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 $65. 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.

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 $ 65 – the departure date for this flight is 11 September 2021.

Sort by: Departure dateCheap flightsFast flightsDirect flights
28.08.2021 Saturday
from $ 171 Trip.com
Economy Found 2 days
1 Stopover 20 hours 52 min
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20.08.2021 Friday
from $ 185 Trip.com
Economy Found 2021-07-21
1 Stopover 16 hours 42 min
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13.08.2021 Friday
from $ 188 JustFly
Economy Found 2021-07-19
1 Stopover 20 hours 26 min
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13.08.2021 Friday
from $ 208 Gotogate
Economy Found 2021-07-21
1 Stopover 23 hours 11 min
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11.08.2021 Wednesday
from $ 212 JustFly
Economy Found 2021-07-20
1 Stopover 17 hours 14 min
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20.08.2021 Friday
from $ 214 Kiwi.com
Economy Found yesterday
1 Stopover 19 hours 51 min
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19.08.2021 Thursday
from $ 214 Kiwi.com
Economy Found yesterday
1 Stopover 16 hours 44 min
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10.08.2021 Tuesday
from $ 225 MyHolidays
Economy Found 2 days
1 Stopover 21 hours 56 min
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31.08.2021 Tuesday
from $ 236 Kiwi.com
Economy Found 2 days
1 Stopover 14 hours 35 min
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19.08.2021 Thursday
from $ 248 JustFly
Economy Found 2021-07-21
1 Stopover 23 hours 55 min
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09.08.2021 Monday
from $ 249 Kiwi.com
Economy Found 2 days
1 Stopover 25 hours 18 min
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06.08.2021 Friday
from $ 253 JustFly
Economy Found 2021-07-18
1 Stopover 19 hours 50 min
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02.08.2021 Monday
from $ 258 Trip.com
Economy Found yesterday
1 Stopover 19 hours 50 min
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10.08.2021 Tuesday
from $ 261 Kissandfly
Economy Found 2021-07-20
2 Stopovers 30 hours 33 min
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04.08.2021 Wednesday
from $ 263 Bravofly
Economy Found 2021-07-19
1 Stopover 21 hours 13 min
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10.08.2021 Tuesday
from $ 267 Thetravelmakers.us
Economy Found 2021-07-19
1 Stopover 19 hours 59 min
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19.08.2021 Thursday
from $ 267 Kiwi.com
Economy Found 2 days
1 Stopover 18 hours 31 min
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09.08.2021 Monday
from $ 276 JustFly
Economy Found 2021-07-18
1 Stopover 43 hours 7 min
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05.08.2021 Thursday
from $ 279 Kissandfly
Economy Found 2 days
2 Stopovers 32 hours 53 min
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07.08.2021 Saturday
from $ 286 SmartFares
Economy Found yesterday
1 Stopover 46 hours 6 min
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02.08.2021 Monday
from $ 289 Kiwi.com
Economy Found 2021-07-21
1 Stopover 19 hours 40 min
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01.08.2021 Sunday
from $ 291 Trip.com
Economy Found 2021-07-21
1 Stopover 16 hours 56 min
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09.08.2021 Monday
from $ 294 Trip.com
Economy Found 2021-07-20
1 Stopover 18 hours 32 min
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05.08.2021 Thursday
from $ 296 Kissandfly
Economy Found 2 days
2 Stopovers 38 hours 39 min
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06.08.2021 Friday
from $ 297 Trip.com
Economy Found 2021-07-21
1 Stopover 18 hours 32 min
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06.08.2021 Friday
from $ 298 Kiwi.com
Economy Found 2 days
1 Stopover 22 hours 5 min
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03.08.2021 Tuesday
from $ 305 Gotogate
Economy Found 2 days
1 Stopover 20 hours 44 min
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02.08.2021 Monday
from $ 315 Lucky2Go
Economy Found 2021-07-21
1 Stopover 25 hours 4 min
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01.08.2021 Sunday
from $ 318 MyHolidays
Economy Found 2021-07-21
Nonstop 10 hours 5 min
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01.08.2021 Sunday
from $ 339 MyHolidays
Economy Found 2021-07-21
Nonstop 10 hours 5 min
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*Prices include: baggage, hand luggage, airline fees and charges.

Flights from Chicago to San Juan are most popular in January, June, December. During this period, the average price of fly tickets is from $ 143. In the low season in February, March, April, air tickets become cheaper and the average price will be from $ 41 one way.

