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Latest Flight Deals from San Juan to Chicago

Book one-way or return flights from San Juan to Chicago from as little as NZD 77. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip
      • SJU12:32
        10h 24m
        1 stop
        ORD21:56
        Tue, May 14|San Juan - Chicago|Spirit Airlines
        NZD 77NZD 171
        55% OFF
        55% OFF
        NZD 171NZD 77
      • SJU09:34
        9h 53m
        1 stop
        MDW18:27
        Wed, May 15|San Juan - Chicago|Frontier Airlines
        NZD 93NZD 171
        46% OFF
        46% OFF
        NZD 171NZD 93
      • SJU09:34
        9h 53m
        1 stop
        MDW18:27
        Wed, May 8|San Juan - Chicago|Frontier Airlines
        NZD 94NZD 171
        45% OFF
        45% OFF
        NZD 171NZD 94
      • SJU19:57
        14h 58m
        1 stop
        ORD09:55
        Tue, May 7|San Juan - Chicago|Spirit Airlines
        NZD 102
        NZD 102
      • SJU21:07
        13h 48m
        1 stop
        ORD09:55
        Wed, May 15|San Juan - Chicago|Spirit Airlines
        NZD 106
        NZD 106
      • SJU21:07
        13h 48m
        1 stop
        ORD09:55
        Wed, May 8|San Juan - Chicago|Spirit Airlines
        NZD 106
        NZD 106
      • SJU06:00
        16h 43m
        1 stop
        MDW21:43
        Wed, May 1|San Juan - Chicago|Frontier Airlines
        NZD 112
        NZD 112
      • SJU09:34
        9h 49m
        1 stop
        MDW18:23
        Tue, May 7|San Juan - Chicago|Frontier Airlines
        NZD 113
        NZD 113
      • SJU22:15
        9h 39m
        1 stop
        MDW06:54
        Wed, May 22|San Juan - Chicago|Frontier Airlines
        NZD 115
        NZD 115
      • SJU03:08
        9h 44m
        1 stop
        MDW11:52
        Thu, May 9|San Juan - Chicago|Frontier Airlines
        NZD 116
        NZD 116
      • SJU13:00
        3h 5m
        Direct
        CHI14:00
        Sun, May 5|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.

Searching for the best last minute flight from San Juan to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from San Juan to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

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

View airlines operating flights from San Juan to Chicago. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Spirit Airlines
From NZD 77
Frontier Airlines
From NZD 93
Jetblue Airways
From NZD 196
American Airlines
From NZD 214
United Airlines
From NZD 289
Southwest Airlines
From NZD 303
Delta Air Lines
From NZD 638
ANA airlines

Find more flights and airlines

Alternative Routes from San Juan to Chicago

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from San Juan to Chicago.

  • Cheapest
    Spirit Airlines
    SJU
    12:32
    10h 24m
    1 transfer
    ORD
    21:56
    Luis Muñoz Marín International Airport - O'Hare International Airport
    Tue, May 14Spirit Airlines
    NZD 77
  • Frontier Airlines
    SJU
    09:34
    9h 53m
    1 transfer
    MDW
    18:27
    Luis Muñoz Marín International Airport - Midway International Airport
    Wed, May 15Frontier Airlines
    NZD 93
  • Frontier Airlines
    SJU
    03:00
    10h 51m
    1 transfer
    RFD
    12:51
    Luis Muñoz Marín International Airport - Chicago Rockford International Airport
    Wed, May 22Frontier Airlines
    NZD 398
  • Frontier Airlines
    SJU
    03:00
    10h 51m
    1 transfer
    RFD
    12:51
    Luis Muñoz Marín International Airport - Chicago Rockford International Airport
    Wed, May 22Frontier Airlines
    NZD 398
    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 NZD 433.

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

How to find a cheap flight from San Juan to Chicago

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 San Juan to Chicago. 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 Information from San Juan to Chicago

Cheapest nonstop flight price

NZD 77

Cheapest round-trip ticket price

NZD 263

Off-season for travel

December

Peak season for travel

July

Flight distance

3,313.11km

Average flight time

5 hours 10 minutes

Popular airline

Frontier Airlines

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