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Cheap flights from Chicago O'Hare Intl Airport to San Juan from $112

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 O'Hare Intl Airport to San Juan departing on 11/20. 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 O'Hare Intl Airport to San Juan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
3:26 pm - 12:32 pmORD-SJU
19h 06m1 stop
Multiple Airlines Logo
1:59 am - 2:03 pmSJU-ORD
14h 04m1 stop
$210Multiple Airlines
Find Deal
Wed, Dec 10 - Sun, Dec 14
Multiple Airlines Logo
12:09 pm - 12:16 amORD-SJU
10h 07m1 stop
Multiple Airlines Logo
1:59 am - 2:03 pmSJU-ORD
14h 04m1 stop
$211Multiple Airlines
Find Deal
Wed, Dec 10 - Sun, Dec 14
Multiple Airlines Logo
10:12 am - 8:27 pmORD-SJU
8h 15m1 stop
Multiple Airlines Logo
2:25 am - 11:11 amSJU-ORD
10h 46m1 stop
$212Multiple Airlines
Find Deal
Thu, Nov 20 - Sun, Nov 23
Multiple Airlines Logo
12:09 pm - 12:16 amORD-SJU
10h 07m1 stop
Multiple Airlines Logo
3:06 pm - 8:42 pmSJU-ORD
7h 36m1 stop
$213Multiple Airlines
Find Deal
Sat, Dec 6 - Fri, Dec 12
Spirit Airlines Logo
11:40 am - 9:50 pmORD-SJU
8h 10m1 stop
Spirit Airlines Logo
8:45 pm - 11:59 pmSJU-ORD
5h 14mnonstop
$215Spirit Airlines
Find Deal
Mon, Nov 24 - Fri, Dec 5
Frontier Logo
6:11 pm - 10:17 amORD-SJU
14h 06m1 stop
Frontier Logo
2:29 am - 2:13 pmSJU-ORD
13h 44m1 stop
$216Frontier
Find Deal
Sat, Jan 10 - Sat, Jan 17
Spirit Airlines Logo
8:41 am - 3:17 pmORD-SJU
4h 36mnonstop
Spirit Airlines Logo
8:45 pm - 11:59 pmSJU-ORD
5h 14mnonstop
$217Spirit Airlines
Find Deal
Wed, Dec 3 - Mon, Dec 15
United Airlines Logo
2:20 pm - 9:00 pmORD-SJU
4h 40mnonstop
United Airlines Logo
4:52 pm - 8:20 pmSJU-ORD
5h 28mnonstop
$218United Airlines
Find Deal
Mon, Jan 19 - Fri, Jan 23
Frontier Logo
7:51 pm - 4:55 pmORD-SJU
19h 04m2 stops
Frontier Logo
4:11 pm - 11:35 pmSJU-ORD
9h 24m1 stop
$220Frontier
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Sun, Jan 18 - Fri, Jan 30
American Airlines Logo
3:15 pm - 9:54 pmORD-SJU
4h 39mnonstop
American Airlines Logo
4:28 pm - 8:00 pmSJU-ORD
5h 32mnonstop
$243American Airlines
Find Deal
Sun, Jan 18 - Thu, Jan 29

Spirit Airlines flights from Chicago O'Hare Intl Airport to San Juan

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to San Juan flight tickets
Spirit Airlines
Nov 24
ORD11:40 amChicago O'Hare Intl
8h 10m
1 stop
SJU9:50 pmSan Juan Luis Munoz Marin Intl
Dec 5
SJU8:45 pmSan Juan Luis Munoz Marin Intl
5h 14m
ORD11:59 pmChicago O'Hare Intl
$215
Find similar
Spirit Airlines
Dec 3
ORD8:41 amChicago O'Hare Intl
4h 36m
SJU3:17 pmSan Juan Luis Munoz Marin Intl
Dec 15
SJU8:45 pmSan Juan Luis Munoz Marin Intl
5h 14m
ORD11:59 pmChicago O'Hare Intl
$217
Find similar
Spirit Airlines
Nov 17
ORD8:00 amChicago O'Hare Intl
4h 36m
SJU2:36 pmSan Juan Luis Munoz Marin Intl
Nov 20
SJU11:55 amSan Juan Luis Munoz Marin Intl
13h 18m
1 stop
ORD11:13 pmChicago O'Hare Intl
$220
Find similar

