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Cheap flights from Puerto Rico to Chicago from $88

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Puerto Rico to Chicago departing on 8/21. 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 Puerto Rico to Chicago

Recent round-trip flight deals from Puerto Rico to Chicago

Spirit Airlines Logo
10:16 pm - 9:22 amSJU-ORD
12h 06m1 stop
Spirit Airlines Logo
5:16 pm - 12:56 amORD-SJU
6h 40m1 stop
$186Spirit Airlines
Find Deal
Fri, Aug 15 - Sun, Aug 17
Spirit Airlines Logo
10:16 pm - 9:22 amSJU-ORD
12h 06m1 stop
Spirit Airlines Logo
6:56 am - 3:10 pmORD-SJU
7h 14m1 stop
$198Spirit Airlines
Find Deal
Fri, Aug 15 - Mon, Aug 18
Logo
8:00 pm - 9:22 amSJU-ORD
14h 22m1 stop
Logo
6:35 am - 3:25 pmORD-SJU
7h 50m1 stop
$240
Find Deal
Thu, Aug 21 - Mon, Aug 25
Logo
10:16 pm - 9:22 amSJU-ORD
12h 06m1 stop
Logo
9:32 am - 12:03 amORD-SJU
13h 31m1 stop
$241
Find Deal
Fri, Aug 15 - Fri, Aug 29
Frontier Logo
3:32 am - 3:17 pmBQN-ORD
12h 45m1 stop
Frontier Logo
8:49 pm - 10:56 amORD-BQN
13h 07m1 stop
$258Frontier
Find Deal
Fri, Sep 19 - Fri, Oct 3
Frontier Logo
3:39 am - 3:17 pmSJU-ORD
12h 38m1 stop
Frontier Logo
8:49 pm - 10:57 amORD-SJU
13h 08m1 stop
$258Frontier
Find Deal
Fri, Sep 26 - Mon, Oct 6
United Airlines Logo
12:15 am - 4:59 pmBQN-ORD
17h 44m2 stops
United Airlines Logo
7:15 am - 11:09 pmORD-BQN
14h 54m2 stops
$415United Airlines
Find Deal
Mon, Sep 15 - Tue, Sep 30
United Airlines Logo
12:15 am - 6:34 pmBQN-ORD
19h 19m2 stops
United Airlines Logo
7:15 am - 11:09 pmORD-BQN
14h 54m2 stops
$422United Airlines
Find Deal
Mon, Sep 15 - Tue, Sep 30
JetBlue Logo
5:01 am - 6:55 pmBQN-ORD
14h 54m2 stops
JetBlue Logo
1:35 pm - 2:33 amORD-BQN
11h 58m1 stop
$423JetBlue
Find Deal
Thu, Sep 18 - Tue, Sep 30
JetBlue Logo
5:01 am - 8:49 pmBQN-ORD
16h 48m1 stop
JetBlue Logo
6:45 am - 2:31 amORD-BQN
18h 46m1 stop
$430JetBlue
Find Deal
Thu, Oct 2 - Sun, Oct 5

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

Our best United Airlines deals on Puerto Rico to Chicago O'Hare Intl Airport flight tickets
United Airlines
Sep 15
BQN12:15 amAguadilla Borinquen
17h 44m
2 stops
ORD4:59 pmChicago O'Hare Intl
Sep 30
ORD7:15 amChicago O'Hare Intl
14h 54m
2 stops
BQN11:09 pmAguadilla Borinquen
$415
Find similar
United Airlines
Sep 15
BQN12:15 amAguadilla Borinquen
19h 19m
2 stops
ORD6:34 pmChicago O'Hare Intl
Sep 30
ORD7:15 amChicago O'Hare Intl
14h 54m
2 stops
BQN11:09 pmAguadilla Borinquen
$422
Find similar
United Airlines
Sep 15
BQN12:15 amAguadilla Borinquen
19h 19m
2 stops
ORD6:34 pmChicago O'Hare Intl
Sep 29
ORD7:25 amChicago O'Hare Intl
14h 44m
2 stops
BQN11:09 pmAguadilla Borinquen
$427
Find similar