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 $ 149, the flight dates are: there on 22 September 2021 year and back on 25 September 2021 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
Spirit Airlines NK 3 Day flight
Departure 22.09.21 12:45, We
1 Stopover Trip 3 days
Return 25.09.21 19:43, Sa
American Airlines AA 922 Evening flight
Departure 10.09.21 22:05, Fr
1 Stopover Trip 8 days
Return 18.09.21 19:43, Sa
Spirit Airlines NK 3 Day flight
Departure 13.09.21 12:45, Mo
1 Stopover Trip 4 days
Return 17.09.21 13:10, Fr
Spirit Airlines NK 3 Day flight
Departure 28.08.21 12:45, Sa
1 Stopover Trip 7 days
Return 04.09.21 11:30, Sa
Frontier Airlines F9 128 Day flight
Departure 13.02.22 12:45, Su
Direct Trip 3 days
Return 16.02.22 18:40, We
Frontier Airlines F9 128 Morning flight
Departure 20.08.21 06:29, Fr
1 Stopover Trip 4 days
Return 24.08.21 13:30, Tu
Spirit Airlines NK 425 Evening flight
Departure 13.08.21 23:30, Fr
1 Stopover Trip 4 days
Return 17.08.21 11:30, Tu
United Airlines UA 4534 Day flight
Departure 22.01.22 14:55, Sa
1 Stopover Trip 11 days
Return 02.02.22 18:40, We
American Airlines AA 2488 Evening flight
Departure 02.10.21 19:07, Sa
2 Stopovers Trip 7 days
Return 09.10.21 10:49, Sa
Frontier Airlines F9 128 Day flight
Departure 13.10.21 11:45, We
Direct Trip 6 days
Return 19.10.21 17:40, Tu
Frontier Airlines F9 128 Morning flight
Departure 02.09.21 06:29, Th
1 Stopover Trip 12 days
Return 14.09.21 12:53, Tu
Spirit Airlines NK 3 Day flight
Departure 28.09.21 12:45, Tu
1 Stopover Trip 6 days
Return 04.10.21 13:10, Mo
Frontier Airlines F9 128 Day flight
Departure 30.10.21 11:45, Sa
Direct Trip 5 days
Return 04.11.21 17:40, Th
Spirit Airlines NK 3 Day flight
Departure 11.08.21 12:45, We
1 Stopover Trip 6 days
Return 17.08.21 11:30, Tu
Spirit Airlines NK 425 Evening flight
Departure 03.09.21 23:35, Fr
1 Stopover Trip 10 days
Return 13.09.21 19:05, Mo
Spirit Airlines NK 3 Day flight
Departure 19.08.21 12:45, Th
1 Stopover Trip 9 days
Return 28.08.21 22:00, Sa
United Airlines UA 2288 Day flight
Departure 10.08.21 12:40, Tu
1 Stopover Trip 3 days
Return 13.08.21 17:40, Fr
Spirit Airlines NK 425 Evening flight
Departure 01.10.21 23:35, Fr
1 Stopover Trip 8 days
Return 09.10.21 17:40, Sa
United Airlines UA 2675 Day flight
Departure 06.10.21 11:00, We
1 Stopover Trip 4 days
Return 10.10.21 17:40, Su
United Airlines UA 2288 Day flight
Departure 04.09.21 12:40, Sa
1 Stopover Trip 9 days
Return 13.09.21 13:50, Mo
Frontier Airlines F9 128 Day flight
Departure 08.10.21 11:45, Fr
Direct Trip 3 days
Return 11.10.21 17:40, Mo
Spirit Airlines NK 3 Day flight
Departure 31.08.21 12:45, Tu
1 Stopover Trip 6 days
Return 06.09.21 11:30, Mo
American Airlines AA 1058 Day flight
Departure 21.03.22 13:49, Mo
2 Stopovers Trip 5 days
Return 26.03.22 21:09, Sa
American Airlines AA 922 Evening flight
Departure 24.09.21 22:05, Fr
1 Stopover Trip 3 days
Return 27.09.21 19:05, Mo
American Airlines AA 583 Night flight
Departure 04.12.21 04:03, Sa
1 Stopover Trip 3 days
Return 06.12.21 22:09, Mo
Spirit Airlines NK 425 Evening flight
Departure 09.08.21 23:30, Mo
1 Stopover Trip 2 days
Return 11.08.21 16:30, We
Spirit Airlines NK 2 Morning flight
Departure 06.08.21 10:25, Fr
1 Stopover Trip 3 days
Return 09.08.21 21:14, Mo
Spirit Airlines NK 2 Morning flight
Departure 02.08.21 10:25, Mo
1 Stopover Trip 4 days
Return 06.08.21 21:14, Fr
Spirit Airlines NK 425 Evening flight
Departure 04.08.21 23:30, We
1 Stopover Trip 5 days
Return 09.08.21 21:14, Mo
Frontier Airlines F9 128 Morning flight
Departure 06.09.21 06:29, Mo
1 Stopover Trip 7 days
Return 13.09.21 13:50, Mo
Spirit Airlines NK 2 Morning flight
Departure 05.08.21 10:25, Th
2 Stopovers Trip 4 days
Return 09.08.21 17:31, Mo
Spirit Airlines NK 729 Night flight
Departure 08.08.21 00:53, Su
1 Stopover Trip 8 days
Return 16.08.21 02:25, Mo
Frontier Airlines F9 128 Morning flight
