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Cheap flights from Chicago O'Hare Intl Airport to Puerto Rico from $107

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 Puerto Rico departing on 10/4. 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 Puerto Rico

Cheap round-trip flights

Frontier Logo
11:00 am - 12:29 amORD-SJU
12h 29m2 stops
Frontier Logo
6:22 am - 11:29 pmSJU-ORD
18h 07m2 stops
$204Frontier
Find Deal
Tue, Oct 7 - Sat, Oct 11
Spirit Airlines Logo
9:06 pm - 2:51 amORD-SJU
4h 45mnonstop
Spirit Airlines Logo
3:19 pm - 9:33 pmSJU-ORD
7h 14m1 stop
$208Spirit Airlines
Find Deal
Fri, Oct 24 - Tue, Oct 28
United Airlines Logo
2:20 pm - 8:00 pmORD-SJU
4h 40mnonstop
United Airlines Logo
8:10 am - 11:32 amSJU-ORD
5h 22mnonstop
$218United Airlines
Find Deal
Tue, Oct 28 - Mon, Nov 3
Multiple Airlines Logo
6:40 am - 2:02 amORD-SJU
18h 22m1 stop
Multiple Airlines Logo
7:43 pm - 11:57 pmSJU-ORD
5h 14mnonstop
$219Multiple Airlines
Find Deal
Wed, Oct 22 - Fri, Oct 31
Multiple Airlines Logo
9:06 pm - 2:51 amORD-SJU
4h 45mnonstop
Multiple Airlines Logo
9:00 am - 1:45 pmSJU-ORD
29h 45m1 stop
$220Multiple Airlines
Find Deal
Fri, Oct 24 - Sat, Nov 1
American Airlines Logo
11:50 am - 11:59 pmORD-SJU
11h 09m1 stop
American Airlines Logo
3:00 pm - 7:20 pmSJU-ORD
5h 20mnonstop
$223American Airlines
Find Deal
Wed, Oct 15 - Wed, Oct 22
American Airlines Logo
9:45 am - 11:59 pmORD-SJU
13h 14m1 stop
American Airlines Logo
5:30 am - 12:04 pmSJU-ORD
7h 34m1 stop
$227American Airlines
Find Deal
Wed, Oct 15 - Wed, Oct 22
JetBlue Logo
6:45 am - 9:37 pmORD-BQN
13h 52m1 stop
JetBlue Logo
6:01 am - 8:52 pmBQN-ORD
16h 51m1 stop
$347JetBlue
Find Deal
Wed, Oct 29 - Wed, Nov 5
JetBlue Logo
1:35 pm - 2:31 amORD-BQN
11h 56m1 stop
JetBlue Logo
5:01 am - 12:22 pmBQN-ORD
8h 21m1 stop
$350JetBlue
Find Deal
Wed, Oct 15 - Wed, Oct 22
United Airlines Logo
12:00 pm - 11:57 pmORD-BQN
9h 57m1 stop
United Airlines Logo
1:09 am - 6:55 pmBQN-ORD
19h 46m2 stops
$442United Airlines
Find Deal
Tue, Dec 9 - Tue, Dec 16

American Airlines flights from Chicago O'Hare Intl Airport to Puerto Rico

Our best American Airlines deals on Chicago O'Hare Intl Airport to Puerto Rico flight tickets
American Airlines
Oct 15
ORD11:50 amChicago O'Hare Intl
11h 09m
1 stop
SJU11:59 pmSan Juan Luis Munoz Marin Intl
Oct 22
SJU3:00 pmSan Juan Luis Munoz Marin Intl
5h 20m
ORD7:20 pmChicago O'Hare Intl
$223
Find similar
American Airlines
Oct 15
ORD9:45 amChicago O'Hare Intl
13h 14m
1 stop
SJU11:59 pmSan Juan Luis Munoz Marin Intl
Oct 22
SJU5:30 amSan Juan Luis Munoz Marin Intl
7h 34m
1 stop
ORD12:04 pmChicago O'Hare Intl
$227
Find similar

Spirit Airlines flights from Chicago O'Hare Intl Airport to Puerto Rico

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Puerto Rico flight tickets
Spirit Airlines
Oct 24
ORD9:06 pmChicago O'Hare Intl
4h 45m
SJU2:51 amSan Juan Luis Munoz Marin Intl
Oct 28
SJU3:19 pmSan Juan Luis Munoz Marin Intl
7h 14m
1 stop
ORD9:33 pmChicago O'Hare Intl
$208
Find similar
Spirit Airlines
Oct 27
ORD9:06 pmChicago O'Hare Intl
4h 45m
SJU2:51 amSan Juan Luis Munoz Marin Intl
Nov 3
SJU8:43 pmSan Juan Luis Munoz Marin Intl
5h 14m
ORD11:57 pmChicago O'Hare Intl
$210
Find similar
Spirit Airlines
Oct 18
ORD7:43 pmChicago O'Hare Intl
14h 13m
1 stop
SJU10:56 amSan Juan Luis Munoz Marin Intl
Oct 25
SJU3:19 pmSan Juan Luis Munoz Marin Intl
7h 14m
1 stop
ORD9:33 pmChicago O'Hare Intl
$213
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport to Puerto Rico 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 September 17, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 10/7

