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Find cheap one-way flights from Chicago to San Juan starting at US$61.

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

  • One way
  • Round-trip

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

When is the cheapest time to book flights 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.
Cheapest airlines flights from Chicago to San Juan

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Spirit Airlines
From US$61
Frontier Airlines
From US$64
Southwest Airlines
From US$91
American Airlines
From US$103
United Airlines
From US$105
Delta Air Lines
From US$144
Allegiant Air
From US$157
Jetblue Airways
From US$178
Avelo Airlines
From US$218
ANA airlines

Find more flights and airlines

Find cheap flights from Chicago to San Juan by different airports

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Chicago to San Juan.

  • Cheapest
    Spirit Airlines
    ORD
    07:27
    10h 35m
    1 transfer
    SJU
    19:02
    O'Hare International Airport - Luis Muñoz Marín International Airport
    Tue, Apr 16Spirit Airlines
    US$61
  • Frontier Airlines
    MDW
    08:51
    16h 16m
    1 transfer
    SJU
    02:07
    Midway International Airport - Luis Muñoz Marín International Airport
    Tue, Apr 9Frontier Airlines
    US$64
  • Allegiant Air
    RFD
    10:35
    22h 37m
    1 transfer
    SJU
    10:12
    Chicago Rockford International Airport - Luis Muñoz Marín International Airport
    Mon, Apr 8Allegiant Air
    US$157
  • Allegiant Air
    RFD
    10:35
    22h 37m
    1 transfer
    SJU
    10:12
    Chicago Rockford International Airport - Luis Muñoz Marín International Airport
    Mon, Apr 8Allegiant Air
    US$157
    Find More Flights

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 $369.
  • How long does it take to fly from Chicago (CHI) to San Juan (SJU) and what is the distance?

    It takes around 4 hours 42 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 11km. 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, Air New Zealand, Air Canada, Alaska Airlines, American Airlines, Southwest Airlines and Spirit Airlines.

Chicago to San Juan Flight Information

Cheapest nonstop flight price

$60

Cheapest round-trip ticket price

$156

Off-season for travel

December

Peak season for travel

September