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Flights from San Juan to Chicago Starting at KRW 91,923

Discover our range of affordable one-way and round-trip flights from San Juan to Chicago and kick-start your next adventure today!

  • One way
  • Round-trip
      • SJU20:41
        12h 55m
        1 stop
        MDW08:36
        Tue, Aug 6|San Juan - Chicago|Frontier Airlines
        KRW 91,923KRW 176,327
        48% OFF
        48% OFF
        KRW 176,327KRW 91,923
      • SJU07:14
        8h 37m
        1 stop
        ORD14:51
        Wed, Aug 28|San Juan - Chicago|Frontier Airlines
        KRW 103,077KRW 176,327
        42% OFF
        42% OFF
        KRW 176,327KRW 103,077
      • SJU21:15
        12h 21m
        1 stop
        MDW08:36
        Thu, Jul 18|San Juan - Chicago|Spirit Airlines
        KRW 112,308KRW 176,327
        36% OFF
        36% OFF
        KRW 176,327KRW 112,308
      • SJU18:20
        15h 16m
        1 stop
        MDW08:36
        Thu, Jul 4|San Juan - Chicago|Frontier Airlines
        KRW 113,846
        KRW 113,846
      • SJU20:54
        13h 20m
        1 stop
        ORD09:14
        Fri, Jul 12|San Juan - Chicago|Spirit Airlines
        KRW 115,769
        KRW 115,769
      • SJU11:15
        8h 18m
        1 stop
        MDW18:33
        Tue, Jul 16|San Juan - Chicago|Frontier Airlines
        KRW 116,154
        KRW 116,154
      • SJU20:41
        26h 5m
        1 stop
        MDW21:46
        Wed, Jul 10|San Juan - Chicago|Frontier Airlines
        KRW 117,885
        KRW 117,885
      • SJU09:10
        24h 26m
        1 stop
        MDW08:36
        Fri, Jul 12|San Juan - Chicago|Frontier Airlines
        KRW 119,231
        KRW 119,231
      • SJU09:42
        10h 36m
        1 stop
        ORD19:18
        Thu, Aug 22|San Juan - Chicago|Frontier Airlines
        KRW 120,769
        KRW 120,769
      • SJU20:41
        13h 10m
        1 stop
        ORD08:51
        Wed, Sep 4|San Juan - Chicago|Frontier Airlines
        KRW 120,769
        KRW 120,769
      • SJU13:00
        3h 5m
        Direct
        CHI14:00
        Wed, Jul 10|San Juan - Chicago|Frontier Airlines
        Find More Flights
        Find More Flights

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

Find the best time to fly from San Juan to Chicago

Price trend charts are a great way of tracking how much your flights cost in the lead up to departure and can help you choose when to book your tickets. See how prices to Chicago from San Juan have changed and are set to move below.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Airlines Flying from San Juan to Chicago

Compare prices from various providers below to understand which option best suits your travel needs, before enjoying a comfortable journey with a trusted airline from San Juan to Chicago.

Frontier Airlines
From KRW 91,923
Spirit Airlines
From KRW 112,308
Jetblue Airways
From KRW 140,962
American Airlines
From KRW 200,962
United Airlines
From KRW 210,192
Southwest Airlines
From KRW 325,769
Delta Air Lines
From KRW 347,500
Sun Country Airlines
From KRW 350,192
Silver Airways
From KRW 690,769
Cape Air
From KRW 877,308
ANA airlines

Find more flights and airlines

Alternative Routes from San Juan to Chicago

Did you know that you can save money and time on an alternative route from San Juan to Chicago? Check out some of the different available routes below.

  • Cheapest
    Frontier Airlines
    SJU
    20:41
    12h 55m
    1 transfer
    MDW
    08:36
    Luis Muñoz Marín International Airport - Midway International Airport
    Tue, Aug 6Frontier Airlines
    KRW 91,923
  • Frontier Airlines
    SJU
    07:14
    8h 37m
    1 transfer
    ORD
    14:51
    Luis Muñoz Marín International Airport - O'Hare International Airport
    Wed, Aug 28Frontier Airlines
    KRW 103,077
  • Spirit Airlines
    SJU
    01:59
    15h 40m
    1 transfer
    RFD
    16:39
    Luis Muñoz Marín International Airport - Chicago Rockford International Airport
    Wed, Jul 17Spirit Airlines
    KRW 237,885
  • Spirit Airlines
    SJU
    01:59
    15h 40m
    1 transfer
    RFD
    16:39
    Luis Muñoz Marín International Airport - Chicago Rockford International Airport
    Wed, Jul 17Spirit Airlines
    KRW 237,885
    Find More Flights

How do I find the cheapest flights?

  • 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 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 San Juan (SJU) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around KRW 426,538.

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

    It takes around 5 hours 10 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 25km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14km. It takes about 30 minutes by taxi.

  • 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): American Airlines, United Airlines, Spirit Airlines, Air New Zealand, Air Canada, Alaska Airlines and Southwest Airlines.

How to find a cheap flight from San Juan to Chicago

Understanding the common pitfalls when booking your flight tickets can help you save massively when it comes time to fly. We’ve listed our six essential steps to keep in mind when you’re booking flight tickets to help you find the best price.
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 Information from San Juan to Chicago

Cheapest nonstop flight price

KRW 91,923

Cheapest round-trip ticket price

KRW 261,346

Off-season for travel

May

Peak season for travel

September

Flight distance

3,313.11km

Average flight time

5 hours 10 minutes

Popular airline

Frontier Airlines

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