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Cheap flights from Puerto Rico to Chicago from $128

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 8/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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.
Southwest Logo
1:20 pm - 7:10 pm-
6h 50m
Southwest Logo
7:30 am - 7:05 pm-
10h 35m
$256Southwest
Wed, Sep 16 - Tue, Sep 22
Southwest Logo
5:05 am - 11:00 am-
6h 55m
Southwest Logo
7:30 am - 7:05 pm-
10h 35m
$266Southwest
Sat, Sep 5 - Wed, Sep 16
Southwest Logo
5:15 am - 12:05 pm-
7h 50m
Southwest Logo
7:30 am - 7:05 pm-
10h 35m
$266Southwest
Wed, Sep 16 - Tue, Sep 22
Southwest Logo
2:25 pm - 8:45 pm-
7h 20m
Southwest Logo
12:45 pm - 10:05 pm-
8h 20m
$266Southwest
Tue, Sep 1 - Tue, Sep 8
Southwest Logo
8:20 am - 4:45 pm-
9h 25m
Southwest Logo
8:30 am - 6:10 pm-
8h 40m
$266Southwest
Sat, Sep 5 - Tue, Sep 15
Southwest Logo
10:25 am - 7:45 pm-
10h 20m
Southwest Logo
9:40 am - 6:10 pm-
7h 30m
$266Southwest
Sat, Sep 5 - Tue, Sep 15
Southwest Logo
6:00 am - 2:30 pm-
9h 30m
Southwest Logo
8:05 pm - 9:10 am-
12h 05m
$266Southwest
Thu, Sep 10 - Sun, Sep 13
Southwest Logo
8:20 am - 5:05 pm-
9h 45m
Southwest Logo
7:30 am - 7:05 pm-
10h 35m
$266Southwest
Sat, Sep 5 - Wed, Sep 16
Delta Logo
2:59 pm - 10:44 pm-
8h 45m
Delta Logo
6:05 am - 1:45 pm-
6h 40m
$276Delta
Wed, Sep 16 - Wed, Sep 23
Delta Logo
2:59 pm - 10:45 pm-
8h 46m
Delta Logo
6:05 am - 1:45 pm-
6h 40m
$348Delta
Thu, Sep 17 - Wed, Sep 23

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Frontier flights from Puerto Rico to Chicago Midway Airport

Our best Frontier deals on Puerto Rico to Chicago Midway Airport flight tickets
Frontier
Oct 21
SJU3:51 pmSan Juan Luis Munoz Marin Intl
7h 07m
1 stop
MDW9:58 pmChicago Midway
Oct 28
MDW7:25 amChicago Midway
7h 00m
1 stop
SJU3:25 pmSan Juan Luis Munoz Marin Intl
$356
Frontier
Sep 9
SJU6:30 amSan Juan Luis Munoz Marin Intl
12h 21m
1 stop
MDW5:51 pmChicago Midway
Sep 16
MDW6:25 amChicago Midway
7h 54m
1 stop
SJU3:19 pmSan Juan Luis Munoz Marin Intl
$370
Frontier
Sep 16
SJU6:30 amSan Juan Luis Munoz Marin Intl
12h 21m
1 stop
MDW5:51 pmChicago Midway
Sep 20
MDW6:25 amChicago Midway
8h 41m
1 stop
SJU4:06 pmSan Juan Luis Munoz Marin Intl
$382

Southwest flights from Puerto Rico to Chicago Midway Airport

Our best Southwest deals on Puerto Rico to Chicago Midway Airport flight tickets
Southwest
Sep 16
SJU1:20 pmSan Juan Luis Munoz Marin Intl
6h 50m
1 stop
MDW7:10 pmChicago Midway
Sep 22
MDW7:30 amChicago Midway
10h 35m
1 stop
SJU7:05 pmSan Juan Luis Munoz Marin Intl
$256
Southwest
Sep 5
SJU10:25 amSan Juan Luis Munoz Marin Intl
10h 20m
1 stop
MDW7:45 pmChicago Midway
Sep 15
MDW9:40 amChicago Midway
7h 30m
1 stop
SJU6:10 pmSan Juan Luis Munoz Marin Intl
$266
Southwest
Nov 3
SJU5:40 amSan Juan Luis Munoz Marin Intl
7h 40m
1 stop
MDW11:20 amChicago Midway
Nov 3
MDW1:20 pmChicago Midway
7h 00m
1 stop
SJU10:20 pmSan Juan Luis Munoz Marin Intl
$271

momondo Fare Finder

 
Customize your flight search to find flights from Puerto Rico to Chicago Midway 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, 2026.
Use the filters below to find and compare flights from Puerto Rico to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 9/16

