Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
Chicago San Juan (Puerto Rico) | Outbound 04/12/25 1 Stopover (MCO) F93044, F91746 14h 58min | Return 04/27/25 direct NK0264 05h 23min | | ![]() | ? | $195 | |
Best option Chicago San Juan (Puerto Rico) | Outbound 06/08/25 direct UA0695 04h 51min | Return 06/12/25 direct UA2089 05h 10min | | ![]() | ? | $424 | |
Chicago San Juan (Puerto Rico) | Outbound 04/21/25 2 Stopovers (ATL, MCO) F91596, F94556, F94726 39h 29min | Return 05/19/25 2 Stopovers (BWI, ATL) F92265, F92509, F91595 35h 43min | | ![]() | ? | $197 | |
Chicago San Juan (Puerto Rico) | Outbound 04/12/25 1 Stopover (MCO) F93044, F91746 14h 58min | Return 04/27/25 direct NK0264 05h 23min | | ![]() | $201 | ||
Chicago San Juan (Puerto Rico) | Outbound 04/12/25 1 Stopover (MCO) F93044, F94726 17h 30min | Return 04/27/25 1 Stopover (MCO) F92249, F92791 18h 39min | | ![]() | ? | $214 | |
Chicago San Juan (Puerto Rico) | Outbound 04/21/25 1 Stopover (MCO) NK1506, NK0980 08h 57min | Return 05/19/25 1 Stopover (ATL) F92871, F93397 13h 25min | | ![]() | $239 | ||
Chicago San Juan (Puerto Rico) | Outbound 04/21/25 1 Stopover (MCO) NK1506, NK0980 08h 57min | Return 05/19/25 direct NK0492 04h 59min | | ![]() | $272 | ||
Chicago San Juan (Puerto Rico) | Outbound 04/21/25 1 Stopover (MCO) F92792, F94726 16h 10min | Return 05/19/25 1 Stopover (ATL) F92871, F93397 13h 25min | | ![]() | ? | $304 | |
Chicago San Juan (Puerto Rico) | Outbound 06/18/25 1 Stopover (CLT) AA2279, AA2830 10h 39min | Return 07/15/25 1 Stopover (MIA) AA0967, AA0581 15h 12min | | ![]() | ? | $412 | |
Chicago San Juan (Puerto Rico) | Outbound 06/08/25 1 Stopover (MCO) F93044, F94726 09h 27min | Return 06/12/25 1 Stopover (MCO) F94725, F92791 08h 04min | | ![]() | $420 |
Airline
- American Airlines
- Frontier Airlines
- Spirit Airlines
- United Airlines
- JetBlue Airways
Tips and tricks to help you find cheap flights from Chicago to San Juan (Puerto Rico)
Favorite airline: American Airlines
79 % of flights booked on the route from Chicago to San Juan (Puerto Rico) are booked with American Airlines, Spirit Airlines and United Airlines.

American Airlines
29 %

Spirit Airlines
27 %

United Airlines
23 %
Direct flights are the cheapest connection
On this route, direct flights are $ 2.00 cheaper than flights with a stopover.
non stop flight
1 stop
2 stops
04h 39min
13h 20min
15h 45min
194 $US
196 $US
451 $US
The favorite connection is non-stop
Flights from Chicago to San Juan (Puerto Rico) are most often booked as a direct flight.
Route
bookings
Direct flights
04h 39min, from 194 $US
39 %
1 stopover Orlando International Airport, FL
07h 00min, from 221 $US
18 %
1 stopover Charlotte Douglas International Airport, NC
13h 01min, from 338 $US
15 %
Important flight information
Flight information: Chicago - San Juan (Puerto Rico)
Roundtrip from | 194,89 $US |
---|---|
Flight duration | min. 04:30 / max. 07:00 |
Return flight duration | min. 05:10/ max. 06:05 |
Distance | 3318 km |
Flights per week | 28 |
Departure airport | Airport Chicago-IL all Airports (ORD, MDW, RFD) (CHI) |
Arrival airport | Airport San Juan - Luis Muñoz Marín International Airport (SJU) |
Destination country | Flights to Puerto Rico |
Alternative flights to San Juan (Puerto Rico)
- Flight Baltimore - San Juan (Puerto Rico) from 128 $US
- Flight Detroit - San Juan (Puerto Rico) from 164 $US
- Flight New York - San Juan (Puerto Rico) from 247 $US
- Flight Philadelphia - San Juan (Puerto Rico) from 235 $US
- Flight Sacramento - San Juan (Puerto Rico) from 317 $US
- Flight Fort Lauderdale - San Juan (Puerto Rico) from 135 $US
- Flight Orlando - San Juan (Puerto Rico) from 179 $US
- Flight Cleveland - San Juan (Puerto Rico) from 217 $US
- Flight Tampa - San Juan (Puerto Rico) from 205 $US
Flight destinations with a similar price
- Flight Chicago - Toronto from 189 $US
- Flight Chicago - San Antonio from 205 $US