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Cheap flights from Puerto Rico to Chicago from $119

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 9/5. 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

Frontier Logo
3:39 am - 9:51 amSJU-MDW
7h 12m1 stop
Frontier Logo
6:15 am - 2:11 pmMDW-SJU
6h 56m1 stop
$236Frontier
Find Deal
Fri, Sep 12 - Sat, Sep 20
Frontier Logo
3:16 pm - 11:17 pmSJU-MDW
9h 01m1 stop
Frontier Logo
10:51 am - 11:59 pmMDW-SJU
12h 08m1 stop
$238Frontier
Find Deal
Sat, Sep 13 - Sat, Sep 20
Frontier Logo
1:06 pm - 7:11 amSJU-MDW
19h 05m1 stop
Frontier Logo
10:51 am - 2:34 amMDW-SJU
14h 43m1 stop
$239Frontier
Find Deal
Wed, Sep 10 - Sat, Sep 13
Frontier Logo
3:39 am - 9:51 amSJU-MDW
7h 12m1 stop
Frontier Logo
6:20 am - 2:11 pmMDW-SJU
6h 51m1 stop
$249Frontier
Find Deal
Fri, Sep 26 - Mon, Oct 6
Frontier Logo
3:39 am - 9:51 amSJU-MDW
7h 12m1 stop
Frontier Logo
6:20 am - 2:11 pmMDW-SJU
6h 51m1 stop
$255Frontier
Find Deal
Fri, Sep 26 - Sun, Oct 5
Southwest Logo
1:20 pm - 10:30 pmSJU-MDW
10h 10m1 stop
Southwest Logo
7:30 am - 2:55 pmMDW-SJU
6h 25m1 stop
$263Southwest
Find Deal
Thu, Sep 4 - Tue, Sep 9
Delta Logo
2:26 pm - 9:10 pmSJU-MDW
7h 44m1 stop
Delta Logo
10:35 am - 9:59 pmMDW-SJU
10h 24m1 stop
$264Delta
Find Deal
Sat, Oct 4 - Tue, Oct 7
Southwest Logo
1:20 pm - 10:30 pmSJU-MDW
10h 10m1 stop
Southwest Logo
1:00 pm - 10:45 pmMDW-SJU
8h 45m2 stops
$307Southwest
Find Deal
Thu, Sep 11 - Tue, Sep 16
Southwest Logo
5:00 am - 12:50 pmSJU-MDW
8h 50m2 stops
Southwest Logo
7:30 am - 2:55 pmMDW-SJU
6h 25m1 stop
$327Southwest
Find Deal
Thu, Sep 4 - Tue, Sep 9
Southwest Logo
7:35 am - 3:45 pmSJU-MDW
9h 10m2 stops
Southwest Logo
1:40 pm - 9:45 pmMDW-SJU
6h 05m1 stop
$343Southwest
Find Deal
Sat, Nov 1 - Sun, Nov 9

