Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Spirit Airlines

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

  • Spirit Airlines Spirit Airlines
  • Frontier Airlines Frontier Airlines
  • American Airlines American Airlines
  • Southwest Airlines Southwest Airlines
  • United Airlines United Airlines
  • JetBlue Airways JetBlue Airways
  • Air Canada Air Canada
Cheapest Month February

Travel Period: January 2025 - December 2025

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

  • 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 Saturday

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

  • 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
      • 08:00 ORD
        14:39 SJU
        4Hrs, 39m Direct
      • ORDChicago O'Hare International Airport 08:00 - SJU 14:39 4h 39m Direct
      • ORDChicago O'Hare International Airport 08:00
      • SJUSan Juan Luis Munoz Marin Intl Airport 14:39
      • 4h 39m
      • Direct
      • Spirit Airlines (NK 491)Airbus A320 Neo
      • Spirit Airlines (NK 491)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Airbus A320 Neo
      • 08:20 MDW
        14:55 SJU
        4Hrs, 35m Direct
      • MDWChicago Midway Airport 08:20 - SJU 14:55 4h 35m Direct
      • MDWChicago Midway Airport 08:20
      • SJUSan Juan Luis Munoz Marin Intl Airport 14:55
      • 4h 35m
      • Direct
      • Southwest Airlines (WN 241)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 241)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 08:30 ORD
        15:10 SJU
        4Hrs, 40m Direct
      • ORDChicago O'Hare International Airport 08:30 - SJU 15:10 4h 40m Direct
      • ORDChicago O'Hare International Airport 08:30
      • SJUSan Juan Luis Munoz Marin Intl Airport 15:10
      • 4h 40m
      • Direct
      • American Airlines (AA 2268)Boeing 737 800
      • American Airlines (AA 2268)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 09:00 ORD
        15:38 SJU
        4Hrs, 38m Direct
      • ORDChicago O'Hare International Airport 09:00 - SJU 15:38 4h 38m Direct
      • ORDChicago O'Hare International Airport 09:00
      • SJUSan Juan Luis Munoz Marin Intl Airport 15:38
      • 4h 38m
      • Direct
      • United Airlines (UA 1996)Boeing 737 Max 9 Passenger
      • United Airlines (UA 1996)
        • M
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        • S
        • S
      • Boeing 737 Max 9 Passenger
      • 09:05 ORD
        15:48 SJU
        4Hrs, 43m Direct
      • ORDChicago O'Hare International Airport 09:05 - SJU 15:48 4h 43m Direct
      • ORDChicago O'Hare International Airport 09:05
      • SJUSan Juan Luis Munoz Marin Intl Airport 15:48
      • 4h 43m
      • Direct
      • Spirit Airlines (NK 850)Airbus A320 Neo
      • Spirit Airlines (NK 850)
        • M
        • T
        • -
        • -
        • -
        • -
        • -
      • Airbus A320 Neo
      • 09:32 ORD
        16:15 SJU
        4Hrs, 43m Direct
      • ORDChicago O'Hare International Airport 09:32 - SJU 16:15 4h 43m Direct
      • ORDChicago O'Hare International Airport 09:32
      • SJUSan Juan Luis Munoz Marin Intl Airport 16:15
      • 4h 43m
      • Direct
      • Spirit Airlines (NK 850)Airbus A320 Neo
      • Spirit Airlines (NK 850)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Airbus A320 Neo
      • 13:00 ORD
        19:36 SJU
        4Hrs, 36m Direct
      • ORDChicago O'Hare International Airport 13:00 - SJU 19:36 4h 36m Direct
      • ORDChicago O'Hare International Airport 13:00
      • SJUSan Juan Luis Munoz Marin Intl Airport 19:36
      • 4h 36m
      • Direct
      • Spirit Airlines (NK 491)Airbus A320 Neo
      • Spirit Airlines (NK 491)
        • M
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        • -
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        • F
        • S
        • S
      • Airbus A320 Neo
      • 14:20 ORD
        20:55 SJU
        4Hrs, 35m Direct
      • ORDChicago O'Hare International Airport 14:20 - SJU 20:55 4h 35m Direct
      • ORDChicago O'Hare International Airport 14:20
      • SJUSan Juan Luis Munoz Marin Intl Airport 20:55
      • 4h 35m
      • Direct
      • United Airlines (UA 695)Boeing 737 Max 9 Passenger
      • United Airlines (UA 695)
        • M
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        • F
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        • S
