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Cheap flights from Chicago to San Juan from $59

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 1/27. 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.
8:44 pm - 9:35 amORD-SJU
10h 51m1 stop
6:35 am - 1:20 pmSJU-ORD
8h 45m1 stop
$116Frontier
Find Deal
Sat, Feb 22 - Thu, Feb 27
3:25 pm - 12:35 amORD-SJU
7h 10m1 stop
6:55 pm - 9:52 amSJU-ORD
16h 57m1 stop
$122Frontier
Find Deal
Mon, Jan 13 - Thu, Jan 30
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$135Spirit Airlines
Find Deal
Tue, Jan 21 - Wed, Jan 29
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$149Spirit Airlines
Find Deal
Sat, Jan 25 - Sat, Feb 1
12:51 pm - 12:36 amORD-SJU
9h 45m1 stop
2:05 am - 10:44 amSJU-ORD
10h 39m1 stop
$234United Airlines
Find Deal
Mon, Feb 3 - Sun, Feb 9
9:00 am - 3:38 pmORD-SJU
4h 38mnonstop
2:05 am - 10:46 amSJU-ORD
10h 41m1 stop
$255United Airlines
Find Deal
Mon, Feb 10 - Wed, Feb 12
8:55 am - 3:30 pmMDW-SJU
4h 35mnonstop
6:00 am - 11:45 amSJU-MDW
7h 45m1 stop
$275Southwest
Find Deal
Sat, Feb 1 - Tue, Feb 4
8:25 am - 9:40 pmMDW-SJU
11h 15m1 stop
6:00 am - 4:50 pmSJU-MDW
12h 50m2 stops
$279Southwest
Find Deal
Fri, Jan 24 - Tue, Jan 28
6:00 am - 2:36 pmMDW-SJU
6h 36m1 stop
2:00 pm - 10:20 pmSJU-MDW
10h 20m1 stop
$324Delta
Find Deal
Tue, Jan 14 - Thu, Jan 23
6:00 am - 5:14 pmMDW-SJU
9h 14m1 stop
4:15 pm - 10:20 pmSJU-MDW
8h 05m1 stop
$369Delta
Find Deal
Mon, Jan 13 - Wed, Jan 15
5:28 pm - 11:30 amORD-SJU
16h 02m1 stop
$59Frontier
Find Deal
Mon, Jan 27
5:28 pm - 2:19 amORD-SJU
6h 51m1 stop
$64Frontier
Find Deal
Mon, Jan 27
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
$70Spirit Airlines
Find Deal
Sun, Jan 19
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
$74Spirit Airlines
Find Deal
Sun, Jan 26
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
$138United Airlines
Find Deal
Thu, Mar 6
6:00 am - 2:36 pmMDW-SJU
6h 36m1 stop
$162Delta
Find Deal
Tue, Jan 14
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
$188United Airlines
Find Deal
Sat, Mar 8
8:15 am - 1:50 pmORD-SJU
4h 35mnonstop
$208American Airlines
Find Deal
Fri, Apr 11
6:00 am - 5:14 pmMDW-SJU
9h 14m1 stop
$222Delta
Find Deal
Sun, Feb 9
7:17 pm - 12:36 pmORD-SJU
16h 19m1 stop
$242American Airlines
Find Deal
Fri, Apr 11
10:29 am - 2:49 amORD-SJU
14h 20m1 stop
9:15 pm - 9:27 amSJU-ORD
14h 12m1 stop
$234Frontier
Find Deal
Wed, Jan 1 - Wed, Jan 15
8:55 pm - 1:05 pmORD-SJU
14h 10m1 stop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$237Spirit Airlines
Find Deal
Wed, Jan 1 - Wed, Jan 15
8:30 am - 3:10 pmORD-SJU
4h 40mnonstop
1:30 am - 8:25 amSJU-ORD
8h 55m1 stop
$414American Airlines
Find Deal
Sun, Dec 29 - Sun, Dec 29
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
2:05 am - 9:28 amSJU-ORD
9h 23m1 stop
$415United Airlines
Find Deal
Mon, Dec 30 - Fri, Jan 17
6:37 am - 4:15 pmORD-SJU
7h 38m1 stop
1:30 am - 9:25 amSJU-ORD
9h 55m1 stop
$418American Airlines
Find Deal
Sun, Dec 29 - Sun, Dec 29
8:00 pm - 6:12 amORD-SJU
8h 12m1 stop
2:05 am - 9:40 amSJU-ORD
9h 35m1 stop
$419United Airlines
Find Deal
Wed, Jan 1 - Tue, Jan 14
10:08 am - 9:12 pmMDW-SJU
9h 04m1 stop
7:30 am - 2:34 pmSJU-MDW
9h 04m1 stop
$557Delta
Find Deal
Sun, Dec 29 - Tue, Dec 31
11:55 am - 12:45 amMDW-SJU
10h 50m2 stops
2:55 pm - 7:45 pmSJU-MDW
6h 50m1 stop
$564Southwest
Find Deal
Tue, Dec 31 - Fri, Jan 10
12:10 pm - 12:40 amMDW-SJU
10h 30m2 stops
1:35 pm - 9:40 pmSJU-MDW
10h 05m1 stop
$603Southwest
Find Deal
Mon, Dec 30 - Tue, Dec 31
12:10 pm - 9:12 pmMDW-SJU
7h 02m1 stop
7:30 am - 2:53 pmSJU-MDW
9h 23m1 stop
$818Delta
Find Deal
Sat, Dec 28 - Sat, Jan 11
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$135Spirit Airlines
Find Deal
Tue, Jan 21 - Wed, Jan 29
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$148Spirit Airlines
Find Deal
Fri, Jan 24 - Fri, Jan 31
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$149Spirit Airlines
Find Deal
Mon, Feb 3 - Sat, Feb 8
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$151Spirit Airlines
Find Deal
Fri, Jan 24 - Fri, Jan 31
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$156Spirit Airlines
Find Deal
Tue, Feb 4 - Sat, Feb 8
8:05 am - 1:45 pmORD-SJU
4h 40mnonstop
3:10 pm - 7:25 pmSJU-ORD
5h 15mnonstop
$225American Airlines
Find Deal
Tue, May 6 - Thu, May 8
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
7:35 am - 11:54 amSJU-ORD
5h 19mnonstop
$289United Airlines
Find Deal
Thu, Mar 6 - Tue, Mar 11
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
7:35 am - 11:54 amSJU-ORD
5h 19mnonstop
$345United Airlines
Find Deal
Thu, Mar 6 - Mon, Mar 10
8:05 am - 1:45 pmORD-SJU
4h 40mnonstop
3:10 pm - 7:25 pmSJU-ORD
5h 15mnonstop
$384American Airlines
Find Deal
Sun, May 25 - Mon, Jun 2
8:55 am - 3:30 pmMDW-SJU
4h 35mnonstop
5:00 pm - 8:15 pmSJU-MDW
5h 15mnonstop
$590Southwest
Find Deal
Sat, Feb 8 - Sat, Feb 15

