10m
      • Southwest Airlines (WN 424)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 138)Boeing 737 800
      • Southwest Airlines (WN 424)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:20 SJU
        12:15 ORD
        7Hrs, 55m 1 Stop (PHL)
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:20 - ORD 12:15 7h 55m 1 Stop (PHL) Philadelphia
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:20
        PHLPhiladelphia International Airport 10:41
      • PHLPhiladelphia International Airport 09:30
        ORDChicago O'Hare International Airport 12:15
      • 7h 55m (1h 11m)
      • 1 Stop PHL · Philadelphia 1h 11m
      • American Airlines (AA 2092)Airbus A321 Neo
        American Airlines (AA 1920)Boeing 737 800
      • American Airlines (AA 2092)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 06:30 SJU
        13:09 MDW
        8Hrs, 39m 1 Stop (PHL)
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:30 - MDW 13:09 8h 39m 1 Stop (PHL) Philadelphia
      • SJUSan Juan Luis Munoz Marin Intl Airport 06:30
        PHLPhiladelphia International Airport 11:43
      • PHLPhiladelphia International Airport 09:34
        MDWChicago Midway Airport 13:09
      • 8h 39m (2h 09m)
      • 1 Stop PHL · Philadelphia 2h 09m
      • Frontier Airlines (F9 1725)Airbus A321 Neo
        Frontier Airlines (F9 1617)Airbus A320 Neo
      • Frontier Airlines (F9 1725)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 07:05 SJU
        14:00 ORD
        8Hrs, 55m 1 Stop (MIA)
      • SJUSan Juan Luis Munoz Marin Intl Airport 07:05 - ORD 14:00 8h 55m 1 Stop (MIA) Miami
      • SJUSan Juan Luis Munoz Marin Intl Airport 07:05
        MIAMiami International Airport 11:30
      • MIAMiami International Airport 09:05
        ORDChicago O'Hare International Airport 14:00
      • 8h 55m (2h 25m)
      • 1 Stop MIA · Miami 2h 25m
      • American Airlines (AA 2817)Boeing 737 800
        American Airlines (AA 1763)Boeing 737 800
      • American Airlines (AA 2817)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 07:20 SJU
        12:10 MDW
        6Hrs, 50m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 07:20 - MDW 12:10 6h 50m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 07:20
        MCOOrlando International Airport 10:20
      • MCOOrlando International Airport 09:35
        MDWChicago Midway Airport 12:10
      • 6h 50m (45m)
      • 1 Stop MCO · Orlando 45m
      • Southwest Airlines (WN 2709)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 546)Boeing 737 800
      • Southwest Airlines (WN 2709)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 07:30 SJU
        13:00 MDW
        7Hrs, 30m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 07:30 - MDW 13:00 7h 30m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 07:30
        MCOOrlando International Airport 11:05
      • MCOOrlando International Airport 09:45
        MDWChicago Midway Airport 13:00
      • 7h 30m (1h 20m)
      • 1 Stop MCO · Orlando 1h 20m
      • Southwest Airlines (WN 1109)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 3764)Boeing 737 800
      • Southwest Airlines (WN 1109)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:30 SJU
        14:25 ORD
        8Hrs, 55m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 07:30 - ORD 14:25 8h 55m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 07:30
        MCOOrlando International Airport 12:15
      • MCOOrlando International Airport 09:45
        ORDChicago O'Hare International Airport 14:25
      • 8h 55m (2h 30m)
      • 1 Stop MCO · Orlando 2h 30m
      • Southwest Airlines (WN 1109)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 350)Boeing 737 800
      • Southwest Airlines (WN 1109)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:30 SJU
        15:05 MDW
        9Hrs, 35m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 07:30 - MDW 15:05 9h 35m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 07:30
        MCOOrlando International Airport 13:15