      • Boeing 737 Max 9 Passenger
      • 18:19 ORD
        06:12 SJU
        9Hrs, 53m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 18:19 - SJU 06:12 9h 53m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 18:19
        IAHHouston George Bush Intercontinental Airport 23:54
      • IAHHouston George Bush Intercontinental Airport 21:22
        SJUSan Juan Luis Munoz Marin Intl Airport 06:12
      • 9h 53m (2h 32m)
      • 1 Stop IAH · Houston 2h 32m
      • United Airlines (UA 1568)Airbus A321 Neo
        United Airlines (UA 1497)Boeing 737 Max 9 Passenger
      • United Airlines (UA 1568)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 18:35 ORD
        05:10 SJU
        8Hrs, 35m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 18:35 - SJU 05:10 8h 35m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 18:35
        DFWDallas/Fort Worth Intl Airport 22:35
      • DFWDallas/Fort Worth Intl Airport 21:42
        SJUSan Juan Luis Munoz Marin Intl Airport 05:10
      • 8h 35m (53m)
      • 1 Stop DFW · Dallas 53m
      • American Airlines (AA 1559)Boeing 737 800
        American Airlines (AA 1823)Airbus
      • American Airlines (AA 1559)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 20:00 ORD
        06:12 SJU
        8Hrs, 12m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 20:00 - SJU 06:12 8h 12m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 20:00
        IAHHouston George Bush Intercontinental Airport 23:54
      • IAHHouston George Bush Intercontinental Airport 23:00
        SJUSan Juan Luis Munoz Marin Intl Airport 06:12
      • 8h 12m (54m)
      • 1 Stop IAH · Houston 54m
      • United Airlines (UA 2155)Boeing 737 800
        United Airlines (UA 1497)Boeing 737 Max 9 Passenger
      • United Airlines (UA 2155)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 20:00 ORD
        06:12 SJU
        8Hrs, 12m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 20:00 - SJU 06:12 8h 12m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 20:00
        IAHHouston George Bush Intercontinental Airport 23:54
      • IAHHouston George Bush Intercontinental Airport 23:00
        SJUSan Juan Luis Munoz Marin Intl Airport 06:12
      • 8h 12m (54m)
      • 1 Stop IAH · Houston 54m
      • United Airlines (UA 2155)Boeing 737 900
        United Airlines (UA 1497)Boeing 737 Max 9 Passenger
      • United Airlines (UA 2155)
        • M
        • T
        • -
        • T
        • -
        • S
        • -
      • 20:00 ORD
        06:12 SJU
        8Hrs, 12m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 20:00 - SJU 06:12 8h 12m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 20:00
        IAHHouston George Bush Intercontinental Airport 23:54
      • IAHHouston George Bush Intercontinental Airport 23:00
        SJUSan Juan Luis Munoz Marin Intl Airport 06:12
      • 8h 12m (54m)
      • 1 Stop IAH · Houston 54m
      • United Airlines (UA 2155)Boeing 737 Max 9 Passenger
        United Airlines (UA 1497)Boeing 737 Max 9 Passenger
      • United Airlines (UA 2155)
        • -
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        • W
        • -
        • F
        • -
        • -
      • 05:00 ORD
        13:35 SJU
        6Hrs, 35m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 05:00 - SJU 13:35 6h 35m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 05:00
        MIAMiami International Airport 09:55
      • MIAMiami International Airport 09:15
        SJUSan Juan Luis Munoz Marin Intl Airport 13:35
      • 6h 35m (40m)
      • 1 Stop MIA · Miami 40m
      • American Airlines (AA 2984)Boeing 737 800
        American Airlines (AA 1613)Boeing 737 Max 8 Passenger
      • American Airlines (AA 2984)
        • M
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        • T
        • F
        • S
        • S
      • 05:00 MDW
        14:45 SJU
        7Hrs, 45m 1 Stop (MCO)
      • MDWChicago Midway Airport 05:00 - SJU 14:45 7h 45m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 05:00
        MCOOrlando International Airport 10:55
      • MCOOrlando International Airport 08:45
        SJUSan Juan Luis Munoz Marin Intl Airport 14:45
      • 7h 45m (2h 10m)
      • 1 Stop MCO · Orlando 2h 10m
      • Southwest Airlines (WN 1519)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2128)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1519)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:00 ORD
