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Cheap flights from Puerto Rico to Chicago from $118

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 11/2. 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 Puerto Rico to Chicago

Recent round-trip flight deals from Puerto Rico to Chicago

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:43 pm - 11:57 pmSJU-ORD
5h 14mnonstop
Multiple Airlines Logo
5:05 am - 2:09 pmORD-SJU
8h 04m1 stop
$203Multiple Airlines
Find Deal
vie., oct. 24 - dom., oct. 26
Spirit Airlines Logo
2:38 pm - 6:00 pmSJU-ORD
5h 22mnonstop
Spirit Airlines Logo
6:55 am - 1:33 pmORD-SJU
4h 38mnonstop
$205Spirit Airlines
Find Deal
jue., dic. 4 - lun., dic. 8
Multiple Airlines Logo
3:40 am - 3:39 pmSJU-ORD
12h 59m1 stop
Multiple Airlines Logo
3:00 pm - 8:40 pmORD-SJU
4h 40mnonstop
$206Multiple Airlines
Find Deal
vie., oct. 17 - sáb., oct. 25
Multiple Airlines Logo
7:43 pm - 11:57 pmSJU-ORD
5h 14mnonstop
Multiple Airlines Logo
5:05 am - 2:06 pmORD-SJU
8h 01m1 stop
$207Multiple Airlines
Find Deal
vie., oct. 24 - lun., oct. 27
Frontier Logo
9:00 am - 12:45 pmSJU-ORD
29h 45m1 stop
Frontier Logo
6:40 am - 5:54 pmORD-SJU
9h 14m1 stop
$246Frontier
Find Deal
jue., nov. 13 - lun., nov. 17
Frontier Logo
12:08 pm - 5:11 pmBQN-ORD
7h 03m1 stop
Frontier Logo
2:33 pm - 3:10 amORD-BQN
10h 37m1 stop
$278Frontier
Find Deal
vie., nov. 21 - sáb., nov. 29
JetBlue Logo
8:15 am - 8:37 pmBQN-ORD
13h 22m2 stops
JetBlue Logo
10:00 am - 10:37 pmORD-BQN
10h 37m2 stops
$481JetBlue
Find Deal
sáb., nov. 1 - sáb., nov. 8
United Airlines Logo
1:09 am - 7:45 amBQN-ORD
8h 36m1 stop
United Airlines Logo
1:01 pm - 11:57 pmORD-BQN
8h 56m1 stop
$485United Airlines
Find Deal
mié., feb. 18 - lun., feb. 23
United Airlines Logo
1:09 am - 2:43 pmBQN-ORD
15h 34m2 stops
United Airlines Logo
11:56 am - 11:57 pmORD-BQN
10h 01m1 stop
$506United Airlines
Find Deal
mié., feb. 18 - lun., feb. 23
JetBlue Logo
5:01 am - 12:23 pmBQN-ORD
8h 22m1 stop
JetBlue Logo
1:35 pm - 2:31 amORD-BQN
11h 56m1 stop
$709JetBlue
Find Deal
dom., oct. 12 - mié., oct. 15

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
Dec 4
SJU2:38 pmSan Juan Luis Munoz Marin Intl
5h 22m
ORD6:00 pmChicago O'Hare Intl
Dec 8
ORD6:55 amChicago O'Hare Intl
4h 38m
SJU1:33 pmSan Juan Luis Munoz Marin Intl
$205
Find similar
Spirit Airlines
Nov 7
SJU3:41 pmSan Juan Luis Munoz Marin Intl
5h 10m
ORD6:51 pmChicago O'Hare Intl
Nov 10
ORD8:00 amChicago O'Hare Intl
4h 36m
SJU2:36 pmSan Juan Luis Munoz Marin Intl
$215
Find similar
Spirit Airlines
Oct 16
SJU11:51 amSan Juan Luis Munoz Marin Intl
12h 54m
1 stop
ORD11:45 pmChicago O'Hare Intl
Oct 20
ORD9:06 pmChicago O'Hare Intl
4h 45m
SJU2:51 amSan Juan Luis Munoz Marin Intl
$218
Find similar

