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 $63. 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.

Mo
Tu
We
Th
Fr
Sa
Sun
 
 
 
 
 
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
 
 
 
 
 

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 $ 63 – the departure date for this flight is 11 January 2022.

Sort by: Departure dateCheap flightsFast flightsDirect flights
09.12.2021 Thursday
from $ 68 SmartFares
Economy Found 2021-11-21
1 Stopover 17 hours 18 min
Find Flights
12.12.2021 Sunday
from $ 71 Gotogate
Economy Found today
1 Stopover 17 hours 18 min
Find Flights
06.12.2021 Monday
from $ 91 Gotogate
Economy Found today
1 Stopover 17 hours 18 min
Find Flights
12.12.2021 Sunday
from $ 105 SmartFares
Economy Found today
2 Stopovers 29 hours 21 min
Find Flights
09.12.2021 Thursday
from $ 119 SmartFares
Economy Found 2021-11-21
2 Stopovers 32 hours 13 min
Find Flights
06.12.2021 Monday
from $ 120 SmartFares
Economy Found today
2 Stopovers 33 hours 4 min
Find Flights
15.12.2021 Wednesday
from $ 124 SmartFares
Economy Found yesterday
1 Stopover 13 hours 6 min
Find Flights
15.12.2021 Wednesday
from $ 149 Kiwi.com
Economy Found yesterday
2 Stopovers 10 hours 36 min
Find Flights
06.12.2021 Monday
from $ 149 SmartFares
Economy Found today
3 Stopovers 35 hours 48 min
Find Flights
09.12.2021 Thursday
from $ 155 SmartFares
Economy Found 2021-11-21
3 Stopovers 19 hours 48 min
Find Flights
06.12.2021 Monday
from $ 175 Trip.com
Economy Found today
Nonstop 4 hours 35 min
Find Flights
28.12.2021 Tuesday
from $ 181 Expedia
Economy Found yesterday
1 Stopover 10 hours 0 min
Find Flights
15.12.2021 Wednesday
from $ 189 Trip.com
Economy Found yesterday
3 Stopovers 19 hours 47 min
Find Flights
24.12.2021 Friday
from $ 198 Kiwi.com
Economy Found 2 days
2 Stopovers 26 hours 22 min
Find Flights
28.12.2021 Tuesday
from $ 210 Kiwi.com
Economy Found yesterday
2 Stopovers 10 hours 39 min
Find Flights
28.12.2021 Tuesday
from $ 213 MyHolidays
Economy Found yesterday
Nonstop 4 hours 40 min
Find Flights
24.12.2021 Friday
from $ 219 Kiwi.com
Economy Found 2 days
1 Stopover 28 hours 55 min
Find Flights
19.12.2021 Sunday
from $ 226 Trip.com
Economy Found 2021-11-21
1 Stopover 11 hours 29 min
Find Flights
27.12.2021 Monday
from $ 231 Wingie
Economy Found 2 days
1 Stopover 18 hours 56 min
Find Flights
15.12.2021 Wednesday
from $ 251 SmartFares
Economy Found yesterday
Nonstop 4 hours 56 min
Find Flights
27.12.2021 Monday
from $ 270 SmartFares
Economy Found 2 days
Nonstop 4 hours 56 min
Find Flights
12.12.2021 Sunday
from $ 279 Kissandfly
Economy Found today
3 Stopovers 51 hours 43 min
Find Flights
12.12.2021 Sunday
from $ 280 Trip.com
Economy Found today
Nonstop 4 hours 40 min
Find Flights
26.12.2021 Sunday
from $ 282 Trip.com
Economy Found 2021-11-23
Nonstop 4 hours 30 min
Find Flights
24.12.2021 Friday
from $ 288 Trip.com
Economy Found 2 days
Nonstop 4 hours 30 min
Find Flights
19.12.2021 Sunday
from $ 290 Kiwi.com
Economy Found 2021-11-21
2 Stopovers 18 hours 3 min
Find Flights
24.12.2021 Friday
from $ 318 Kissandfly
Economy Found 2 days
3 Stopovers 26 hours 4 min
Find Flights
26.12.2021 Sunday
from $ 322 Trip.com
Economy Found 2021-11-23
1 Stopover 10 hours 44 min
Find Flights
26.12.2021 Sunday
from $ 324 Trip.com
Economy Found 2021-11-23
2 Stopovers 16 hours 9 min
Find Flights