        14:58 SJU
        7Hrs, 58m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 05:00 - SJU 14:58 7h 58m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 08:28
      • DFWDallas/Fort Worth Intl Airport 07:47
        SJUSan Juan Luis Munoz Marin Intl Airport 14:58
      • 7h 58m (41m)
      • 1 Stop DFW · Dallas 41m
      • American Airlines (AA 370)Boeing 737 800
        American Airlines (AA 2437)Boeing 777 200
      • American Airlines (AA 370)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 05:00 MDW
        15:05 SJU
        8Hrs, 05m 1 Stop (MCO)
      • MDWChicago Midway Airport 05:00 - SJU 15:05 8h 05m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 05:00
        MCOOrlando International Airport 11:15
      • MCOOrlando International Airport 08:45
        SJUSan Juan Luis Munoz Marin Intl Airport 15:05
      • 8h 05m (2h 30m)
      • 1 Stop MCO · Orlando 2h 30m
      • Southwest Airlines (WN 2538)Boeing 737 800
        Southwest Airlines (WN 2128)Boeing 737 700
      • Southwest Airlines (WN 2538)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:00 ORD
        15:08 SJU
        8Hrs, 08m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 05:00 - SJU 15:08 8h 08m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 08:28
      • DFWDallas/Fort Worth Intl Airport 07:47
        SJUSan Juan Luis Munoz Marin Intl Airport 15:08
      • 8h 08m (41m)
      • 1 Stop DFW · Dallas 41m
      • American Airlines (AA 370)Boeing 737 800
        American Airlines (AA 2437)Airbus
      • American Airlines (AA 370)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:00 ORD
        16:15 SJU
        9Hrs, 15m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 05:00 - SJU 16:15 9h 15m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 05:00
        MIAMiami International Airport 12:30
      • MIAMiami International Airport 09:15
        SJUSan Juan Luis Munoz Marin Intl Airport 16:15
      • 9h 15m (3h 15m)
      • 1 Stop MIA · Miami 3h 15m
      • American Airlines (AA 2984)Boeing 737 800
        American Airlines (AA 1699)Boeing 737 800
      • American Airlines (AA 2984)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 05:00 ORD
        16:15 SJU
        9Hrs, 15m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 05:00 - SJU 16:15 9h 15m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 05:00
        MIAMiami International Airport 12:30
      • MIAMiami International Airport 09:15
        SJUSan Juan Luis Munoz Marin Intl Airport 16:15
      • 9h 15m (3h 15m)
      • 1 Stop MIA · Miami 3h 15m
      • American Airlines (AA 2984)Boeing 737 800
        American Airlines (AA 1329)Boeing 737 800
      • American Airlines (AA 2984)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 05:00 ORD
        16:25 SJU
        9Hrs, 25m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 05:00 - SJU 16:25 9h 25m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 05:00
        MIAMiami International Airport 12:30
      • MIAMiami International Airport 09:15
        SJUSan Juan Luis Munoz Marin Intl Airport 16:25
      • 9h 25m (3h 15m)
      • 1 Stop MIA · Miami 3h 15m
      • American Airlines (AA 2984)Boeing 737 800
        American Airlines (AA 1699)Airbus A321 Neo
      • American Airlines (AA 2984)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 05:00 ORD
        16:36 SJU
        9Hrs, 36m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 05:00 - SJU 16:36 9h 36m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 05:00
        IAHHouston George Bush Intercontinental Airport 10:14
      • IAHHouston George Bush Intercontinental Airport 07:58
        SJUSan Juan Luis Munoz Marin Intl Airport 16:36
      • 9h 36m (2h 16m)
      • 1 Stop IAH · Houston 2h 16m
      • United Airlines (UA 2163)Boeing 737 800
        United Airlines (UA 1192)Boeing 737 Max 9 Passenger
      • United Airlines (UA 2163)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 05:00 ORD
        16:36 SJU
        9Hrs, 36m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 05:00 - SJU 16:36 9h 36m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 05:00
        IAHHouston George Bush Intercontinental Airport 10:14
      • IAHHouston George Bush Intercontinental Airport 07:58
        SJUSan Juan Luis Munoz Marin Intl Airport 16:36
      • 9h 36m (2h 16m)