Frontier flights from Puerto Rico to Chicago Midway Airport

Our best Frontier deals on Puerto Rico to Chicago Midway Airport flight tickets
Frontier
Sep 12
SJU3:39 amSan Juan Luis Munoz Marin Intl
7h 12m
1 stop
MDW9:51 amChicago Midway
Sep 20
MDW6:15 amChicago Midway
6h 56m
1 stop
SJU2:11 pmSan Juan Luis Munoz Marin Intl
$236
Find similar
Frontier
Sep 13
SJU3:16 pmSan Juan Luis Munoz Marin Intl
9h 01m
1 stop
MDW11:17 pmChicago Midway
Sep 20
MDW10:51 amChicago Midway
12h 08m
1 stop
SJU11:59 pmSan Juan Luis Munoz Marin Intl
$238
Find similar
Frontier
Sep 10
SJU1:06 pmSan Juan Luis Munoz Marin Intl
19h 05m
1 stop
MDW7:11 amChicago Midway
Sep 13
MDW10:51 amChicago Midway
14h 43m
1 stop
SJU2:34 amSan Juan Luis Munoz Marin Intl
$239
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
Sep 4
SJU1:20 pmSan Juan Luis Munoz Marin Intl
10h 10m
1 stop
MDW10:30 pmChicago Midway
Sep 9
MDW7:30 amChicago Midway
6h 25m
1 stop
SJU2:55 pmSan Juan Luis Munoz Marin Intl
$263
Find similar
Southwest
Sep 11
SJU1:20 pmSan Juan Luis Munoz Marin Intl
10h 10m
1 stop
MDW10:30 pmChicago Midway
Sep 16
MDW1:00 pmChicago Midway
8h 45m
2 stops
SJU10:45 pmSan Juan Luis Munoz Marin Intl
$307
Find similar
Southwest
Sep 4
SJU5:00 amSan Juan Luis Munoz Marin Intl
8h 50m
2 stops
MDW12:50 pmChicago Midway
Sep 9
MDW7:30 amChicago Midway
6h 25m
1 stop
SJU2:55 pmSan Juan Luis Munoz Marin Intl
$327
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 August 6, 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 9/12

3:39 am-9:51 am

1 stop7h 12m

Chicago Midway

Sat 9/20

6:15 am-2:11 pm

1 stop6h 56m

$236

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 9/13

3:16 pm-11:17 pm

1 stop9h 01m

Chicago Midway

Sat 9/20

10:51 am-11:59 pm

1 stop12h 08m

$238

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 9/10

1:06 pm-7:11 am

1 stop19h 05m

Chicago Midway

Sat 9/13

10:51 am-2:34 am

1 stop14h 43m

$239

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 9/26

3:39 am-9:51 am

1 stop7h 12m

Chicago Midway

Mon 10/6

6:20 am-2:11 pm

1 stop6h 51m

$249

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 9/26

3:39 am-9:51 am

1 stop7h 12m

Chicago Midway

Sun 10/5

6:20 am-2:11 pm

1 stop6h 51m

$255

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/4

1:20 pm-10:30 pm

1 stop10h 10m

Chicago Midway

Tue 9/9

7:30 am-2:55 pm

1 stop6h 25m

$263

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 10/4

2:26 pm-9:10 pm

1 stop7h 44m

Chicago Midway

Tue 10/7

10:35 am-9:59 pm

1 stop10h 24m

$264

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/11

1:20 pm-10:30 pm

1 stop10h 10m

Chicago Midway

Tue 9/16

1:00 pm-10:45 pm

2 stops8h 45m

$307

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/4

5:00 am-12:50 pm

2 stops8h 50m

Chicago Midway

Tue 9/9

7:30 am-2:55 pm

1 stop6h 25m

$327

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 11/1

7:35 am-3:45 pm

2 stops9h 10m

Chicago Midway

Sun 11/9

1:40 pm-9:45 pm

1 stop6h 05m

$343

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 $252. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Puerto Rico during the month September is also very affordable. Most momondo users find prices during this month for around $278.

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 $580.

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 $610. 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

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from Puerto Rico when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $402 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Puerto Rico for as low as $285 on momondo.

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

There are 1 cabin classes 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

Best Price Found

$119

Fastest flight time

5h 15m

Direct flights

Sun
The best one-way flight to Chicago Midway Airport from Puerto Rico in the past 72 hours is $119. The best round-trip flight deal from Puerto Rico to Chicago Midway Airport found on momondo in the last 72 hours is $236.
The fastest flight from Puerto Rico to Chicago Midway Airport takes 5h 15m
Direct flights go from Puerto Rico to Chicago Midway Airport on Sunday. The only airline offering direct flights is Southwest.
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 $130Free CancellationRating
5.8
3,232 reviews
Search Frontier flights
SouthwestPriceFrom $312Free CancellationRating
8.0
4,246 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
Lansing
Portage
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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