Cheap $72 Flights From Chicago to Puerto Rico
Easily compare flights from Chicago to Puerto Rico and find the cheapest tickets available!
Flying From Chicago to Puerto Rico: What You Need to Know
| Cheapest one-way flight price | $72 |
|---|---|
| Cheapest round-trip ticket price | $153 |
| Off-season for travel | October |
| Peak season for travel | July |
| Popular airline | Spirit Airlines |
| Cheapest month | September |
Compare multiple airlines at once to find the best flight deals from Chicago to Puerto Rico.
Airlines Flying From Chicago to Puerto Rico
Spirit Airlines 
United Airlines 
Jetblue Airways 
American Airlines 
Delta Air Lines 
Frontier Airlines Search Flights From Chicago to Puerto Rico
Easily compare flights from Chicago to Puerto Rico and find the cheapest tickets available!
Find the Cheapest Flights to Puerto Rico From Chicago
Looking for cheap flights from Chicago to Puerto Rico? Check out prices for the next 90 days, starting at just $72 for a one-way ticket and $153 for a round trip.
- Round-trip
- One way
-
- Cheapest nonstop
Tue, May 5ORD|SJUChicagoSan JuanNonstop | Spirit AirlinesThu, May 7SJU|ORDSan JuanChicagoNonstop | Spirit Airlines$153 $19421% off21% off$194 $153 -
Sun, Apr 26ORD|SJUChicagoSan JuanNonstop | Spirit Airlines
Fri, May 1SJU|ORDSan JuanChicagoNonstop | Spirit Airlines$175 $19410% off10% off$194 $175
-
Mon, Apr 27ORD|SJUChicagoSan JuanNonstop | Spirit Airlines
Fri, May 1SJU|ORDSan JuanChicagoNonstop | Spirit Airlines$175 $19410% off10% off$194 $175
-
Mon, May 4ORD|SJUChicagoSan JuanNonstop | Spirit Airlines
Sat, May 9SJU|ORDSan JuanChicago1 stop | Frontier Airlines$15321% off$194 $153 -
Sat, May 16ORD|SJUChicagoSan Juan1 stop | Frontier Airlines
Fri, May 22SJU|ORDSan JuanChicagoNonstop | Frontier Airlines$15719% off$194 $157
-
Mon, May 18ORD|SJUChicagoSan Juan1 stop | Frontier Airlines
Fri, May 22SJU|ORDSan JuanChicagoNonstop | Frontier Airlines$15918% off$194 $159
-
Wed, Apr 22ORD|SJUChicagoSan Juan1 stop | Spirit Airlines
Fri, Apr 24SJU|ORDSan JuanChicagoNonstop | Spirit Airlines$16714% off$194 $167
-
Sat, Apr 25ORD|SJUChicagoSan JuanNonstop | Spirit Airlines
Fri, May 1SJU|ORDSan JuanChicago1 stop | Frontier Airlines$17311% off$194 $173
-
Thu, Apr 23ORD|SJUChicagoSan Juan1 stop | Frontier Airlines
Fri, May 1SJU|ORDSan JuanChicago1 stop | Spirit Airlines$1798% off$194 $179
-
Fri, May 8MDW|SJUChicagoSan Juan1 stop | Frontier Airlines
Fri, May 15SJU|ORDSan JuanChicago1 stop | Frontier Airlines$1807% off$194 $180
-
Tue, Apr 21CHI|SJUChicagoSan Juan1 stop | Normal Airline
Thu, Apr 23SJU|CHISan JuanChicagoNonstop | Normal AirlineFind more flightsFind more flights
-
Cheapest nonstopTue, May 5ORD|SJUChicagoSan JuanNonstop | Spirit Airlines$72 $10028% off28% off$100 $72
-
Fri, May 15ORD|SJUChicagoSan Juan1 stop | Frontier Airlines$89 $10011% off11% off$100 $89
-
Mon, Apr 27ORD|SJUChicagoSan Juan1 stop | Spirit Airlines$89 $10011% off11% off$100 $89
-
Fri, May 8ORD|SJUChicagoSan Juan1 stop | Frontier Airlines$9010% off$100 $90
-
Sun, Apr 26ORD|SJUChicagoSan Juan1 stop | Frontier Airlines$9010% off$100 $90
-
Sun, May 10ORD|SJUChicagoSan Juan1 stop | Frontier Airlines$919% off$100 $91
-
Mon, May 18MDW|SJUChicagoSan Juan1 stop | Frontier Airlines$919% off$100 $91
-
Tue, May 12ORD|SJUChicagoSan Juan1 stop | Frontier Airlines$919% off$100 $91
-
Mon, May 4MDW|SJUChicagoSan Juan1 stop | Frontier Airlines$928% off$100 $92
-
Wed, Apr 22ORD|SJUChicagoSan Juan1 stop | Frontier Airlines$937% off$100 $93
-
Tue, Apr 21CHI|SJUChicagoSan Juan1 stop | Normal AirlineFind more flightsFind more flights
Displayed flight fares from Chicago to San Juan are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.
FAQs: Flights From Chicago to Puerto Rico
What is the cheapest Chicago to Puerto Rico flight route?
The cheapest round-trip flight from Chicago to Puerto Rico is on the route from Chicago to San Juan, with prices starting at $150 for a round trip between 2026-05-16 and 2026-05-22.When is it the cheapest time to fly from Chicago to Puerto Rico?
According to our flights calendar over the next 90 days, it seems the cheapest date is on 2026-05-05 for one-way flights.How long does it take to fly to Puerto Rico from Chicago?
Based on our flight data, the average flight time from Chicago to Puerto Rico is approximately 4 hours 49 minutes based on our most popular routes from Chicago to San Juan. The time may also vary depending on your destination.What is the cheapest airline that flies to Puerto Rico from Chicago?
The cheapest airline flying to Puerto Rico from Chicago is Spirit Airlines serving route from Chicago to San Juan.Where can I fly to Puerto Rico from Chicago?
There are direct flights from Chicago to Puerto Rico. San Juan, Aguadilla, and Ponce are all popular destinations in Puerto Rico.
Trending Searches
- Cheap tickets from Chicago to El Salvador
- Book flights from Chicago to Bangladesh
- Direct flights from Chicago to France
- Book flights from Chicago to Syria
- Direct flights from Chicago to Hungary
- Cheap tickets from Chicago to Switzerland
- Cheap tickets from Chicago to Romania
- Book flights from Chicago to Curacao
- Direct flights from Chicago to Moldova
- Direct flights from Chicago to Lithuania