1:20 pm-7:10 pm

1 stop6h 50m

Chicago Midway

Tue 9/22

7:30 am-7:05 pm

1 stop10h 35m

$256

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 9/5

5:05 am-11:00 am

1 stop6h 55m

Chicago Midway

Wed 9/16

7:30 am-7:05 pm

1 stop10h 35m

$266

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 9/16

5:15 am-12:05 pm

2 stops7h 50m

Chicago Midway

Tue 9/22

7:30 am-7:05 pm

1 stop10h 35m

$266

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 9/1

2:25 pm-8:45 pm

1 stop7h 20m

Chicago Midway

Tue 9/8

12:45 pm-10:05 pm

2 stops8h 20m

$266

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 9/5

8:20 am-4:45 pm

2 stops9h 25m

Chicago Midway

Tue 9/15

8:30 am-6:10 pm

1 stop8h 40m

$266

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 9/5

10:25 am-7:45 pm

1 stop10h 20m

Chicago Midway

Tue 9/15

9:40 am-6:10 pm

1 stop7h 30m

$266

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/10

6:00 am-2:30 pm

2 stops9h 30m

Chicago Midway

Sun 9/13

8:05 pm-9:10 am

1 stop12h 05m

$266

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 9/5

8:20 am-5:05 pm

2 stops9h 45m

Chicago Midway

Wed 9/16

7:30 am-7:05 pm

1 stop10h 35m

$266
Quickest round-trip

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 9/16

2:59 pm-10:44 pm

1 stop8h 45m

Chicago Midway

Wed 9/23

6:05 am-1:45 pm

1 stop6h 40m

$276

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/17

2:59 pm-10:45 pm

1 stop8h 46m

Chicago Midway

Wed 9/23

6:05 am-1:45 pm

1 stop6h 40m

$348

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Puerto Rico to Chicago Midway 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 Midway Airport?

The month of March is, on average, the cheapest month to fly to Chicago Midway Airport from Puerto Rico, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Puerto Rico during the month August is also very affordable. Most momondo users find prices during this month for around $301.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Puerto Rico. The lowest ticket price found for a Saturday departure recently was $552. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. 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 $726.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Puerto Rico in the morning is the least expensive time of day to depart. momondo users have found prices as low as $552 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $726. 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 Midway flight route?

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

What cabin class options are available on Puerto Rico to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Puerto Rico to Chicago Midway Airport 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 Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Puerto Rico to Chicago Midway Airport.

Cheap Puerto Rico to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Puerto Rico to Chicago Midway Airport

Best Price Found

$279

Fastest flight time

4h 55m

Direct flights

Sun
The best one-way flight to Chicago Midway Airport from Puerto Rico in the past 72 hours is $279. The best round-trip flight deal from Puerto Rico to Chicago Midway Airport found on momondo in the last 72 hours is $565.
The fastest flight from Puerto Rico to Chicago Midway Airport takes 4h 55m
Direct flights go from Puerto Rico to Chicago Midway Airport on Sunday. There are no airlines offering direct flights.
Search flight deals

Frequently asked questions about flying from Puerto Rico to Chicago Midway Airport

  • When did momondo last update prices for flights from Puerto Rico to Chicago Midway Airport?

    Prices for flights from Puerto Rico to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Puerto Rico to Chicago Midway Airport?

  • How old do you have to be to fly from Puerto Rico to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Puerto Rico to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport 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 Chicago Midway Airport. 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 Puerto Rico to Chicago Midway Airport?

Best airlines flying from Puerto Rico to Chicago Midway Airport

Compare and see reviews for airlines that fly from Puerto Rico to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $266Free CancellationRating
8.0
4,220 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Saint John

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. All flights to Chicago from Puerto Rico on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo helps you find the best flight between Puerto Rico and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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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