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.

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 $ 69 – the departure date for this flight is 02 October 2020.

Sort by: Departure dateCheap flightsFast flightsDirect flights
05.10.2020 Monday
from $ 53 Gotogate
Economy Found 2020-09-20
1 transfer 6 hours 22 min
Find
16.10.2020 Friday
from $ 54 Gotogate
Economy Found 2020-09-16
1 transfer 6 hours 22 min
Find
06.10.2020 Tuesday
from $ 56 Kiwi.com
Economy Found 2020-09-21
1 transfer 10 hours 47 min
Find
29.10.2020 Thursday
from $ 62 JustFly
Economy Found 2020-09-20
1 transfer 27 hours 25 min
Find
05.10.2020 Monday
from $ 63 Kiwi.com
Economy Found 2020-09-20
2 transfers 29 hours 5 min
Find
16.10.2020 Friday
from $ 64 Kiwi.com
Economy Found 2020-09-16
2 transfers 23 hours 27 min
Find
29.10.2020 Thursday
from $ 65 Kiwi.com
Economy Found 2020-09-20
2 transfers 29 hours 8 min
Find
03.10.2020 Saturday
from $ 73 Kiwi.com
Economy Found 2020-09-20
1 transfer 18 hours 34 min
Find
01.10.2020 Thursday
from $ 79 Kiwi.com
Economy Found yesterday
1 transfer 26 hours 31 min
Find
02.10.2020 Friday
from $ 79 Kiwi.com
Economy Found yesterday
1 transfer 14 hours 31 min
Find
18.10.2020 Sunday
from $ 79 Kiwi.com
Economy Found 2 days
1 transfer 27 hours 32 min
Find
02.10.2020 Friday
from $ 85 Kiwi.com
Economy Found yesterday
2 transfers 26 hours 9 min
Find
01.10.2020 Thursday
from $ 85 Kiwi.com
Economy Found yesterday
2 transfers 27 hours 41 min
Find
18.10.2020 Sunday
from $ 88 Kiwi.com
Economy Found 2 days
2 transfers 25 hours 10 min
Find
03.10.2020 Saturday
from $ 90 Kiwi.com
Economy Found 2020-09-20
2 transfers 22 hours 23 min
Find
06.10.2020 Tuesday
from $ 100 Gotogate
Economy Found 2020-09-21
2 transfers 12 hours 58 min
Find
29.10.2020 Thursday
from $ 138 Lucky2Go
Economy Found 2020-09-20
no transfers 4 hours 45 min
Find
16.10.2020 Friday
from $ 156 MyHolidays
Economy Found 2020-09-16
no transfers 4 hours 45 min
Find
18.10.2020 Sunday
from $ 170 MyHolidays
Economy Found 2 days
no transfers 4 hours 45 min
Find
06.10.2020 Tuesday
from $ 201 Lucky2Go
Economy Found 2020-09-21
no transfers 4 hours 52 min
Find
03.10.2020 Saturday
from $ 207 Trip.com
Economy Found 2020-09-20
no transfers 4 hours 52 min
Find
05.10.2020 Monday
from $ 207 Trip.com
Economy Found 2020-09-20
no transfers 4 hours 52 min
Find
01.10.2020 Thursday
from $ 224 Lucky2Go
Economy Found yesterday
no transfers 4 hours 52 min
Find
02.10.2020 Friday
from $ 224 Lucky2Go
Economy Found yesterday
no transfers 4 hours 52 min
Find
*Prices include: baggage, hand luggage, airline fees and charges.

