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Cheap flights from Chicago to San Juan from $57

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to San Juan departing on 11/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago to San Juan

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to San Juan that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to San Juan.

Cheap last minute flights

Planning a quick getaway from Chicago to San Juan? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to San Juan, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to San Juan

Find recent round-trip train or bus tickets from Chicago to San Juan.

All round-trip flight deals to San Juan

The cheapest plane tickets to San Juan found on KAYAK recently.
3:16 pm - 12:59 amORD-SJU
7h 43m1 stop
6:00 am - 10:04 pmSJU-ORD
18h 04m1 stop
$158Frontier
Find Deal
Mon, Jan 27 - Mon, Feb 3
6:49 pm - 9:25 amMDW-SJU
12h 36m1 stop
9:15 pm - 10:02 amSJU-MDW
14h 47m1 stop
$158Frontier
Find Deal
Sat, Jan 4 - Sat, Jan 11
8:26 pm - 2:52 amORD-SJU
28h 26m1 stop
5:40 am - 9:04 amSJU-ORD
5h 24mnonstop
Mon, Nov 11 - Fri, Nov 22
1:50 pm - 8:20 pmORD-SJU
4h 30mnonstop
8:35 pm - 11:56 pmSJU-ORD
5h 21mnonstop
$160Spirit Airlines
Find Deal
Wed, Nov 13 - Fri, Nov 15
8:26 pm - 10:10 amORD-SJU
11h 44m1 stop
9:44 pm - 1:13 amSJU-ORD
5h 29mnonstop
Mon, Nov 11 - Thu, Nov 14
6:11 pm - 12:43 amORD-SJU
4h 32mnonstop
6:40 pm - 7:45 pmSJU-ORD
27h 05m1 stop
$171Spirit Airlines
Find Deal
Tue, Dec 3 - Mon, Dec 9
1:05 pm - 11:44 pmMDW-SJU
8h 39m1 stop
6:00 am - 11:59 amSJU-MDW
7h 59m1 stop
$349Delta
Find Deal
Thu, Jan 16 - Mon, Jan 27
11:55 am - 12:30 amMDW-SJU
10h 35m1 stop
2:55 pm - 6:10 pmSJU-MDW
5h 15mnonstop
$370Southwest
Find Deal
Sat, Jan 4 - Sat, Jan 18
12:10 pm - 12:40 amMDW-SJU
10h 30m2 stops
5:35 am - 2:45 pmSJU-MDW
11h 10m2 stops
$374Southwest
Find Deal
Thu, Jan 2 - Fri, Jan 17
10:49 am - 10:21 pmMDW-SJU
10h 32m1 stop
1:50 pm - 9:46 pmSJU-MDW
9h 56m1 stop
$384Delta
Find Deal
Sat, Oct 26 - Wed, Nov 13
6:30 am - 1:49 amORD-SJU
17h 19m1 stop
$57Frontier
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Thu, Nov 7
8:23 pm - 2:52 amORD-SJU
28h 29m1 stop
$63Frontier
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Fri, Nov 8
7:48 am - 4:28 pmMDW-SJU
6h 40m1 stop
$63Frontier
Find Deal
Sat, Feb 22
8:32 am - 3:05 pmORD-SJU
4h 33mnonstop
$68Spirit Airlines
Find Deal
Thu, Nov 28
1:10 pm - 7:40 pmORD-SJU
4h 30mnonstop
$74Spirit Airlines
Find Deal
Fri, Nov 15
1:05 pm - 11:44 pmMDW-SJU
8h 39m1 stop
$162Delta
Find Deal
Tue, Jan 21
6:00 am - 2:31 pmMDW-SJU
6h 31m1 stop
$187Delta
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Wed, Nov 20
2:20 pm - 7:55 pmORD-SJU
4h 35mnonstop
$193United Airlines
Find Deal
Mon, Oct 28
10:31 am - 10:20 pmORD-SJU
9h 49m2 stops
$197American Airlines
Find Deal
