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 $62. 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 $ 62 – the departure date for this flight is 02 June 2021.

Sort by: Departure dateCheap flightsFast flightsDirect flights
18.05.2021 Tuesday
from $ 65 Trip.com
Economy Found today
1 Stopover 7 hours 54 min
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23.05.2021 Sunday
from $ 65 MyHolidays
Economy Found 2021-04-25
Nonstop 4 hours 49 min
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23.05.2021 Sunday
from $ 65 MyHolidays
Economy Found 2021-04-25
1 Stopover 8 hours 14 min
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10.05.2021 Monday
from $ 65 MyHolidays
Economy Found 2021-04-26
1 Stopover 11 hours 11 min
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05.05.2021 Wednesday
from $ 66 MyHolidays
Economy Found yesterday
1 Stopover 11 hours 24 min
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18.05.2021 Tuesday
from $ 73 City.Travel
Economy Found today
Nonstop 4 hours 49 min
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06.05.2021 Thursday
from $ 78 Cheapflightsfreak
Economy Found today
Nonstop 4 hours 50 min
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06.05.2021 Thursday
from $ 80 Kiwi.com
Economy Found today
1 Stopover 6 hours 40 min
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18.05.2021 Tuesday
from $ 101 Kiwi.com
Economy Found today
2 Stopovers 16 hours 24 min
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10.05.2021 Monday
from $ 101 MyHolidays
Economy Found 2021-04-26
Nonstop 4 hours 46 min
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16.05.2021 Sunday
from $ 102 MyHolidays
Economy Found 2021-04-24
1 Stopover 8 hours 32 min
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10.05.2021 Monday
from $ 114 Gotogate
Economy Found 2021-04-26
2 Stopovers 19 hours 13 min
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02.05.2021 Sunday
from $ 114 SmartFares
Economy Found yesterday
1 Stopover 6 hours 45 min
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16.05.2021 Sunday
from $ 115 MyHolidays
Economy Found 2021-04-24
Nonstop 4 hours 46 min
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30.05.2021 Sunday
from $ 132 SmartFares
Economy Found 2021-04-26
Nonstop 4 hours 49 min
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05.05.2021 Wednesday
from $ 136 MyHolidays
Economy Found yesterday
Nonstop 4 hours 46 min
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01.05.2021 Saturday
from $ 138 Kiwi.com
Economy Found yesterday
1 Stopover 6 hours 45 min
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30.05.2021 Sunday
from $ 142 Kiwi.com
Economy Found 2021-04-26
2 Stopovers 33 hours 12 min
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05.05.2021 Wednesday
from $ 143 Kiwi.com
Economy Found yesterday
2 Stopovers 18 hours 36 min
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30.05.2021 Sunday
from $ 149 SmartFares
Economy Found 2021-04-26
1 Stopover 6 hours 38 min
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06.05.2021 Thursday
from $ 152 Kiwi.com
Economy Found today
2 Stopovers 30 hours 49 min
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16.05.2021 Sunday
from $ 153 Kiwi.com
Economy Found 2021-04-24
2 Stopovers 41 hours 24 min
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02.05.2021 Sunday
from $ 153 Kiwi.com
Economy Found yesterday
2 Stopovers 28 hours 15 min
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23.05.2021 Sunday
from $ 166 FlyFar
Economy Found 2021-04-25
2 Stopovers 12 hours 45 min
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16.05.2021 Sunday
from $ 173 Kissandfly.com
Economy Found 2021-04-24
3 Stopovers 45 hours 32 min
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18.05.2021 Tuesday
from $ 180 Tickets.ru
Economy Found today
3 Stopovers 28 hours 9 min
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10.05.2021 Monday
from $ 182 FlightNetwork
Economy Found 2021-04-26
3 Stopovers 29 hours 23 min
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05.05.2021 Wednesday
from $ 196 Kissandfly.com
Economy Found yesterday
3 Stopovers 52 hours 48 min
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23.05.2021 Sunday
from $ 197 FlyFar
Economy Found 2021-04-25
3 Stopovers 28 hours 3 min
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01.05.2021 Saturday
from $ 232 Kiwi.com
Economy Found yesterday
2 Stopovers 45 hours 12 min
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02.05.2021 Sunday
from $ 277 Gotogate
Economy Found yesterday
3 Stopovers 29 hours 16 min
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02.05.2021 Sunday
from $ 279 TrustFares
Economy Found yesterday
Nonstop 4 hours 41 min
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01.05.2021 Saturday
from $ 287 Bravofly
Economy Found yesterday
Nonstop 4 hours 46 min
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01.05.2021 Saturday
from $ 393 SuperSaver
Economy Found yesterday
3 Stopovers 16 hours 4 min
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30.05.2021 Sunday
from $ 441 FlyFar
Economy Found 2021-04-26
3 Stopovers 27 hours 19 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 $ 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 $ 127, the flight dates are: there on 03 May 2021 year and back on 05 May 2021 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