Departure 01.08.21 06:29, Su
1 Stopover Trip 7 days
Return 08.08.21 02:38, Su
Spirit Airlines NK 3 Day flight
Departure 03.08.21 12:45, Tu
1 Stopover Trip 2 days
Return 05.08.21 13:30, Th
American Airlines AA 1159 Day flight
Departure 25.07.21 13:30, Su
1 Stopover Trip 7 days
Return 01.08.21 13:45, Su
American Airlines AA 595 Evening flight
Departure 26.07.21 22:09, Mo
Direct Trip 3 days
Return 30.07.21 10:00, Fr
Frontier Airlines F9 1155 Day flight
Departure 30.07.21 11:45, Fr
1 Stopover Trip 4 days
Return 03.08.21 13:30, Tu
American Airlines AA 1179 Night flight
Departure 01.08.21 01:50, Su
1 Stopover Trip 3 days
Return 03.08.21 19:24, Tu
United Airlines UA 2288 Day flight
Departure 28.07.21 12:45, We
1 Stopover Trip 4 days
Return 01.08.21 11:30, Su
Spirit Airlines NK 425 Evening flight
Departure 27.07.21 23:30, Tu
1 Stopover Trip 5 days
Return 01.08.21 16:30, Su
Southwest Airlines WN 2754 Day flight
Departure 20.11.21 13:00, Sa
1 Stopover Trip 4 days
Return 24.11.21 19:17, We
United Airlines UA 695 Evening flight
Departure 22.11.21 20:05, Mo
Direct Trip 7 days
Return 29.11.21 19:35, Mo
Frontier Airlines F9 128 Morning flight
Departure 09.07.22 06:29, Sa
Direct Trip 13 days
Return 22.07.22 11:25, Fr
United Airlines UA 3856 Day flight
Departure 22.12.21 16:50, We
2 Stopovers Trip 6 days
Return 28.12.21 18:33, Tu
American Airlines AA 742 Day flight
Departure 23.12.21 16:25, Th
1 Stopover Trip 11 days
Return 03.01.22 18:13, Mo
*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 3 flights every day, from 4hours 45min. Local departure and arrival times are indicated.
01:2907:24
Frontier Airlines F9128 Frontier Airlines F9128
ORD → SJU
Mo Tu We Th Fr Sa Su
Check price
05:1014:45
Southwest Airlines WN1419 Southwest Airlines WN1419
MDW → SJU
Mo - - Th Fr - -
Check price
07:5015:05
Southwest Airlines WN5472 Southwest Airlines WN5472
MDW → SJU
- - - - - - Su
Check price
08:2517:40
Southwest Airlines WN4649 Southwest Airlines WN4649
MDW → SJU
- - - - - - Su
Check price
08:4514:30
Southwest Airlines WN4682 Southwest Airlines WN4682
MDW → SJU
- Tu We - - - -
Check price
08:4514:30
Southwest Airlines WN3246 Southwest Airlines WN3246
MDW → SJU
- - - - - - Su
Check price
08:4514:30
Southwest Airlines WN2310 Southwest Airlines WN2310
MDW → SJU
Mo - - Th Fr - -
Check price
10:0015:52
American Airlines AA593 American Airlines AA593
ORD → SJU
Mo Tu We Th Fr Sa Su
Check price
14:4522:25
Southwest Airlines WN5385 Southwest Airlines WN5385
ORD → SJU
- - - - - - Su
Check price
17:0923:01
American Airlines AA595 American Airlines AA595
ORD → SJU
Mo Tu - Th - - Su
Check price
17:0923:01
American Airlines AA595 American Airlines AA595
ORD → SJU
- - - - Fr - -
Check price
17:0923:01
American Airlines AA595 American Airlines AA595
ORD → SJU
- - We - - Sa -
Check price

*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.

time

Average 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

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.

*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 $ 67

San 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 $ 65
11 September 2021
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
Find
31 July 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 $ 110
31 July 2021
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
Find
31 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 $ 60
17 August 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 $ 136
28 August 2021
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 $ 82
11 September 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
11 September 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 $ 175
16 August 2021

All flights to San Juan

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 city

To start searching for tickets, Specify dates.

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