      • MCOOrlando International Airport 09:45
        MDWChicago Midway Airport 15:05
      • 9h 35m (3h 30m)
      • 1 Stop MCO · Orlando 3h 30m
      • Southwest Airlines (WN 1109)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 5113)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1109)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:45 SJU
        14:40 ORD
        8Hrs, 55m 1 Stop (IAH)
      • SJUSan Juan Luis Munoz Marin Intl Airport 07:45 - ORD 14:40 8h 55m 1 Stop (IAH) Houston
      • SJUSan Juan Luis Munoz Marin Intl Airport 07:45
        IAHHouston George Bush Intercontinental Airport 12:00
      • IAHHouston George Bush Intercontinental Airport 10:52
        ORDChicago O'Hare International Airport 14:40
      • 8h 55m (1h 08m)
      • 1 Stop IAH · Houston 1h 08m
      • United Airlines (UA 1644)Boeing 737 Max 9 Passenger
        United Airlines (UA 1168)Boeing 777
      • United Airlines (UA 1644)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 07:45 SJU
        14:41 ORD
        8Hrs, 56m 1 Stop (IAH)
      • SJUSan Juan Luis Munoz Marin Intl Airport 07:45 - ORD 14:41 8h 56m 1 Stop (IAH) Houston
      • SJUSan Juan Luis Munoz Marin Intl Airport 07:45
        IAHHouston George Bush Intercontinental Airport 11:55
      • IAHHouston George Bush Intercontinental Airport 10:52
        ORDChicago O'Hare International Airport 14:41
      • 8h 56m (1h 03m)
      • 1 Stop IAH · Houston 1h 03m
      • United Airlines (UA 1644)Boeing 737 Max 9 Passenger
        United Airlines (UA 1168)Airbus A321 Neo
      • United Airlines (UA 1644)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:55 SJU
        14:30 MDW
        8Hrs, 35m 1 Stop (MCO)
      • SJUSan Juan Luis Munoz Marin Intl Airport 07:55 - MDW 14:30 8h 35m 1 Stop (MCO) Orlando
      • SJUSan Juan Luis Munoz Marin Intl Airport 07:55
        MCOOrlando International Airport 12:40
      • MCOOrlando International Airport 10:10
        MDWChicago Midway Airport 14:30
      • 8h 35m (2h 30m)
      • 1 Stop MCO · Orlando 2h 30m
      • Southwest Airlines (WN 1109)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 4265)Boeing 737 800
      • Southwest Airlines (WN 1109)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 08:10 SJU
        14:00 ORD
        7Hrs, 50m 1 Stop (IAD)
      • SJUSan Juan Luis Munoz Marin Intl Airport 08:10 - ORD 14:00 7h 50m 1 Stop (IAD) Washington
      • SJUSan Juan Luis Munoz Marin Intl Airport 08:10
        IADWashington Dulles International Airport 12:40
      • IADWashington Dulles International Airport 11:10
        ORDChicago O'Hare International Airport 14:00
      • 7h 50m (1h 30m)
      • 1 Stop IAD · Washington 1h 30m
      • United Airlines (UA 2022)Boeing 737 Max 9 Passenger
        United Airlines (UA 1581)Airbus
      • United Airlines (UA 2022)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 08:10 SJU
        14:05 ORD
        7Hrs, 55m 1 Stop (IAD)
      • SJUSan Juan Luis Munoz Marin Intl Airport 08:10 - ORD 14:05 7h 55m 1 Stop (IAD) Washington
      • SJUSan Juan Luis Munoz Marin Intl Airport 08:10
        IADWashington Dulles International Airport 12:45
      • IADWashington Dulles International Airport 11:10
        ORDChicago O'Hare International Airport 14:05
      • 7h 55m (1h 35m)
      • 1 Stop IAD · Washington 1h 35m
      • United Airlines (UA 2022)Boeing 737 Max 9 Passenger
        United Airlines (UA 1581)Boeing 737 700
      • United Airlines (UA 2022)
        • M
        • -
        • -
        • -
        • F
        • -
        • -
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      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 15 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 00:55. The last flight of the day departs at 20:31. See the full list of flight times on Wego.

      How many airlines offer direct flights from San Juan to Chicago?

      There are 4 airlines that offer direct flights from San Juan to Chicago. Find out the list of airlines on Wego.

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