Cheap Flights from San Juan to Chicago, IL from $89
Return flight: Chicago – San Juan
On Cheapflightsplus.com you will find 6 direct and 276 connecting flights from San Juan to Chicago. You can compare airfare deals from 6 airlines and multiple travel sites from $89, 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: $89 (one-way), $153 (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 $89. The fastest direct flight takes 4h 59m and the fastest connecting – 7h 20m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $89 | 16:46 San Juan Luis Munoz Marin Intl | 20:50 Chicago O'Hare International | 5h 4m | Spirit Airlines | NK1531 |
| from $93 | 06:50 San Juan Luis Munoz Marin Intl | 11:06 Chicago O'Hare International | 5h 16m | Spirit Airlines | NK2534 |
| from $105 | 06:00 San Juan Luis Munoz Marin Intl | 10:16 Chicago O'Hare International | 5h 16m | Spirit Airlines | NK1632 |
| from $132 | 20:59 San Juan Luis Munoz Marin Intl | 00:58 Chicago O'Hare International | 4h 59m | Spirit Airlines | NK492 |
| from $163 | 15:56 San Juan Luis Munoz Marin Intl | 20:03 Chicago O'Hare International | 5h 7m | United Airlines | UA2088 |
| from $95 | 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 $95 | 03:40 San Juan Luis Munoz Marin Intl | 11:56 Chicago Midway | 9h 16m layover 3h 18m - Orlando | Frontier Airlines | F91823 F93853 |
| from $95 | 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 $96 | 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 $96 | 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 $96 | 07:58 San Juan Luis Munoz Marin Intl | 17:34 Chicago Midway | 10h 36m layover 4h 40m - Baltimore | Frontier Airlines | F92265 F93087 |
| from $96 | 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 $99 | 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 $110 | 10:51 San Juan Luis Munoz Marin Intl | 18:43 Chicago O'Hare International | 8h 52m layover 2h 39m - Orlando | Spirit Airlines | NK3160 NK506 |
| from $146 | 17:41 San Juan Luis Munoz Marin Intl | 22:28+1 день Chicago O'Hare International | 29h 47m layover 7h 9m - Detroit 13h 34m - Atlanta | Spirit Airlines | NK3899 NK1205 NK1200 |
| from $168 | 02:06 San Juan Luis Munoz Marin Intl | 19:17 Chicago O'Hare International | 18h 11m layover 4h 5m - Orlando 5h 48m - New York | Spirit Airlines | NK3164 NK3053 NK918 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on June 26, 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$105 |
|
|
06:50 — 11:06
|
06:50 — 11:06
NK2534
Spirit Airlines
San Juan — Chicago
|
5h 16m |
Find flight
from$93 |
|
|
07:45 — 11:55
|
07:45 — 11:55
UA2089
United Airlines
San Juan — Chicago
|
5h 10m |
Find flight
from$165 |
|
|
15:56 — 20:03
|
15:56 — 20:03
UA2088
United Airlines
San Juan — Chicago
|
5h 7m |
Find flight
from$163 |
|
|
16:46 — 20:50
|
16:46 — 20:50
NK1531
Spirit Airlines
San Juan — Chicago
|
5h 4m |
Find flight
from$89 |
|
|
20:59 — 00:58
|
20:59 — 00:58
NK492
Spirit Airlines
San Juan — Chicago
|
4h 59m |
Find flight
from$132 |
|
|
01:05 — 08:39
|
01:05 — 05:14
UA2219
United Airlines
San Juan — Newark
1h 46m stop
07:00 — 08:39
UA2050
United Airlines
Newark — Chicago
|
8h 34m including layover |
Find flight
from$155 |
|
|
01:05 — 07:38
|
01:05 — 05:14
UA2219
United Airlines
San Juan — Newark
45m stop
06:00 — 07:38
UA2164
United Airlines
Newark — Chicago
|
7h 33m including layover |
Find flight
from$162 |
|
|
02:06 — 14:15
|
02:06 — 05:05
NK3164
Spirit Airlines
San Juan — Orlando
7h 3m stop
12:08 — 14:15
NK3201
Spirit Airlines
Orlando — Chicago
|
13h 9m including layover |
Find flight
from$137 |
|
|
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$126 |
|
|
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$95 |
|
|
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$95 |
|
|
07:00 — 14:48
|
