Cheap Flights from San Juan to Chicago, IL from $85

Return flight: Chicago – San Juan

On Cheapflightsplus.com you will find 6 direct and 319 connecting flights from San Juan to Chicago. You can compare airfare deals from 7 airlines and multiple travel sites from $85, 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: $85 (one-way), $146 (round-trip).
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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
06:00 — 10:16
06:00 — 10:16 NK1632 Spirit Airlines
San Juan — Chicago
5h 16m
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from$102
06:50 — 11:06
06:50 — 11:06 NK2534 Spirit Airlines
San Juan — Chicago
5h 16m
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from$87
07:45 — 11:55
07:45 — 11:55 UA2089 United Airlines
San Juan — Chicago
5h 10m
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from$162
15:56 — 20:03
15:56 — 20:03 UA2088 United Airlines
San Juan — Chicago
5h 7m
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from$160
16:46 — 20:50
16:46 — 20:50 NK1531 Spirit Airlines
San Juan — Chicago
5h 4m
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from$87
20:59 — 00:58
20:59 — 00:58 NK492 Spirit Airlines
San Juan — Chicago
4h 59m
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from$129
01:33 — 19:17
01:33 — 05:50 NK2530 Spirit Airlines
San Juan — Dallas
10h 54m stop
16:44 — 19:17 NK2046 Spirit Airlines
Dallas — Chicago
18h 44m
including layover
Find flight
from$108
02:36 — 17:44
01:59 — 05:05 NK2396 Spirit Airlines
San Juan — Orlando
9h 52m stop
21:25 — 23:29 NK2190 Spirit Airlines
Orlando — Chicago
16h 8m
including layover
Find flight
from$128
02:40 — 10:06
02:40 — 05:47 NK1515 Spirit Airlines
San Juan — Orlando
2h 13m stop
08:00 — 10:06 NK1114 Spirit Airlines
Orlando — Chicago
8h 26m
including layover
Find flight
from$123
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
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from$93
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
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from$93
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
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from$94
08:30 — 19:14
08:30 — 12:59 NK1800 Spirit Airlines
San Juan — Dallas
3h 58m stop
16:57 — 19:14 NK2046 Spirit Airlines
Dallas — Chicago
11h 44m
including layover
Find flight
from$131
09:00 — 17:10
09:00 — 12:40 F91225 Frontier Airlines
San Juan — Raleigh
2h 58m stop
15:38 — 17:10 F93351 Frontier Airlines
Raleigh — Chicago
9h 10m
including layover
Find flight
from$120
10:04 — 23:31
06:00 — 09:26 F92249 Frontier Airlines
San Juan — Orlando
8h 7m stop
22:17 — 00:20 F92791 Frontier Airlines
Orlando — Chicago
14h 27m
including layover
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from$105
10:51 — 18:43
10:51 — 13:54 NK3160 Spirit Airlines
San Juan — Orlando
2h 39m stop
16:33 — 18:43 NK506 Spirit Airlines
Orlando — Chicago
8h 52m
including layover
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from$108
11:25 — 19:52
11:05 — 15:07 F91165 Frontier Airlines
San Juan — Philadelphia
3h 12m stop
18:39 — 19:55 F91617 Frontier Airlines
Philadelphia — Chicago
9h 27m
including layover
Find flight
from$120
11:25 — 18:04
11:25 — 15:23 F91165 Frontier Airlines
San Juan — Philadelphia
1h 5m stop
16:28 — 18:04 F92111 Frontier Airlines
Philadelphia — Chicago
7h 39m
including layover
Find flight
from$143
14:14 — 22:47
14:14 — 17:00 NK1845 Spirit Airlines
San Juan — Miami
3h 21m stop
20:21 — 22:47 NK3203 Spirit Airlines
Miami — Chicago
9h 33m
including layover
Find flight
from$150
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
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from$93
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
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from$94
17:43 — 00:25
17:43 — 20:58 F92215 Frontier Airlines
San Juan — Tampa
1h 27m stop
20:25 — 22:29 F92317 Frontier Airlines
Tampa — Chicago
7h 42m
including layover
Find flight
from$94
17:43 — 19:12
+1 day
18:10 — 21:28 F92215 Frontier Airlines
San Juan — Tampa
20h 14m stop
17:43 — 19:48 F91415 Frontier Airlines
Tampa — Chicago
26h 29m
including layover
Find flight
from$99
19:28 — 08:07
+1 day
16:38 — 20:04 F92981 Frontier Airlines
San Juan — Orlando
7h 24m stop
06:10 — 08:22 F93043 Frontier Airlines