Spirit Airlines flights from Chicago to San Juan

Our best Spirit Airlines deals on Chicago to San Juan flight tickets
Spirit Airlines
Jan 21
ORD1:44 pmChicago O'Hare Intl
4h 37m
SJU8:21 pmSan Juan Luis Munoz Marin Intl
Jan 29
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 amChicago O'Hare Intl
Spirit Airlines
Jan 25
ORD1:44 pmChicago O'Hare Intl
4h 37m
SJU8:21 pmSan Juan Luis Munoz Marin Intl
Feb 1
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 amChicago O'Hare Intl
Spirit Airlines
Feb 3
ORD1:44 pmChicago O'Hare Intl
4h 37m
SJU8:21 pmSan Juan Luis Munoz Marin Intl
Feb 6
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 amChicago O'Hare Intl

Frontier flights from Chicago to San Juan

Our best Frontier deals on Chicago to San Juan flight tickets
Frontier
Feb 22
ORD8:44 pmChicago O'Hare Intl
10h 51m
1 stop
SJU9:35 amSan Juan Luis Munoz Marin Intl
Feb 27
SJU6:35 amSan Juan Luis Munoz Marin Intl
8h 45m
1 stop
ORD1:20 pmChicago O'Hare Intl
Frontier
Jan 13
ORD3:25 pmChicago O'Hare Intl
7h 10m
1 stop
SJU12:35 amSan Juan Luis Munoz Marin Intl
Jan 30
SJU6:55 pmSan Juan Luis Munoz Marin Intl
16h 57m
1 stop
ORD9:52 amChicago O'Hare Intl
Frontier
Mar 3
ORD4:58 pmChicago O'Hare Intl
7h 56m
1 stop
SJU2:54 amSan Juan Luis Munoz Marin Intl
Mar 4
SJU6:35 amSan Juan Luis Munoz Marin Intl
8h 45m
1 stop
ORD1:20 pmChicago O'Hare Intl

See travel insights to San Juan from

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 to San Juan?

If you’re not able to fly to San Juan in August, then September is your next best option. Flight prices from Chicago to San Juan during September average around $293.

What is the cheapest day to depart on your flight to San Juan?

The cheapest day to depart from Chicago to San Juan is on a Tuesday when prices can be found for as low as $335. The most expensive day to fly to San Juan is Sunday, with ticket prices averaging around $405.

What is the cheapest time of day to depart on your flight to San Juan?

The cheapest time of day to fly to San Juan is in the afternoon when flights can be purchased for as low as $295. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $385 on average. Flights to San Juan from Chicago in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago to San Juan flight route?

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago - San Juan flight prices

How far in advance should I book a flight to San Juan?

We recommend purchasing flights from Chicago to San Juan 59 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to San Juan for $361. However, in the past 72 hours, people saw flights from Chicago for as low as $268.

What cabin class options are available on Chicago to San Juan flights?

There are 4 cabin classes available to choose from on Chicago to San Juan flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

You could potentially save up to 15% 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

$59

Fastest flight time

4h 31m

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 $59. The best round-trip flight deal from Chicago to San Juan found on momondo in the last 72 hours is $116.
The fastest flight from Chicago to San Juan takes 4h 31m
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 31m 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
6.0
3,463 reviews
Search Frontier flights
JetBluePriceFrom $137Free CancellationRating
7.4
3,240 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $159Free CancellationRating
6.3
8,104 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $254Free CancellationRating
7.4
9,001 reviews
Search United Airlines flights
SouthwestPriceFrom $304Free CancellationRating
8.1
4,749 reviews
Search Southwest flights
DeltaPriceFrom $307Free CancellationRating
8.0
8,560 reviews
Search Delta flights
American AirlinesPriceFrom $324Free 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