Airfare Deals San Juan to Chicago

On HolidayPrice.com you will find 4 direct and 6 connecting flights from San Juan to Chicago 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 SJU - CHI flight schedule to find best flight time, convenient departure and arrival airports.

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The cost of airline tickets from San Juan to Chicago (United States) 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 Chicago.

One way flight from San Juan to Chicago

Below are the prices of tickets for direct one-way flights from San Juan to Chicago. The cheapest flight from San Juan to Chicago starts from $ 65 – the departure date for this flight is 13 January 2022.

Sort by: Departure dateCheap flightsFast flightsDirect flights
19.12.2021 Sunday
from $ 77 SmartFares
Economy Found 2021-11-20
Nonstop 5 hours 28 min
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20.12.2021 Monday
from $ 81 Trip.com
Economy Found 2021-11-20
Nonstop 5 hours 28 min
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13.12.2021 Monday
from $ 86 Gotogate
Economy Found 2021-11-23
1 Stopover 7 hours 14 min
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08.12.2021 Wednesday
from $ 88 SmartFares
Economy Found 2021-11-23
1 Stopover 8 hours 3 min
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24.12.2021 Friday
from $ 94 SmartFares
Economy Found yesterday
Nonstop 5 hours 28 min
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12.12.2021 Sunday
from $ 104 SmartFares
Economy Found today
1 Stopover 12 hours 10 min
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20.12.2021 Monday
from $ 105 Kiwi.com
Economy Found 2021-11-20
1 Stopover 17 hours 45 min
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13.12.2021 Monday
from $ 106 SmartFares
Economy Found 2021-11-23
2 Stopovers 22 hours 50 min
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08.12.2021 Wednesday
from $ 108 SmartFares
Economy Found 2021-11-23
2 Stopovers 24 hours 17 min
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12.12.2021 Sunday
from $ 118 SmartFares
Economy Found today
2 Stopovers 22 hours 38 min
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08.12.2021 Wednesday
from $ 128 SmartFares
Economy Found 2021-11-23
3 Stopovers 24 hours 3 min
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19.12.2021 Sunday
from $ 145 SmartFares
Economy Found 2021-11-20
2 Stopovers 22 hours 11 min
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19.12.2021 Sunday
from $ 146 Gotogate
Economy Found 2021-11-20
1 Stopover 7 hours 46 min
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08.12.2021 Wednesday
from $ 158 Wingie
Economy Found 2021-11-23
Nonstop 5 hours 21 min
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20.12.2021 Monday
from $ 159 Aviakassa
Economy Found 2021-11-20
2 Stopovers 28 hours 55 min
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24.12.2021 Friday
from $ 160 SmartFares
Economy Found yesterday
2 Stopovers 34 hours 9 min
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12.12.2021 Sunday
from $ 165 FlightNetwork
Economy Found today
3 Stopovers 29 hours 59 min
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24.12.2021 Friday
from $ 174 Wingie
Economy Found yesterday
1 Stopover 17 hours 45 min
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13.12.2021 Monday
from $ 175 SmartFares
Economy Found 2021-11-23
3 Stopovers 17 hours 55 min
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24.12.2021 Friday
from $ 179 SmartFares
Economy Found yesterday
3 Stopovers 27 hours 4 min
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20.12.2021 Monday
from $ 182 Mytrip.com
Economy Found 2021-11-20
3 Stopovers 24 hours 41 min
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26.12.2021 Sunday
from $ 214 SmartFares
Economy Found 2 days
Nonstop 5 hours 28 min
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13.12.2021 Monday
from $ 223 Trip.com
Economy Found 2021-11-23
Nonstop 5 hours 12 min
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19.12.2021 Sunday
from $ 231 Gotogate
Economy Found 2021-11-20
3 Stopovers 23 hours 18 min
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26.12.2021 Sunday
from $ 246 TrustFares
Economy Found 2 days
1 Stopover 11 hours 48 min
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12.12.2021 Sunday
from $ 280 Trip.com
Economy Found today
Nonstop 5 hours 12 min
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26.12.2021 Sunday
from $ 286 Gotogate
Economy Found 2 days
2 Stopovers 15 hours 25 min
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26.12.2021 Sunday
from $ 360 Gotogate
Economy Found 2 days
3 Stopovers 39 hours 25 min
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*Prices include: baggage, hand luggage, airline fees and charges.

