Worldwide Coverage
Worldwide Coverage
Flights to over 5,000 cities
One-stop Service Guarantee
One-stop Service Guarantee
Price guaranteed upon confirmed payment, booking guaranteed once tickets issued
Secure Payment
Secure Payment
Convenient & reliable booking and payment system

Flights from Chicago to San Juan Starting at £46

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

  • One way
  • Round-trip

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

Find the best 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.
Airlines Flying 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.

Southwest Airlines
From £72
Spirit Airlines
From £79
United Airlines
From £82
American Airlines
From £83
Frontier Airlines
From £87
Delta Air Lines
From £114
Allegiant Air
From £124
Jetblue Airways
From £141
ANA airlines

Find more flights and airlines

Alternative Routes from Chicago to San Juan

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

  • Cheapest
    Spirit Airlines
    ORD
    22:00
    13h 42m
    1 transfer
    SJU
    12:42
    O'Hare International Airport - Luis Muñoz Marín International Airport
    Mon, Apr 8Spirit Airlines
    £79
  • Frontier Airlines
    MDW
    08:51
    16h 16m
    1 transfer
    SJU
    02:07
    Midway International Airport - Luis Muñoz Marín International Airport
    Tue, Apr 9Frontier Airlines
    £87
  • 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
    £124
  • 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
    £124
    Find More Flights

How do I find the cheapest flights?

  • 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 date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much are flights from Chicago (CHI) to San Juan (SJU) cost?

    According to Trip.com's data, the lowest price is around £293.
  • How long is the flight from Chicago (CHI) to San Juan (SJU)?

    It takes about 4 hours 43 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, by taxi about 30 minutes.
  • 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.
  • What's the most popular airline for direct flights from Chicago (CHI) to San Juan (SJU)?

    United Airlines operates 1 direct flights from Chicago (CHI) to San Juan (SJU).
  • How many airports in San Juan (SJU)?

Flight Information from Chicago to San Juan

Cheapest direct flight price

£45

Cheapest return ticket price

£125

Cheapest month

December

Peak season for travel

September