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

Our best Spirit Airlines deals on Puerto Rico to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Aug 15
SJU10:16 pmSan Juan Luis Munoz Marin Intl
12h 06m
1 stop
ORD9:22 amChicago O'Hare Intl
Aug 17
ORD5:16 pmChicago O'Hare Intl
6h 40m
1 stop
SJU12:56 amSan Juan Luis Munoz Marin Intl
$186
Find similar
Spirit Airlines
Aug 15
SJU10:16 pmSan Juan Luis Munoz Marin Intl
12h 06m
1 stop
ORD9:22 amChicago O'Hare Intl
Aug 18
ORD5:05 amChicago O'Hare Intl
15h 43m
1 stop
SJU9:48 pmSan Juan Luis Munoz Marin Intl
$191
Find similar
Spirit Airlines
Aug 15
SJU10:16 pmSan Juan Luis Munoz Marin Intl
12h 06m
1 stop
ORD9:22 amChicago O'Hare Intl
Aug 18
ORD6:56 amChicago O'Hare Intl
7h 14m
1 stop
SJU3:10 pmSan Juan Luis Munoz Marin Intl
$198
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Puerto Rico to Chicago O'Hare Intl Airport 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 August 5, 2025.
Use the filters below to find and compare flights from Puerto Rico to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 8/15

10:16 pm-9:22 am

1 stop12h 06m

Chicago O'Hare Intl

Sun 8/17

5:16 pm-12:56 am

1 stop6h 40m

$186

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 8/15

10:16 pm-9:22 am

1 stop12h 06m

Chicago O'Hare Intl

Mon 8/18

6:56 am-3:10 pm

1 stop7h 14m

$198

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 8/21

8:00 pm-9:22 am

1 stop14h 22m

Chicago O'Hare Intl

Mon 8/25

6:35 am-3:25 pm

1 stop7h 50m

$240

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 8/15

10:16 pm-9:22 am

1 stop12h 06m

Chicago O'Hare Intl

Fri 8/29

9:32 am-12:03 am

1 stop13h 31m

$241

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Fri 9/19

3:32 am-3:17 pm

1 stop12h 45m

Chicago O'Hare Intl

Fri 10/3

8:49 pm-10:56 am

1 stop13h 07m

$258

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 9/26

3:39 am-3:17 pm

1 stop12h 38m

Chicago O'Hare Intl

Mon 10/6

8:49 pm-10:57 am

1 stop13h 08m

$258

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Mon 9/15

12:15 am-4:59 pm

2 stops17h 44m

Chicago O'Hare Intl

Tue 9/30

7:15 am-11:09 pm

2 stops14h 54m

$415

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Mon 9/15

12:15 am-6:34 pm

2 stops19h 19m

Chicago O'Hare Intl

Tue 9/30

7:15 am-11:09 pm

2 stops14h 54m

$422

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Thu 9/18

5:01 am-6:55 pm

2 stops14h 54m

Chicago O'Hare Intl

Tue 9/30

1:35 pm-2:33 am

1 stop11h 58m

$423

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Thu 10/2

5:01 am-8:49 pm

1 stop16h 48m

Chicago O'Hare Intl

Sun 10/5

6:45 am-2:31 am

1 stop18h 46m

$430

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 Chicago from

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

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 Chicago O'Hare Intl Airport?

The month of August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Puerto Rico averaging around $254.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $347. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Puerto Rico because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $490.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Puerto Rico in the evening is the least expensive time of day to depart. momondo users have found prices as low as $244 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $481. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Puerto Rico when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $318 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Puerto Rico for as low as $254 on momondo.

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

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

No. A direct flight is the cheapest option for a flight between Puerto Rico to Chicago O'Hare Intl Airport.

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

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

Best Price Found

$88

Fastest flight time

5h 03m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Puerto Rico in the past 72 hours is $88. The best round-trip flight deal from Puerto Rico to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $186.
The fastest flight from Puerto Rico to Chicago O'Hare Intl Airport takes 5h 03m
Direct flights go from Puerto Rico to Chicago O'Hare Intl Airport every day.
Search flight deals

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

    Prices for flights from Puerto Rico to Chicago O'Hare Intl Airport were last updated today.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Puerto Rico to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

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

Compare and see reviews for airlines that fly from Puerto Rico to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $136Free CancellationRating
6.3
8,053 reviews
Search Spirit Airlines flights
FrontierPriceFrom $137Free CancellationRating
5.8
3,232 reviews
Search Frontier flights
DeltaPriceFrom $162Free CancellationRating
8.0
7,987 reviews
Search Delta flights
United AirlinesPriceFrom $218Free CancellationRating
7.4
8,912 reviews
Search United Airlines flights
SouthwestPriceFrom $257Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
American AirlinesPriceFrom $329Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Rockford
Schaumburg
South Haven
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Tinley Park
Elgin
Orland Park
Aurora
Janesville
Benton Harbor

Why use momondo?

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

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 Chicago from Puerto Rico.

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

Yes. momondo allows you to filter the results for Puerto Rico to Chicago flights to just show those with flexible booking policies.

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

Once all potential Puerto Rico to Chicago 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 Puerto Rico to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Puerto Rico to Chicago 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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