Flights from San Juan to Chicago are most popular in May, June, July. During this period, the average price of fly tickets is from $ 81. In the low season in February, March, April, air tickets become cheaper and the average price will be from $ 48 one way.

Round trip from San Juan to Chicago

You can buy a round-trip ticket from San Juan to Chicago (United States) and back using the table below. The best offer starts from $ 139, the flight dates are: there on 15 January 2022 year and back on 18 January 2022 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
Frontier Airlines F9 111 Evening flight
Departure 15.01.22 22:15, Sa
1 Stopover Trip 3 days
Return 18.01.22 12:34, Tu
Frontier Airlines F9 111 Evening flight
Departure 13.01.22 22:15, Th
1 Stopover Trip 7 days
Return 20.01.22 12:34, Th
Spirit Airlines NK 851 Evening flight
Departure 14.01.22 21:26, Fr
1 Stopover Trip 2 days
Return 16.01.22 12:15, Su
Frontier Airlines F9 129 Day flight
Departure 19.12.21 11:55, Su
1 Stopover Trip 21 day
Return 09.01.22 12:15, Su
Frontier Airlines F9 129 Day flight
Departure 21.12.21 11:55, Tu
Direct Trip 11 days
Return 01.01.22 05:14, Sa
Frontier Airlines F9 119 Morning flight
Departure 18.04.22 06:20, Mo
1 Stopover Trip 7 days
Return 25.04.22 11:12, Mo
United Airlines UA 2022 Day flight
Departure 06.06.22 15:10, Mo
1 Stopover Trip 8 days
Return 14.06.22 12:19, Tu
Frontier Airlines F9 138 Evening flight
Departure 25.12.21 17:54, Sa
2 Stopovers Trip 6 days
Return 31.12.21 13:22, Fr
Frontier Airlines F9 129 Day flight
Departure 25.11.21 11:55, Th
1 Stopover Trip 2 days
Return 27.11.21 14:00, Sa
Spirit Airlines NK 851 Evening flight
Departure 06.05.22 20:26, Fr
1 Stopover Trip 7 days
Return 14.05.22 01:27, Sa
American Airlines AA 1852 Evening flight
Departure 27.05.22 19:47, Fr
1 Stopover Trip 8 days
Return 04.06.22 17:54, Sa
United Airlines UA 2022 Morning flight
Departure 24.12.21 10:30, Fr
1 Stopover Trip 10 days
Return 03.01.22 04:56, Mo
United Airlines UA 2022 Morning flight
Departure 01.01.22 10:30, Sa
1 Stopover Trip 1 day
Return 02.01.22 05:14, Su
United Airlines UA 1644 Day flight
Departure 26.12.21 12:00, Su
1 Stopover Trip 7 days
Return 02.01.22 12:00, Su
*Prices include: baggage, hand luggage, airline fees and charges.

Flight Schedule San Juan to Chicago 2021

The current flight schedule for the route from San Juan to Chicago 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 57min. Local departure and arrival times are indicated.
07:4013:25
Southwest Airlines WN4693 Southwest Airlines WN4693
SJU → MDW
- - - - - - Su
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08:4512:42
United Airlines UA1511 United Airlines UA1511
SJU → ORD
Mo Tu We Th Fr Sa Su
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10:1517:10
Southwest Airlines WN3065 Southwest Airlines WN3065
SJU → MDW
- - - - - Sa -
Check price
10:4016:15
Southwest Airlines WN2035 Southwest Airlines WN2035
SJU → ORD
- - - - - Sa -
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14:0018:05
Southwest Airlines WN2860 Southwest Airlines WN2860
SJU → MDW
- - - - - Sa -
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15:2419:43
American Airlines AA395 American Airlines AA395
SJU → ORD
Mo - We Th Fr - Su
Check price
17:0522:45
Southwest Airlines WN2523 Southwest Airlines WN2523
SJU → MDW
- - - - - Sa -
Check price
17:0721:20
American Airlines AA395 American Airlines AA395
SJU → ORD
- Tu - - - Sa -
Check price

*Schedule is indicated only for direct scheduled flights and low-cost airlines.

