Cheap Flights from San Juan to Chicago, IL from $102

Return flight: Chicago – San Juan

On you will find 1 direct and 2 connecting flights from San Juan to Chicago. You can compare airfare deals from 2 airlines and multiple travel sites from $102, book and save on cheap plane tickets and last minute offers. Also check out SJU-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip San Juan to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $102 (one-way), $175 (round-trip).
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Full flight schedule will help you in detecting at what time planes fly from San Juan to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
15:35 — 18:45
15:35 — 18:45 UA841 United Airlines
San Juan — Chicago
5h 10m
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17:15 — 00:01
+1 day
17:15 — 20:09 UA668 United Airlines
San Juan — Houston
1h 24m stop
21:33 — 00:01 UA1854 United Airlines
Houston — Chicago
8h 46m
including layover
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17:28 — 23:59
17:28 — 19:17 NK240 Spirit Airlines
San Juan — Miami
2h 20m stop
21:37 — 23:59 NK464 Spirit Airlines
Miami — Chicago
8h 31m
including layover
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*Departure and arrival times - local. Updated on June 18, 2024

Flight Information

Below we will explain in detail what the flights cost on the destination from San Juan to Chicago depends on and how to choose the most interesting flight option for you.

Distance between San Juan and Chicago is 3314 miles. Time difference between the cities is 2h. Airplanes depart 15:35 to 17:28 from 2 San Juan airports and arrive 15:35 to 17:28 to 7 Chicago airports. Average flight time is 5h 10m.

  • The fastest flight 5h 10m
  • Average flight time 5h 10m
  • The earliest flight 15:35
  • The latest flight 17:28
  • Distance 2060 ml

The cheapest months to travel to Chicago are june (from 102 $).

What is the lowest airfare San Juan to Chicago?

The cheapest plane ticket found by our users is $102. This airfare is for economy class on one-way NK240 flight by Spirit Airlines for June 19, 2024 which leaves Luis Munoz Marin Intl in San Juan at 17:28 am and arrives at Chicago O'Hare International at 23:59.

Economy class
Business class
First class

Popular Airlines on the Route

The flight San Juan — Chicago is served by 2 regular airlines and 1 low-cost airline. Most of the flights on this route are operated by United Airlines - 2 departures per week at the price of from $ 126 . And the most expensive tickets are offered by United Airlines airline - from $ 129.

Direct flights

There are 1 nonstop flights on the route. The fastest direct flight is UA841 by United Airlines takes 5h 10m and the cheapest is NK240 by Spirit Airlines for $129.

  • UA - United Airlines
    from $129
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Connecting Flights

There are 2 flights with layovers on the route. The fastest connecting flight is NK240 by Spirit Airlines takes 8h 31m and the cheapest is NK240 by Spirit Airlines for $102.

  • UA - United Airlines
    from $126
  • NK - Spirit Airlines
    from $102
See more connecting flights


You can fly from San Juan to Chicago from 2 airports (Isla Grande, Luis Munoz Marin Intl).

San Juan airports

  • Isla Grande-SIG
  • Luis Munoz Marin Intl-SJU
    from $102

Chicago airports

  • O'Hare International-ORD
  • Midway-MDW
  • Dupage County-DPA
  • Chicago FSS-CHI
  • Merrill C Meigs (closed)-CGX
  • Pal-Waukee-PWK
  • Chicago NAS-NOH

How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.