Cheap Flights from San Juan to Chicago, IL from $79

One way Round trip

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Return flight: Chicago – San Juan

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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 $79, 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: $79 (one-way), $135 (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 $79. The fastest direct flight takes 4h 59m and the fastest connecting – 7h 6m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $116 Find flight	21:59 San Juan Luis Munoz Marin Intl	00:58+1 день Chicago O'Hare International	4h 59m	Spirit Airlines	NK492
from $294 Find flight	16:52 San Juan Luis Munoz Marin Intl	20:11 Chicago O'Hare International	5h 19m	United Airlines	UA2088
from $386 Find flight	16:00 San Juan Luis Munoz Marin Intl	19:26 Chicago O'Hare International	5h 26m	Spirit Airlines	NK518
from $79 Find flight	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 $82 Find flight	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 $97 Find flight	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 $97 Find flight	14:00 San Juan Luis Munoz Marin Intl	21:55 Chicago Midway	9h 55m layover 3h 58m - Raleigh	Frontier Airlines	F91225 F93717
from $97 Find flight	11:16 San Juan Luis Munoz Marin Intl	19:13 Chicago Midway	9h 57m layover 3h 39m - Philadelphia	Frontier Airlines	F91015 F94367
from $97 Find flight	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 $97 Find flight	10:42 San Juan Luis Munoz Marin Intl	19:18 Chicago Midway	10h 36m layover 4h 36m - Miami	Frontier Airlines	F92283 F92109
from $97 Find flight	16:15 San Juan Luis Munoz Marin Intl	00:59+1 день Chicago O'Hare International	10h 44m layover 4h 18m - Orlando	Frontier Airlines	F92981 F93043
from $97 Find flight	13:54 San Juan Luis Munoz Marin Intl	22:41 Chicago Midway	10h 47m layover 3h 14m - Dallas	Frontier Airlines	F94249 F92882
from $97 Find flight	13:55 San Juan Luis Munoz Marin Intl	23:47 Chicago O'Hare International	11h 52m layover 5h 20m - Philadelphia	Frontier Airlines	F91015 F92111
from $97 Find flight	22:47 San Juan Luis Munoz Marin Intl	09:08+1 день Chicago O'Hare International	12h 21m layover 6h 22m - Atlanta	Frontier Airlines	F92081 F91441
from $97 Find flight	06:20 San Juan Luis Munoz Marin Intl	17:12 Chicago Midway	12h 52m layover 6h 40m - Atlanta	Frontier Airlines	F92871 F92143
from $121 Find flight	11:45 San Juan Luis Munoz Marin Intl	17:37 Chicago Midway	7h 52m layover 1h 41m - Baltimore	Frontier Airlines	F92265 F93087

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on May 14, 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
08:35 — 11:54	08:35 — 11:54 UA2089 United Airlines San Juan — Chicago	5h 19m	Find flight from$297
14:17 — 17:47	14:17 — 17:47 NK851 Spirit Airlines San Juan — Chicago	5h 30m	Find flight from$121
16:00 — 19:26	16:00 — 19:26 NK518 Spirit Airlines San Juan — Chicago	5h 26m	Find flight from$386
16:52 — 20:11	16:52 — 20:11 UA2088 United Airlines San Juan — Chicago	5h 19m	Find flight from$294
17:41 — 20:44	17:41 — 20:44 NK1531 Spirit Airlines San Juan — Chicago	5h 3m	Find flight from$116
21:26 — 00:51 +1 day	21:26 — 00:51 NK173 Spirit Airlines San Juan — Chicago	5h 25m	Find flight from$116
21:59 — 00:58 +1 day	21:59 — 00:58 NK492 Spirit Airlines San Juan — Chicago	4h 59m	Find flight from$116
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$97
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$97
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$103
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$80
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$97
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$104
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$153
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$97
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$97
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$121
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$97
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$97
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$97
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$97
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$79
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$82
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$97
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$97
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$149
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$175
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$97
21:15 — 09:52 +1 day	21:15 — 23:37 F94725 Frontier Airlines San Juan — Orlando 7h 53m stop 07:30 — 09:52 F92041 Frontier Airlines Orlando — Chicago	14h 37m including layover	Find flight from$97
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$149
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$97
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$192
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$212
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$226
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$233
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$233
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$236
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$164
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$218
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$217

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

*Departure and arrival times - local. Updated on May 14, 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 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 79 $), december (from 80 $), january (from 82 $).

The most expensive months are february (from 97 $), january (from 82 $), december (from 80 $).

What is the lowest airfare San Juan to Chicago?

The cheapest plane ticket found by our users is $79. 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.

Economy class

$79

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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 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 $ 433 . And the most expensive tickets are offered by United Airlines airline - from $ 1004.

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 $116.

UA - United Airlines

from $294

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NK - Spirit Airlines

from $116

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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 $79.

9K - Cape Air

from $433

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F9 - Frontier Airlines

from $79

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3M - Gulfstream International Airlines

from $452

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UA - United Airlines

from $300

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NK - Spirit Airlines

from $149

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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 $79
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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 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.

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»
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.
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