Cheap Flights from San Juan to Chicago, IL from $116

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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 $116, 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: $116 (one-way), $199 (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 $116. The fastest direct flight takes 4h 59m and the fastest connecting – 6h 51m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $120 Find flight	16:46 San Juan Luis Munoz Marin Intl	20:50 Chicago O'Hare International	5h 4m	Spirit Airlines	NK1531
from $120 Find flight	06:50 San Juan Luis Munoz Marin Intl	11:06 Chicago O'Hare International	5h 16m	Spirit Airlines	NK2534
from $176 Find flight	20:59 San Juan Luis Munoz Marin Intl	00:58 Chicago O'Hare International	4h 59m	Spirit Airlines	NK492
from $217 Find flight	06:00 San Juan Luis Munoz Marin Intl	10:16 Chicago O'Hare International	5h 16m	Spirit Airlines	NK1632
from $219 Find flight	15:56 San Juan Luis Munoz Marin Intl	20:03 Chicago O'Hare International	5h 7m	United Airlines	UA2088
from $116 Find flight	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 $127 Find flight	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 $127 Find flight	03:40 San Juan Luis Munoz Marin Intl	11:56 Chicago Midway	9h 16m layover 3h 18m - Orlando	Frontier Airlines	F91823 F93853
from $127 Find flight	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 $128 Find flight	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 $128 Find flight	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 $128 Find flight	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 $133 Find flight	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 $134 Find flight	21:30 San Juan Luis Munoz Marin Intl	15:06+1 день Chicago Midway	18h 36m layover 12h 32m - Orlando	Frontier Airlines	F91745 F93853
from $120 Find flight	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 $149 Find flight	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 August 08, 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	Flight Details	Flight Duration	Price
06:00 — 10:16	06:00 — 10:16 NK1632 Spirit Airlines San Juan — Chicago	5h 16m	Find flight from$217
06:50 — 11:06	06:50 — 11:06 NK2534 Spirit Airlines San Juan — Chicago	5h 16m	Find flight from$120
07:45 — 11:55	07:45 — 11:55 UA2089 United Airlines San Juan — Chicago	5h 10m	Find flight from$221
15:56 — 20:03	15:56 — 20:03 UA2088 United Airlines San Juan — Chicago	5h 7m	Find flight from$219
16:46 — 20:50	16:46 — 20:50 NK1531 Spirit Airlines San Juan — Chicago	5h 4m	Find flight from$120
20:59 — 00:58	20:59 — 00:58 NK492 Spirit Airlines San Juan — Chicago	4h 59m	Find flight from$176
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$147
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$174
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$168
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$127
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$127
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$143
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$164
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$143
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$148
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$154
11:43 — 22:19	11:50 — 15:50 NK2528 Spirit Airlines San Juan — Houston 4h 8m stop 19:54 — 22:39 NK2174 Spirit Airlines Houston — Chicago	11h 36m including layover	Find flight from$148
12:36 — 08:55 +1 day	12:36 — 16:49 NK2405 Spirit Airlines San Juan — Atlanta 14h 59m stop 07:48 — 08:55 NK2707 Spirit Airlines Atlanta — Chicago	21h 19m including layover	Find flight from$155
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$127
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$128
16:31 — 00:17	16:31 — 20:50 F92871 Frontier Airlines San Juan — Atlanta 2h 8m stop 22:58 — 00:17 F93397 Frontier Airlines Atlanta — Chicago	8h 46m including layover	Find flight from$154
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$128
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$134
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$128
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$116
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$134
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$134
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$168
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$149
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$151
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$151
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$156
18:21 — 08:55 +1 day	18:21 — 21:34 NK2536 Spirit Airlines San Juan — Orlando 43m stop 22:17 — 23:59 NK2302 Spirit Airlines Orlando — Atlanta 7h 49m stop 07:48 — 08:55 NK2707 Spirit Airlines Atlanta — Chicago	15h 34m including layover	Find flight from$168
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$120

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times - local. Updated on August 8, 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 116 $), may (from 120 $), august (from 120 $).

The most expensive months are november (from 319 $), february (from 307 $), december (from 307 $).

What is the lowest airfare San Juan to Chicago?

The cheapest plane ticket found by our users is $116. 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

$116

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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 $ 396 . And the most expensive tickets are offered by Finnair airline - from $ 4255.

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 $120.

UA - United Airlines

from $219

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NK - Spirit Airlines

from $120

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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 $116.

9K - Cape Air

from $396

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F9 - Frontier Airlines

from $127

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SY - Sun Country Airlines

from $283

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AY - Finnair

from $4255

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DM - Aero-Charter

from $375

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UA - United Airlines

from $208

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NK - Spirit Airlines

from $116

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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 $116
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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

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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.

San Juan — Miami

from $72

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San Juan — New York

from $60

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San Juan — Orlando

from $69

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San Juan — Boston

from $68

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San Juan — Chicago

from $65

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San Juan — Tampa

from $57

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San Juan — Atlanta

from $73

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San Juan — Houston

from $73

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San Juan — Dallas

from $58

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San Juan — Denver

from $62

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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»
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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.
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