Frontier flights from Puerto Rico to Chicago O'Hare Intl Airport

Our best Frontier deals on Puerto Rico to Chicago O'Hare Intl Airport flight tickets
Frontier
Nov 13
SJU9:00 amSan Juan Luis Munoz Marin Intl
29h 45m
1 stop
ORD12:45 pmChicago O'Hare Intl
Nov 17
ORD6:40 amChicago O'Hare Intl
9h 14m
1 stop
SJU5:54 pmSan Juan Luis Munoz Marin Intl
$246
Find similar
Frontier
Nov 21
BQN12:08 pmAguadilla Borinquen
7h 03m
1 stop
ORD5:11 pmChicago O'Hare Intl
Nov 29
ORD2:33 pmChicago O'Hare Intl
10h 37m
1 stop
BQN3:10 amAguadilla Borinquen
$278
Find similar
Frontier
Oct 4
SJU8:00 amSan Juan Luis Munoz Marin Intl
24h 10m
1 stop
ORD7:10 amChicago O'Hare Intl
Oct 6
ORD8:49 pmChicago O'Hare Intl
28h 41m
1 stop
SJU2:30 amSan Juan Luis Munoz Marin Intl
$279
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 octubre 2, 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

vie. 10/24

7:43 pm-11:57 pm

Nonstop5h 14m

Chicago O'Hare Intl

dom. 10/26

5:05 am-2:09 pm

1 stop8h 04m

$203

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 12/4

2:38 pm-6:00 pm

Nonstop5h 22m

Chicago O'Hare Intl

lun. 12/8

6:55 am-1:33 pm

Nonstop4h 38m

$205

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 10/17

3:40 am-3:39 pm

1 stop12h 59m

Chicago O'Hare Intl

sáb. 10/25

3:00 pm-8:40 pm

Nonstop4h 40m

$206

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 10/24

7:43 pm-11:57 pm

Nonstop5h 14m

Chicago O'Hare Intl

lun. 10/27

5:05 am-2:06 pm

1 stop8h 01m

$207

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 11/13

9:00 am-12:45 pm

1 stop29h 45m

Chicago O'Hare Intl

lun. 11/17

6:40 am-5:54 pm

1 stop9h 14m

$246

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

vie. 11/21

12:08 pm-5:11 pm

1 stop7h 03m

Chicago O'Hare Intl

sáb. 11/29

2:33 pm-3:10 am

1 stop10h 37m

$278

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

sáb. 11/1

8:15 am-8:37 pm

2 stops13h 22m

Chicago O'Hare Intl

sáb. 11/8

10:00 am-10:37 pm

2 stops10h 37m

$481

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

mié. 2/18

1:09 am-7:45 am

1 stop8h 36m

Chicago O'Hare Intl

lun. 2/23

1:01 pm-11:57 pm

1 stop8h 56m

$485

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

mié. 2/18

1:09 am-2:43 pm

2 stops15h 34m

Chicago O'Hare Intl

lun. 2/23

11:56 am-11:57 pm

1 stop10h 01m

$506

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

dom. 10/12

5:01 am-12:23 pm

1 stop8h 22m

Chicago O'Hare Intl

mié. 10/15

1:35 pm-2:31 am

1 stop11h 56m

$709

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 September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Puerto Rico averaging around $291.

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 $374. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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 $506.

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 $251 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $475. 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 $328 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 $275 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?

You could potentially save up to 2% on your flight if you consider stops on a Puerto Rico to Chicago O'Hare Intl Airport flight.

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

$162

Fastest flight time

5h 07m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Puerto Rico in the past 72 hours is $162. The best round-trip flight deal from Puerto Rico to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $299.
The fastest flight from Puerto Rico to Chicago O'Hare Intl Airport takes 5h 07m
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
8,070 reviews
Search Spirit Airlines flights
FrontierPriceFrom $137Free CancellationRating
5.8
3,155 reviews
Search Frontier flights
DeltaPriceFrom $162Free CancellationRating
7.9
7,962 reviews
Search Delta flights
United AirlinesPriceFrom $257Free CancellationRating
7.4
8,933 reviews
Search United Airlines flights
SouthwestPriceFrom $260Free CancellationRating
8.0
4,248 reviews
Search Southwest flights
American AirlinesPriceFrom $338Free 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
South Haven
Rockford
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Orland Park
Hammond
Tinley Park
Elgin
Janesville
Aurora
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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