27.12.2021 Monday
from $ 327 Wingie
Economy Found 2 days
2 Stopovers 19 hours 56 min
Find Flights
*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 $ 141. In the low season in February, March, April, air tickets become cheaper and the average price will be from $ 40 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 $ 137, the flight dates are: there on 14 January 2022 year and back on 20 January 2022 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
Frontier Airlines F9 1155 Day flight
Departure 03.02.22 12:34, Th
1 Stopover Trip 7 days
Return 10.02.22 22:15, Th
Frontier Airlines F9 1155 Day flight
Departure 09.03.22 12:24, We
1 Stopover Trip 8 days
Return 17.03.22 21:35, Th
Frontier Airlines F9 128 Night flight
Departure 09.03.22 02:00, We
1 Stopover Trip 4 days
Return 12.03.22 17:30, Sa
Frontier Airlines F9 1155 Day flight
Departure 02.03.22 12:24, We
1 Stopover Trip 5 days
Return 07.03.22 07:29, Mo
Frontier Airlines F9 1423 Evening flight
Departure 10.03.22 18:16, Th
1 Stopover Trip 7 days
Return 17.03.22 21:35, Th
Frontier Airlines F9 1423 Day flight
Departure 27.01.22 12:30, Th
1 Stopover Trip 4 days
Return 31.01.22 07:29, Mo
Frontier Airlines F9 1425 Night flight
Departure 27.02.22 01:21, Su
1 Stopover Trip 3 days
Return 02.03.22 07:29, We
Frontier Airlines F9 1155 Day flight
Departure 28.01.22 12:24, Fr
1 Stopover Trip 4 days
Return 01.02.22 21:26, Tu
Spirit Airlines NK 3165 Day flight
Departure 01.02.22 12:30, Tu
1 Stopover Trip 7 days
Return 08.02.22 21:26, Tu
Spirit Airlines NK 3165 Day flight
Departure 02.02.22 12:30, We
1 Stopover Trip 7 days
Return 09.02.22 21:26, We
Spirit Airlines NK 3165 Day flight
Departure 07.02.22 12:15, Mo
1 Stopover Trip 5 days
Return 12.02.22 21:26, Sa
Spirit Airlines NK 3165 Day flight
Departure 05.02.22 12:15, Sa
1 Stopover Trip 7 days
Return 12.02.22 21:26, Sa
Spirit Airlines NK 3165 Day flight
Departure 11.02.22 12:15, Fr
1 Stopover Trip 3 days
Return 14.02.22 21:26, Mo
Spirit Airlines NK 3165 Day flight
Departure 06.02.22 12:15, Su
1 Stopover Trip 5 days
Return 11.02.22 21:26, Fr
Frontier Airlines F9 1575 Evening flight
Departure 18.05.22 23:15, We
1 Stopover Trip 7 days
Return 25.05.22 14:54, We
Frontier Airlines F9 128 Night flight
Departure 04.03.22 02:00, Fr
1 Stopover Trip 3 days
Return 07.03.22 07:29, Mo
Spirit Airlines NK 3165 Day flight
Departure 20.01.22 12:15, Th
1 Stopover Trip 10 days
Return 30.01.22 22:14, Su
Spirit Airlines NK 2 Day flight
Departure 04.02.22 11:15, Fr
1 Stopover Trip 7 days
Return 11.02.22 21:26, Fr
Frontier Airlines F9 1155 Day flight
Departure 22.01.22 12:24, Sa
1 Stopover Trip 7 days
Return 29.01.22 21:26, Sa
Frontier Airlines F9 1423 Evening flight
Departure 27.02.22 23:30, Su
1 Stopover Trip 2 days
Return 02.03.22 07:29, We
Frontier Airlines F9 1155 Day flight
Departure 15.02.22 12:34, Tu
1 Stopover Trip 5 days
Return 20.02.22 07:47, Su
Frontier Airlines F9 1155 Day flight
Departure 11.01.22 12:34, Tu
1 Stopover Trip 5 days
Return 16.01.22 22:15, Su
Spirit Airlines NK 3165 Day flight
Departure 04.12.21 12:00, Sa
2 Stopovers Trip 6 days
Return 10.12.21 23:54, Fr
Spirit Airlines NK 3165 Day flight
Departure 09.12.21 12:00, Th
1 Stopover Trip 3 days
Return 12.12.21 07:45, Su
Frontier Airlines F9 128 Morning flight
Departure 12.03.22 05:14, Sa
Direct Trip 6 days
Return 18.03.22 10:55, Fr