Frontier flights from Chicago O'Hare Intl Airport to San Juan

Our best Frontier deals on Chicago O'Hare Intl Airport to San Juan flight tickets
Frontier
Jan 10
ORD6:11 pmChicago O'Hare Intl
14h 06m
1 stop
SJU10:17 amSan Juan Luis Munoz Marin Intl
Jan 17
SJU2:29 amSan Juan Luis Munoz Marin Intl
13h 44m
1 stop
ORD2:13 pmChicago O'Hare Intl
$216
Find similar
Frontier
Jan 18
ORD7:51 pmChicago O'Hare Intl
19h 04m
2 stops
SJU4:55 pmSan Juan Luis Munoz Marin Intl
Jan 30
SJU4:11 pmSan Juan Luis Munoz Marin Intl
9h 24m
1 stop
ORD11:35 pmChicago O'Hare Intl
$220
Find similar
Frontier
Nov 18
ORD6:40 amChicago O'Hare Intl
9h 14m
1 stop
SJU5:54 pmSan Juan Luis Munoz Marin Intl
Nov 21
SJU7:11 amSan Juan Luis Munoz Marin Intl
12h 48m
1 stop
ORD5:59 pmChicago O'Hare Intl
$227
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport 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 5, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport 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 12/10

3:26 pm-12:32 pm

1 stop19h 06m

San Juan Luis Munoz Marin Intl

Sun 12/14

1:59 am-2:03 pm

1 stop14h 04m

$210

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 12/10

12:09 pm-12:16 am

1 stop10h 07m

San Juan Luis Munoz Marin Intl

Sun 12/14

1:59 am-2:03 pm

1 stop14h 04m

$211

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 11/20

10:12 am-8:27 pm

1 stop8h 15m

San Juan Luis Munoz Marin Intl

Sun 11/23

2:25 am-11:11 am

1 stop10h 46m

$212

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 12/6

12:09 pm-12:16 am

1 stop10h 07m

San Juan Luis Munoz Marin Intl

Fri 12/12

3:06 pm-8:42 pm

1 stop7h 36m

$213

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 11/24

11:40 am-9:50 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

Fri 12/5

8:45 pm-11:59 pm

Nonstop5h 14m

$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

Sat 1/17

2:29 am-2:13 pm

1 stop13h 44m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 12/3

8:41 am-3:17 pm

Nonstop4h 36m

San Juan Luis Munoz Marin Intl

Mon 12/15

8:45 pm-11:59 pm

Nonstop5h 14m

$217

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/19

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Fri 1/23

4:52 pm-8:20 pm

Nonstop5h 28m

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/18

7:51 pm-4:55 pm

2 stops19h 04m

San Juan Luis Munoz Marin Intl

Fri 1/30

4:11 pm-11:35 pm

1 stop9h 24m

$220

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/18

3:15 pm-9:54 pm

Nonstop4h 39m

San Juan Luis Munoz Marin Intl

Thu 1/29

4:28 pm-8:00 pm

Nonstop5h 32m

$243

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 O'Hare Intl Airport 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 O'Hare Intl Airport and San Juan?

What is the cheapest month to fly to San Juan?

If you’re not able to fly to San Juan in January, then April is your next best option. Flight prices from Chicago O'Hare Intl Airport to San Juan during April average around $348.

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

The cheapest day to depart from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago O'Hare Intl to San Juan flight route?

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago O'Hare Intl - 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 O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to San Juan for around $389 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 O'Hare Intl Airport for as low as $323 on momondo.

What cabin class options are available on Chicago O'Hare Intl to San Juan flights?

There are 4 cabin classes available to choose from on Chicago O'Hare Intl 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 O'Hare Intl Airport to San Juan flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to San Juan

Fastest flight time

4h 24m

Direct flights

Every day

Airports in San Juan

1 airport
The fastest flight from Chicago O'Hare Intl Airport to San Juan takes 4h 24m
Direct flights go from Chicago O'Hare Intl Airport 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 O'Hare Intl to San Juan by plane?

    There are 2067.2 mi between Chicago O'Hare Intl and San Juan. By plane, this route typically takes 4h 36m.

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to San Juan?

    Prices for flights from Chicago O'Hare Intl Airport to San Juan are updated daily.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to San Juan?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to San Juan.

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

    The travel and health documents you'll need for your trip to San Juan may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San Juan. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Chicago O'Hare Intl Airport to San Juan

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to San Juan with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $106Free CancellationRating
5.8
3,115 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $139Free CancellationRating
6.3
8,113 reviews
Search Spirit Airlines flights
DeltaPriceFrom $196Free CancellationRating
7.9
8,004 reviews
Search Delta flights
JetBluePriceFrom $271Free CancellationRating
7.2
2,908 reviews
Search JetBlue flights
United AirlinesPriceFrom $276Free CancellationRating
7.4
9,001 reviews
Search United Airlines flights
American AirlinesPriceFrom $358Free CancellationRating
7.2
11,039 reviews
Search American Airlines flights
SouthwestPriceFrom $385Free CancellationRating
8.0
4,239 reviews
Search Southwest flights

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to San Juan. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Chicago to San Juan on momondo can be filtered to show those which offer flexible booking policies.

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