Cheap Flights from San Juan to Chicago, IL from $73
On Cheapflightsplus.com you will find 7 direct and 270 connecting flights from San Juan to Chicago. You can compare airfare deals from 5 airlines and multiple travel sites from $73, 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
Best Flights from San Juan to Chicago Today
Price | Departure | Arrival | Flight Duration | Airline | Flight |
---|---|---|---|---|---|
from $107 | 21:59 San Juan Luis Munoz Marin Intl | 00:58+1 день Chicago O'Hare International | 4h 59m | Spirit Airlines | NK492 |
from $270 | 16:52 San Juan Luis Munoz Marin Intl | 20:11 Chicago O'Hare International | 5h 19m | United Airlines | UA2088 |
from $356 | 16:00 San Juan Luis Munoz Marin Intl | 19:26 Chicago O'Hare International | 5h 26m | Spirit Airlines | NK518 |
from $73 | 16:32 San Juan Luis Munoz Marin Intl | 20:25+1 день Chicago Midway | 29h 53m layover 23h 56m - Tampa | Frontier Airlines | F93979 F93899 |
from $76 | 16:49 San Juan Luis Munoz Marin Intl | 13:43+1 день Chicago O'Hare International | 22h 54m layover 16h 29m - Tampa | Frontier Airlines | F92215 F91415 |
from $89 | 03:59 San Juan Luis Munoz Marin Intl | 12:05 Chicago O'Hare International | 10h 6m layover 3h 47m - Orlando | Frontier Airlines | F91823 F93043 |
from $89 | 06:20 San Juan Luis Munoz Marin Intl | 17:12 Chicago Midway | 12h 52m layover 6h 40m - Atlanta | Frontier Airlines | F92871 F92143 |
from $89 | 21:49 San Juan Luis Munoz Marin Intl | 09:54+1 день Chicago O'Hare International | 14h 5m layover 7h 20m - Orlando | Frontier Airlines | F94725 F93043 |
from $89 | 12:45 San Juan Luis Munoz Marin Intl | 00:59+1 день Chicago O'Hare International | 14h 14m layover 7h 58m - Orlando | Frontier Airlines | F93505 F93043 |
from $90 | 17:03 San Juan Luis Munoz Marin Intl | 23:47 Chicago O'Hare International | 8h 44m layover 2h 12m - Philadelphia | Frontier Airlines | F94461 F92111 |
from $90 | 17:03 San Juan Luis Munoz Marin Intl | 00:20+1 день Chicago Midway | 9h 17m layover 2h 50m - Philadelphia | Frontier Airlines | F94461 F94367 |
from $90 | 02:25 San Juan Luis Munoz Marin Intl | 10:09 Chicago Midway | 9h 44m layover 3h 23m - Philadelphia | Frontier Airlines | F94461 F91617 |
from $90 | 14:00 San Juan Luis Munoz Marin Intl | 21:55 Chicago Midway | 9h 55m layover 3h 58m - Raleigh | Frontier Airlines | F91225 F93717 |
from $90 | 11:16 San Juan Luis Munoz Marin Intl | 19:13 Chicago Midway | 9h 57m layover 3h 39m - Philadelphia | Frontier Airlines | F91015 F94367 |
from $90 | 10:42 San Juan Luis Munoz Marin Intl | 19:18 Chicago Midway | 10h 36m layover 4h 36m - Miami | Frontier Airlines | F92283 F92109 |
from $112 | 11:45 San Juan Luis Munoz Marin Intl | 17:37 Chicago Midway | 7h 52m layover 1h 41m - Baltimore | Frontier Airlines | F92265 F93087 |
Flight Schedule San Juan to Chicago (Illinois)
Departure | Arrival | Flight Details | Flight Duration | Price |
---|---|---|---|---|
08:35 — 11:54
|
08:35 — 11:54
UA2089
United Airlines
San Juan — Chicago
|
5h 19m |
Find flight
from$274 |
|
14:17 — 17:47
|
14:17 — 17:47
NK851
Spirit Airlines
San Juan — Chicago
|
5h 30m |
Find flight
from$111 |
|
16:00 — 19:26
|
16:00 — 19:26
NK518
Spirit Airlines
San Juan — Chicago
|
5h 26m |
Find flight
from$356 |
|
16:52 — 20:11
|
16:52 — 20:11
UA2088
United Airlines
San Juan — Chicago
|