Frontier Airlines F9 1425 Night flight
Departure 09.01.22 01:21, Su
1 Stopover Trip 2 days
Return 11.01.22 11:00, Tu
Spirit Airlines NK 3165 Day flight
Departure 12.01.22 12:30, We
2 Stopovers Trip 12 days
Return 24.01.22 01:27, Mo
Spirit Airlines NK 3165 Day flight
Departure 20.02.22 12:30, Su
1 Stopover Trip 4 days
Return 24.02.22 22:15, Th
American Airlines AA 396 Evening flight
Departure 14.01.22 23:55, Fr
1 Stopover Trip 3 days
Return 18.01.22 11:00, Tu
Spirit Airlines NK 3165 Day flight
Departure 06.12.21 12:00, Mo
1 Stopover Trip 5 days
Return 11.12.21 22:27, Sa
Frontier Airlines F9 1155 Day flight
Departure 23.03.22 11:00, We
1 Stopover Trip 5 days
Return 28.03.22 21:18, Mo
Frontier Airlines F9 1155 Day flight
Departure 13.01.22 12:34, Th
1 Stopover Trip 11 days
Return 24.01.22 02:40, Mo
Spirit Airlines NK 3165 Day flight
Departure 08.12.21 12:00, We
1 Stopover Trip 7 days
Return 15.12.21 14:20, We
Spirit Airlines NK 425 Evening flight
Departure 02.12.21 23:43, Th
2 Stopovers Trip 2 days
Return 04.12.21 22:27, Sa
Frontier Airlines F9 1423 Evening flight
Departure 27.11.21 18:21, Sa
1 Stopover Trip 9 days
Return 07.12.21 04:59, Tu
Frontier Airlines F9 128 Night flight
Departure 18.02.22 02:00, Fr
Direct Trip 2 days
Return 20.02.22 07:47, Su
Frontier Airlines F9 1155 Day flight
Departure 22.03.22 11:12, Tu
1 Stopover Trip 5 days
Return 27.03.22 16:30, Su
Frontier Airlines F9 1155 Day flight
Departure 26.11.21 12:12, Fr
1 Stopover Trip 7 days
Return 03.12.21 07:24, Fr
Spirit Airlines NK 3165 Day flight
Departure 30.11.21 12:15, Tu
1 Stopover Trip 8 days
Return 08.12.21 22:27, We
Spirit Airlines NK 3165 Day flight
Departure 31.12.21 13:22, Fr
2 Stopovers Trip 7 days
Return 07.01.22 22:14, Fr
United Airlines UA 640 Evening flight
Departure 14.12.21 20:45, Tu
1 Stopover Trip 23 days
Return 07.01.22 04:59, Fr
Frontier Airlines F9 1155 Day flight
Departure 25.02.22 12:24, Fr
1 Stopover Trip 4 days
Return 01.03.22 21:08, Tu
Spirit Airlines NK 927 Evening flight
Departure 10.12.21 23:21, Fr
1 Stopover Trip 1 day
Return 12.12.21 07:45, Su
Spirit Airlines NK 3165 Day flight
Departure 07.12.21 12:00, Tu
1 Stopover Trip 29 days
Return 05.01.22 22:14, We
Frontier Airlines F9 1423 Evening flight
Departure 27.03.22 17:16, Su
1 Stopover Trip 7 days
Return 03.04.22 16:26, Su
Frontier Airlines F9 1423 Evening flight
Departure 24.03.22 17:16, Th
1 Stopover Trip 3 days
Return 27.03.22 16:30, Su
Frontier Airlines F9 1155 Day flight
Departure 01.04.22 11:25, Fr
1 Stopover Trip 3 days
Return 04.04.22 16:30, Mo
Frontier Airlines F9 1575 Evening flight
Departure 01.06.22 23:15, We
1 Stopover Trip 1 day
Return 02.06.22 19:47, Th
Frontier Airlines F9 1155 Day flight
Departure 25.11.21 12:12, Th
1 Stopover Trip 5 days
Return 30.11.21 12:43, Tu
Frontier Airlines F9 1155 Day flight
Departure 28.11.21 12:12, Su
1 Stopover Trip 8 days
Return 06.12.21 22:27, Mo
Frontier Airlines F9 128 Night flight
Departure 31.12.21 04:55, Fr
1 Stopover Trip 6 days
Return 05.01.22 22:14, We
Spirit Airlines NK 425 Evening flight
Departure 21.12.21 23:43, Tu
1 Stopover Trip 3 days
Return 24.12.21 11:55, Fr
American Airlines AA 2576 Evening flight
Departure 16.12.21 23:20, Th
1 Stopover Trip 5 days
Return 21.12.21 11:55, Tu
Spirit Airlines NK 1190 Day flight
Departure 15.12.21 15:00, We
1 Stopover Trip 13 days