Mon, Nov 4
5:44 pm - 11:00 amORD-SJU
16h 16m1 stop
$225American Airlines
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Fri, Apr 11
10:16 am - 2:40 amORD-SJU
15h 24m1 stop
9:20 pm - 12:49 amSJU-ORD
5h 29mnonstop
$205Spirit Airlines
Find Deal
Sat, Oct 26 - Wed, Nov 13
10:16 am - 2:40 amORD-SJU
15h 24m1 stop
10:20 pm - 9:26 amSJU-ORD
12h 06m1 stop
$221Spirit Airlines
Find Deal
Fri, Oct 25 - Fri, Nov 1
10:16 am - 2:40 amORD-SJU
15h 24m1 stop
8:35 pm - 11:56 pmSJU-ORD
5h 21mnonstop
$231Spirit Airlines
Find Deal
Sat, Oct 26 - Fri, Nov 8
2:54 pm - 3:48 amMDW-SJU
11h 54m1 stop
9:30 pm - 8:34 amSJU-MDW
13h 04m1 stop
$238Frontier
Find Deal
Sat, Oct 26 - Sat, Nov 16
1:39 pm - 3:48 amORD-SJU
13h 09m1 stop
10:30 am - 7:43 pmSJU-ORD
11h 13m1 stop
$258Frontier
Find Deal
Sat, Oct 26 - Thu, Nov 14
12:49 pm - 10:21 pmMDW-SJU
8h 32m1 stop
1:50 pm - 9:46 pmSJU-MDW
9h 56m1 stop
$384Delta
Find Deal
Thu, Oct 24 - Wed, Nov 13
7:35 am - 8:35 pmORD-SJU
12h 00m1 stop
1:05 am - 7:34 amSJU-ORD
7h 29m1 stop
$393United Airlines
Find Deal
Fri, Oct 25 - Fri, Oct 25
8:35 pm - 10:51 amORD-SJU
13h 16m1 stop
12:00 pm - 9:06 pmSJU-ORD
10h 06m2 stops
$394American Airlines
Find Deal
Fri, Oct 25 - Mon, Oct 28
6:00 am - 1:41 pmMDW-SJU
6h 41m1 stop
12:57 pm - 9:38 pmSJU-MDW
9h 41m1 stop
$394Delta
Find Deal
Sat, Oct 26 - Sat, Nov 2
2:20 pm - 7:55 pmORD-SJU
4h 35mnonstop
2:05 am - 9:44 amSJU-ORD
9h 39m1 stop
$470United Airlines
Find Deal
Sun, Oct 27 - Tue, Nov 12
1:50 pm - 8:20 pmORD-SJU
4h 30mnonstop
9:44 pm - 1:13 amSJU-ORD
5h 29mnonstop
$160Spirit Airlines
Find Deal
Wed, Nov 13 - Thu, Nov 14
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
2:17 pm - 5:47 pmSJU-ORD
5h 30mnonstop
$173Spirit Airlines
Find Deal
Wed, Dec 11 - Mon, Dec 16
1:50 pm - 8:20 pmORD-SJU
4h 30mnonstop
5:40 am - 9:04 amSJU-ORD
5h 24mnonstop
$174Spirit Airlines
Find Deal
Wed, Nov 20 - Sun, Nov 24
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
2:17 pm - 5:47 pmSJU-ORD
5h 30mnonstop
$182Spirit Airlines
Find Deal
Fri, Dec 6 - Fri, Dec 13
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
2:17 pm - 5:47 pmSJU-ORD
5h 30mnonstop
$186Spirit Airlines
Find Deal
Tue, Dec 10 - Sat, Dec 14
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
$380United Airlines
Find Deal
Tue, Nov 19 - Tue, Nov 26
8:55 am - 3:30 pmMDW-SJU
4h 35mnonstop
2:55 pm - 6:10 pmSJU-MDW
5h 15mnonstop
$385Southwest
Find Deal
Sat, Jan 25 - Sat, Feb 1
2:20 pm - 7:55 pmORD-SJU
4h 35mnonstop
7:35 am - 11:54 amSJU-ORD
5h 19mnonstop
$387United Airlines
Find Deal
Wed, Oct 30 - Fri, Nov 1
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
8:35 am - 11:54 amSJU-ORD
5h 19mnonstop
$390United Airlines
Find Deal
Sat, Nov 16 - Wed, Nov 20
8:45 am - 3:20 pmMDW-SJU
4h 35mnonstop
5:00 pm - 8:15 pmSJU-MDW
5h 15mnonstop
$1,273Southwest
Find Deal
Sat, Feb 15 - Sat, Feb 22

