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Flights from Chicago to San Juan

Cheap flight deals from Chicago to San Juan

Here are our top budget-friendly flights, offering flexible one-way or round-trip options. Additional flights with other timings and airlines are also available.

  • 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 Chicago to San Juan?

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

Cheapest flights
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  • 11 18
  • 18 25

  • Jun

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

  • Jul

    29 6
  • 6 13
  • 13 20
  • 20 27

  • Aug

    27 3
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 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 PHP 22,590.

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

    It takes around 4 hours 43 minutes to fly from Chicago (CHI) to San Juan (SJU).

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

How to find a cheap flight from Chicago to San Juan

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 Chicago to San Juan. 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

Flying from Chicago to San Juan

Cheapest one-way flight price PHP 5,111
Cheapest round-trip ticket price PHP 8,237
Off-season for travel April
Peak season for travel June
Flight distance 3,313.11 km
Average flight time 4 hours 43 minutes
Popular airline United Airlines

More Travel Options

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  • Popular Airlines to San Juan
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  • Popular San Juan Hotels