Cheap Flights from San Juan to Chicago, IL from $109

Return flight: Chicago – San Juan
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On Cheapflightsplus.com you will find 6 direct and 397 connecting flights from San Juan to Chicago. You can compare airfare deals from 7 airlines and multiple travel sites from $109, 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.

Find One-Way and Round-Trip San Juan to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $109 (one-way), $187 (round-trip).
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Best Flights from San Juan to Chicago Today

Take a look at the list of non stop flights and flights with layovers from San Juan to Chicago with the lowest price of $109. The fastest direct flight takes 4h 59m and the fastest connecting – 6h 51m.
Price Departure Arrival Flight Duration Airline Flight
from $113
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16:46
San Juan
Luis Munoz Marin Intl
 20:50
Chicago
O'Hare International
 5h 4m Spirit Airlines
NK1531
from $132
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06:00
San Juan
Luis Munoz Marin Intl
 10:16
Chicago
O'Hare International
 5h 16m Spirit Airlines
NK1632
from $166
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20:59
San Juan
Luis Munoz Marin Intl
 00:58
Chicago
O'Hare International
 4h 59m Spirit Airlines
NK492
from $109
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20:12
San Juan
Luis Munoz Marin Intl
 08:50+1 день
Chicago
O'Hare International
 13h 38m
layover
7h 27m - Miami
 Spirit Airlines
NK2222
NK2188
from $120
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15:21
San Juan
Luis Munoz Marin Intl
 23:21
Chicago
O'Hare International
 9h 0m
layover
2h 36m - Atlanta
 Frontier Airlines
F92871
F91595
from $113
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20:24
San Juan
Luis Munoz Marin Intl
 18:44+1 день
Chicago
O'Hare International
 23h 20m
layover
7h 3m - Miami
9h 20m - Orlando
 Spirit Airlines
NK2222
NK2195
NK2190
from $140
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01:33
San Juan
Luis Munoz Marin Intl
 06:42+1 день
Chicago
O'Hare International
 30h 9m
layover
14h 43m - Dallas
2h 40m - Los Angeles
 Spirit Airlines
NK2530
NK2452
NK2549
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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on September 18, 2025
Full flight schedule will help you in detecting at what time planes fly from San Juan to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
03:40 — 11:56
03:40 — 06:54 F91823 Frontier Airlines
San Juan — Orlando
3h 18m stop
18:20 — 20:17 F93853 Frontier Airlines
Orlando — Chicago
9h 16m
including layover
Find flight
from$120
03:40 — 14:53
03:40 — 06:54 F91823 Frontier Airlines
San Juan — Orlando
6h 1m stop
06:10 — 08:22 F93043 Frontier Airlines
Orlando — Chicago
12h 13m
including layover
Find flight
from$120
06:00 — 10:16
06:00 — 10:16 NK1632 Spirit Airlines
San Juan — Chicago
5h 16m
Find flight
from$132
06:50 — 11:06
06:50 — 11:06 NK2534 Spirit Airlines
San Juan — Chicago
5h 16m
Find flight
from$113
07:45 — 11:55
07:45 — 11:55 UA2089 United Airlines
San Juan — Chicago
5h 10m
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from$208
07:58 — 17:34
07:55 — 11:56 F92265 Frontier Airlines
San Juan — Baltimore
4h 40m stop
16:32 — 17:36 F93087 Frontier Airlines
Baltimore — Chicago
10h 36m
including layover
Find flight
from$121
15:21 — 23:21
15:21 — 19:33 F92871 Frontier Airlines
San Juan — Atlanta
2h 36m stop
22:09 — 23:21 F91595 Frontier Airlines
Atlanta — Chicago
9h
including layover
Find flight
from$120
15:27 — 23:44
14:30 — 18:28 F93003 Frontier Airlines
San Juan — Charlotte
2h 55m stop
22:09 — 23:42 F93141 Frontier Airlines
Charlotte — Chicago
9h 17m
including layover
Find flight
from$121
15:56 — 20:03
15:56 — 20:03 UA2088 United Airlines
San Juan — Chicago
5h 7m
Find flight
from$206
16:46 — 20:50
16:46 — 20:50 NK1531 Spirit Airlines
San Juan — Chicago
5h 4m
Find flight
from$113
20:12 — 08:50
+1 day
20:12 — 23:03 NK2222 Spirit Airlines
San Juan — Miami
7h 27m stop
06:30 — 08:50 NK2188 Spirit Airlines
Miami — Chicago
13h 38m
including layover
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from$109
20:12 — 20:03
+1 day
20:12 — 23:03 NK2222 Spirit Airlines
San Juan — Miami
6h 57m stop
06:00 — 07:07 NK2195 Spirit Airlines
Miami — Orlando
10h 48m stop
17:55 — 20:03 NK2541 Spirit Airlines
Orlando — Chicago
24h 51m
including layover
Find flight
from$113
20:24 — 18:44
+1 day
20:12 — 23:03 NK2222 Spirit Airlines
San Juan — Miami
7h 3m stop
06:00 — 07:07 NK2195 Spirit Airlines
Miami — Orlando
9h 20m stop
21:25 — 23:29 NK2190 Spirit Airlines
Orlando — Chicago
23h 20m
including layover
Find flight
from$113
20:24 — 15:33
+1 day
20:12 — 23:03 NK2222 Spirit Airlines
San Juan — Miami
8h 8m stop
07:00 — 08:20 NK2025 Spirit Airlines
Miami — Nashville
5h 4m stop
14:28 — 16:25 NK2028 Spirit Airlines
Nashville — Chicago
20h 9m
including layover
Find flight
from$119
20:59 — 00:58
20:59 — 00:58 NK492 Spirit Airlines
San Juan — Chicago
4h 59m
Find flight
from$166
*Departure and arrival times - local. Updated on September 18, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from San Juan to Chicago depends on and how to choose the most interesting flight option for you.