United Airlines UA 3686 Day flight
Departure 05.05.21 14:00, We
1 Stopover Trip 6 days
Return 11.05.21 19:44, Tu
United Airlines UA 467 Day flight
Departure 25.05.21 14:15, Tu
1 Stopover Trip 5 days
Return 30.05.21 03:44, Su
Spirit Airlines NK 3 Day flight
Departure 02.06.21 13:01, We
1 Stopover Trip 4 days
Return 06.06.21 16:49, Su
Spirit Airlines NK 927 Evening flight
Departure 18.05.21 18:30, Tu
1 Stopover Trip 13 days
Return 01.06.21 00:34, Tu
American Airlines AA 337 Day flight
Departure 01.05.21 12:30, Sa
2 Stopovers Trip 9 days
Return 10.05.21 04:58, Mo
United Airlines UA 1996 Day flight
Departure 18.10.21 12:50, Mo
1 Stopover Trip 4 days
Return 22.10.21 02:45, Fr
United Airlines UA 2161 Evening flight
Departure 07.08.21 21:05, Sa
1 Stopover Trip 6 days
Return 13.08.21 23:46, Fr
Spirit Airlines NK 425 Evening flight
Departure 03.06.21 23:30, Th
1 Stopover Trip 3 days
Return 06.06.21 16:49, Su
Spirit Airlines NK 3 Day flight
Departure 10.07.21 12:45, Sa
1 Stopover Trip 5 days
Return 15.07.21 05:10, Th
Spirit Airlines NK 425 Evening flight
Departure 07.05.21 23:35, Fr
1 Stopover Trip 3 days
Return 10.05.21 22:58, Mo
Spirit Airlines NK 425 Evening flight
Departure 30.04.21 23:25, Fr
1 Stopover Trip 3 days
Return 04.05.21 04:57, Tu
United Airlines UA 2161 Evening flight
Departure 28.07.21 21:05, We
1 Stopover Trip 4 days
Return 02.08.21 02:45, Mo
United Airlines UA 1166 Evening flight
Departure 06.07.21 17:45, Tu
1 Stopover Trip 14 days
Return 21.07.21 05:17, We
United Airlines UA 1996 Evening flight
Departure 14.05.21 19:20, Fr
Direct Trip 2 days
Return 16.05.21 17:55, Su
American Airlines AA 357 Night flight
Departure 19.10.21 01:30, Tu
2 Stopovers Trip 3 days
Return 21.10.21 18:42, Th
Spirit Airlines NK 3 Day flight
Departure 09.06.21 12:45, We
1 Stopover Trip 5 days
Return 14.06.21 05:48, Mo
Frontier Airlines F9 128 Day flight
Departure 06.11.21 11:45, Sa
1 Stopover Trip 9 days
Return 15.11.21 17:28, Mo
American Airlines AA 1277 Night flight
Departure 08.05.21 00:35, Sa
2 Stopovers Trip 3 days
Return 11.05.21 00:39, Tu
Spirit Airlines NK 2 Morning flight
Departure 27.05.21 10:15, Th
1 Stopover Trip 3 days
Return 30.05.21 16:49, Su
United Airlines UA 2161 Evening flight
Departure 29.07.21 21:05, Th
1 Stopover Trip 3 days
Return 02.08.21 02:45, Mo
United Airlines UA 695 Night flight
Departure 06.08.21 00:44, Fr
1 Stopover Trip 4 days
Return 10.08.21 02:45, Tu
Spirit Airlines NK 425 Evening flight
Departure 08.07.21 23:25, Th
1 Stopover Trip 5 days
Return 14.07.21 02:27, We
Spirit Airlines NK 425 Evening flight
Departure 01.07.21 23:25, Th
1 Stopover Trip 5 days
Return 07.07.21 05:17, We
United Airlines UA 2288 Day flight
Departure 12.06.21 12:45, Sa
1 Stopover Trip 9 days
Return 21.06.21 23:46, Mo
Spirit Airlines NK 924 Day flight
Departure 02.07.21 16:28, Fr
2 Stopovers Trip 10 days
Return 12.07.21 05:17, Mo
Spirit Airlines NK 2 Morning flight
Departure 12.07.21 10:25, Mo
1 Stopover Trip 7 days
Return 19.07.21 02:27, Mo
American Airlines AA 335 Day flight
Departure 14.06.21 16:55, Mo
2 Stopovers Trip 8 days
Return 22.06.21 12:30, Tu
JetBlue Airways B6 563 Morning flight
Departure 30.06.21 10:40, We
1 Stopover Trip 21 day
Return 21.07.21 04:06, We
Sun Country Airlines SY 262 Evening flight
Departure 28.05.21 23:45, Fr
1 Stopover Trip 5 days
Return 02.06.21 14:31, We
Spirit Airlines NK 630 Morning flight
Departure 15.07.21 10:49, Th
1 Stopover Trip 4 days
Return 19.07.21 02:27, Mo
American Airlines AA 593 Day flight
Departure 05.08.21 15:00, Th
Direct Trip 4 days
Return 10.08.21 00:46, Tu
United Airlines UA 2161 Evening flight
Departure 18.06.21 21:05, Fr
1 Stopover Trip 3 days
Return 21.06.21 22:08, Mo
United Airlines UA 695 Night flight
Departure 13.07.21 00:44, Tu
Direct Trip 6 days
Return 18.07.21 23:42, Su
United Airlines UA 695 Night flight
Departure 19.06.21 00:44, Sa
Direct Trip 3 days
Return 21.06.21 23:42, Mo
United Airlines UA 695 Night flight
Departure 07.07.21 00:44, We
Direct Trip 14 days
Return 20.07.21 15:43, Tu
Frontier Airlines F9 128 Day flight
Departure 25.12.21 12:45, Sa
Direct Trip 7 days
Return 02.01.22 00:01, Su
Frontier Airlines F9 128 Morning flight
Departure 13.04.22 05:59, We
1 Stopover Trip 4 days
Return 17.04.22 04:20, Su
Frontier Airlines F9 1423 Evening flight
Departure 27.12.21 18:09, Mo
1 Stopover Trip 7 days
Return 04.01.22 05:36, Tu
United Airlines UA 1973 Night flight
Departure 28.12.21 03:05, Tu
2 Stopovers Trip 7 days
Return 03.01.22 15:51, 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 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 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 $ 62
02 June 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
07 May 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 $ 89
07 May 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
from $ 124
16 May 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 $ 56
31 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 $ 108
03 June 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 $ 42
11 May 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 $ 62
02 June 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 $ 126
07 May 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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