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Cheap flights from Puerto Rico to Chicago from $97

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 3/4. 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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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
6:30 am - 3:33 pm
SJU
-
MDW
10h 03m1 stop
Frontier Logo
11:19 am - 2:03 am
MDW
-
SJU
13h 44m1 stop
$176Frontier
Tue, Mar 24 - Tue, Mar 31
Frontier Logo
3:22 pm - 10:19 pm
SJU
-
MDW
7h 57m1 stop
Frontier Logo
11:19 am - 8:54 am
MDW
-
SJU
20h 35m1 stop
$177Frontier
Wed, Mar 11 - Tue, Mar 17
Frontier Logo
8:00 am - 7:52 pm
SJU
-
MDW
13h 52m1 stop
Frontier Logo
7:00 pm - 12:57 pm
MDW
-
SJU
15h 57m1 stop
$182Frontier
Thu, Feb 5 - Mon, Feb 9
Frontier Logo
6:00 am - 2:26 pm
SJU
-
MDW
10h 26m1 stop
Frontier Logo
6:15 am - 12:39 pm
MDW
-
SJU
28h 24m1 stop
$183Frontier
Thu, Feb 19 - Thu, Feb 26
Frontier Logo
3:22 pm - 10:19 pm
SJU
-
MDW
7h 57m1 stop
Frontier Logo
6:00 am - 2:12 pm
MDW
-
SJU
7h 12m1 stop
$187Frontier
Tue, Mar 17 - Tue, Mar 24
Frontier Logo
6:39 pm - 1:41 pm
SJU
-
MDW
20h 02m1 stop
Frontier Logo
6:00 am - 2:12 pm
MDW
-
SJU
7h 12m1 stop
$192Frontier
Wed, Mar 18 - Wed, Mar 25
Frontier Logo
6:39 pm - 1:41 pm
SJU
-
MDW
20h 02m1 stop
Frontier Logo
4:33 pm - 2:03 am
MDW
-
SJU
8h 30m1 stop
$193Frontier
Wed, Mar 18 - Tue, Mar 24
Frontier Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m1 stop
Frontier Logo
11:19 am - 10:45 pm
MDW
-
SJU
10h 26m1 stop
$198Frontier
Thu, Mar 5 - Wed, Mar 18
Frontier Logo
4:36 pm - 7:52 pm
SJU
-
MDW
29h 16m1 stop
Frontier Logo
1:00 pm - 12:57 pm
MDW
-
SJU
21h 57m1 stop
$203Frontier
Wed, Feb 4 - Mon, Feb 9
Frontier Logo
4:36 pm - 7:52 pm
SJU
-
MDW
29h 16m1 stop
Frontier Logo
1:00 pm - 6:40 pm
MDW
-
SJU
27h 40m1 stop
$209Frontier
Thu, Jan 29 - Sun, Feb 1

Frontier flights from Puerto Rico to Chicago Midway Airport

Our best Frontier deals on Puerto Rico to Chicago Midway Airport flight tickets
Frontier
Mar 10
SJU3:22 pmSan Juan Luis Munoz Marin Intl
7h 57m
1 stop
MDW10:19 pmChicago Midway
Mar 25
MDW6:00 amChicago Midway
7h 12m
1 stop
SJU2:12 pmSan Juan Luis Munoz Marin Intl
$176
Frontier
Mar 11
SJU3:22 pmSan Juan Luis Munoz Marin Intl
7h 57m
1 stop
MDW10:19 pmChicago Midway
Mar 17
MDW11:19 amChicago Midway
20h 35m
1 stop
SJU8:54 amSan Juan Luis Munoz Marin Intl
$177
Frontier
Feb 26
SJU6:00 amSan Juan Luis Munoz Marin Intl
9h 56m
1 stop
MDW1:56 pmChicago Midway
Mar 2
MDW9:22 pmChicago Midway
10h 32m
1 stop
SJU9:54 amSan Juan Luis Munoz Marin Intl
$182

Southwest flights from Puerto Rico to Chicago Midway Airport

Our best Southwest deals on Puerto Rico to Chicago Midway Airport flight tickets
Southwest
Jan 23
SJU6:10 amSan Juan Luis Munoz Marin Intl
9h 45m
2 stops
MDW1:55 pmChicago Midway
Jan 26
MDW7:35 amChicago Midway
9h 30m
1 stop
SJU7:05 pmSan Juan Luis Munoz Marin Intl
$266
Southwest
Jan 23
SJU6:10 amSan Juan Luis Munoz Marin Intl
9h 45m
2 stops
MDW1:55 pmChicago Midway
Jan 26
MDW8:10 amChicago Midway
8h 55m
2 stops
SJU7:05 pmSan Juan Luis Munoz Marin Intl
$296
Southwest
Jan 16
SJU8:00 amSan Juan Luis Munoz Marin Intl
8h 20m
1 stop
MDW2:20 pmChicago Midway
Jan 20
MDW8:10 amChicago Midway
8h 55m
2 stops
SJU7:05 pmSan Juan Luis Munoz Marin Intl
$326

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 January 12, 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

Tue 3/24

6:30 am-3:33 pm

1 stop10h 03m

Chicago Midway

Tue 3/31

11:19 am-2:03 am

1 stop13h 44m

$176

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 3/11

3:22 pm-10:19 pm

1 stop7h 57m

Chicago Midway

Tue 3/17

11:19 am-8:54 am

1 stop20h 35m

$177

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/5

8:00 am-7:52 pm

1 stop13h 52m

Chicago Midway

Mon 2/9

7:00 pm-12:57 pm

1 stop15h 57m

$182

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/19

6:00 am-2:26 pm

1 stop10h 26m

Chicago Midway

Thu 2/26

6:15 am-12:39 pm

1 stop28h 24m

$183

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 3/17

3:22 pm-10:19 pm

1 stop7h 57m

Chicago Midway

Tue 3/24

6:00 am-2:12 pm

1 stop7h 12m

$187

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

Wed 3/25

6:00 am-2:12 pm

1 stop7h 12m

$192

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-2:03 am

1 stop8h 30m

$193

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/5

6:00 am-1:56 pm

1 stop9h 56m

Chicago Midway

Wed 3/18

11:19 am-10:45 pm

1 stop10h 26m

$198

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 2/4

4:36 pm-7:52 pm

1 stop29h 16m

Chicago Midway

Mon 2/9

1:00 pm-12:57 pm

1 stop21h 57m

$203

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/29

4:36 pm-7:52 pm

1 stop29h 16m

Chicago Midway

Sun 2/1

1:00 pm-6:40 pm

1 stop27h 40m

$209

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 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 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?

You could potentially save up to 12% 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

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
4,253 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
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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