      • 1 Stop IAH · Houston 2h 16m
      • United Airlines (UA 2163)Boeing 737 900
        United Airlines (UA 1192)Boeing 737 Max 9 Passenger
      • United Airlines (UA 2163)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 05:02 ORD
        13:34 SJU
        6Hrs, 32m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 05:02 - SJU 13:34 6h 32m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 05:02
        CLTCharlotte Airport 08:59
      • CLTCharlotte Airport 08:08
        SJUSan Juan Luis Munoz Marin Intl Airport 13:34
      • 6h 32m (51m)
      • 1 Stop CLT · Charlotte 51m
      • American Airlines (AA 2842)Boeing 737 Max 8 Passenger
        American Airlines (AA 750)Airbus
      • American Airlines (AA 2842)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 05:02 ORD
        15:35 SJU
        8Hrs, 33m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 05:02 - SJU 15:35 8h 33m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 05:02
        CLTCharlotte Airport 11:00
      • CLTCharlotte Airport 08:08
        SJUSan Juan Luis Munoz Marin Intl Airport 15:35
      • 8h 33m (2h 52m)
      • 1 Stop CLT · Charlotte 2h 52m
      • American Airlines (AA 2842)Boeing 737 Max 8 Passenger
        American Airlines (AA 783)Airbus
      • American Airlines (AA 2842)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 05:05 MDW
        17:05 SJU
        10Hrs, 00m 1 Stop (HOU)
      • MDWChicago Midway Airport 05:05 - SJU 17:05 10h 1 Stop (HOU) Houston
      • MDWChicago Midway Airport 05:05
        HOUHouston Hobby Airport 10:55
      • HOUHouston Hobby Airport 07:55
        SJUSan Juan Luis Munoz Marin Intl Airport 17:05
      • 10h (3h)
      • 1 Stop HOU · Houston 3h
      • Southwest Airlines (WN 1050)Boeing 737 700
        Southwest Airlines (WN 5156)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1050)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:10 MDW
        16:00 SJU
        8Hrs, 50m 1 Stop (TPA)
      • MDWChicago Midway Airport 05:10 - SJU 16:00 8h 50m 1 Stop (TPA) Tampa
      • MDWChicago Midway Airport 05:10
        TPATampa International Airport 12:05
      • TPATampa International Airport 08:50
        SJUSan Juan Luis Munoz Marin Intl Airport 16:00
      • 8h 50m (3h 15m)
      • 1 Stop TPA · Tampa 3h 15m
      • Southwest Airlines (WN 3315)Boeing 737 800
        Southwest Airlines (WN 2410)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3315)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:15 MDW
        13:50 SJU
        6Hrs, 35m 1 Stop (FLL)
      • MDWChicago Midway Airport 05:15 - SJU 13:50 6h 35m 1 Stop (FLL) Broward County
      • MDWChicago Midway Airport 05:15
        FLLFort Lauderdale/Hollywood Intl Airport 10:20
      • FLLFort Lauderdale/Hollywood Intl Airport 09:20
        SJUSan Juan Luis Munoz Marin Intl Airport 13:50
      • 6h 35m (1h)
      • 1 Stop FLL · Broward County 1h
      • Southwest Airlines (WN 527)Boeing 737 700
        Southwest Airlines (WN 2149)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 527)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:15 MDW
        14:35 SJU
        7Hrs, 20m 1 Stop (BNA)
      • MDWChicago Midway Airport 05:15 - SJU 14:35 7h 20m 1 Stop (BNA) Nashville
      • MDWChicago Midway Airport 05:15
        BNANashville Airport 08:45
      • BNANashville Airport 06:45
        SJUSan Juan Luis Munoz Marin Intl Airport 14:35
      • 7h 20m (2h)
      • 1 Stop BNA · Nashville 2h
      • Southwest Airlines (WN 2665)Boeing 737 700
        Southwest Airlines (WN 4295)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2665)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 11:15 MCO
        06:45 BNA
        7Hrs, 50m 1 Stop (SJU)
      • MCOOrlando International Airport 11:15 - BNA 06:45 7h 50m 1 Stop (SJU) San Juan
      • MCOOrlando International Airport 11:15
        MDWChicago Midway Airport 05:15
      • SJUSan Juan Luis Munoz Marin Intl Airport 15:05
        BNANashville Airport 06:45
      • 7h 50m (1h 30m)
      • 1 Stop SJU · San Juan 1h 30m
      • Southwest Airlines (WN 2128)Boeing 737 700
        Southwest Airlines (WN 2665)Boeing 737 700
      • Southwest Airlines (WN 2128)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:45 ORD
        14:30 SJU
        6Hrs, 45m 1 Stop (BWI)
      • ORDChicago O'Hare International Airport 05:45 - SJU 14:30 6h 45m 1 Stop (BWI) Baltimore
      • ORDChicago O'Hare International Airport 05:45
