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Cheap flight deals from San Juan to Chicago Starting at JPY 8,898

For as little as JPY 8,898, you can take your next adventure to Chicago without breaking the bank. Choose between one-way and return tickets from San Juan below.

  • One way
  • Round-trip
      • Cheapest nonstop
        SJU19:57
        5h 23m
        Nonstop
        ORD23:20
        Thu, Feb 20|San Juan - Chicago|Spirit Airlines
        JPY 17,377JPY 22,155
        22% OFF
        22% OFF
        JPY 22,155JPY 17,377

        Choose Spirit Airlines flights from San Juan to Chicago. The one-way direct flight with Spirit Airlines departs from Luis Muñoz Marín International Airport on Thu, Feb 20, arriving at O'Hare International Airport. One-way Prices start from JPY 17,377 including taxes and charges.

      • SJU19:57
        5h 23m
        Nonstop
        ORD23:20
        Thu, Feb 27|San Juan - Chicago|Spirit Airlines
        JPY 19,496JPY 22,155
        12% OFF
        12% OFF
        JPY 22,155JPY 19,496

        Choose Spirit Airlines flights from San Juan to Chicago. The one-way direct flight with Spirit Airlines departs from Luis Muñoz Marín International Airport on Thu, Feb 27, arriving at O'Hare International Airport. One-way Prices start from JPY 19,496 including taxes and charges.

      • SJU08:55
        25h 18m
        1 stop
        ORD08:13
        Tue, Mar 4|San Juan - Chicago|Frontier Airlines
        JPY 8,898JPY 22,155
        60% OFF
        60% OFF
        JPY 22,155JPY 8,898

        Choose Frontier Airlines flights from San Juan to Chicago. The one-way connecting flight with Frontier Airlines departs from Luis Muñoz Marín International Airport on Tue, Mar 4, arriving at O'Hare International Airport. One-way Prices start from JPY 8,898 including taxes and charges.

      • SJU06:00
        10h 32m
        1 stop
        MDW15:32
        Tue, Mar 11|San Juan - Chicago|Frontier Airlines
        JPY 9,129
        JPY 9,129

        Choose Frontier Airlines flights from San Juan to Chicago. The one-way connecting flight with Frontier Airlines departs from Luis Muñoz Marín International Airport on Tue, Mar 11, arriving at Midway International Airport. One-way Prices start from JPY 9,129 including taxes and charges.

      • SJU06:00
        11h 21m
        1 stop
        MDW16:21
        Tue, Mar 18|San Juan - Chicago|Frontier Airlines
        JPY 9,780
        JPY 9,780

        Choose Frontier Airlines flights from San Juan to Chicago. The one-way connecting flight with Frontier Airlines departs from Luis Muñoz Marín International Airport on Tue, Mar 18, arriving at Midway International Airport. One-way Prices start from JPY 9,780 including taxes and charges.

      • SJU06:00
        12h 31m
        1 stop
        MDW17:31
        Thu, Apr 3|San Juan - Chicago|Frontier Airlines
        JPY 9,780
        JPY 9,780

        Choose Frontier Airlines flights from San Juan to Chicago. The one-way connecting flight with Frontier Airlines departs from Luis Muñoz Marín International Airport on Thu, Apr 3, arriving at Midway International Airport. One-way Prices start from JPY 9,780 including taxes and charges.

      • SJU09:00
        12h 29m
        1 stop
        MDW19:29
        Thu, Feb 27|San Juan - Chicago|Frontier Airlines
        JPY 9,801
        JPY 9,801

        Choose Frontier Airlines flights from San Juan to Chicago. The one-way connecting flight with Frontier Airlines departs from Luis Muñoz Marín International Airport on Thu, Feb 27, arriving at Midway International Airport. One-way Prices start from JPY 9,801 including taxes and charges.

      • SJU07:00
        14h 39m
        1 stop
        ORD19:39
        Sat, Mar 1|San Juan - Chicago|Frontier Airlines
        JPY 9,801
        JPY 9,801

        Choose Frontier Airlines flights from San Juan to Chicago. The one-way connecting flight with Frontier Airlines departs from Luis Muñoz Marín International Airport on Sat, Mar 1, arriving at O'Hare International Airport. One-way Prices start from JPY 9,801 including taxes and charges.

      • SJU10:46
        13h 25m
        1 stop
        ORD23:11
        Thu, May 8|San Juan - Chicago|Frontier Airlines
        JPY 9,801
        JPY 9,801

        Choose Frontier Airlines flights from San Juan to Chicago. The one-way connecting flight with Frontier Airlines departs from Luis Muñoz Marín International Airport on Thu, May 8, arriving at O'Hare International Airport. One-way Prices start from JPY 9,801 including taxes and charges.

