Find cheap flights from San Juan to Chicago starting at $46.
Book one-way or return flights from San Juan to Chicago from as little as $46. Choose from the popular airlines below and book your flight today!
- One way
- Round-trip
- SJU12:3210h 24m1 stopORD21:56Tue, May 14|San Juan - Chicago|Spirit Airlines$46$10255% OFF55% OFF$102$46
- SJU09:349h 53m1 stopMDW18:27Wed, May 15|San Juan - Chicago|Frontier Airlines$55$10246% OFF46% OFF$102$55
- SJU09:349h 53m1 stopMDW18:27Wed, May 8|San Juan - Chicago|Frontier Airlines$56$10245% OFF45% OFF$102$56
- SJU19:5714h 58m1 stopORD09:55Tue, May 7|San Juan - Chicago|Spirit Airlines$61$61
- SJU21:0713h 48m1 stopORD09:55Wed, May 15|San Juan - Chicago|Spirit Airlines$63$63
- SJU21:0713h 48m1 stopORD09:55Wed, May 8|San Juan - Chicago|Spirit Airlines$63$63
- SJU06:0016h 43m1 stopMDW21:43Wed, May 1|San Juan - Chicago|Frontier Airlines$66$66
- SJU09:349h 49m1 stopMDW18:23Tue, May 7|San Juan - Chicago|Frontier Airlines$67$67
- SJU22:159h 39m1 stopMDW06:54Wed, May 22|San Juan - Chicago|Frontier Airlines$68$68
- SJU03:089h 44m1 stopMDW11:52Thu, May 9|San Juan - Chicago|Frontier Airlines$69$69
- SJU13:003h 5mDirectCHI14:00Sun, May 5|San Juan - Chicago|Spirit AirlinesFind More FlightsFind More Flights
Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
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Discover different routes, airlines, and transfers and find the best alternative flights for your journey from San Juan to Chicago.
- CheapestSJU12:3210h 24m1 transferORD21:56Luis Muñoz Marín International Airport - O'Hare International AirportTue, May 14Spirit Airlines$46
- SJU09:349h 53m1 transferMDW18:27Luis Muñoz Marín International Airport - Midway International AirportWed, May 15Frontier Airlines$55
- SJU03:0010h 51m1 transferRFD12:51Luis Muñoz Marín International Airport - Chicago Rockford International AirportWed, May 22Frontier Airlines$237
- SJU03:0010h 51m1 transferRFD12:51Luis Muñoz Marín International Airport - Chicago Rockford International AirportWed, May 22Frontier Airlines$237Find More Flights
Frequently Asked Questions
How to find a cheap flight from San Juan to Chicago
Cheapest nonstop flight price | $45 |
---|---|
Cheapest round-trip ticket price | $156 |
Off-season for travel | December |
Peak season for travel | July |
Flight distance | 3,313.11km |
Average flight time | 5 hours 10 minutes |
Popular airline | Frontier Airlines |
Plan Your Trip Around Chicago
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