Airfare Deals from Chicago to San Juan

Find cheap flights from Chicago to San Juan at Tripsta.co.uk in just 5 minutes. On the site you can compare flight prices on this route, buy airline tickets costing from £65 and see the aircraft schedule.

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The cheapest flight ticket from Chicago to San Juan was found 3 days ago. Its one way cost starts from £65, the departure date is 01 December 2021. The minimum price for a round trip flight starts from £115. This flight fare was found 4 days ago, with the following departure dates: Chicago on 08 September 2021 year, and back from San Juan on 15 September 2021 year.

Plane tickets from Chicago to San Juan, one way

The table shows the prices of direct flight plane tickets to San Juan from Chicago. If you find an interesting air travel offer, do not delay your purchase, last minute offers run out very quickly.

Sort by: Departure dateCheap flightsFast flightsDirect flights
02.07.2021 Friday
from £176 Kiwi.com
Economy Found 2021-06-11
1 Stopover 16 hours 53 min
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10.07.2021 Saturday
from £182 MyHolidays
Economy Found yesterday
Nonstop 10 hours 14 min
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09.07.2021 Friday
from £185 MyHolidays
Economy Found 2021-06-15
1 Stopover 12 hours 21 min
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02.07.2021 Friday
from £187 Kiwi.com
Economy Found 2021-06-11
1 Stopover 16 hours 45 min
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14.07.2021 Wednesday
from £187 CheapOair.com
Economy Found 2021-06-15
1 Stopover 17 hours 4 min
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12.07.2021 Monday
from £187 CheapOair.com
Economy Found yesterday
1 Stopover 17 hours 4 min
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11.07.2021 Sunday
from £188 SmartFares
Economy Found yesterday
Nonstop 10 hours 14 min
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02.07.2021 Friday
from £189 MyHolidays
Economy Found 2021-06-11
1 Stopover 16 hours 45 min
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13.07.2021 Tuesday
from £191 JustFly
Economy Found yesterday
Nonstop 10 hours 14 min
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08.07.2021 Thursday
from £192 Bravofly
Economy Found 2021-06-15
1 Stopover 18 hours 27 min
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08.07.2021 Thursday
from £193 Bravofly
Economy Found 2021-06-14
1 Stopover 21 hours 13 min
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03.07.2021 Saturday
from £194 Kiwi.com
Economy Found yesterday
1 Stopover 23 hours 48 min
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02.07.2021 Friday
from £195 Kiwi.com
Economy Found 2021-06-11
1 Stopover 16 hours 45 min
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18.07.2021 Sunday
from £195 Kiwi.com
Economy Found 2021-06-14
Nonstop 10 hours 14 min
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20.07.2021 Tuesday
from £197 Kiwi.com
Economy Found 2021-06-11
1 Stopover 18 hours 27 min
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Flights from Chicago to San Juan are most popular in January, June, December. During this period, the average price of fly tickets is from £103. In the low season in February, March, April, air tickets become cheaper and the average price will be from £29 one way.