        BWIBaltimore Washington International Airport 09:30
      • BWIBaltimore Washington International Airport 08:40
        SJUSan Juan Luis Munoz Marin Intl Airport 14:30
      • 6h 45m (50m)
      • 1 Stop BWI · Baltimore 50m
      • Southwest Airlines (WN 1266)Boeing 737 800
        Southwest Airlines (WN 758)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1266)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:45 ORD
        14:45 SJU
        7Hrs, 00m 1 Stop (MCO)
      • ORDChicago O'Hare International Airport 05:45 - SJU 14:45 7h 1 Stop (MCO) Orlando
      • ORDChicago O'Hare International Airport 05:45
        MCOOrlando International Airport 10:55
      • MCOOrlando International Airport 09:30
        SJUSan Juan Luis Munoz Marin Intl Airport 14:45
      • 7h (1h 25m)
      • 1 Stop MCO · Orlando 1h 25m
      • Southwest Airlines (WN 425)Boeing 737 700
        Southwest Airlines (WN 2128)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 425)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:45 ORD
        17:20 SJU
        9Hrs, 35m 1 Stop (MCO)
      • ORDChicago O'Hare International Airport 05:45 - SJU 17:20 9h 35m 1 Stop (MCO) Orlando
      • ORDChicago O'Hare International Airport 05:45
        MCOOrlando International Airport 13:30
      • MCOOrlando International Airport 09:30
        SJUSan Juan Luis Munoz Marin Intl Airport 17:20
      • 9h 35m (4h)
      • 1 Stop MCO · Orlando 4h
      • Southwest Airlines (WN 425)Boeing 737 700
        Southwest Airlines (WN 807)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 425)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:00 ORD
        16:36 SJU
        8Hrs, 36m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 06:00 - SJU 16:36 8h 36m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 06:00
        IAHHouston George Bush Intercontinental Airport 10:14
      • IAHHouston George Bush Intercontinental Airport 08:57
        SJUSan Juan Luis Munoz Marin Intl Airport 16:36
      • 8h 36m (1h 17m)
      • 1 Stop IAH · Houston 1h 17m
      • United Airlines (UA 2160)Boeing 757 200 Series
        United Airlines (UA 1192)Boeing 737 Max 9 Passenger
      • United Airlines (UA 2160)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 06:00 MDW
        17:30 SJU
        9Hrs, 30m 1 Stop (MCO)
      • MDWChicago Midway Airport 06:00 - SJU 17:30 9h 30m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 06:00
        MCOOrlando International Airport 13:45
      • MCOOrlando International Airport 09:45
        SJUSan Juan Luis Munoz Marin Intl Airport 17:30
      • 9h 30m (4h)
      • 1 Stop MCO · Orlando 4h
      • Southwest Airlines (WN 1601)Boeing 737 800
        Southwest Airlines (WN 2728)Boeing 737 700
      • Southwest Airlines (WN 1601)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:10 ORD
        15:51 SJU
        7Hrs, 41m 1 Stop (PUJ)
      • ORDChicago O'Hare International Airport 06:10 - SJU 15:51 7h 41m 1 Stop (PUJ) Punta Cana
      • ORDChicago O'Hare International Airport 06:10
        PUJPunta Cana Airport 14:53
      • PUJPunta Cana Airport 12:39
        SJUSan Juan Luis Munoz Marin Intl Airport 15:51
      • 7h 41m (2h 14m)
      • 1 Stop PUJ · Punta Cana 2h 14m
      • Frontier Airlines (F9 80)Airbus A321 Neo
        Frontier Airlines (F9 238)Airbus A321 Neo
      • Frontier Airlines (F9 80)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 06:10 ORD
        15:53 SJU
        7Hrs, 43m 1 Stop (PUJ)
      • ORDChicago O'Hare International Airport 06:10 - SJU 15:53 7h 43m 1 Stop (PUJ) Punta Cana
      • ORDChicago O'Hare International Airport 06:10
        PUJPunta Cana Airport 14:55
      • PUJPunta Cana Airport 12:39
        SJUSan Juan Luis Munoz Marin Intl Airport 15:53
      • 7h 43m (2h 16m)
      • 1 Stop PUJ · Punta Cana 2h 16m
      • Frontier Airlines (F9 80)Airbus A321 Neo
        Frontier Airlines (F9 238)Airbus A321 Neo
      • Frontier Airlines (F9 80)
        • -
        • -
        • -
        • T
        • -
        • -
        • S
      • 06:15 ORD
        15:05 SJU
        6Hrs, 50m 1 Stop (MCO)
      • ORDChicago O'Hare International Airport 06:15 - SJU 15:05 6h 50m 1 Stop (MCO) Orlando
      • ORDChicago O'Hare International Airport 06:15
        MCOOrlando International Airport 11:15
      • MCOOrlando International Airport 10:00
        SJUSan Juan Luis Munoz Marin Intl Airport 15:05