11:00 am-12:29 am

2 stops12h 29m

San Juan Luis Munoz Marin Intl

Sat 10/11

6:22 am-11:29 pm

2 stops18h 07m

$204

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 10/24

9:06 pm-2:51 am

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Tue 10/28

3:19 pm-9:33 pm

1 stop7h 14m

$208

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 10/28

2:20 pm-8:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Mon 11/3

8:10 am-11:32 am

Nonstop5h 22m

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 10/22

6:40 am-2:02 am

1 stop18h 22m

San Juan Luis Munoz Marin Intl

Fri 10/31

7:43 pm-11:57 pm

Nonstop5h 14m

$219

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 10/24

9:06 pm-2:51 am

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Sat 11/1

9:00 am-1:45 pm

1 stop29h 45m

$220

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 10/15

11:50 am-11:59 pm

1 stop11h 09m

San Juan Luis Munoz Marin Intl

Wed 10/22

3:00 pm-7:20 pm

Nonstop5h 20m

$223

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 10/15

9:45 am-11:59 pm

1 stop13h 14m

San Juan Luis Munoz Marin Intl

Wed 10/22

5:30 am-12:04 pm

1 stop7h 34m

$227

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Wed 10/29

6:45 am-9:37 pm

1 stop13h 52m

Aguadilla Borinquen

Wed 11/5

6:01 am-8:52 pm

1 stop16h 51m

$347

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Wed 10/15

1:35 pm-2:31 am

1 stop11h 56m

Aguadilla Borinquen

Wed 10/22

5:01 am-12:22 pm

1 stop8h 21m

$350

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Tue 12/9

12:00 pm-11:57 pm

1 stop9h 57m

Aguadilla Borinquen

Tue 12/16

1:09 am-6:55 pm

2 stops19h 46m

$442

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 Puerto Rico from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Puerto Rico

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 cheapest month to fly to Puerto Rico?

If you don’t want to visit Puerto Rico in January, then you should wait until November to fly from Chicago O'Hare Intl Airport, when ticket prices are also cheap, with an average price of $349.

What is the cheapest day to depart on your flight to Puerto Rico?

On average, the least expensive day to fly to Puerto Rico from Chicago O'Hare Intl Airport is on a Monday. momondo users have found tickets for Monday departures for as low as $396. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Puerto Rico is Thursday, with ticket prices averaging around $448.

What is the cheapest time of day to depart on your flight to Puerto Rico?

Our most recent data shows that the best time of day to fly to Puerto Rico is in the evening. Flights from Chicago O'Hare Intl Airport to Puerto Rico during this time can be as low as $305. In contrast, the most expensive time of day to depart to Puerto Rico is in the morning when prices are around $447.

What is the cheapest Chicago O'Hare Intl to Puerto Rico flight route?

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

How far in advance should I book a flight to Puerto Rico?

You are more likely to see cheaper flights to Puerto Rico from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Puerto Rico for around $390 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Puerto Rico from Chicago O'Hare Intl Airport for as low as $319 on momondo.

What cabin class options are available on Chicago O'Hare Intl to Puerto Rico flights?

There are 4 cabin classes available to choose from on Chicago O'Hare Intl to Puerto Rico 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 O'Hare Intl Airport to Puerto Rico flights?

You could potentially save up to 10% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Puerto Rico flight.

Cheap Chicago O'Hare Intl Airport to Puerto Rico flight deals and tips

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

Best Price Found

$187

Fastest flight time

4h 35m

Direct flights

Every day

Airports in Puerto Rico

1 airport
The best one-way flight to Puerto Rico from Chicago O'Hare Intl Airport in the past 72 hours is $187. The best round-trip flight deal from Chicago O'Hare Intl Airport to Puerto Rico found on momondo in the last 72 hours is $360.
The fastest flight from Chicago O'Hare Intl Airport to Puerto Rico takes 4h 35m
Direct flights go from Chicago O'Hare Intl Airport to Puerto Rico every day.
There is 1 airport near Puerto Rico: San Juan Luis Munoz Marin Intl (SJU)
Search flight deals

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

    Prices for flights from Chicago O'Hare Intl Airport to Puerto Rico are updated daily.

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

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to Puerto Rico?

    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 Puerto Rico.

  • What documentation or ID do you need to fly to Puerto Rico?

    The travel and health documents you'll need for your trip to Puerto Rico 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 Puerto Rico. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago O'Hare Intl Airport to Puerto Rico?

Best airlines flying from Chicago O'Hare Intl Airport to Puerto Rico

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Puerto Rico with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $106Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $139Free CancellationRating
6.3
8,023 reviews
Search Spirit Airlines flights
DeltaPriceFrom $196Free CancellationRating
7.9
7,961 reviews
Search Delta flights
JetBluePriceFrom $271Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
United AirlinesPriceFrom $277Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
American AirlinesPriceFrom $350Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $389Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Puerto Rico?

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 Puerto Rico from Chicago.

Can I find flights from Chicago to Puerto Rico with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Puerto Rico from Chicago with this policy.

How can momondo help me find flights from Chicago to Puerto Rico?

Once all potential Chicago to Puerto Rico flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes. momondo can track prices for Chicago to Puerto Rico flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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