Best Flights: Chicago to San Juan and back

The cost of a round trip flight on the Chicago - San Juan (Puerto Rico) route. The cheapest ticket was purchased 4 days ago, its price was from £115. It flies to San Juan on 08 September 2021 year and returns to Chicago on 15 September 2021 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
United Airlines UA 2202 Night flight
Departure 09.09.21 00:40, Th
1 Stopover Trip 7 days
Return 15.09.21 20:45, We
United Airlines UA 2161 Evening flight
Departure 28.01.22 22:05, Fr
1 Stopover Trip 6 days
Return 03.02.22 18:40, Th
United Airlines UA 2354 Day flight
Departure 07.09.21 15:52, Tu
1 Stopover Trip 7 days
Return 14.09.21 06:55, Tu
United Airlines UA 2288 Day flight
Departure 01.09.21 12:40, We
1 Stopover Trip 3 days
Return 04.09.21 13:30, Sa
Frontier Airlines F9 128 Day flight
Departure 09.09.21 11:45, Th
1 Stopover Trip 4 days
Return 13.09.21 06:55, Mo
Frontier Airlines F9 128 Day flight
Departure 01.12.21 12:45, We
Direct Trip 4 days
Return 05.12.21 17:40, Su
Frontier Airlines F9 128 Morning flight
Departure 04.09.21 06:29, Sa
1 Stopover Trip 8 days
Return 12.09.21 06:55, Su
United Airlines UA 2161 Evening flight
Departure 04.11.21 21:05, Th
1 Stopover Trip 5 days
Return 09.11.21 17:40, Tu
Frontier Airlines F9 128 Morning flight
Departure 06.09.21 06:29, Mo
1 Stopover Trip 7 days
Return 13.09.21 06:55, Mo
Frontier Airlines F9 128 Morning flight
Departure 07.08.21 06:29, Sa
1 Stopover Trip 5 days
Return 12.08.21 07:25, Th
Spirit Airlines NK 425 Evening flight
Departure 28.07.21 23:30, We
1 Stopover Trip 6 days
Return 03.08.21 13:30, Tu
Frontier Airlines F9 1155 Morning flight
Departure 17.06.21 10:44, Th
1 Stopover Trip 8 days
Return 25.06.21 19:19, Fr
United Airlines UA 2288 Day flight
Departure 02.07.21 12:45, Fr
1 Stopover Trip 1 day
Return 03.07.21 11:25, Sa
Spirit Airlines NK 2 Morning flight
Departure 29.06.21 10:25, Tu
1 Stopover Trip 4 days
Return 03.07.21 22:03, Sa
Frontier Airlines F9 128 Morning flight
Departure 10.07.21 06:29, Sa
Direct Trip 4 days
Return 14.07.21 11:30, We
Frontier Airlines F9 1155 Day flight
Departure 18.06.21 11:45, Fr
1 Stopover Trip 4 days
Return 22.06.21 11:25, Tu
Frontier Airlines F9 1155 Day flight
Departure 09.07.21 11:45, Fr
1 Stopover Trip 5 days
Return 14.07.21 11:30, We
Frontier Airlines F9 128 Day flight
Departure 10.11.21 12:45, We
1 Stopover Trip 4 days
Return 14.11.21 08:07, Su
Spirit Airlines NK 425 Evening flight
Departure 16.08.21 23:30, Mo
1 Stopover Trip 7 days
Return 23.08.21 13:30, Mo
Spirit Airlines NK 2 Morning flight
Departure 14.07.21 10:25, We
1 Stopover Trip 6 days
Return 20.07.21 11:30, Tu
Spirit Airlines NK 2 Morning flight
Departure 12.07.21 10:25, Mo
1 Stopover Trip 4 days
Return 16.07.21 11:30, Fr
Frontier Airlines F9 128 Morning flight
Departure 11.07.21 06:29, Su
Direct Trip 4 days
Return 15.07.21 11:30, Th
American Airlines AA 395 Day flight
Departure 02.09.21 13:30, Th
1 Stopover Trip 5 days
Return 07.09.21 13:30, Tu
Frontier Airlines F9 128 Morning flight
Departure 13.07.21 06:29, Tu
Direct Trip 4 days
Return 17.07.21 11:30, Sa
Spirit Airlines NK 425 Evening flight
Departure 08.07.21 23:30, Th
1 Stopover Trip 9 days
Return 17.07.21 11:30, Sa
Spirit Airlines NK 425 Evening flight
Departure 03.07.21 23:21, Sa
1 Stopover Trip 3 days
Return 06.07.21 22:03, Tu
Frontier Airlines F9 128 Morning flight
Departure 18.07.21 06:29, Su
Direct Trip 9 days
Return 27.07.21 11:30, Tu
United Airlines UA 2288 Day flight
Departure 04.08.21 12:40, We
1 Stopover Trip 4 days
Return 08.08.21 16:30, Su
United Airlines UA 2161 Evening flight
Departure 07.10.21 21:05, Th
1 Stopover Trip 2 days
Return 10.10.21 06:55, Su
Spirit Airlines NK 425 Evening flight
Departure 16.07.21 23:30, Fr
1 Stopover Trip 4 days
Return 20.07.21 11:30, Tu
Spirit Airlines NK 425 Evening flight
Departure 24.07.21 23:30, Sa
1 Stopover Trip 8 days
Return 01.08.21 11:30, Su
United Airlines UA 2288 Day flight
Departure 29.07.21 12:45, Th
1 Stopover Trip 3 days
Return 01.08.21 13:30, Su
Spirit Airlines NK 425 Evening flight
Departure 17.07.21 23:30, Sa
1 Stopover Trip 8 days
Return 25.07.21 17:31, Su
Spirit Airlines NK 425 Evening flight
Departure 24.06.21 23:21, Th
1 Stopover Trip 5 days
Return 29.06.21 21:27, Tu
Frontier Airlines F9 128 Morning flight
Departure 05.07.21 06:29, Mo
1 Stopover Trip 7 hours
Return 05.07.21 13:41, Mo
Frontier Airlines F9 128 Morning flight
Departure 20.06.21 06:29, Su
1 Stopover Trip 6 days
Return 25.06.21 19:19, Fr
United Airlines UA 2161 Evening flight
Departure 05.11.21 21:05, Fr
1 Stopover Trip 2 days
Return 07.11.21 11:14, Su
American Airlines AA 595 Evening flight
Departure 19.06.21 22:09, Sa
Direct Trip 3 days
Return 22.06.21 10:30, Tu
United Airlines UA 2288 Day flight
Departure 07.07.21 12:45, We
1 Stopover Trip 4 days
Return 11.07.21 21:16, Su
Frontier Airlines F9 1447 Evening flight
Departure 01.07.21 22:20, Th
1 Stopover Trip 11 days
Return 12.07.21 15:45, Mo
Frontier Airlines F9 128 Morning flight
Departure 21.05.22 06:29, Sa
Direct Trip 10 days
Return 31.05.22 11:25, Tu
Frontier Airlines F9 128 Morning flight
Departure 21.06.21 06:29, Mo
Direct Trip 8 days
Return 29.06.21 11:25, Tu
United Airlines UA 509 Evening flight
Departure 17.12.21 19:00, Fr
1 Stopover Trip 10 days
Return 27.12.21 17:56, Mo
United Airlines UA 1996 Day flight
Departure 20.11.21 16:50, Sa
1 Stopover Trip 8 days
Return 28.11.21 11:14, Su