      • 6h 50m (1h 15m)
      • 1 Stop MCO · Orlando 1h 15m
      • Southwest Airlines (WN 425)Boeing 737 700
        Southwest Airlines (WN 2128)Boeing 737 700
      • Southwest Airlines (WN 425)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:20 ORD
        15:31 SJU
        7Hrs, 11m 1 Stop (PUJ)
      • ORDChicago O'Hare International Airport 06:20 - SJU 15:31 7h 11m 1 Stop (PUJ) Punta Cana
      • ORDChicago O'Hare International Airport 06:20
        PUJPunta Cana Airport 14:33
      • PUJPunta Cana Airport 12:49
        SJUSan Juan Luis Munoz Marin Intl Airport 15:31
      • 7h 11m (1h 44m)
      • 1 Stop PUJ · Punta Cana 1h 44m
      • Frontier Airlines (F9 80)Airbus A321 Neo
        Frontier Airlines (F9 238)Airbus A320 Neo
      • Frontier Airlines (F9 80)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:20 ORD
        15:33 SJU
        7Hrs, 13m 1 Stop (PUJ)
      • ORDChicago O'Hare International Airport 06:20 - SJU 15:33 7h 13m 1 Stop (PUJ) Punta Cana
      • ORDChicago O'Hare International Airport 06:20
        PUJPunta Cana Airport 14:35
      • PUJPunta Cana Airport 12:49
        SJUSan Juan Luis Munoz Marin Intl Airport 15:33
      • 7h 13m (1h 46m)
      • 1 Stop PUJ · Punta Cana 1h 46m
      • Frontier Airlines (F9 80)Airbus A321 Neo
        Frontier Airlines (F9 238)Airbus A321 Neo
      • Frontier Airlines (F9 80)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 06:25 MDW
        14:55 SJU
        6Hrs, 30m 1 Stop (BWI)
      • MDWChicago Midway Airport 06:25 - SJU 14:55 6h 30m 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 06:25
        BWIBaltimore Washington International Airport 10:07
      • BWIBaltimore Washington International Airport 09:17
        SJUSan Juan Luis Munoz Marin Intl Airport 14:55
      • 6h 30m (50m)
      • 1 Stop BWI · Baltimore 50m
      • Frontier Airlines (F9 3088)Airbus A320 Neo
        Frontier Airlines (F9 2266)Airbus A321 Neo
      • Frontier Airlines (F9 3088)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 06:31 ORD
        15:40 SJU
        7Hrs, 09m 1 Stop (PHL)
      • ORDChicago O'Hare International Airport 06:31 - SJU 15:40 7h 09m 1 Stop (PHL) Philadelphia
      • ORDChicago O'Hare International Airport 06:31
        PHLPhiladelphia International Airport 10:45
      • PHLPhiladelphia International Airport 09:33
        SJUSan Juan Luis Munoz Marin Intl Airport 15:40
      • 7h 09m (1h 12m)
      • 1 Stop PHL · Philadelphia 1h 12m
      • American Airlines (AA 1854)Boeing 737 800
        American Airlines (AA 2433)Airbus A321 Neo
      • American Airlines (AA 1854)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:37 ORD
        16:15 SJU
        7Hrs, 38m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 06:37 - SJU 16:15 7h 38m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 06:37
        MIAMiami International Airport 12:30
      • MIAMiami International Airport 10:55
        SJUSan Juan Luis Munoz Marin Intl Airport 16:15
      • 7h 38m (1h 35m)
      • 1 Stop MIA · Miami 1h 35m
      • American Airlines (AA 1411)Boeing 737 800
        American Airlines (AA 1699)Boeing 737 800
      • American Airlines (AA 1411)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 06:37 ORD
        16:15 SJU
        7Hrs, 38m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 06:37 - SJU 16:15 7h 38m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 06:37
        MIAMiami International Airport 12:30
      • MIAMiami International Airport 10:55
        SJUSan Juan Luis Munoz Marin Intl Airport 16:15
      • 7h 38m (1h 35m)
      • 1 Stop MIA · Miami 1h 35m
      • American Airlines (AA 1411)Boeing 737 800
        American Airlines (AA 1329)Boeing 737 800
      • American Airlines (AA 1411)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 06:37 ORD
        16:25 SJU
        7Hrs, 48m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 06:37 - SJU 16:25 7h 48m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 06:37
        MIAMiami International Airport 12:30
      • MIAMiami International Airport 10:55
        SJUSan Juan Luis Munoz Marin Intl Airport 16:25
      • 7h 48m (1h 35m)
      • 1 Stop MIA · Miami 1h 35m
      • American Airlines (AA 1411)Boeing 737 800
        American Airlines (AA 1699)Airbus A321 Neo
      • American Airlines (AA 1411)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 06:37 ORD
