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Cheap flights from Puerto Rico to Chicago from $108

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 12/4. 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.
Multiple Airlines Logo
6:14 pm - 1:59 pmSJU-MDW
21h 45m2 stops
Multiple Airlines Logo
2:59 pm - 9:37 amMDW-SJU
16h 38m1 stop
$189Multiple Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 7
Frontier Logo
7:10 am - 1:01 pmSJU-MDW
31h 51m1 stop
Frontier Logo
2:59 pm - 9:37 amMDW-SJU
16h 38m1 stop
$194Frontier
Find Deal
Wed, Dec 3 - Sun, Dec 7
Frontier Logo
9:15 am - 1:59 pmSJU-MDW
30h 44m2 stops
Frontier Logo
2:59 pm - 9:37 amMDW-SJU
16h 38m1 stop
$195Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Multiple Airlines Logo
4:10 am - 10:12 pmSJU-MDW
20h 02m2 stops
Multiple Airlines Logo
2:59 pm - 9:37 amMDW-SJU
16h 38m1 stop
$203Multiple Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7
Frontier Logo
1:59 am - 9:28 pmSJU-MDW
21h 29m2 stops
Frontier Logo
2:59 pm - 9:37 amMDW-SJU
16h 38m1 stop
$206Frontier
Find Deal
Thu, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
6:00 am - 6:54 pmSJU-MDW
14h 54m1 stop
Multiple Airlines Logo
9:13 am - 1:20 amMDW-SJU
14h 07m2 stops
$207Multiple Airlines
Find Deal
Fri, Jan 16 - Sun, Jan 18
Frontier Logo
3:55 am - 10:39 pmSJU-MDW
20h 44m1 stop
Frontier Logo
2:59 pm - 9:37 amMDW-SJU
16h 38m1 stop
$211Frontier
Find Deal
Thu, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
8:00 am - 8:46 amSJU-MDW
26h 46m2 stops
Multiple Airlines Logo
2:59 pm - 9:37 amMDW-SJU
16h 38m1 stop
$213Multiple Airlines
Find Deal
Tue, Dec 2 - Sun, Dec 7
Multiple Airlines Logo
7:10 am - 1:01 pmSJU-MDW
31h 51m1 stop
Multiple Airlines Logo
2:49 pm - 12:32 pmMDW-SJU
19h 43m2 stops
$215Multiple Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
Multiple Airlines Logo
6:14 pm - 1:59 pmSJU-MDW
21h 45m2 stops
Multiple Airlines Logo
2:16 pm - 7:50 pmMDW-SJU
27h 34m1 stop
$217Multiple Airlines
Find Deal
Fri, Dec 5 - Thu, Dec 11

Frontier flights from Puerto Rico to Chicago Midway Airport

Our best Frontier deals on Puerto Rico to Chicago Midway Airport flight tickets
Frontier
Dec 3
SJU7:10 amSan Juan Luis Munoz Marin Intl
31h 51m
1 stop
MDW1:01 pmChicago Midway
Dec 7
MDW2:59 pmChicago Midway
16h 38m
1 stop
SJU9:37 amSan Juan Luis Munoz Marin Intl
$194
Find similar
Frontier
Dec 4
SJU1:59 amSan Juan Luis Munoz Marin Intl
21h 29m
2 stops
MDW9:28 pmChicago Midway
Dec 7
MDW2:59 pmChicago Midway
16h 38m
1 stop
SJU9:37 amSan Juan Luis Munoz Marin Intl
$206
Find similar
Frontier
Dec 4
SJU3:55 amSan Juan Luis Munoz Marin Intl
20h 44m
1 stop
MDW10:39 pmChicago Midway
Dec 7
MDW2:59 pmChicago Midway
16h 38m
1 stop
SJU9:37 amSan Juan Luis Munoz Marin Intl
$211
Find similar

Southwest flights from Puerto Rico to Chicago Midway Airport

Our best Southwest deals on Puerto Rico to Chicago Midway Airport flight tickets
Southwest
Jan 21
SJU10:20 amSan Juan Luis Munoz Marin Intl
10h 20m
1 stop
MDW6:40 pmChicago Midway
Jan 28
MDW3:15 pmChicago Midway
7h 20m
1 stop
SJU12:35 amSan Juan Luis Munoz Marin Intl
$225
Find similar
Southwest
Jan 21
SJU6:10 amSan Juan Luis Munoz Marin Intl
9h 45m
2 stops
MDW1:55 pmChicago Midway
Jan 28
MDW1:50 pmChicago Midway
8h 45m
2 stops
SJU12:35 amSan Juan Luis Munoz Marin Intl
$245
Find similar
Southwest
Jan 16
SJU5:35 amSan Juan Luis Munoz Marin Intl
11h 20m
2 stops
MDW2:55 pmChicago Midway
Jan 18
MDW8:25 amChicago Midway
6h 40m
1 stop
SJU5:05 pmSan Juan Luis Munoz Marin Intl
$295
Find similar

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 November 17, 2025.
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

Fri 12/5

6:14 pm-1:59 pm

2 stops21h 45m

Chicago Midway

Sun 12/7

2:59 pm-9:37 am

1 stop16h 38m

$189

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 12/3

7:10 am-1:01 pm

1 stop31h 51m

Chicago Midway

Sun 12/7

2:59 pm-9:37 am

1 stop16h 38m

$194

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/5

9:15 am-1:59 pm

2 stops30h 44m

Chicago Midway

Sun 12/7

2:59 pm-9:37 am

1 stop16h 38m

$195

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 12/4

4:10 am-10:12 pm

2 stops20h 02m

Chicago Midway

Sun 12/7

2:59 pm-9:37 am

1 stop16h 38m

$203

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 12/4

1:59 am-9:28 pm

2 stops21h 29m

Chicago Midway

Sun 12/7

2:59 pm-9:37 am

1 stop16h 38m

$206

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/16

6:00 am-6:54 pm

1 stop14h 54m

Chicago Midway

Sun 1/18

9:13 am-1:20 am

2 stops14h 07m

$207

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 12/4

3:55 am-10:39 pm

1 stop20h 44m

Chicago Midway

Sun 12/7

2:59 pm-9:37 am

1 stop16h 38m

$211

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 12/2

8:00 am-8:46 am

2 stops26h 46m

Chicago Midway

Sun 12/7

2:59 pm-9:37 am

1 stop16h 38m

$213

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 12/3

7:10 am-1:01 pm

1 stop31h 51m

Chicago Midway

Wed 12/10

2:49 pm-12:32 pm

2 stops19h 43m

$215

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/5

6:14 pm-1:59 pm

2 stops21h 45m

Chicago Midway

Thu 12/11

2:16 pm-7:50 pm

1 stop27h 34m

$217

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 $292. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Puerto Rico during the month February is also very affordable. Most momondo users find prices during this month for around $325.

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

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Puerto Rico. The lowest ticket price found for a Friday departure recently was $154. 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, Saturday 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 $610.

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 evening is the least expensive time of day to depart. momondo users have found prices as low as $237 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $580. 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 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.

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

Fastest flight time

5h 20m

Direct flights

Mon and Sun
The fastest flight from Puerto Rico to Chicago Midway Airport takes 5h 20m
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
FrontierPriceFrom $148Free CancellationRating
5.8
3,106 reviews
Search Frontier flights
SouthwestPriceFrom $394Free CancellationRating
8.0
4,244 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
Schererville
Valparaiso
Crown Point
Munster
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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