5h 19m |
Find flight
from$270 |
|
17:41 — 20:44
|
17:41 — 20:44
NK1531
Spirit Airlines
San Juan — Chicago
|
5h 3m |
Find flight
from$107 |
|
21:26 — 00:51
+1 day
|
21:26 — 00:51
NK173
Spirit Airlines
San Juan — Chicago
|
5h 25m |
Find flight
from$107 |
|
21:59 — 00:58
+1 day
|
21:59 — 00:58
NK492
Spirit Airlines
San Juan — Chicago
|
4h 59m |
Find flight
from$107 |
|
02:25 — 10:09
|
02:25 — 05:33
F94461
Frontier Airlines
San Juan — Philadelphia
3h 23m stop
08:56 — 10:09
F91617
Frontier Airlines
Philadelphia — Chicago
|
9h 44m including layover |
Find flight
from$90 |
|
03:59 — 12:05
|
03:59 — 06:09
F91823
Frontier Airlines
San Juan — Orlando
3h 47m stop
09:56 — 12:05
F93043
Frontier Airlines
Orlando — Chicago
|
10h 6m including layover |
Find flight
from$89 |
|
04:08 — 12:23
|
03:59 — 06:09
F91823
Frontier Airlines
San Juan — Orlando
4h 17m stop
06:00 — 07:55
F91457
Frontier Airlines
Orlando — Chicago
|
10h 15m including layover |
Find flight
from$95 |
|
06:00 — 11:41
|
11:45 — 14:05
F93979
Frontier Airlines
San Juan — Tampa
1h 35m stop
09:54 — 11:41
F91185
Frontier Airlines
Tampa — Chicago
|
7h 41m including layover |
Find flight
from$74 |
|
06:20 — 17:12
|
06:20 — 09:32
F92871
Frontier Airlines
San Juan — Atlanta
6h 40m stop
16:18 — 17:18
F92143
Frontier Airlines
Atlanta — Chicago
|
12h 52m including layover |
Find flight
from$89 |
|
08:00 — 00:59
+1 day
|
15:03 — 17:27
F92249
Frontier Airlines
San Juan — Orlando
12h 43m stop
07:30 — 09:54
F93043
Frontier Airlines
Orlando — Chicago
|
18h 59m including layover |
Find flight
from$96 |
|
10:34 — 18:50
|
11:12 — 13:29
NK3160
Spirit Airlines
San Juan — Orlando
3h 53m stop
18:05 — 20:15
NK1147
Spirit Airlines
Orlando — Chicago
|
10h 16m including layover |
Find flight
from$141 |
|
10:42 — 19:18
|
10:29 — 12:19
F92283
Frontier Airlines
San Juan — Miami
4h 36m stop
17:21 — 19:36
F92109
Frontier Airlines
Miami — Chicago
|
10h 36m including layover |
Find flight
from$90 |
|
11:16 — 19:13
|
13:55 — 16:59
F91015
Frontier Airlines
San Juan — Philadelphia
3h 39m stop
22:57 — 00:20
F94367
Frontier Airlines
Philadelphia — Chicago
|
9h 57m including layover |
Find flight
from$90 |
|
11:45 — 17:37
|
11:45 — 14:52
F92265
Frontier Airlines
San Juan — Baltimore
1h 41m stop
16:33 — 17:37
F93087
Frontier Airlines
Baltimore — Chicago
|
7h 52m including layover |
Find flight
from$112 |
|
12:45 — 00:59
+1 day
|
11:18 — 13:35
F93505
Frontier Airlines
San Juan — Orlando
7h 58m stop
09:56 — 12:05
F93043
Frontier Airlines
Orlando — Chicago
|
14h 14m including layover |
Find flight
from$89 |
|
13:54 — 22:41
|
13:54 — 17:05
F94249
Frontier Airlines
San Juan — Dallas
3h 14m stop
20:19 — 22:41
F92882
Frontier Airlines
Dallas — Chicago
|
10h 47m including layover |
Find flight
from$90 |
|
13:55 — 23:47
|
13:55 — 16:59
F91015
Frontier Airlines
San Juan — Philadelphia
5h 20m stop
22:19 — 23:47
F92111
Frontier Airlines
Philadelphia — Chicago
|
11h 52m including layover |
Find flight
from$90 |
|
14:00 — 21:55
|
14:00 — 16:56
F91225
Frontier Airlines
San Juan — Raleigh
3h 58m stop
20:54 — 21:55
F93717
Frontier Airlines
Raleigh — Chicago
|
9h 55m including layover |
Find flight
from$90 |
|
16:32 — 20:25
+1 day
|
16:32 — 18:44
F93979
Frontier Airlines
San Juan — Tampa
23h 56m stop
18:40 — 20:25
F93899
Frontier Airlines
Tampa — Chicago
|
29h 53m including layover |
