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Cheap flights from Puerto Rico to Chicago from $109

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 4/21. 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

Enter your travel dates to find the best prices.
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
9:14 am - 10:48 pm
MDW
-
SJU
12h 34m
1 stop
$202Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
3:19 pm - 4:13 pm
SJU
-
MDW
25h 54m
1 stop
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
$213Frontier
Fri, May 8 - Mon, May 11
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
$214Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
6:00 am - 2:13 pm
MDW
-
SJU
7h 13m
1 stop
$223Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
6:07 pm - 2:01 pm
SJU
-
MDW
20h 54m
1 stop
Frontier Logo
6:30 am - 11:53 pm
MDW
-
SJU
16h 23m
1 stop
$229Frontier
Thu, Apr 9 - Mon, Apr 13
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
$233Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
6:39 pm - 1:41 pm
SJU
-
MDW
20h 02m
1 stop
Frontier Logo
4:33 pm - 10:45 pm
MDW
-
SJU
29h 12m
1 stop
$235Frontier
Wed, Mar 18 - Tue, Mar 24
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
$237Frontier
Fri, May 8 - Mon, May 11
Multiple Airlines Logo
6:30 am - 10:19 pm
SJU
-
MDW
16h 49m
2 stops
Multiple Airlines Logo
6:00 am - 5:31 pm
MDW
-
SJU
10h 31m
1 stop
$241Multiple Airlines
Tue, May 5 - Fri, May 8
Multiple Airlines Logo
2:58 am - 2:59 pm
BQN
-
MDW
13h 01m
2 stops
Multiple Airlines Logo
7:41 pm - 11:51 am
MDW
-
BQN
15h 10m
1 stop
$460Multiple Airlines
Sun, Aug 9 - Thu, Aug 20

Southwest flights from Puerto Rico to Chicago Midway Airport

Our best Southwest deals on Puerto Rico to Chicago Midway Airport flight tickets
Southwest
Apr 21
SJU5:35 amSan Juan Luis Munoz Marin Intl
9h 10m
1 stop
MDW1:45 pmChicago Midway
Apr 24
MDW4:35 pmChicago Midway
6h 20m
1 stop
SJU11:55 pmSan Juan Luis Munoz Marin Intl
$281
Southwest
Mar 7
SJU3:35 pmSan Juan Luis Munoz Marin Intl
5h 20m
MDW6:55 pmChicago Midway
Mar 10
MDW3:45 pmChicago Midway
7h 30m
1 stop
SJU12:15 amSan Juan Luis Munoz Marin Intl
$297
Southwest
May 5
SJU8:10 amSan Juan Luis Munoz Marin Intl
10h 20m
1 stop
MDW5:30 pmChicago Midway
May 8
MDW1:00 pmChicago Midway
9h 25m
1 stop
SJU11:25 pmSan Juan Luis Munoz Marin Intl
$321

Frontier flights from Puerto Rico to Chicago Midway Airport

Our best Frontier deals on Puerto Rico to Chicago Midway Airport flight tickets
Frontier
May 7
SJU3:18 pmSan Juan Luis Munoz Marin Intl
8h 01m
1 stop
MDW10:19 pmChicago Midway
May 10
MDW9:14 amChicago Midway
12h 34m
1 stop
SJU10:48 pmSan Juan Luis Munoz Marin Intl
$202
Frontier
May 8
SJU3:19 pmSan Juan Luis Munoz Marin Intl
25h 54m
1 stop
MDW4:13 pmChicago Midway
May 11
MDW9:14 amChicago Midway
15h 47m
1 stop
SJU2:01 amSan Juan Luis Munoz Marin Intl
$213
Frontier
May 7
SJU3:18 pmSan Juan Luis Munoz Marin Intl
8h 01m
1 stop
MDW10:19 pmChicago Midway
May 10
MDW9:14 amChicago Midway
15h 47m
1 stop
SJU2:01 amSan Juan Luis Munoz Marin Intl
$214

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 March 3, 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

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/7

3:18 pm-10:19 pm

1 stop8h 01m

Chicago Midway

Sun 5/10

9:14 am-10:48 pm

1 stop12h 34m

$202

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/8

3:19 pm-4:13 pm

1 stop25h 54m

Chicago Midway

Mon 5/11

9:14 am-2:01 am

1 stop15h 47m

$213

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/7

3:18 pm-10:19 pm

1 stop8h 01m

Chicago Midway

Sun 5/10

9:14 am-2:01 am

1 stop15h 47m

$214

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/1

3:23 pm-10:26 pm

1 stop8h 03m

Chicago Midway

Mon 5/4

6:00 am-2:13 pm

1 stop7h 13m

$223

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 4/9

6:07 pm-2:01 pm

1 stop20h 54m

Chicago Midway

Mon 4/13

6:30 am-11:53 pm

1 stop16h 23m

$229

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/7

3:18 pm-10:19 pm

1 stop8h 01m

Chicago Midway

Sun 5/10

9:14 am-2:01 am

1 stop15h 47m

$233

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 3/18

6:39 pm-1:41 pm

1 stop20h 02m

Chicago Midway

Tue 3/24

4:33 pm-10:45 pm

1 stop29h 12m

$235

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/8

3:18 pm-10:19 pm

1 stop8h 01m

Chicago Midway

Mon 5/11

9:14 am-2:01 am

1 stop15h 47m

$237

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 5/5

6:30 am-10:19 pm

2 stops16h 49m

Chicago Midway

Fri 5/8

6:00 am-5:31 pm

1 stop10h 31m

$241

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Sun 8/9

2:58 am-2:59 pm

2 stops13h 01m

Chicago Midway

Thu 8/20

7:41 pm-11:51 am

1 stop15h 10m

$460

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 December is, on average, the cheapest month to fly to Chicago Midway Airport from Puerto Rico, with most prices found around $302. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Puerto Rico during the month November is also very affordable. Most momondo users find prices during this month for around $336.

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 flights?

There is only 1 cabin class available to choose from on Puerto Rico to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

4h 50m

Direct flights

Mon and Sun
The fastest flight from Puerto Rico to Chicago Midway Airport takes 4h 50m
Direct flights go from Puerto Rico to Chicago Midway Airport on Monday and Sunday. There are no airlines offering direct flights.
Search flight deals

  • 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 $419Free CancellationRating
8.0
4,302 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
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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