Flights from Chicago to San Juan from $69
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Airfare Deals Chicago to San Juan
On HolidayPrice.com you will find 4 direct and 6 connecting flights from Chicago to San Juan at a price of from $69. You can compare airfare deals from airlines and multiple travel sites, book and save on cheap plane tickets and last minute offers. Also check out CHI - SJU flight schedule to find best flight time, convenient departure and arrival airports.
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The cost of airline tickets from Chicago to San Juan (Puerto Rico) and back without transfers can be found with the help of the calendar. Specify the search parameters: one way or round-trip, payment currency, click on the month/day you need and we will search for flights to San Juan.
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Cheap flights from ChicagoCheap flights to San Juan
Airline tickets to Puerto Rico
One way flight from Chicago to San Juan
Below are the prices of tickets for direct one-way flights from Chicago to San Juan. The cheapest flight from Chicago to San Juan starts from $69 – the departure date for this flight is 19 March 2025.
19.04.2025
Saturday
from $150
Flightnetwork
Economy
Found today
1 Stopover
9 hours 31 min
Find Flights
Round trip from Chicago to San Juan
You can buy a round-trip ticket from Chicago to San Juan (Puerto Rico) and back using the table below. The best offer starts from $154, the flight dates are: there on 19 March 2025 year and back on 30 March 2025 year.
Frontier Airlines F9 2144
Day flight
Departure
01.05.25
13:30, Th
1 Stopover
Trip 5 days
Return
06.05.25
07:56, Tu
Not found promotions and sales.
Flight Schedule Chicago to San Juan 2025
The current flight schedule for the route from Chicago to San Juan for today, tomorrow and the next few days. This schedule will help you decide on the time of departure and arrival, the airline, the flight number and the day of the week.
More than 6 flights every day, from 4hours 30min. Local departure and arrival times are indicated.
*Schedule is indicated only for direct scheduled flights and low-cost airlines.
Flight Information
Flying to San Juan from Chicago takes 04:56 minutes (excluding transfers). The distance between Chicago and San Juan is 2049 miles (3299 kilometers). Planes depart from Chicago between 00:30 and 23:30. The fastest flight from the company American Airlines with flight number AA 1174. Flies for just 04:38 minutes with departure from O'Hare and arrival in Luis Munoz Marin.
Average flight time
04:56 min
Distance
2049 mi
The earliest flight
00:30
The latest flight
23:30
The fastest flight
04:38
Airlines
Direct flight
There are 4 airlines that fly directly from Chicago to San Juan. The most popular company carrying out non-stop flights is Southwest Airlines.
- Southwest Airlines: WN 1314, WN 4226, WN 2772
- JetBlue Airways: B6 563
- United Airlines: UA 1996, UA 1841, UA 1896
- American Airlines: AA 395, AA 1187, AA 1174
*Flight number
Flights with Transfers
Flights with transfers from Chicago to San Juan can be bought from 6 airlines:
- Delta Air Lines: New York
- United Airlines: Grand Rapids, Houston,
- Southwest Airlines: Tampa, Orlando, Philadelphia
- American Airlines: West Palm Beach, Orlando, New York
- Spirit Airlines: Orlando
- JetBlue Airways: New York
*Transit cities
Airports
Airports serving the air communication between Chicago and San Juan. You can fly to San Juan from 2 Chicago airports. Planes arrive at 1 airport in San Juan.
Chicago airports:
Chicago Midway ~ 14 km* from $ 99O'Hare ~ 25 km* from $ 67San Juan airports:
Luis Munoz Marin ~ 12 km* from $ 35*Distance from the airport to the city center
Aircraft
You can fly from Chicago to San Juan on board of 4 airlines that utilize 4 aircraft models.
- Airbus A320
- Boeing 737-700
- Boeing 737-800
- Boeing 737-900
Connecting cities
The list of cities on transfer flights to San Juan from Chicago. The best options are to fly through: New York, Grand Rapids, Tampa, West Palm Beach, Orlando, Philadelphia, Houston, , Baltimore, Atlanta, Hartford, Charlotte, Boston.
Cheap airline tickets from Chicago to Puerto Rico
Here is a list of flights from Chicago to Puerto Rico purchased on HolidayPrice.com in the past 48 hours. If you find an interesting offer for cheap tickets, do not delay your purchase, prices change every 15 minutes.
Chicago - San Juan AA 1174
American Airlines Boeing 737-800
23:30
O'Hare
in a way 4 hours 38 min
Direct
04:08
Luis Munoz Marin
Flights
from $69 19 March 2025
from $69 19 March 2025
Chicago - Ponce NK 929
Spirit Airlines Airbus A320
22:20
O'Hare
in a way 7 hours 13 min
1 Stopover
05:33
Mercedita Airport
Flights
from $226 23 March 2025
from $226 23 March 2025
Chicago - Aguadilla WN 3023
Southwest Airlines Boeing 737-800
22:40
Chicago Midway
in a way 6 hours 58 min
1 Stopover
05:38
Rafael Hernandez Airport
Flights
from $71 23 March 2025
from $71 23 March 2025
Chicago - Mayaguez AA 395
American Airlines Boeing 737-800
14:40
O'Hare
in a way 8 hours 15 min
1 Stopover
22:55
Eugenio M. De Hostos Airport
Flights
from $402 23 March 2025
from $402 23 March 2025
Flights from United States to San Juan
Here are the cheapest flight bookings from United States to San Juan made by users of our website. If you didn’t find your flight destination, use the search bar at the top of the page.
New York - San Juan B6 1403
JetBlue Airways Airbus A321
12:00
John F. Kennedy
in a way 3 hours 43 min
Direct
15:43
Luis Munoz Marin
Flights
from $76 19 March 2025
from $76 19 March 2025
Los Angeles - San Juan UA 2410
United Airlines Boeing 737-900
06:45
Los Angeles
in a way 8 hours 45 min
1 Stopover
15:30
Luis Munoz Marin
Flights
from $135 23 March 2025
from $135 23 March 2025
Miami - San Juan AA 316
American Airlines Boeing 757
04:56
Miami
in a way 2 hours 4 min
Direct
07:00
Luis Munoz Marin
Flights
from $44 17 March 2025
from $44 17 March 2025
Chicago - San Juan AA 1174
American Airlines Boeing 737-800
23:30
O'Hare
in a way 4 hours 38 min
Direct
04:08
Luis Munoz Marin
Flights
from $69 19 March 2025
from $69 19 March 2025
San Francisco - San Juan UA 1996
United Airlines Boeing 737-800
10:20
San Francisco
in a way 10 hours 15 min
Direct
20:35
Luis Munoz Marin
Flights
from $152 23 March 2025
from $152 23 March 2025
Tips for buying a ticket
Chicago – San Juan – Chicago round-trip route are always cheaper than tickets purchased there and back separately.
To start searching for tickets, Specify dates.