Airfare Deals

On HolidayPrice.com you will find 4 direct and 6 connecting flights from Chicago to San Juan at a price of from $34. 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 $ 34 – the departure date for this flight is 27 July 2020.

27.07.2020 Monday
from $ 34 FlightNetwork
Economy Found 2020-07-10
1 transfer 10 hours 40 min
Find
29.07.2020 Wednesday
from $ 34 FlightNetwork
Economy Found 2020-07-10
1 transfer 10 hours 40 min
Find
16.07.2020 Thursday
from $ 38 Gotogate
Economy Found 2020-07-08
1 transfer 13 hours 40 min
Find
22.07.2020 Wednesday
from $ 43 FlyFar
Economy Found 2020-07-10
1 transfer 10 hours 40 min
Find
23.07.2020 Thursday
from $ 43 FlightNetwork
Economy Found today
1 transfer 8 hours 3 min
Find
14.07.2020 Tuesday
from $ 46 Gotogate
Economy Found 2020-07-08
1 transfer 13 hours 40 min
Find
14.07.2020 Tuesday
from $ 67 Kiwi.com
Economy Found 2020-07-08
2 transfers 26 hours 43 min
Find
29.07.2020 Wednesday
from $ 68 Gotogate
Economy Found 2020-07-10
2 transfers 16 hours 2 min
Find
27.07.2020 Monday
from $ 68 Gotogate
Economy Found 2020-07-10
2 transfers 14 hours 38 min
Find
13.07.2020 Monday
from $ 70 Kiwi.com
Economy Found 2020-07-08
2 transfers 37 hours 26 min
Find
16.07.2020 Thursday
from $ 70 Kiwi.com
Economy Found 2020-07-08
2 transfers 39 hours 6 min
Find
22.07.2020 Wednesday
from $ 77 Gotogate
Economy Found 2020-07-10
2 transfers 16 hours 2 min
Find
23.07.2020 Thursday
from $ 81 Gotogate
Economy Found today
2 transfers 14 hours 50 min
Find
13.07.2020 Monday
from $ 97 Kiwi.com
Economy Found 2020-07-08
1 transfer 28 hours 56 min
Find
16.07.2020 Thursday
from $ 152 SmartFares
Economy Found 2020-07-08
no transfers 4 hours 49 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 $ 124. In the low season in April, May, June, air tickets become cheaper and the average price will be from $ 54 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 $ 72, the flight dates are: there on 14 July 2020 year and back on 21 July 2020 year.

Spirit Airlines NK 929 Evening flight
Departure 14.07.20 20:14, Tu
2 transfers Trip 7 days
Return 21.07.20 23:49, Tu
Spirit Airlines NK 425 Evening flight
Departure 31.07.20 17:10, Fr
2 transfers Trip 1 day
Return 01.08.20 23:49, Sa
Spirit Airlines NK 929 Evening flight
Departure 01.08.20 20:14, Sa
1 transfer Trip 32 days
Return 02.09.20 20:16, We
Spirit Airlines NK 425 Evening flight
Departure 17.07.20 17:10, Fr
1 transfer Trip 3 days
Return 20.07.20 17:28, Mo
Frontier Airlines F9 1157 Day flight
Departure 27.08.20 16:47, Th
1 transfer Trip 4 days
Return 31.08.20 22:36, Mo
Spirit Airlines NK 929 Evening flight
Departure 26.08.20 18:15, We
1 transfer Trip 5 days
Return 31.08.20 22:36, Mo
Spirit Airlines NK 929 Evening flight
Departure 30.07.20 20:14, Th
1 transfer Trip 6 days
Return 05.08.20 09:35, We
Spirit Airlines NK 903 Evening flight
Departure 26.09.20 20:44, Sa
2 transfers Trip 9 days
Return 05.10.20 09:13, Mo
Spirit Airlines NK 929 Evening flight
Departure 13.07.20 20:14, Mo
1 transfer Trip 4 days
Return 17.07.20 09:27, Fr
Frontier Airlines F9 1462 Morning flight
Departure 06.08.20 06:09, Th
2 transfers Trip 6 days
Return 12.08.20 12:40, We
American Airlines AA 1121 Morning flight
Departure 23.10.20 08:40, Fr
1 transfer Trip 8 days
Return 31.10.20 11:39, Sa
American Airlines AA 1121 Morning flight
Departure 16.10.20 08:40, Fr
1 transfer Trip 8 days
Return 24.10.20 09:00, Sa
Frontier Airlines F9 128 Morning flight
Departure 03.07.21 06:45, Sa
Direct Trip 3 days
Return 06.07.21 18:01, Tu
Frontier Airlines F9 128 Morning flight
Departure 02.07.21 06:45, Fr
Direct Trip 3 days
Return 05.07.21 18:01, Mo
United Airlines UA 2058 Evening flight
Departure 29.12.20 18:04, Tu
1 transfer Trip 5 days
Return 03.01.21 23:20, Su
*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 6 flights every day, from 4hours 28min. Local departure and arrival times are indicated.
05:1512:50
Southwest Airlines WN5163 Southwest Airlines WN5163
MDW → SJU
- - - - - Sa -
Check price
07:4913:37
United Airlines UA1996 United Airlines UA1996
ORD → SJU
Mo Tu We Th Fr Sa Su
Check price
07:5913:35
United Airlines UA1996 United Airlines UA1996
ORD → SJU
Mo Tu We Th Fr Sa Su
Check price
08:0015:56
Frontier Airlines F9106 Frontier Airlines F9106
ORD → SJU
Mo Tu We Th Fr Sa Su
Check price
08:3514:19
American Airlines AA395 American Airlines AA395
ORD → SJU
Mo Tu We Th Fr Sa Su
Check price
08:3716:16
Frontier Airlines F9106 Frontier Airlines F9106
ORD → SJU
Mo Tu We Th Fr Sa Su
Check price
09:0014:35
Southwest Airlines WN4305 Southwest Airlines WN4305
MDW → SJU
- - - - - Sa Su
Check price
09:2515:00
Southwest Airlines WN1585 Southwest Airlines WN1585
MDW → SJU
Mo Tu We Th Fr - -
Check price
15:3021:09
American Airlines AA1187 American Airlines AA1187
ORD → SJU
- - - - - Sa -
Check price
18:0123:40
United Airlines UA1841 United Airlines UA1841
ORD → SJU
- - - - - Sa -
Check price
22:4204:10
United Airlines UA1896 United Airlines UA1896
ORD → SJU
- - - - - Sa -
Check price
22:5504:40
United Airlines UA1806 United Airlines UA1806
ORD → SJU
- - - - Fr 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 $ 66

San Juan airports:

Luis Munoz Marin  ~ 12 km* from $ 64

*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 $ 34 27 July 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 20 July 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 20 July 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 20 July 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 $ 38 19 July 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 $ 175 15 January 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
from $ 31 16 July 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 $ 34 27 July 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 $ 157 20 July 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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