        17:30 SJU
        8Hrs, 53m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 06:37 - SJU 17:30 8h 53m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 06:37
        MIAMiami International Airport 14:00
      • MIAMiami International Airport 10:55
        SJUSan Juan Luis Munoz Marin Intl Airport 17:30
      • 8h 53m (3h 05m)
      • 1 Stop MIA · Miami 3h 05m
      • American Airlines (AA 1411)Boeing 737 800
        American Airlines (AA 967)Airbus A321 Neo
      • American Airlines (AA 1411)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 06:50 MDW
        15:50 SJU
        7Hrs, 00m 1 Stop (TPA)
      • MDWChicago Midway Airport 06:50 - SJU 15:50 7h 1 Stop (TPA) Tampa
      • MDWChicago Midway Airport 06:50
        TPATampa International Airport 11:55
      • TPATampa International Airport 10:30
        SJUSan Juan Luis Munoz Marin Intl Airport 15:50
      • 7h (1h 25m)
      • 1 Stop TPA · Tampa 1h 25m
      • Southwest Airlines (WN 215)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2410)Boeing 737 800
      • Southwest Airlines (WN 215)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 07:00 ORD
        15:35 SJU
        6Hrs, 35m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 07:00 - SJU 15:35 6h 35m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 07:00
        CLTCharlotte Airport 11:00
      • CLTCharlotte Airport 10:01
        SJUSan Juan Luis Munoz Marin Intl Airport 15:35
      • 6h 35m (59m)
      • 1 Stop CLT · Charlotte 59m
      • American Airlines (AA 1784)Airbus
        American Airlines (AA 783)Airbus
      • American Airlines (AA 1784)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 07:10 ORD
        18:25 SJU
        9Hrs, 15m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 07:10 - SJU 18:25 9h 15m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 07:10
        DENDenver Intl Airport 09:46
      • DENDenver Intl Airport 09:00
        SJUSan Juan Luis Munoz Marin Intl Airport 18:25
      • 9h 15m (46m)
      • 1 Stop DEN · Denver 46m
      • United Airlines (UA 711)Airbus A321 Neo
        United Airlines (UA 1339)Boeing 737 Max 9 Passenger
      • United Airlines (UA 711)
        • -
        • -
        • W
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        • F
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        • S
      • 07:10 ORD
        18:25 SJU
        9Hrs, 15m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 07:10 - SJU 18:25 9h 15m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 07:10
        DENDenver Intl Airport 09:46
      • DENDenver Intl Airport 09:00
        SJUSan Juan Luis Munoz Marin Intl Airport 18:25
      • 9h 15m (46m)
      • 1 Stop DEN · Denver 46m
      • United Airlines (UA 711)Boeing 737 900
        United Airlines (UA 1339)Boeing 737 Max 9 Passenger
      • United Airlines (UA 711)
        • M
        • T
        • -
        • T
        • -
        • -
        • -
      • 07:15 MDW
        16:15 SJU
        7Hrs, 00m 1 Stop (STL)
      • MDWChicago Midway Airport 07:15 - SJU 16:15 7h 1 Stop (STL) Saint Louis
      • MDWChicago Midway Airport 07:15
        STLSt Louis Lambert Intl Airport 10:00
      • STLSt Louis Lambert Intl Airport 08:35
        SJUSan Juan Luis Munoz Marin Intl Airport 16:15
      • 7h (1h 25m)
      • 1 Stop STL · Saint Louis 1h 25m
      • Southwest Airlines (WN 4604)Boeing 737 700
        Southwest Airlines (WN 4860)Boeing 737 700
      • Southwest Airlines (WN 4604)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:25 ORD
        15:50 SJU
        6Hrs, 25m 1 Stop (STT)
      • ORDChicago O'Hare International Airport 07:25 - SJU 15:50 6h 25m 1 Stop (STT) St Thomas Island
      • ORDChicago O'Hare International Airport 07:25
        STTSt Thomas Cyril E King Airport 15:15
      • STTSt Thomas Cyril E King Airport 14:15
        SJUSan Juan Luis Munoz Marin Intl Airport 15:50
      • 6h 25m (1h)
      • 1 Stop STT · St Thomas Island 1h
      • United Airlines (UA 2176)Boeing 737 Max 8 Passenger
        Silver Airways (3M 116)Aerospatiale Alenia Atr 42
      • United Airlines (UA 2176)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 07:25 MDW
        18:20 SJU
        8Hrs, 55m 1 Stop (BWI)
      • MDWChicago Midway Airport 07:25 - SJU 18:20 8h 55m 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 07:25
        BWIBaltimore Washington International Airport 13:20
