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Flights from San Juan to Chicago

Cheap flight deals from San Juan to Chicago

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

  • Round-trip
  • One way

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

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

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

Cheapest flights
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  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
  • 8 15
  • 15 22
  • 22 29

  • Jul

    29 6
  • 6 13
  • 13 20
  • 20 27
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 San Juan (SJU) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from San Juan to Chicago based on the date and time of your booking. By analyzing data from all airlines, 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 AED 1,237.

  • How long does it take to fly from San Juan (SJU) to Chicago (CHI)?

    It takes about 5 hours 49 minutes to fly from San Juan (SJU) to Chicago (CHI).

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

  • How many airports are there in Chicago (CHI)?

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
Being flexible with your dates to get the cheapest San Juan to Chicago ticket.
Tap "Date" on flight search bar to scan through the calender for San Juan to Chicago airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Tue, Jun 3 at AED 372 for one-way flights.
2
Compare cheap San Juan to Chicago flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from San Juan to Chicago. The cheapest airline operating is Spirit Airlines.
3
Set up a Price Alert
By setting up a Price Alert for your San Juan to Chicago route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap San Juan to Chicago flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
5
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
6
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from San Juan to Chicago to get exclusive deals for you.

Flight Info | San Juan to Chicago

Cheapest one-way flight price AED 251
Cheapest return ticket price AED 761
Off-season for travel March
Peak season for travel June
Flight distance 3,313.11 km
Average flight time 5 hours 49 minutes
Popular airline Frontier Airlines

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