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Cheap flights from Chicago to San Juan from $113

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 12/31. 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.
Multiple Airlines Logo
12:22 pm - 6:54 pmORD-SJU
4h 32mnonstop
Multiple Airlines Logo
4:11 pm - 11:35 pmSJU-ORD
9h 24m1 stop
$211Multiple Airlines
Find Deal
Fri, Feb 20 - Fri, Feb 27
Frontier Logo
8:56 pm - 9:55 amMDW-SJU
10h 59m1 stop
Frontier Logo
4:11 pm - 11:25 pmSJU-MDW
9h 14m1 stop
$211Frontier
Find Deal
Sun, Mar 1 - Thu, Mar 5
Multiple Airlines Logo
2:00 pm - 12:49 amORD-SJU
8h 49m1 stop
Multiple Airlines Logo
8:45 pm - 11:59 pmSJU-ORD
5h 14mnonstop
$212Multiple Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 14
Frontier Logo
6:40 am - 5:54 pmORD-SJU
9h 14m1 stop
Frontier Logo
4:11 pm - 10:23 pmSJU-ORD
8h 12m1 stop
$213Frontier
Find Deal
Thu, Feb 19 - Tue, Mar 3
Multiple Airlines Logo
6:23 pm - 8:27 pmORD-SJU
24h 04m2 stops
Multiple Airlines Logo
3:06 pm - 8:42 pmSJU-ORD
7h 36m1 stop
$214Multiple Airlines
Find Deal
Thu, Nov 27 - Fri, Dec 5
Frontier Logo
5:50 am - 3:19 pmORD-SJU
7h 29m1 stop
Frontier Logo
8:57 am - 2:39 pmSJU-ORD
7h 42m1 stop
$215Frontier
Find Deal
Sun, Jan 11 - Sat, Jan 17
Frontier Logo
6:11 pm - 10:17 amORD-SJU
14h 06m1 stop
Frontier Logo
4:06 pm - 12:12 amSJU-ORD
10h 06m1 stop
$216Frontier
Find Deal
Sat, Jan 10 - Thu, Jan 15
Spirit Airlines Logo
12:22 pm - 6:54 pmORD-SJU
4h 32mnonstop
Spirit Airlines Logo
1:22 pm - 4:37 pmSJU-ORD
5h 15mnonstop
$217Spirit Airlines
Find Deal
Sat, Jan 24 - Mon, Feb 9
Spirit Airlines Logo
12:22 pm - 6:54 pmORD-SJU
4h 32mnonstop
Spirit Airlines Logo
1:22 pm - 4:37 pmSJU-ORD
5h 15mnonstop
$218Spirit Airlines
Find Deal
Fri, Jan 23 - Mon, Jan 26
Delta Logo
10:53 am - 11:44 pmMDW-SJU
10h 51m1 stop
Delta Logo
3:55 pm - 10:26 pmSJU-MDW
8h 31m1 stop
$225Delta
Find Deal
Tue, Jan 20 - Tue, Jan 27

United Airlines flights from Chicago to San Juan

Our best United Airlines deals on Chicago to San Juan flight tickets
United Airlines
Jan 20
ORD2:20 pmChicago O'Hare Intl
4h 40m
SJU9:00 pmSan Juan Luis Munoz Marin Intl
Jan 26
SJU2:05 amSan Juan Luis Munoz Marin Intl
10h 48m
1 stop
ORD10:53 amChicago O'Hare Intl
$222
Find similar
United Airlines
Feb 15
ORD6:20 pmChicago O'Hare Intl
9h 51m
1 stop
SJU6:11 amSan Juan Luis Munoz Marin Intl
Feb 19
SJU8:10 amSan Juan Luis Munoz Marin Intl
8h 10m
1 stop
ORD2:20 pmChicago O'Hare Intl
$257
Find similar

Delta flights from Chicago to San Juan

Our best Delta deals on Chicago to San Juan flight tickets
Delta
Jan 20
MDW10:53 amChicago Midway
10h 51m
1 stop
SJU11:44 pmSan Juan Luis Munoz Marin Intl
Jan 27
SJU3:55 pmSan Juan Luis Munoz Marin Intl
8h 31m
1 stop
MDW10:26 pmChicago Midway
$225
Find similar
Delta
Feb 3
ORD9:52 amChicago O'Hare Intl
9h 05m
1 stop
SJU8:57 pmSan Juan Luis Munoz Marin Intl
Feb 14
SJU6:15 amSan Juan Luis Munoz Marin Intl
9h 24m
1 stop
ORD1:39 pmChicago O'Hare Intl
$227
Find similar
Delta
Nov 27
MDW10:47 amChicago Midway
10h 26m
1 stop
SJU11:13 pmSan Juan Luis Munoz Marin Intl
Dec 5
SJU6:38 pmSan Juan Luis Munoz Marin Intl
7h 09m
1 stop
MDW11:47 pmChicago Midway
$290
Find similar

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 November 13, 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

Fri 2/20

12:22 pm-6:54 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Fri 2/27

4:11 pm-11:35 pm

1 stop9h 24m

$211

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 3/1

8:56 pm-9:55 am

1 stop10h 59m

San Juan Luis Munoz Marin Intl

Thu 3/5

4:11 pm-11:25 pm

1 stop9h 14m

$211

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 12/5

2:00 pm-12:49 am

1 stop8h 49m

San Juan Luis Munoz Marin Intl

Sun 12/14

8:45 pm-11:59 pm

Nonstop5h 14m

$212

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 2/19

6:40 am-5:54 pm

1 stop9h 14m

San Juan Luis Munoz Marin Intl

Tue 3/3

4:11 pm-10:23 pm

1 stop8h 12m

$213

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 11/27

6:23 pm-8:27 pm

2 stops24h 04m

San Juan Luis Munoz Marin Intl

Fri 12/5

3:06 pm-8:42 pm

1 stop7h 36m

$214

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/11

5:50 am-3:19 pm

1 stop7h 29m

San Juan Luis Munoz Marin Intl

Sat 1/17

8:57 am-2:39 pm

1 stop7h 42m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/10

6:11 pm-10:17 am

1 stop14h 06m

San Juan Luis Munoz Marin Intl

Thu 1/15

4:06 pm-12:12 am

1 stop10h 06m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/24

12:22 pm-6:54 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Mon 2/9

1:22 pm-4:37 pm

Nonstop5h 15m

$217

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 1/23

12:22 pm-6:54 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Mon 1/26

1:22 pm-4:37 pm

Nonstop5h 15m

$218

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/20

10:53 am-11:44 pm

1 stop10h 51m

San Juan Luis Munoz Marin Intl

Tue 1/27

3:55 pm-10:26 pm

1 stop8h 31m

$225

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 May is your next best option. Flight prices from Chicago to San Juan during May average around $352.

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 $444.

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 $314. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $450 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 $392 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 $335 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)
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  • How far is Chicago to San Juan by plane?

    San Juan is 2052.1 mi away from Chicago. 4h 32m 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
3,114 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $139Free CancellationRating
6.3
8,139 reviews
Search Spirit Airlines flights
DeltaPriceFrom $196Free CancellationRating
7.9
8,007 reviews
Search Delta flights
JetBluePriceFrom $271Free CancellationRating
7.2
2,907 reviews
Search JetBlue flights
United AirlinesPriceFrom $276Free CancellationRating
7.4
9,015 reviews
Search United Airlines flights
American AirlinesPriceFrom $358Free CancellationRating
7.2
11,050 reviews
Search American Airlines flights
SouthwestPriceFrom $380Free CancellationRating
8.0
4,236 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