Distance between San Juan and Chicago is 3314 miles. Time difference between the cities is 2h. Airplanes depart 01:05 to 23:59 from 2 San Juan airports and arrive 01:05 to 23:59 to 7 Chicago airports. Average flight time is 5h 9m.

  • The fastest flight 4h 59m
  • Average flight time 5h 9m
  • The earliest flight 01:05
  • The latest flight 23:59
  • Distance 2060 ml

The cheapest months to travel to Chicago are june (from 109 $), may (from 113 $), august (from 113 $).

The most expensive months are november (from 300 $), february (from 289 $), december (from 289 $).

What is the lowest airfare San Juan to Chicago?

The cheapest plane ticket found by our users is $109. This airfare is for economy class on one-way NK2222 flight by Spirit Airlines for June 5, 2025 which leaves Luis Munoz Marin Intl in San Juan at 20:12 am and arrives at Chicago O'Hare International at 08:50.

Economy class
$109
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Business class
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First class
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Popular Airlines on the Route

The flight San Juan — Chicago is served by 7 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by Cape Air - 10 departures per week at the price of from $ 373 . And the most expensive tickets are offered by Finnair airline - from $ 4005.

Direct flights

There are 6 nonstop flights on the route. The fastest direct flight is NK492 by Spirit Airlines takes 4h 59m and the cheapest is NK2222 by Spirit Airlines for $113.

  • UA - United Airlines
    from $206
    Find
  • NK - Spirit Airlines
    from $113
    Find
See more direct flights

Connecting Flights

There are 397 flights with layovers on the route. The fastest connecting flight is F92215 by Frontier Airlines takes 6h 51m and the cheapest is NK2222 by Spirit Airlines for $109.

  • 9K - Cape Air
    from $373
    Find
  • F9 - Frontier Airlines
    from $120
    Find
  • SY - Sun Country Airlines
    from $267
    Find
  • AY - Finnair
    from $4005
    Find
  • DM - Aero-Charter
    from $353
    Find
  • UA - United Airlines
    from $196
    Find
  • NK - Spirit Airlines
    from $109
    Find
See more connecting flights

Airports

You can fly from San Juan to Chicago from 2 airports (Isla Grande, Luis Munoz Marin Intl).

San Juan airports

  • Isla Grande-SIG
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  • Luis Munoz Marin Intl-SJU
    from $109
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Chicago airports

  • O'Hare International-ORD
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  • Midway-MDW
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
    Find

Airplanes

There are flights to Chicago from San Juan by 7 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.

Top International Destinations from San Juan

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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