Flight Information

Flying to Chicago from San Juan takes 04:56 minutes (excluding transfers). The distance between San Juan and Chicago is 2049 miles (3299 kilometers). Planes depart from San Juan between 00:04 and 22:55. The fastest flight from the company Southwest Airlines with flight number WN 3197. Flies for just 04:50 minutes with departure from Luis Munoz Marin and arrival in Chicago Midway.

time

Average flight time

04:56 min

distance

Distance

2049 mi

The earliest flight

The earliest flight

00:04

The latest flight

The latest flight

22:55

Airplane

The fastest flight

04:50

Airlines

Direct flight

There are 4 airlines that fly directly from San Juan to Chicago. The most popular company carrying out non-stop flights is United Airlines.

*Flight number

Flights with Transfers

Flights with transfers from San Juan to Chicago can be bought from 6 airlines:

  • JetBlue Airways: Orlando, West Palm Beach, New York
  • Frontier Airlines: Philadelphia, New York
  • Southwest Airlines: Orlando, West Palm Beach
  • Delta Air Lines: Atlanta
  • Spirit Airlines: Tampa, Philadelphia
  • American Airlines: West Palm Beach

*Transit cities

Airports

Airports serving the air communication between San Juan and Chicago. You can fly to Chicago from 1 San Juan airports. Planes arrive at 2 airport in Chicago.

San Juan airports:

Luis Munoz Marin  ~ 12 km* from $ 33

Chicago airports:

O'Hare  ~ 25 km* from $ 66Chicago Midway  ~ 14 km* from $ 101

*Distance from the airport to the city center

Aircraft

You can fly from San Juan to Chicago 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 Chicago from San Juan. The best options are to fly through: Orlando, Philadelphia, New York, West Palm Beach, Atlanta, Baltimore, Tampa, Boston.

Cheap airline tickets from San Juan to United States

Here is a list of flights from San Juan to United States 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.

San Juan - New York DL 332 Delta Air Lines Boeing 757-200
00:25 Luis Munoz Marin
in a way 3 hours 35 min Direct
04:00 John F. Kennedy
Flights
from $ 43
04 February 2022
San Juan - Los Angeles UA 668 United Airlines Boeing 737-900
23:45 Luis Munoz Marin
in a way 8 hours 53 min Direct
08:38 Los Angeles
Flights
from $ 121
20 July 2022
San Juan - Miami B6 754 JetBlue Airways Airbus A320
10:46 Luis Munoz Marin
in a way 2 hours 14 min Direct
13:00 Fort Lauderdale Executive Airport
Flights
from $ 47
14 January 2022
San Juan - Chicago WN 3197 Southwest Airlines Boeing 737-800
19:40 Luis Munoz Marin
in a way 4 hours 50 min Direct
00:30 Chicago Midway
Flights
from $ 65
13 January 2022
San Juan - San Francisco WN 5614 Southwest Airlines Boeing 737-800
12:30 Luis Munoz Marin
in a way 9 hours 15 min Direct
21:45 Norman Y. Mineta San Jose
Flights
from $ 155
12 December 2021

All flights from San Juan

Flights from Puerto Rico to Chicago

Here are the cheapest flight bookings from Puerto Rico to Chicago made by users of our website. If you didn’t find your flight destination, use the search bar at the top of the page.

San Juan - Chicago WN 3197 Southwest Airlines Boeing 737-800
19:40 Luis Munoz Marin
in a way 4 hours 50 min Direct
00:30 Chicago Midway
Flights
from $ 65
13 January 2022
Ponce - Chicago B6 668 JetBlue Airways Airbus A320
06:43 Mercedita Airport
in a way 7 hours 42 min 1 Stopover
14:25 Chicago Midway
Flights
Find
03 December 2021
Aguadilla - Chicago UA 1162 United Airlines Boeing 737-900
08:50 Rafael Hernandez Airport
in a way 7 hours 24 min Direct
16:14 O'Hare
Flights
Find
03 December 2021
Mayaguez - Chicago 9K 32 Cape Air Cessna Light Aircraft
15:42 Eugenio M. De Hostos Airport
in a way 9 hours 4 min 1 Stopover
00:46 O'Hare
Flights
Find
03 December 2021

All flights to Chicago

Tips for buying a ticket

San Juan – Chicago – San Juan round-trip route are always cheaper than tickets purchased there and back separately.

Cheap flights from San Juan to Chicago
Chicago city

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