Orlando — Chicago
13h 39m
including layover
Find flight
from$94
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
Find flight
from$85
20:12 — 00:05
+1 day
20:12 — 23:03 NK2222 Spirit Airlines
San Juan — Miami
22h 49m stop
21:52 — 00:05 NK1 Spirit Airlines
Miami — Chicago
28h 53m
including layover
Find flight
from$99
21:30 — 15:06
+1 day
21:30 — 00:43 F91745 Frontier Airlines
San Juan — Orlando
12h 32m stop
18:20 — 20:17 F93853 Frontier Airlines
Orlando — Chicago
18h 36m
including layover
Find flight
from$99
21:30 — 23:31
+1 day
21:30 — 00:43 F91745 Frontier Airlines
San Juan — Orlando
20h 40m stop
21:57 — 00:04 F92791 Frontier Airlines
Orlando — Chicago
27h 1m
including layover
Find flight
from$99
23:59 — 14:41
+1 day
23:59 — 04:11 NK1227 Spirit Airlines
San Juan — Newark
8h 46m stop
12:57 — 14:41 NK1183 Spirit Airlines
Newark — Chicago
15h 42m
including layover
Find flight
from$123
01:33 — 06:42
+1 day
01:33 — 05:50 NK2530 Spirit Airlines
San Juan — Dallas
14h 43m stop
20:33 — 22:01 NK2452 Spirit Airlines
Dallas — Los Angeles
2h 40m stop
00:41 — 06:42 NK2549 Spirit Airlines
Los Angeles — Chicago
30h 9m
including layover
Find flight
from$109
12:36 — 23:29
+1 day
12:36 — 16:49 NK2405 Spirit Airlines
San Juan — Atlanta
22h 30m stop
15:19 — 16:50 NK2460 Spirit Airlines
Atlanta — Orlando
4h 35m stop
21:25 — 23:29 NK2190 Spirit Airlines
Orlando — Chicago
35h 53m
including layover
Find flight
from$111
12:36 — 00:05
12:36 — 16:49 NK2405 Spirit Airlines
San Juan — Atlanta
2h 27m stop
19:16 — 21:11 NK2061 Spirit Airlines
Atlanta — Miami
41m stop
21:52 — 00:05 NK1 Spirit Airlines
Miami — Chicago
12h 29m
including layover
Find flight
from$116
13:02 — 20:23
+1 day
12:36 — 16:49 NK2405 Spirit Airlines
San Juan — Atlanta
21h 33m stop
15:19 — 16:50 NK2460 Spirit Airlines
Atlanta — Orlando
2h 2m stop
17:55 — 20:03 NK2541 Spirit Airlines
Orlando — Chicago
32h 21m
including layover
Find flight
from$111
13:39 — 23:29
+1 day
13:39 — 17:40 NK2532 Spirit Airlines
San Juan — Baltimore
19h 11m stop
12:51 — 15:14 NK1961 Spirit Airlines
Baltimore — Orlando
6h 11m stop
21:25 — 23:29 NK2190 Spirit Airlines
Orlando — Chicago
34h 50m
including layover
Find flight
from$114
23:59 — 17:17
+1 day
23:59 — 04:11 NK1227 Spirit Airlines
San Juan — Newark
7h 19m stop
11:30 — 13:24 NK1810 Spirit Airlines
Newark — Myrtle Beach
2h 28m stop
15:52 — 17:17 NK1637 Spirit Airlines
Myrtle Beach — Chicago
18h 18m
including layover
Find flight
from$146
*Departure and arrival times - local. Updated on June 6, 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 114 $), may (from 117 $), august (from 117 $).

The most expensive months are november (from 312 $), february (from 301 $), december (from 301 $).

What is the lowest airfare San Juan to Chicago?

The cheapest plane ticket found by our users is $85. This airfare is for economy class on one-way NK2222 flight by Spirit Airlines for June 6, 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
$85
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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 - 3 departures per week at the price of from $ 324 . And the most expensive tickets are offered by Finnair airline - from $ 3192.

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 $87.

  • UA - United Airlines
    from $160
    Find
  • NK - Spirit Airlines
    from $87
    Find
See more direct flights

Connecting Flights

There are 319 flights with layovers on the route. The fastest connecting flight is UA2024 by United Airlines takes 7h 20m and the cheapest is NK2222 by Spirit Airlines for $85.

  • 9K - Cape Air
    from $324
    Find
  • F9 - Frontier Airlines
    from $93
    Find
  • SY - Sun Country Airlines
    from $208
    Find
  • AY - Finnair
    from $3192
    Find
  • DM - Aero-Charter
    from $275
    Find
  • UA - United Airlines
    from $153
    Find
  • NK - Spirit Airlines
    from $85
    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 $85
    Find

Chicago airports

  • O'Hare International-ORD
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  • Midway-MDW
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  • Dupage County-DPA
    Find
  • 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

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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