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Cheap flights from Chicago to San Juan from $108

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 11/17. 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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0 bags

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Find the cheapest flights from Chicago to San Juan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:40 am - 5:54 pmORD-SJU
10h 14m1 stop
Frontier Logo
1:59 am - 11:52 amSJU-ORD
10h 53m1 stop
$201Frontier
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Wed, Oct 29 - Sat, Nov 1
Frontier Logo
6:30 pm - 8:45 amORD-SJU
36h 15m2 stops
Frontier Logo
9:00 am - 12:45 pmSJU-ORD
29h 45m1 stop
$202Frontier
Find Deal
Fri, Nov 7 - Wed, Nov 12
Frontier Logo
12:37 pm - 1:32 amORD-SJU
34h 55m2 stops
Frontier Logo
9:00 am - 12:45 pmSJU-ORD
29h 45m1 stop
$203Frontier
Find Deal
Wed, Nov 5 - Wed, Nov 12
Multiple Airlines Logo
6:40 am - 5:54 pmORD-SJU
10h 14m1 stop
Multiple Airlines Logo
9:00 am - 9:47 amSJU-ORD
50h 47m2 stops
$209Multiple Airlines
Find Deal
Wed, Oct 29 - Thu, Nov 13
Multiple Airlines Logo
2:31 pm - 3:33 amORD-SJU
11h 02m1 stop
Multiple Airlines Logo
4:12 pm - 7:23 pmSJU-ORD
5h 11mnonstop
$211Multiple Airlines
Find Deal
Wed, Nov 12 - Thu, Nov 20
Spirit Airlines Logo
8:41 am - 3:17 pmORD-SJU
4h 36mnonstop
Spirit Airlines Logo
9:47 pm - 12:59 amSJU-ORD
5h 12mnonstop
$217Spirit Airlines
Find Deal
Tue, Dec 2 - Sun, Dec 7
Spirit Airlines Logo
5:55 am - 12:36 pmORD-SJU
4h 41mnonstop
Spirit Airlines Logo
7:08 pm - 10:30 pmSJU-ORD
5h 22mnonstop
$218Spirit Airlines
Find Deal
Sat, Dec 6 - Tue, Dec 16
United Airlines Logo
2:20 pm - 9:00 pmORD-SJU
4h 40mnonstop
United Airlines Logo
8:35 am - 11:57 amSJU-ORD
5h 22mnonstop
$254United Airlines
Find Deal
Mon, Jan 12 - Fri, Jan 16
Southwest Logo
12:50 pm - 11:00 pmMDW-SJU
8h 10m2 stops
Southwest Logo
3:00 pm - 6:20 pmSJU-MDW
5h 20mnonstop
$259Southwest
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Sat, Jan 24 - Sat, Jan 31
Southwest Logo
7:10 am - 9:30 pmMDW-SJU
12h 20m1 stop
Southwest Logo
10:50 am - 4:10 pmSJU-MDW
7h 20m1 stop
$263Southwest
Find Deal
Tue, Dec 9 - Thu, Feb 26

Spirit Airlines flights from Chicago to San Juan

Our best Spirit Airlines deals on Chicago to San Juan flight tickets
Spirit Airlines
Dec 2
ORD8:41 amChicago O'Hare Intl
4h 36m
SJU3:17 pmSan Juan Luis Munoz Marin Intl
Dec 7
SJU9:47 pmSan Juan Luis Munoz Marin Intl
5h 12m
ORD12:59 amChicago O'Hare Intl
$217
Find similar
Spirit Airlines
Dec 6
ORD5:55 amChicago O'Hare Intl
4h 41m
SJU12:36 pmSan Juan Luis Munoz Marin Intl
Dec 16
SJU7:08 pmSan Juan Luis Munoz Marin Intl
5h 22m
ORD10:30 pmChicago O'Hare Intl
$218
Find similar
Spirit Airlines
Dec 8
ORD5:55 amChicago O'Hare Intl
4h 41m
SJU12:36 pmSan Juan Luis Munoz Marin Intl
Dec 17
SJU7:08 pmSan Juan Luis Munoz Marin Intl
5h 22m
ORD10:30 pmChicago O'Hare Intl
$231
Find similar