      • SJU10:46
        13h 25m
        1 stop
        ORD23:11
        Thu, May 15|San Juan - Chicago|Frontier Airlines
        JPY 9,822
        JPY 9,822

        Choose Frontier Airlines flights from San Juan to Chicago. The one-way connecting flight with Frontier Airlines departs from Luis Muñoz Marín International Airport on Thu, May 15, arriving at O'Hare International Airport. One-way Prices start from JPY 9,822 including taxes and charges.

      • SJU01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Sun, Feb 23|San Juan - Chicago|Spirit Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

San Juan to Chicago flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. F91823

    Frontier Airlines

    03:56

    SJU

    3.2h

    07:10

    MCO

    SM--TFS
    Search

  2. F93853

    Frontier Airlines

    10:30

    MCO

    2.9h

    12:24

    MDW

    -M-----

  3. F92249

    Frontier Airlines

    06:00

    SJU

    3.4h

    09:26

    MCO

    S--WT--
    Search

  4. F91457

    Frontier Airlines

    17:26

    MCO

    3.0h

    19:29

    MDW

    SMTWTFS

  5. F93979

    Frontier Airlines

    06:35

    SJU

    3.4h

    08:57

    TPA

    SMTWTFS
    Search

  6. F91415

    Frontier Airlines

    05:01

    TPA

    3.1h

    07:06

    ORD

    SMTWTFS

  7. F92215

    Frontier Airlines

    11:20

    SJU

    3.4h

    14:41

    TPA

    S--WT-S
    Search

  8. F93899

    Frontier Airlines

    20:48

    TPA

    2.9h

    22:40

    MDW

    SMTWTF-

  9. F92215

    Frontier Airlines

    11:20

    SJU

    3.4h

    14:41

    TPA

    S--WT-S
    Search

  10. F91415

    Frontier Airlines

    05:01

    TPA

    3.1h

    07:06

    ORD

    SMTWTFS

  11. F92081

    Frontier Airlines

    16:28

    SJU

    4.4h

    19:53

    ATL

    SM-WT-S
    Search

  12. F91595

    Frontier Airlines

    15:16

    ATL

    2.5h

    16:43

    ORD

    SMTWTFS

  13. F92081

    Frontier Airlines

    16:28

    SJU

    4.4h

    19:53

    ATL

    SM-WT-S
    Search

  14. F92143

    Frontier Airlines

    10:25

    ATL

    2.0h

    11:26

    MDW

    -MT---S

  15. F92081

    Frontier Airlines

    16:28

    SJU

    4.4h

    19:53

    ATL

    SM-WT-S
    Search

  16. F92779

    Frontier Airlines

    22:52

    ATL

    2.0h

    23:55

    MDW

    SM-WTFS

  17. F94725

    Frontier Airlines

    16:29

    SJU

    3.4h

    19:55

    MCO

    -MTWTFS
    Search

  18. F93853

    Frontier Airlines

    10:30

    MCO

    2.9h

    12:24

    MDW

    -M-----

  19. F93247

    Frontier Airlines

    21:58

    SJU

    4.0h

    01:59

    PHL

    S---T--
    Search

  20. F92111

    Frontier Airlines

    05:17

    PHL

    2.4h

    06:42

    ORD

    ------S
Find more flights and airlines

When is the cheapest time to fly from San Juan to Chicago?

Explore the best time to buy affordable tickets to Chicago with our price trend chart, which predicts how flight prices will change in the coming weeks from previous data.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

  • When are flight tickets from San Juan (SJU) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from San Juan to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from San Juan (SJU) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around JPY 38,195.

  • How long does it take to fly from San Juan (SJU) to Chicago (CHI)?

    It takes about 5 hours 11 minutes to fly from San Juan (SJU) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14 km, by taxi about 30 minutes.

  • What are the most popular airlines that fly from San Juan (SJU) to Chicago (CHI)?

    Airlines with flights from San Juan (SJU) to Chicago (CHI): Air New Zealand, United Airlines, Alaska Airlines, Spirit Airlines, Air Canada, American Airlines and Southwest Airlines.

  • What's the most popular airline for non-stop flights from San Juan (SJU) to Chicago (CHI)?

    American Airlines operates 6 non-stop flights from San Juan (SJU) to Chicago (CHI).

  • How many airports are there in Chicago (CHI)?

How to find a cheap flight from San Juan to Chicago

If you don’t know some of the key things to look out for when buying flight tickets, prices can often end up sky high or, worse, sold out! We’ve carefully compiled our six most important steps to help ensure you’re getting the best deals when planning your next journey.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Info | San Juan to Chicago

Cheapest direct flight priceJPY 8,898
Cheapest return ticket priceJPY 24,365
Off-season for travelMarch
Peak season for travelNovember
Flight distance3,313.11 km
Average flight time5 hours 11 minutes
Popular airlineJetblue Airways

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