Frontier flights from Chicago to San Juan

Our best Frontier deals on Chicago to San Juan flight tickets
Frontier
Jan 4
MDW6:49 pmChicago Midway
12h 36m
1 stop
SJU9:25 amSan Juan Luis Munoz Marin Intl
Jan 11
SJU9:15 pmSan Juan Luis Munoz Marin Intl
14h 47m
1 stop
MDW10:02 amChicago Midway
Frontier
Nov 16
MDW2:52 pmChicago Midway
11h 55m
1 stop
SJU4:47 amSan Juan Luis Munoz Marin Intl
Nov 20
SJU11:18 amSan Juan Luis Munoz Marin Intl
22h 37m
1 stop
MDW7:55 amChicago Midway
Frontier
Nov 13
ORD1:11 pmChicago O'Hare Intl
11h 41m
1 stop
SJU2:52 amSan Juan Luis Munoz Marin Intl
Nov 14
SJU10:30 amSan Juan Luis Munoz Marin Intl
11h 13m
1 stop
ORD7:43 pmChicago O'Hare Intl

Spirit Airlines flights from Chicago to San Juan

Our best Spirit Airlines deals on Chicago to San Juan flight tickets
Spirit Airlines
Nov 13
ORD1:50 pmChicago O'Hare Intl
4h 30m
SJU8:20 pmSan Juan Luis Munoz Marin Intl
Nov 15
SJU8:35 pmSan Juan Luis Munoz Marin Intl
5h 21m
ORD11:56 pmChicago O'Hare Intl
Spirit Airlines
Dec 3
ORD6:11 pmChicago O'Hare Intl
4h 32m
SJU12:43 amSan Juan Luis Munoz Marin Intl
Dec 9
SJU6:40 pmSan Juan Luis Munoz Marin Intl
27h 05m
1 stop
ORD7:45 pmChicago O'Hare Intl
Spirit Airlines
Dec 11
ORD1:00 pmChicago O'Hare Intl
4h 36m
SJU7:36 pmSan Juan Luis Munoz Marin Intl
Feb 5
SJU5:41 pmSan Juan Luis Munoz Marin Intl
5h 03m
ORD8:44 pmChicago O'Hare Intl

How to get the cheapest flight ticket from Chicago to San Juan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago and San Juan?

What is the cheapest month to fly from Chicago to San Juan?

January. The cheapest time of year to fly to San Juan from Chicago is January. Most expensive is March

What is the cheapest day to depart Chicago for San Juan?

Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Sunday

When is the cheapest time to fly from Chicago to San Juan?

In the afternoon. Chicago to San Juan flights are approximately 27% more expensive at noon than in the afternoon

What is the cheapest airline that flies to San Juan from Chicago?

Spirit Airlines. Spirit Airlines, Frontier, and JetBlue are the most popular carriers operating from Chicago to San Juan

What is the cheapest Chicago to San Juan flight route?

Chicago Midway - San Juan Luis Munoz Marin Intl. Fly from Chicago Midway to San Juan Luis Munoz Marin Intl for the best Chicago - San Juan flight prices

How far in advance should you book Chicago to San Juan flights?

38 days before. The cheapest time to buy a flight from Chicago to San Juan is approximately 38 days to departure

How many flights depart from Chicago to San Juan on average per day?

2 flights are operational weekly from Chicago to San Juan as of October 2024. The most popular departure time for this route is 9:00AM, with 100% of flights per day taking off at noon.

How many flights depart from Chicago to San Juan on average per week?

As of October 2024, there are 20 flights per week flying from Chicago to San Juan. The most common day of the week flights depart is Monday, with 20% of flights taking off on this day.

Can stopping save me money on Chicago to San Juan flights?

You could potentially save up to 16% on your flight if you consider stops on a Chicago to San Juan flight.

Cheap Chicago to San Juan flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to San Juan

Best Price Found

$57

Fastest flight time

4h 30m

Direct flights

Every day

Airports in San Juan

1 airport
The best one-way flight to San Juan from Chicago in the past 72 hours is $57. The best round-trip flight deal from Chicago to San Juan found on momondo in the last 72 hours is $158.
The fastest flight from Chicago to San Juan takes 4h 30m
Direct flights go from Chicago to San Juan every day.
There is 1 airport near San Juan: San Juan Luis Munoz Marin Intl (SJU)

  • How far is Chicago to San Juan by plane?

    San Juan is 2052.1 mi away from Chicago. 4h 30m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago to San Juan?

    Prices for flights from Chicago to San Juan refresh daily.

  • How many operators does momondo search for flights from Chicago to San Juan?

  • How old do you have to be to fly from Chicago to San Juan?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to San Juan.

  • What documentation or ID do you need to fly to San Juan?

    The travel and health documents required for your trip to San Juan can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at San Juan. We always recommend checking with your airline or a trusted third party such as IATA to get advice.


Best airlines flying from Chicago to San Juan

Compare and see reviews for airlines that fly from Chicago to San Juan with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $119Free CancellationRating
6.1
3,612 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $159Free CancellationRating
6.3
8,199 reviews
Search Spirit Airlines flights
JetBluePriceFrom $173Free CancellationRating
7.5
3,552 reviews
Search JetBlue flights
DeltaPriceFrom $204Free CancellationRating
8.0
8,885 reviews
Search Delta flights
SouthwestPriceFrom $267Free CancellationRating
8.1
5,156 reviews
Search Southwest flights
United AirlinesPriceFrom $268Free CancellationRating
7.4
9,283 reviews
Search United Airlines flights
American AirlinesPriceFrom $325Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San Juan?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to San Juan from Chicago.

Can I find flights from Chicago to San Juan with flexible booking policies on momondo?

Yes. All flights to San Juan from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to San Juan?

momondo provides multiple filters to help you find the best flight to San Juan from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San Juan right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to San Juan from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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Find better results for your trip to Puerto Rico

Fly into one of these airports located in San Juan
Airports listed have a maximum distance of 7.1 mi from San Juan