07:00 — 10:51
UA1644
United Airlines
San Juan — Houston
1h 4m stop
11:55 — 14:51
UA2417
United Airlines
Houston — Chicago
|
8h 48m including layover |
Find flight
from$164 |
|
|
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$96 |
|
|
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$133 |
|
|
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$106 |
|
|
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$110 |
|
|
13:30 — 20:11
|
13:30 — 17:40
UA1173
United Airlines
San Juan — Newark
50m stop
18:30 — 20:11
UA254
United Airlines
Newark — Chicago
|
7h 41m including layover |
Find flight
from$162 |
|
|
13:44 — 09:23
+1 day
|
13:39 — 17:40
NK2532
Spirit Airlines
San Juan — Baltimore
14h 12m stop
08:10 — 09:24
NK2439
Spirit Airlines
Baltimore — Chicago
|
20h 39m including layover |
Find flight
from$144 |
|
|
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$153 |
|
|
14:55 — 22:41
|
14:55 — 18:46
UA668
United Airlines
San Juan — Houston
1h 4m stop
19:50 — 22:41
UA1752
United Airlines
Houston — Chicago
|
8h 46m including layover |
Find flight
from$167 |
|
|
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$95 |
|
|
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$96 |
|
|
16:55 — 23:15
|
16:55 — 20:54
UA2024
United Airlines
San Juan — Washington D.C.
1h 18m stop
22:18 — 23:30
UA1738
United Airlines
Washington D.C. — Chicago
|
7h 20m including layover |
Find flight
from$162 |
|
|
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$96 |
|
|
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$100 |
|
|
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$96 |
|
|
20:24 — 08:50
+1 day
|
20:24 — 23:12
NK2222
Spirit Airlines
San Juan — Miami
7h 18m stop
06:30 — 08:50
NK2
Spirit Airlines
Miami — Chicago
|
13h 26m including layover |
Find flight
from$126 |
|
|
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$100 |
|
|
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$100 |
|
|
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$126 |
|
|
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$148 |
|
*Departure and arrival times - local. Updated on June 26, 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 may (from 119 $), june (from 119 $), august (from 119 $).
The most expensive months are november (from 317 $), february (from 306 $), december (from 306 $).
What is the lowest airfare San Juan to Chicago?
The cheapest plane ticket found by our users is $89. This airfare is for economy class on one-way NK1531 flight by Spirit Airlines for August 27, 2025 which leaves Luis Munoz Marin Intl in San Juan at 16:46 am and arrives at Chicago O'Hare International at 20:50.
Economy class
$89
Business class
?
First class
?
Popular Airlines on the Route
The flight San Juan — Chicago is served by 6 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 $ 330 . And the most expensive tickets are offered by United Airlines airline - from $ 474.
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 NK1531 by Spirit Airlines for $89.
- UA - United Airlinesfrom $163Find
- NK - Spirit Airlinesfrom $89Find
See more direct flights
Connecting Flights
There are 276 flights with layovers on the route. The fastest connecting flight is UA2024 by United Airlines takes 7h 20m and the cheapest is NK1531 by Spirit Airlines for $95.
- 9K - Cape Airfrom $330Find
- F9 - Frontier Airlinesfrom $95Find
- SY - Sun Country Airlinesfrom $211Find
- DM - Aero-Charterfrom $279Find
- UA - United Airlinesfrom $155Find
- NK - Spirit Airlinesfrom $99Find
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 $89Find
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 6 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 $73Find
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- 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.