Flights from Chicago to San Juan are most popular in September, October, November. During this period, the average price of fly tickets is from $ 112. In the low season in April, May, June, air tickets become cheaper and the average price will be from $ 48 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 $ 99, the flight dates are: there on 05 November 2020 year and back on 09 November 2020 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
Spirit Airlines NK 929 Day flight
Departure 05.11.20 14:29, Th
1 transfer Trip 4 days
Return 09.11.20 20:54, Mo
Spirit Airlines NK 929 Day flight
Departure 10.11.20 14:29, Tu
1 transfer Trip 7 days
Return 17.11.20 20:54, Tu
Spirit Airlines NK 929 Day flight
Departure 07.11.20 14:29, Sa
1 transfer Trip 10 days
Return 17.11.20 20:54, Tu
Spirit Airlines NK 929 Day flight
Departure 12.11.20 14:29, Th
1 transfer Trip 5 days
Return 17.11.20 20:54, Tu
Spirit Airlines NK 903 Evening flight
Departure 06.11.20 20:44, Fr
2 transfers Trip 6 days
Return 12.11.20 20:49, Th
Frontier Airlines F9 1423 Morning flight
Departure 09.12.20 06:30, We
1 transfer Trip 8 days
Return 17.12.20 15:30, Th
JetBlue Airways B6 563 Morning flight
Departure 19.11.20 05:55, Th
1 transfer Trip 4 days
Return 22.11.20 23:34, Su
American Airlines AA 367 Morning flight
Departure 01.10.20 08:30, Th
1 transfer Trip 12 days
Return 13.10.20 17:31, Tu
Spirit Airlines NK 929 Morning flight
Departure 02.11.20 07:20, Mo
1 transfer Trip 25 days
Return 27.11.20 16:55, Fr
American Airlines AA 1033 Morning flight
Departure 31.12.20 06:30, Th
2 transfers Trip 6 days
Return 06.01.21 08:56, We
American Airlines AA 357 Evening flight
Departure 02.10.20 20:30, Fr
1 transfer Trip 3 days
Return 05.10.20 10:20, Mo
American Airlines AA 2501 Evening flight
Departure 26.09.20 17:00, Sa
2 transfers Trip 9 days
Return 05.10.20 11:00, Mo
American Airlines AA 1386 Morning flight
Departure 27.02.21 06:30, Sa
1 transfer Trip 8 days
Return 07.03.21 10:29, Su
United Airlines UA 1996 Morning flight
Departure 25.12.20 07:59, Fr
1 transfer Trip 6 days
Return 31.12.20 10:42, Th
American Airlines AA 1452 Morning flight
Departure 23.12.20 07:00, We
1 transfer Trip 5 days
Return 27.12.20 23:28, Su
American Airlines AA 2425 Day flight
Departure 22.12.20 11:45, Tu
1 transfer Trip 13 days
Return 04.01.21 23:20, Mo
*Prices include: baggage, hand luggage, airline fees and charges.

Flight Schedule Chicago to San Juan 2020

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 5 flights every day, from 4hours 40min. Local departure and arrival times are indicated.
05:5013:35
Southwest Airlines WN5793 Southwest Airlines WN5793
MDW → SJU
Mo Tu We Th Fr - -
Check price
06:4512:40
Frontier Airlines F9128 Frontier Airlines F9128
ORD → SJU
Mo Tu We Th Fr Sa Su
Check price
07:0015:45
Southwest Airlines WN3366 Southwest Airlines WN3366
MDW → SJU
- - - - - - Su
Check price
07:4913:37
United Airlines UA1996 United Airlines UA1996
ORD → SJU
Mo Tu We Th Fr Sa Su
Check price
08:5514:35
Southwest Airlines WN444 Southwest Airlines WN444
MDW → SJU
Mo Tu We Th Fr - -
Check price
09:0017:55
Southwest Airlines WN3477 Southwest Airlines WN3477
MDW → SJU
- - - - - - Su
Check price
09:0014:45
Southwest Airlines WN3479 Southwest Airlines WN3479
MDW → SJU
- - - - - Sa -
Check price
09:0014:45
Southwest Airlines WN2891 Southwest Airlines WN2891
MDW → SJU
- - - - - - Su
Check price
09:5517:25
Southwest Airlines WN3167 Southwest Airlines WN3167
MDW → SJU
- - - - - - Su
Check price
12:5523:35
Southwest Airlines WN4129 Southwest Airlines WN4129
MDW → SJU
- - - - - - Su
Check price
13:1023:05
Southwest Airlines WN2819 Southwest Airlines WN2819
MDW → SJU
- - - - - Sa -
Check price
13:2501:20
Southwest Airlines WN2920 Southwest Airlines WN2920
MDW → SJU
- - - - - - Su
Check price
Show all

*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
from $ 69 02 October 2020
Chicago - Ponce NK 929 Spirit Airlines Airbus A320
22:20 O'Hare
in a way 7 hours 13 min 1 transfer
05:33 Mercedita Airport
Find 03 October 2020
Chicago - Aguadilla WN 3023 Southwest Airlines Boeing 737-800
22:40 Chicago Midway
in a way 6 hours 58 min 1 transfer
05:38 Rafael Hernandez Airport
Find 03 October 2020
Chicago - Mayaguez AA 395 American Airlines Boeing 737-800
14:40 O'Hare
in a way 8 hours 15 min 1 transfer
22:55 Eugenio M. De Hostos Airport
Find 03 October 2020

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
from $ 25 10 November 2020
Los Angeles - San Juan UA 2410 United Airlines Boeing 737-900
06:45 Los Angeles
in a way 8 hours 45 min 1 transfer
15:30 Luis Munoz Marin
from $ 91 08 October 2020
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
from $ 34 04 October 2020
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
from $ 69 02 October 2020
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
from $ 113 04 December 2020

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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