*Prices include: baggage, hand luggage, airline fees and charges.

Flight Schedule Chicago to San Juan 2021

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 4 flights every day, from 4hours 44min. Local departure and arrival times are indicated.
06:4512:40
Frontier Airlines F9128 Frontier Airlines F9128
ORD → SJU
Mo Tu We Th Fr Sa Su
Check price
07:5313:37
United Airlines UA1996 United Airlines UA1996
ORD → SJU
Mo Tu We Th Fr Sa Su
Check price
08:3014:25
American Airlines AA395 American Airlines AA395
ORD → SJU
Mo Tu We Th Fr Sa Su
Check price
15:3021:25
American Airlines AA396 American Airlines AA396
ORD → SJU
- - - - - Sa -
Check price
22:5604:40
United Airlines UA1806 United Airlines UA1806
ORD → SJU
Mo Tu We Th Fr Sa Su
Check price

*Schedule is indicated only for direct scheduled flights and lowcost airlines.

Flight information

It takes 04:56 minutes to fly from Chicago to San Juan excluding transfers. The distance between the cities is 3299 km or 2049 miles. The earliest morning plane from Chicago leaves for San Juan at 00:30. And the latest evening flight departs at 23:30.

time

Non-stop flight time

04:56 min

distance

Distance

2049 mi

The earliest flight

The earliest flight

00:30

The latest flight

The latest flight

23:30

Airplane

The fastest flight

04:38

The fastest Chicago - San Juan flight ticket is provided by American Airlines, the flight number is AA 1174. It is in the air for 04:38 mins, departing from O'Hare at 23:30 and arriving at 04:08 in Luis Munoz Marin. This flight is carried out on a modern Boeing 737-800 airliner.

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

Airfare from airports. In Chicago, 2 airports serve all air communications with San Juan. Airplanes arrive at 1 airport in San Juan.

Chicago airports:

Chicago Midway  ~ 14 km* from £59O'Hare  ~ 25 km* from £44

San Juan airports:

Luis Munoz Marin  ~ 12 km* from £44

*Distance from the airport to the city center

Airplanes

4 aircraft models from 4 airlines fly on the Chicago - San Juan route. The fastest airliner is the Boeing 737-800, from the company American Airlines.

  • Airbus A320
  • Boeing 737-700
  • Boeing 737-800
  • Boeing 737-900

Connecting cities

The list of cities on transfer flights from Chicago to San Juan. 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 Tripsta.co.uk 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 £65
01 December 2021
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 £129
05 July 2021

All flights from Chicago

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 £41
08 September 2021
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 £101
13 January 2022
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 £41
07 October 2021
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 £65
01 December 2021
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 £137
12 July 2021

All flights to San Juan

Frequently asked question

How much does a plane ticket from Chicago to San Juan cost?

The cost of the cheapest one-way flight from Chicago to San Juan starts from £65. The departure date of that flight is 01 December 2021.

Round trip costs start from £115, with the departure date there being on 08 September 2021 year, and back on 15 September 2021 year.

Which airlines fly on the Chicago - San Juan route?

There are 4 airlines flying directly from Chicago to San Juan: Southwest Airlines, JetBlue Airways, United Airlines, American Airlines

And 6 airlines fly with transfers: Delta Air Lines, United Airlines, Southwest Airlines, American Airlines, Spirit Airlines, JetBlue Airways

How long does it take to fly from Chicago to San Juan?

The flight time from Chicago to San Juan averages 04:56 mins.

Which planes fly to San Juan from Chicago?

4 aircraft models fly from Chicago to San Juan, overcoming 2049 miles in an average of 04:56 mins. The fastest aircraft on this route is Boeing 737-800 from American Airlines, it flies for 04:38 min.

  • Airbus A320
  • Boeing 737-700
  • Boeing 737-800
  • Boeing 737-900

Tips for buying a ticket

Chicago – San Juan – Chicago round-trip route are always cheaper than tickets purchased there and back separately.

Cheap flights from Chicago to San Juan
San Juan

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