Cheap Flights from San Juan to Chicago, IL from $89

One way Round trip

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Return flight: Chicago – San Juan

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On Cheapflightsplus.com you will find 3 direct and 39 connecting flights from San Juan to Chicago. You can compare airfare deals from 3 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).

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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 $89. The fastest direct flight takes 4h 59m and the fastest connecting – 7h 6m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $107 Find flight	21:59 San Juan Luis Munoz Marin Intl	00:58+1 день Chicago O'Hare International	4h 59m	Spirit Airlines	NK492
from $107 Find flight	17:41 San Juan Luis Munoz Marin Intl	20:44 Chicago O'Hare International	5h 3m	Spirit Airlines	NK1531
from $270 Find flight	16:52 San Juan Luis Munoz Marin Intl	20:11 Chicago O'Hare International	5h 19m	United Airlines	UA2088
from $89 Find flight	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 Find flight	02:25 San Juan Luis Munoz Marin Intl	10:09 Chicago Midway	9h 44m layover 3h 23m - Philadelphia	Frontier Airlines	F94461 F91617
from $90 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 $90 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 $90 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 $90 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 $90 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 $90 Find flight	21:09 San Juan Luis Munoz Marin Intl	09:13+1 день Chicago Midway	14h 4m layover 7h 50m - Orlando	Frontier Airlines	F94725 F91457
from $95 Find flight	04:08 San Juan Luis Munoz Marin Intl	12:23 Chicago Midway	10h 15m layover 4h 17m - Orlando	Frontier Airlines	F91823 F91457
from $96 Find flight	08:00 San Juan Luis Munoz Marin Intl	00:59+1 день Chicago O'Hare International	18h 59m layover 12h 43m - Orlando	Frontier Airlines	F92249 F93043
from $96 Find flight	17:30 San Juan Luis Munoz Marin Intl	14:02+1 день Chicago Midway	22h 32m layover 16h 43m - Tampa	Frontier Airlines	F92215 F91185
from $137 Find flight	11:46 San Juan Luis Munoz Marin Intl	16:52 Chicago O'Hare International	7h 6m layover 0h 56m - Orlando	Spirit Airlines	NK3160 NK506
from $169 Find flight	16:15 San Juan Luis Munoz Marin Intl	16:46+1 день Chicago O'Hare International	26h 31m layover 19h 56m - Orlando	Frontier Airlines	F92981 F92041

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on March 03, 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
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
21:59 — 00:58 +1 day	21:59 — 00:58 NK492 Spirit Airlines San Juan — Chicago	4h 59m	Find flight from$107
02:05 — 08:47	02:05 — 05:22 UA2219 United Airlines San Juan — Newark 1h 38m stop 07:00 — 08:47 UA1215 United Airlines Newark — Chicago	8h 42m including layover	Find flight from$279
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
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
07:45 — 19:05	07:45 — 10:52 UA1644 United Airlines San Juan — Houston 5h 28m stop 16:20 — 19:05 UA2659 United Airlines Houston — Chicago	13h 20m including layover	Find flight from$553
07:45 — 17:06	07:45 — 10:52 UA1644 United Airlines San Juan — Houston 3h 28m stop 14:20 — 17:06 UA2097 United Airlines Houston — Chicago	11h 21m including layover	Find flight from$604
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
08:10 — 14:03	08:10 — 11:10 UA2022 United Airlines San Juan — Washington D.C. 1h 35m stop 12:45 — 14:03 UA1709 United Airlines Washington D.C. — Chicago	7h 53m including layover	Find flight from$364
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
11:46 — 16:52	11:46 — 13:49 NK3160 Spirit Airlines San Juan — Orlando 56m stop 14:45 — 16:52 NK506 Spirit Airlines Orlando — Chicago	7h 6m including layover	Find flight from$137
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
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
14:25 — 23:58	14:25 — 18:09 UA1368 United Airlines San Juan — Denver 2h 21m stop 20:29 — 23:59 UA377 United Airlines Denver — Chicago	11h 33m including layover	Find flight from$715
15:46 — 00:15 +1 day	15:46 — 18:54 UA668 United Airlines San Juan — Houston 2h 44m stop 21:38 — 00:15 UA1692 United Airlines Houston — Chicago	10h 29m including layover	Find flight from$507
16:15 — 00:59 +1 day	21:49 — 00:10 F92981 Frontier Airlines San Juan — Orlando 4h 18m stop 06:05 — 08:24 F93043 Frontier Airlines Orlando — Chicago	10h 44m including layover	Find flight from$90
16:15 — 16:46 +1 day	16:15 — 18:41 F92981 Frontier Airlines San Juan — Orlando 19h 56m stop 14:37 — 16:46 F92041 Frontier Airlines Orlando — Chicago	26h 31m including layover	Find flight from$169
17:30 — 14:02 +1 day	17:30 — 19:36 F92215 Frontier Airlines San Juan — Tampa 16h 43m stop 12:19 — 14:02 F91185 Frontier Airlines Tampa — Chicago	22h 32m including layover	Find flight from$96
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
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

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

*Departure and arrival times - local. Updated on March 3, 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 3m.

The fastest flight 4h 59m
Average flight time 5h 3m
The earliest flight 02:05
The latest flight 22:47
Distance 2060 ml

The cheapest months to travel to Chicago are december (from 89 $), february (from 90 $), november (from 95 $).

The most expensive months are january (from 270 $), november (from 95 $), february (from 90 $).

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 F93505 flight by Frontier Airlines for February 21, 2025 which leaves Luis Munoz Marin Intl in San Juan at 12:45 am and arrives at Chicago O'Hare International at 00:59.

Economy class

$89

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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 3 regular airlines and 2 low-cost airlines. Most of the flights on this route are operated by Frontier Airlines - 13 departures per week at the price of from $ 89 . And the most expensive tickets are offered by United Airlines airline - from $ 739.

Direct flights

There are 3 nonstop flights on the route. The fastest direct flight is NK492 by Spirit Airlines takes 4h 59m and the cheapest is F93505 by Frontier Airlines for $107.

UA - United Airlines

from $270

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NK - Spirit Airlines

from $107

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Connecting Flights

There are 39 flights with layovers on the route. The fastest connecting flight is NK3160 by Spirit Airlines takes 7h 6m and the cheapest is F93505 by Frontier Airlines for $89.

F9 - Frontier Airlines

from $89

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UA - United Airlines

from $279

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NK - Spirit Airlines

from $137

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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 $89
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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 3 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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