Southwest flights from Chicago to San Juan

Our best Southwest deals on Chicago to San Juan flight tickets
Southwest
Jan 24
MDW12:50 pmChicago Midway
8h 10m
2 stops
SJU11:00 pmSan Juan Luis Munoz Marin Intl
Jan 31
SJU3:00 pmSan Juan Luis Munoz Marin Intl
5h 20m
MDW6:20 pmChicago Midway
$259
Find similar
Southwest
Dec 9
MDW7:10 amChicago Midway
12h 20m
1 stop
SJU9:30 pmSan Juan Luis Munoz Marin Intl
Feb 26
SJU10:50 amSan Juan Luis Munoz Marin Intl
7h 20m
1 stop
MDW4:10 pmChicago Midway
$263
Find similar
Southwest
Dec 3
MDW4:35 pmChicago Midway
6h 00m
1 stop
SJU12:35 amSan Juan Luis Munoz Marin Intl
Dec 8
SJU11:20 amSan Juan Luis Munoz Marin Intl
7h 15m
1 stop
MDW4:35 pmChicago Midway
$289
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momondo Fare Finder

 
Customize your flight search to find flights from Chicago to San Juan that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated October 16, 2025.
Use the filters below to find and compare flights from Chicago to San Juan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 10/29

6:40 am-5:54 pm

1 stop10h 14m

San Juan Luis Munoz Marin Intl

Sat 11/1

1:59 am-11:52 am

1 stop10h 53m

$201

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 11/7

6:30 pm-8:45 am

2 stops36h 15m

San Juan Luis Munoz Marin Intl

Wed 11/12

9:00 am-12:45 pm

1 stop29h 45m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 11/5

12:37 pm-1:32 am

2 stops34h 55m

San Juan Luis Munoz Marin Intl

Wed 11/12

9:00 am-12:45 pm

1 stop29h 45m

$203

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 10/29

6:40 am-5:54 pm

1 stop10h 14m

San Juan Luis Munoz Marin Intl

Thu 11/13

9:00 am-9:47 am

2 stops50h 47m

$209

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 11/12

2:31 pm-3:33 am

1 stop11h 02m

San Juan Luis Munoz Marin Intl

Thu 11/20

4:12 pm-7:23 pm

Nonstop5h 11m

$211

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 12/2

8:41 am-3:17 pm

Nonstop4h 36m

San Juan Luis Munoz Marin Intl

Sun 12/7

9:47 pm-12:59 am

Nonstop5h 12m

$217

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 12/6

5:55 am-12:36 pm

Nonstop4h 41m

San Juan Luis Munoz Marin Intl

Tue 12/16

7:08 pm-10:30 pm

Nonstop5h 22m

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/12

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Fri 1/16

8:35 am-11:57 am

Nonstop5h 22m

$254

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/24

12:50 pm-11:00 pm

2 stops8h 10m

San Juan Luis Munoz Marin Intl

Sat 1/31

3:00 pm-6:20 pm

Nonstop5h 20m

$259

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 12/9

7:10 am-9:30 pm

1 stop12h 20m

San Juan Luis Munoz Marin Intl

Thu 2/26

10:50 am-4:10 pm

1 stop7h 20m

$263

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 April, then October is your next best option. Flight prices from Chicago to San Juan during October average around $353.

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 $393. The most expensive day to fly to San Juan is Thursday, with ticket prices averaging around $443.

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 evening when flights can be purchased for as low as $306. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $448 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?

You are more likely to see cheaper flights to San Juan from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San Juan for around $388 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Juan from Chicago for as low as $319 on momondo.

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.

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

Fastest flight time

4h 24m

Direct flights

Every day

Airports in San Juan

1 airport
The fastest flight from Chicago to San Juan takes 4h 24m
Direct flights go from Chicago to San Juan every day.
There is 1 airport near San Juan: San Juan Luis Munoz Marin Intl (SJU)
Search flight deals

  • How far is Chicago to San Juan by plane?

    San Juan is 2052.1 mi away from Chicago. 4h 36m 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 $106Free CancellationRating
5.8
3,137 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $139Free CancellationRating
6.3
8,099 reviews
Search Spirit Airlines flights
DeltaPriceFrom $196Free CancellationRating
7.9
7,982 reviews
Search Delta flights
JetBluePriceFrom $271Free CancellationRating
7.2
2,907 reviews
Search JetBlue flights
United AirlinesPriceFrom $271Free CancellationRating
7.4
8,982 reviews
Search United Airlines flights
American AirlinesPriceFrom $358Free CancellationRating
7.2
11,040 reviews
Search American Airlines flights
SouthwestPriceFrom $379Free CancellationRating
8.0
4,240 reviews
Search Southwest 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
San Juan Isla Grande Airport
San Juan Luis Munoz Marin Intl Airport