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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 8/31. 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
6:30 am - 1:45 pm
SJU
-
MDW
8h 15m
2 stops
Southwest Logo
6:15 am - 1:35 pm
MDW
-
SJU
6h 20m
1 stop
$236Southwest
Thu, Aug 20 - Tue, Sep 8
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
Delta Logo
6:05 am - 4:38 pm
MDW
-
SJU
9h 33m
1 stop
$246Delta
Wed, Aug 19 - Sun, Sep 6
Southwest Logo
9:25 pm - 10:00 am
SJU
-
MDW
13h 35m
1 stop
Southwest Logo
7:50 pm - 9:10 am
MDW
-
SJU
12h 20m
1 stop
$256Southwest
Sun, Aug 23 - Thu, Aug 27
Southwest Logo
6:30 am - 1:45 pm
SJU
-
MDW
8h 15m
2 stops
Southwest Logo
12:45 pm - 10:00 pm
MDW
-
SJU
8h 15m
2 stops
$266Southwest
Fri, Sep 4 - Tue, Sep 8
Delta Logo
12:58 pm - 9:46 pm
SJU
-
MDW
9h 48m
1 stop
Delta Logo
6:05 am - 4:31 pm
MDW
-
SJU
9h 26m
1 stop
$276Delta
Fri, Sep 11 - Tue, Sep 15
Southwest Logo
6:30 am - 3:35 pm
SJU
-
MDW
10h 05m
1 stop
Southwest Logo
3:15 pm - 11:05 pm
MDW
-
SJU
6h 50m
1 stop
$286Southwest
Thu, Sep 3 - Mon, Sep 7
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
Delta Logo
6:05 am - 1:42 pm
MDW
-
SJU
6h 37m
1 stop
$296Delta
Wed, Aug 19 - Mon, Aug 24
Southwest Logo
8:55 pm - 8:45 am
SJU
-
MDW
12h 50m
1 stop
Southwest Logo
7:30 am - 7:00 pm
MDW
-
SJU
10h 30m
1 stop
$300Southwest
Thu, Aug 6 - Tue, Aug 25
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
2 stops
Southwest Logo
3:15 pm - 11:05 pm
MDW
-
SJU
6h 50m
1 stop
$301Southwest
Wed, Aug 5 - Mon, Aug 10
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
Delta Logo
6:05 am - 4:38 pm
MDW
-
SJU
9h 33m
1 stop
$306Delta
Fri, Aug 21 - Sat, Sep 5

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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
Aug 6
SJU6:32 amSan Juan Luis Munoz Marin Intl
15h 00m
1 stop
MDW8:32 pmChicago Midway
Aug 11
MDW5:46 pmChicago Midway
10h 16m
1 stop
SJU5:02 amSan Juan Luis Munoz Marin Intl
$416
Frontier
Jun 22
SJU6:45 pmSan Juan Luis Munoz Marin Intl
28h 26m
2 stops
MDW10:11 pmChicago Midway
Jun 26
MDW6:00 amChicago Midway
17h 37m
2 stops
SJU12:37 amSan Juan Luis Munoz Marin Intl
$924

Southwest flights from Puerto Rico to Chicago Midway Airport

Our best Southwest deals on Puerto Rico to Chicago Midway Airport flight tickets
Southwest
Aug 20
SJU6:30 amSan Juan Luis Munoz Marin Intl
8h 15m
2 stops
MDW1:45 pmChicago Midway
Sep 8
MDW6:15 amChicago Midway
6h 20m
1 stop
SJU1:35 pmSan Juan Luis Munoz Marin Intl
$236
Southwest
Aug 23
SJU9:25 pmSan Juan Luis Munoz Marin Intl
13h 35m
1 stop
MDW10:00 amChicago Midway
Aug 27
MDW2:55 pmChicago Midway
6h 15m
1 stop
SJU10:10 pmSan Juan Luis Munoz Marin Intl
$256
Southwest
Sep 4
SJU6:30 amSan Juan Luis Munoz Marin Intl
8h 15m
2 stops
MDW1:45 pmChicago Midway
Sep 8
MDW12:45 pmChicago Midway
8h 15m
2 stops
SJU10:00 pmSan Juan Luis Munoz Marin Intl
$266

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 June 9, 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
Quickest round-trip

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/20

6:30 am-1:45 pm

2 stops8h 15m

Chicago Midway

Tue 9/8

6:15 am-1:35 pm

1 stop6h 20m

$236

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 8/19

2:59 pm-10:36 pm

1 stop8h 37m

Chicago Midway

Sun 9/6

6:05 am-4:38 pm

1 stop9h 33m

$246

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 8/23

9:25 pm-10:00 am

1 stop13h 35m

Chicago Midway

Thu 8/27

7:50 pm-9:10 am

1 stop12h 20m

$256

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 9/4

6:30 am-1:45 pm

2 stops8h 15m

Chicago Midway

Tue 9/8

12:45 pm-10:00 pm

2 stops8h 15m

$266

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 9/11

12:58 pm-9:46 pm

1 stop9h 48m

Chicago Midway

Tue 9/15

6:05 am-4:31 pm

1 stop9h 26m

$276

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/3

6:30 am-3:35 pm

1 stop10h 05m

Chicago Midway

Mon 9/7

3:15 pm-11:05 pm

1 stop6h 50m

$286

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 8/19

2:59 pm-10:36 pm

1 stop8h 37m

Chicago Midway

Mon 8/24

6:05 am-1:42 pm

1 stop6h 37m

$296

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/6

8:55 pm-8:45 am

1 stop12h 50m

Chicago Midway

Tue 8/25

7:30 am-7:00 pm

1 stop10h 30m

$300

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 8/5

5:15 am-12:05 pm

2 stops7h 50m

Chicago Midway

Mon 8/10

3:15 pm-11:05 pm

1 stop6h 50m

$301

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 8/21

2:59 pm-10:36 pm

1 stop8h 37m

Chicago Midway

Sat 9/5

6:05 am-4:38 pm

1 stop9h 33m

$306

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 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 December is also very affordable. Most momondo users find prices during this month for around $104.

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?

You could potentially save up to 14% on your flight if you consider stops on a Puerto Rico to Chicago Midway Airport flight.

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

Fastest flight time

8h 15m

Direct flights

Mon and Sun
The fastest flight from Puerto Rico to Chicago Midway Airport takes 8h 15m
Direct flights go from Puerto Rico to Chicago Midway Airport on Monday and 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 $326Free CancellationRating
7.9
4,240 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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New Buffalo
Hammond
Saint Joseph
Portage
Benton Harbor
Lansing
Valparaiso
Schererville
Munster
Crown Point
Monticello
Chesterton
Porter
Griffith
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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