Find flight
from$73 |
|
16:49 — 13:43
+1 day
|
16:49 — 19:14
F92215
Frontier Airlines
San Juan — Tampa
16h 29m stop
11:43 — 13:43
F91415
Frontier Airlines
Tampa — Chicago
|
22h 54m including layover |
Find flight
from$76 |
|
17:03 — 23:47
|
17:03 — 20:07
F94461
Frontier Airlines
San Juan — Philadelphia
2h 12m stop
22:19 — 23:47
F92111
Frontier Airlines
Philadelphia — Chicago
|
8h 44m including layover |
Find flight
from$90 |
|
17:03 — 00:20
+1 day
|
17:03 — 20:07
F94461
Frontier Airlines
San Juan — Philadelphia
2h 50m stop
22:57 — 00:20
F94367
Frontier Airlines
Philadelphia — Chicago
|
9h 17m including layover |
Find flight
from$90 |
|
18:14 — 10:06
+1 day
|
18:14 — 20:08
NK1637
Spirit Airlines
San Juan — Miami
11h 27m stop
07:35 — 10:06
NK396
Spirit Airlines
Miami — Chicago
|
17h 52m including layover |
Find flight
from$137 |
|
19:16 — 13:54
+1 day
|
11:18 — 13:35
F93505
Frontier Airlines
San Juan — Orlando
14h 17m stop
06:00 — 07:55
F91457
Frontier Airlines
Orlando — Chicago
|
20h 38m including layover |
Find flight
from$161 |
|
21:09 — 09:13
+1 day
|
21:49 — 00:10
F94725
Frontier Airlines
San Juan — Orlando
7h 50m stop
11:56 — 13:54
F91457
Frontier Airlines
Orlando — Chicago
|
14h 4m including layover |
Find flight
from$90 |
|
21:49 — 09:54
+1 day
|
21:49 — 00:10
F94725
Frontier Airlines
San Juan — Orlando
7h 20m stop
07:30 — 09:54
F93043
Frontier Airlines
Orlando — Chicago
|
14h 5m including layover |
Find flight
from$89 |
|
22:09 — 09:52
+1 day
|
22:09 — 23:58
NK1690
Spirit Airlines
San Juan — Miami
7h 32m stop
07:30 — 09:52
NK1986
Spirit Airlines
Miami — Chicago
|
13h 43m including layover |
Find flight
from$137 |
|
22:47 — 09:08
+1 day
|
22:47 — 01:38
F92081
Frontier Airlines
San Juan — Atlanta
6h 22m stop
08:00 — 09:08
F91441
Frontier Airlines
Atlanta — Chicago
|
12h 21m including layover |
Find flight
from$90 |
|
03:20 — 00:24
+1 day
|
03:20 — 06:26
NK838
Spirit Airlines
San Juan — Atlanta
11h 9m stop
17:35 — 18:56
NK967
Spirit Airlines
Atlanta — Houston
2h 51m stop
21:47 — 00:24
NK962
Spirit Airlines
Houston — Chicago
|
23h 4m including layover |
Find flight
from$177 |
|
04:39 — 20:48
|
04:39 — 07:47
NK3124
Spirit Airlines
San Juan — Baltimore
4h 42m stop
12:29 — 15:10
NK223
Spirit Airlines
Baltimore — Miami
3h 15m stop
18:25 — 20:48
NK7
Spirit Airlines
Miami — Chicago
|
18h 9m including layover |
Find flight
from$195 |
|
05:10 — 17:40
|
07:00 — 09:19
NK3164
Spirit Airlines
San Juan — Orlando
5h 4m stop
13:29 — 15:32
NK1096
Spirit Airlines
Orlando — Dallas
34m stop
17:58 — 20:26
NK241
Spirit Airlines
Dallas — Chicago
|
14h 30m including layover |
Find flight
from$208 |
|
07:00 — 22:55
|
07:00 — 10:36
NK1380
Spirit Airlines
San Juan — Dallas
2h 34m stop
13:10 — 17:31
NK1353
Spirit Airlines
Dallas — New York
3h 44m stop
21:15 — 22:55
NK225
Spirit Airlines
New York — Chicago
|
17h 55m including layover |
Find flight
from$215 |
|
12:27 — 22:51
|
12:27 — 14:46
NK1758
Spirit Airlines
San Juan — Orlando
3h 19m stop
18:05 — 19:19
NK359
Spirit Airlines
Orlando — Miami
1h 11m stop
20:30 — 22:51
NK718
Spirit Airlines
Miami — Chicago
|
12h 24m including layover |
Find flight
from$215 |
|
18:40 — 09:43
+1 day
|
18:40 — 20:33
NK1845
Spirit Airlines
San Juan — Miami
1h 55m stop
22:28 — 00:55
NK3175
Spirit Airlines
Miami — Dallas
6h 16m stop
07:11 — 09:43
