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Cheap flight deals from Chicago to San Juan Starting at PHP 3,584

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

  • One way
  • Round-trip
      • Cheapest nonstop
        ORD02:20 pm
        4h 35m
        Nonstop
        SJU08:55 pm
        Thu, Mar 6|Chicago - San Juan|United Airlines
        PHP 7,950PHP 8,912
        11% OFF
        11% OFF
        PHP 8,912PHP 7,950

        Choose United Airlines flights from Chicago to San Juan. The one-way direct flight with United Airlines departs from O'Hare International Airport on Thu, Mar 6, arriving at Luis Muñoz Marín International Airport. One-way Prices start from PHP 7,950 including taxes and charges.

      • ORD08:10 am
        4h 30m
        Nonstop
        SJU01:40 pm
        Tue, Mar 11|Chicago - San Juan|American Airlines
        PHP 8,377PHP 8,912
        6% OFF
        6% OFF
        PHP 8,912PHP 8,377

        Choose American Airlines flights from Chicago to San Juan. The one-way direct flight with American Airlines departs from O'Hare International Airport on Tue, Mar 11, arriving at Luis Muñoz Marín International Airport. One-way Prices start from PHP 8,377 including taxes and charges.

      • ORD04:58 pm
        7h 56m
        1 stop
        SJU02:54 am
        Mon, Feb 24|Chicago - San Juan|Frontier Airlines
        PHP 3,584PHP 8,912
        60% OFF
        60% OFF
        PHP 8,912PHP 3,584

        Choose Frontier Airlines flights from Chicago to San Juan. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Mon, Feb 24, arriving at Luis Muñoz Marín International Airport. One-way Prices start from PHP 3,584 including taxes and charges.

      • MDW12:26 pm
        11h 44m
        1 stop
        SJU01:10 am
        Mon, Mar 10|Chicago - San Juan|Frontier Airlines
        PHP 3,737
        PHP 3,737

        Choose Frontier Airlines flights from Chicago to San Juan. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Mon, Mar 10, arriving at Luis Muñoz Marín International Airport. One-way Prices start from PHP 3,737 including taxes and charges.

      • ORD08:44 pm
        10h 51m
        1 stop
        SJU09:35 am
        Sat, Feb 15|Chicago - San Juan|Frontier Airlines
        PHP 3,745
        PHP 3,745

        Choose Frontier Airlines flights from Chicago to San Juan. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Sat, Feb 15, arriving at Luis Muñoz Marín International Airport. One-way Prices start from PHP 3,745 including taxes and charges.

      • ORD03:14 pm
        16h 35m
        1 stop
        SJU09:49 am
        Tue, Feb 18|Chicago - San Juan|Frontier Airlines
        PHP 3,745
        PHP 3,745

        Choose Frontier Airlines flights from Chicago to San Juan. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Tue, Feb 18, arriving at Luis Muñoz Marín International Airport. One-way Prices start from PHP 3,745 including taxes and charges.

      • MDW07:10 pm
        13h 34m
        1 stop
        SJU10:44 am
        Sat, Feb 22|Chicago - San Juan|Frontier Airlines
        PHP 3,745
        PHP 3,745

        Choose Frontier Airlines flights from Chicago to San Juan. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Sat, Feb 22, arriving at Luis Muñoz Marín International Airport. One-way Prices start from PHP 3,745 including taxes and charges.

      • MDW08:30 am
        12h 6m
        1 stop
        SJU10:36 pm
        Tue, Mar 4|Chicago - San Juan|Frontier Airlines
        PHP 3,745
        PHP 3,745

        Choose Frontier Airlines flights from Chicago to San Juan. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Tue, Mar 4, arriving at Luis Muñoz Marín International Airport. One-way Prices start from PHP 3,745 including taxes and charges.

      • ORD03:14 pm
        16h 35m
        1 stop
        SJU09:49 am
        Tue, Feb 25|Chicago - San Juan|Frontier Airlines
        PHP 3,745
        PHP 3,745

        Choose Frontier Airlines flights from Chicago to San Juan. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Tue, Feb 25, arriving at Luis Muñoz Marín International Airport. One-way Prices start from PHP 3,745 including taxes and charges.