Return 28.12.21 11:55, Tu
Frontier Airlines F9 128 Morning flight
Departure 30.12.21 05:14, Th
1 Stopover Trip 11 days
Return 09.01.22 22:14, Su
American Airlines AA 649 Evening flight
Departure 26.05.22 21:50, Th
1 Stopover Trip 3 days
Return 29.05.22 16:00, Su
United Airlines UA 616 Evening flight
Departure 10.06.22 19:00, Fr
1 Stopover Trip 3 days
Return 13.06.22 15:10, Mo
United Airlines UA 1216 Day flight
Departure 24.12.21 12:00, Fr
1 Stopover Trip 15 days
Return 08.01.22 22:15, Sa
Frontier Airlines F9 128 Night flight
Departure 03.01.22 04:56, Mo
1 Stopover Trip 7 days
Return 09.01.22 22:15, Su
Spirit Airlines NK 815 Day flight
Departure 17.12.21 12:05, Fr
2 Stopovers Trip 7 days
Return 24.12.21 17:00, Fr
United Airlines UA 695 Night flight
Departure 19.12.21 03:50, Su
Direct Trip 7 days
Return 26.12.21 11:55, Su
United Airlines UA 1216 Day flight
Departure 22.12.21 12:00, We
1 Stopover Trip 14 days
Return 05.01.22 12:00, We
United Airlines UA 4475 Day flight
Departure 23.12.21 14:50, Th
1 Stopover Trip 4 days
Return 27.12.21 10:30, Mo
United Airlines UA 4475 Day flight
Departure 20.12.21 14:50, Mo
1 Stopover Trip 12 days
Return 01.01.22 12:40, Sa
United Airlines UA 695 Night flight
Departure 27.12.21 03:50, Mo
Direct Trip 8 days
Return 04.01.22 12:40, Tu
United Airlines UA 2200 Day flight
Departure 19.12.21 16:50, Su
2 Stopovers Trip 14 days
Return 02.01.22 10:30, Su
United Airlines UA 2669 Evening flight
Departure 28.12.21 21:35, Tu
1 Stopover Trip 5 days
Return 02.01.22 10:30, Su
Frontier Airlines F9 128 Morning flight
Departure 28.12.21 05:14, Tu
1 Stopover Trip 7 days
Return 03.01.22 22:18, 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 2 flights every day, from 4hours 45min. Local departure and arrival times are indicated.
07:1014:35
Southwest Airlines WN3698 Southwest Airlines WN3698
MDW → SJU
- - - - - - Su
Check price
08:1013:55
Southwest Airlines WN4674 Southwest Airlines WN4674
MDW → SJU
- - - - - Sa -
Check price
08:3014:18
American Airlines AA2277 American Airlines AA2277
ORD → SJU
Mo - - - - - -
Check price
10:3016:17
American Airlines AA2277 American Airlines AA2277
ORD → SJU
- Tu We Th Fr Sa Su
Check price
13:3023:50
Southwest Airlines WN2948 Southwest Airlines WN2948
MDW → SJU
- - - - - Sa -
Check price
14:2020:10
United Airlines UA1996 United Airlines UA1996
ORD → SJU
Mo Tu We Th Fr Sa Su
Check price
15:3523:00
Southwest Airlines WN380 Southwest Airlines WN380
MDW → SJU
- - - - - - Su
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 $ 63
11 January 2022
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
03 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 $ 92
06 December 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
03 December 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 $ 44
07 December 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 $ 158
22 May 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 $ 42
18 January 2022
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 $ 63
11 January 2022
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 $ 159
03 December 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.

Copyright © 2018-2020. All rights reserved. HolidayPrice.com is part of HolidayPrice Inc., the European leader in online tourism and related services. Terms of use. Privacy policy. Cookie Policy.