NK3670
Spirit Airlines
Dallas — Chicago
|
17h 3m including layover |
Find flight
from$217 |
|
19:59 — 12:52
+1 day
|
19:59 — 21:50
NK1845
Spirit Airlines
San Juan — Miami
8h 6m stop
05:56 — 09:00
NK1897
Spirit Airlines
Miami — Newark
2h 14m stop
12:08 — 13:44
NK329
Spirit Airlines
Newark — Chicago
|
18h 53m including layover |
Find flight
from$151 |
|
20:31 — 21:07
+1 day
|
20:31 — 22:51
NK1647
Spirit Airlines
San Juan — New Orleans
11h 22m stop
10:13 — 13:08
NK2057
Spirit Airlines
New Orleans — Miami
5h 37m stop
18:45 — 21:07
NK7
Spirit Airlines
Miami — Chicago
|
26h 36m including layover |
Find flight
from$201 |
|
20:39 — 12:52
+1 day
|
20:39 — 22:25
NK262
Spirit Airlines
San Juan — Miami
7h 40m stop
06:05 — 09:00
NK385
Spirit Airlines
Miami — Newark
2h 13m stop
12:08 — 13:44
NK329
Spirit Airlines
Newark — Chicago
|
18h 13m including layover |
Find flight
from$200 |
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 02:05 to 22:47 from 2 San Juan airports and arrive 02:05 to 22:47 to 7 Chicago airports. Average flight time is 5h 19m.
- The fastest flight 4h 59m
- Average flight time 5h 19m
- The earliest flight 02:05
- The latest flight 22:47
- Distance 2060 ml
The cheapest months to travel to Chicago are november (from 73 $), december (from 74 $), january (from 76 $).
The most expensive months are february (from 90 $), january (from 76 $), december (from 74 $).
What is the lowest airfare San Juan to Chicago?
The cheapest plane ticket found by our users is $73. This airfare is for economy class on one-way F93979 flight by Frontier Airlines for November 13, 2024 which leaves Luis Munoz Marin Intl in San Juan at 16:32 am and arrives at Chicago Midway at 20:25.
Popular Airlines on the Route
The flight San Juan — Chicago is served by 5 regular airlines and 2 low-cost airlines. Most of the flights on this route are operated by Cape Air - 4 departures per week at the price of from $ 399 . And the most expensive tickets are offered by United Airlines airline - from $ 925.
Direct flights
There are 7 nonstop flights on the route. The fastest direct flight is NK492 by Spirit Airlines takes 4h 59m and the cheapest is F93979 by Frontier Airlines for $107.
- UA - United Airlinesfrom $270Find
- NK - Spirit Airlinesfrom $107Find
Connecting Flights
There are 270 flights with layovers on the route. The fastest connecting flight is NK3160 by Spirit Airlines takes 7h 6m and the cheapest is F93979 by Frontier Airlines for $73.
- 9K - Cape Airfrom $399Find
- F9 - Frontier Airlinesfrom $73Find
- 3M - Gulfstream International Airlinesfrom $416Find
- UA - United Airlinesfrom $276Find
- NK - Spirit Airlinesfrom $137Find
Airports
You can fly from San Juan to Chicago from 2 airports (Isla Grande, Luis Munoz Marin Intl).
San Juan airports
- Isla Grande-SIGFind
- Luis Munoz Marin Intl-SJUfrom $73Find
Chicago airports
- O'Hare International-ORDFind
- Midway-MDWFind
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Airplanes
There are flights to Chicago from San Juan by 5 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.
- from $72Find
- from $60Find
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- from $68Find
- from $65Find
- from $57Find
- from $73Find
- from $73Find
- from $58Find
- from $62Find
How to book a plane 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.