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).
Direct flights
Check prices for return flight
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 $85. The fastest direct flight takes 4h 59m and the fastest connecting – 7h 20m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $87 | 16:46 San Juan Luis Munoz Marin Intl | 20:50 Chicago O'Hare International | 5h 4m | Spirit Airlines | NK1531 |
| from $87 | 06:50 San Juan Luis Munoz Marin Intl | 11:06 Chicago O'Hare International | 5h 16m | Spirit Airlines | NK2534 |
| from $102 | 06:00 San Juan Luis Munoz Marin Intl | 10:16 Chicago O'Hare International | 5h 16m | Spirit Airlines | NK1632 |
| from $129 | 20:59 San Juan Luis Munoz Marin Intl | 00:58 Chicago O'Hare International | 4h 59m | Spirit Airlines | NK492 |
| from $160 | 15:56 San Juan Luis Munoz Marin Intl | 20:03 Chicago O'Hare International | 5h 7m | United Airlines | UA2088 |
| from $85 | 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 $93 | 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 $93 | 03:40 San Juan Luis Munoz Marin Intl | 11:56 Chicago Midway | 9h 16m layover 3h 18m - Orlando | Frontier Airlines | F91823 F93853 |
| from $93 | 03:40 San Juan Luis Munoz Marin Intl | 14:53 Chicago O'Hare International | 12h 13m layover 6h 1m - Orlando | Frontier Airlines | F91823 F93043 |
| from $94 | 17:43 San Juan Luis Munoz Marin Intl | 00:25 Chicago O'Hare International | 7h 42m layover 1h 27m - Tampa | Frontier Airlines | F92215 F92317 |
| from $94 | 15:27 San Juan Luis Munoz Marin Intl | 23:44 Chicago O'Hare International | 9h 17m layover 2h 55m - Charlotte | Frontier Airlines | F93003 F93141 |
| from $94 | 07:58 San Juan Luis Munoz Marin Intl | 17:34 Chicago Midway | 10h 36m layover 4h 40m - Baltimore | Frontier Airlines | F92265 F93087 |
| from $94 | 19:28 San Juan Luis Munoz Marin Intl | 08:07+1 день Chicago O'Hare International | 13h 39m layover 7h 24m - Orlando | Frontier Airlines | F92981 F93043 |
| from $98 | 15:50 San Juan Luis Munoz Marin Intl | 07:04+1 день Chicago O'Hare International | 16h 14m layover 9h 55m - Atlanta | Spirit Airlines | NK1390 NK1116 |
| from $109 | 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 |
| from $126 | 20:24 San Juan Luis Munoz Marin Intl | 22:19+1 день Chicago O'Hare International | 26h 55m layover 14h 27m - Miami 4h 6m - Houston | Spirit Airlines | NK2222 NK2678 NK2174 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on June 06, 2025
Flight Schedule San Juan to Chicago (Illinois)
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 |
Find flight
from$102 |
|
|
06:50 — 11:06
|
06:50 — 11:06
NK2534
Spirit Airlines
San Juan — Chicago
|
5h 16m |
Find flight
from$87 |
|
|
07:45 — 11:55
|
07:45 — 11:55
UA2089
United Airlines
San Juan — Chicago
|
5h 10m |
Find flight
from$162 |
|
|
15:56 — 20:03
|
15:56 — 20:03
UA2088
United Airlines
San Juan — Chicago
|
5h 7m |
Find flight
from$160 |
|
|
16:46 — 20:50
|
16:46 — 20:50
NK1531
Spirit Airlines
San Juan — Chicago
|
5h 4m |
Find flight
from$87 |
|
|
20:59 — 00:58
|
20:59 — 00:58
NK492
Spirit Airlines
San Juan — Chicago
|
4h 59m |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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
Business class
?
First class
?
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 Airlinesfrom $160Find
- NK - Spirit Airlinesfrom $87Find
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 Airfrom $324Find
- F9 - Frontier Airlinesfrom $93Find
- SY - Sun Country Airlinesfrom $208Find
- AY - Finnairfrom $3192Find
- DM - Aero-Charterfrom $275Find
- UA - United Airlinesfrom $153Find
- NK - Spirit Airlinesfrom $85Find
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-SIGFind
- Luis Munoz Marin Intl-SJUfrom $85Find
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 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.
- from $72Find
- from $60Find
- from $69Find
- 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.