      • MDW07:10 pm
        13h 34m
        1 stop
        SJU10:44 am
        Sat, Mar 1|Chicago - San Juan|Frontier Airlines
        PHP 3,754
        PHP 3,754

        Choose Frontier Airlines flights from Chicago to San Juan. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Sat, Mar 1, arriving at Luis Muñoz Marín International Airport. One-way Prices start from PHP 3,754 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        SJU02:00 pm
        Thu, Feb 6|Chicago - San Juan|United Airlines
        Find More Flights
        Find More Flights

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

Chicago to San Juan Flight Time

Flight info.
Departure
Arrival
Weekly Schedule

  1. F92144

    Frontier Airlines

    04:28 pm

    MDW

    2.1h

    07:33 pm

    ATL

    SMTWTFS
    Search

  2. F92082

    Frontier Airlines

    06:00 am

    ATL

    3.6h

    09:35 am

    SJU

    SMTWTFS

  3. F92110

    Frontier Airlines

    08:00 am

    MDW

    3.1h

    12:08 pm

    MIA

    S--WTFS
    Search

  4. F92284

    Frontier Airlines

    07:15 am

    MIA

    2.6h

    09:50 am

    SJU

    SM-WTFS

  5. F91416

    Frontier Airlines

    08:10 am

    ORD

    2.8h

    11:58 am

    TPA

    S--WT-S
    Search

  6. F92542

    Frontier Airlines

    08:48 pm

    TPA

    2.9h

    12:44 am

    SJU

    S--WTFS

  7. F91186

    Frontier Airlines

    08:56 am

    MDW

    2.8h

    12:41 pm

    TPA

    S--WTFS
    Search

  8. F92542

    Frontier Airlines

    08:48 pm

    TPA

    2.9h

    12:44 am

    SJU

    S--WTFS

  9. F93088

    Frontier Airlines

    09:51 am

    MDW

    1.9h

    12:48 pm

    BWI

    S---T--
    Search

  10. F92268

    Frontier Airlines

    09:28 pm

    BWI

    3.9h

    01:24 am

    SJU

    S-T-T--

  11. F92042

    Frontier Airlines

    10:02 pm

    ORD

    2.9h

    01:57 am

    MCO

    S---T-S
    Search

  12. F92250

    Frontier Airlines

    06:00 am

    MCO

    2.9h

    08:53 am

    SJU

    SMTWTFS

  13. F93044

    Frontier Airlines

    10:59 am

    ORD

    2.9h

    02:51 pm

    MCO

    SM-WTFS
    Search

  14. F92982

    Frontier Airlines

    03:23 pm

    MCO

    2.9h

    07:18 pm

    SJU

    SMTWTFS

  15. F93044

    Frontier Airlines

    10:59 am

    ORD

    2.9h

    02:51 pm

    MCO

    SM-WTFS
    Search

  16. F92250

    Frontier Airlines

    06:00 am

    MCO

    2.9h

    08:53 am

    SJU

    SMTWTFS

  17. F93044

    Frontier Airlines

    10:59 am

    ORD

    2.9h

    02:51 pm

    MCO

    SM-WTFS
    Search

  18. F93506

    Frontier Airlines

    06:53 pm

    MCO

    2.9h

    09:46 pm

    SJU

    SMTWTFS

  19. F91458

    Frontier Airlines

    12:58 pm

    MDW

    2.9h

    04:52 pm

    MCO

    S--WTFS
    Search

  20. F93506

    Frontier Airlines

    06:53 pm

    MCO

    2.9h

    09:46 pm

    SJU

    SMTWTFS
Find more flights and airlines

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

We monitor flight fares to help you find the best deals effortlessly

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 Chicago (CHI) to San Juan (SJU) the cheapest?

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

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

    According to Trip.com's data, the lowest price is around PHP 17,092.

  • How long does it take to fly from Chicago (CHI) to San Juan (SJU) and what is the distance?

    It takes around 4 hours 54 minutes to fly from Chicago (CHI) to San Juan (SJU).

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

    • The distance from Luis Muñoz Marín International Airport to downtown is about 11 km. It takes about 30 minutes by taxi.

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

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

How to find a cheap flight from Chicago to San Juan

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to San Juan. Book your flights at the right time and save more.
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 | Chicago to San Juan

Cheapest nonstop flight pricePHP 3,584
Cheapest round-trip ticket pricePHP 12,090
Off-season for travelJanuary
Peak season for travelOctober
Flight distance3,313.11 km
Average flight time4 hours 54 minutes
Popular airlineFrontier Airlines

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