      • BWIBaltimore Washington International Airport 10:15
        SJUSan Juan Luis Munoz Marin Intl Airport 18:20
      • 8h 55m (3h 05m)
      • 1 Stop BWI · Baltimore 3h 05m
      • Southwest Airlines (WN 3286)Boeing 737 700
        Southwest Airlines (WN 541)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3286)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:25 ORD
        18:40 SJU
        9Hrs, 15m 1 Stop (STT)
      • ORDChicago O'Hare International Airport 07:25 - SJU 18:40 9h 15m 1 Stop (STT) St Thomas Island
      • ORDChicago O'Hare International Airport 07:25
        STTSt Thomas Cyril E King Airport 18:05
      • STTSt Thomas Cyril E King Airport 14:15
        SJUSan Juan Luis Munoz Marin Intl Airport 18:40
      • 9h 15m (3h 50m)
      • 1 Stop STT · St Thomas Island 3h 50m
      • United Airlines (UA 2176)Boeing 737 Max 8 Passenger
        Silver Airways (3M 123)Aerospatiale Alenia Atr 42
      • United Airlines (UA 2176)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • 07:30 MDW
        17:20 SJU
        7Hrs, 50m 1 Stop (MCO)
      • MDWChicago Midway Airport 07:30 - SJU 17:20 7h 50m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 07:30
        MCOOrlando International Airport 13:30
      • MCOOrlando International Airport 11:10
        SJUSan Juan Luis Munoz Marin Intl Airport 17:20
      • 7h 50m (2h 20m)
      • 1 Stop MCO · Orlando 2h 20m
      • Southwest Airlines (WN 669)Boeing 737 700
        Southwest Airlines (WN 807)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 669)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 07:35 MDW
        18:04 SJU
        8Hrs, 29m 1 Stop (MIA)
      • MDWChicago Midway Airport 07:35 - SJU 18:04 8h 29m 1 Stop (MIA) Miami
      • MDWChicago Midway Airport 07:35
        MIAMiami International Airport 14:30
      • MIAMiami International Airport 11:48
        SJUSan Juan Luis Munoz Marin Intl Airport 18:04
      • 8h 29m (2h 42m)
      • 1 Stop MIA · Miami 2h 42m
      • Frontier Airlines (F9 2110)Airbus A320 Neo
        Frontier Airlines (F9 2284)Airbus A320 Neo
      • Frontier Airlines (F9 2110)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 07:40 MDW
        17:30 SJU
        7Hrs, 50m 1 Stop (TPA)
      • MDWChicago Midway Airport 07:40 - SJU 17:30 7h 50m 1 Stop (TPA) Tampa
      • MDWChicago Midway Airport 07:40
        TPATampa International Airport 13:40
      • TPATampa International Airport 11:15
        SJUSan Juan Luis Munoz Marin Intl Airport 17:30
      • 7h 50m (2h 25m)
      • 1 Stop TPA · Tampa 2h 25m
      • Southwest Airlines (WN 1343)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1427)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1343)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:45 MDW
        19:25 SJU
        9Hrs, 40m 1 Stop (MCO)
      • MDWChicago Midway Airport 07:45 - SJU 19:25 9h 40m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 07:45
        MCOOrlando International Airport 15:40
      • MCOOrlando International Airport 11:25
        SJUSan Juan Luis Munoz Marin Intl Airport 19:25
      • 9h 40m (4h 15m)
      • 1 Stop MCO · Orlando 4h 15m
      • Southwest Airlines (WN 3210)Boeing 737 800
        Southwest Airlines (WN 2728)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3210)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
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      What’s the fastest flight time from Chicago to San Juan?

      The fastest flight time for direct flights from Chicago to San Juan is 4 hours 35 minutes. Check latest flight schedules & prices on Wego.

      What’s the most popular airline flying from Chicago to San Juan?

      The most popular airline flying from Chicago to San Juan is Spirit Airlines. Find the latest flight deals on Wego.

      How far is San Juan from Chicago?

      The flight distance between Chicago and San Juan 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 05:00. The last flight of the day departs at 18:19. See the full list of flight times on Wego.

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

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

      Popular Airlines Flying From Chicago to San Juan

      Spirit Airlines ‏()

      Popular Destinations From San Juan

      Popular Destinations From Chicago

      Popular Hotels in San Juan

      Hotels In Popular Destinations