HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$102+ Cheap flights from Puerto Rico to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Jan 20 — Jan 271
Tue 1/20
Tue 1/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Puerto Rico to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Puerto Rico to Midway

Cheapest flights from Puerto Rico to Midway
Explore the most affordable flight options available from Puerto Rico to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 21, 2025.

This Expedia deal was found by Cheapflights users on 12/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:54 amSJU - MDW
1 stop12h 43mFrontier
Mon 1/56:15 amMDW - SJU
1 stop18h 24mFrontier
Deal found 12/19$192
This Priceline deal was found by Cheapflights users on 12/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:54 amSJU - MDW
1 stop12h 43mFrontier
Thu 1/13:10 pmMDW - SJU
1 stop16h 13mFrontier
Deal found 12/19$204
This Priceline deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:30 amSJU - MDW
1 stop7h 51mFrontier
Sat 1/106:10 amMDW - SJU
1 stop8h 11mFrontier
Deal found 12/21$213
This Priceline deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/293:55 amSJU - MDW
1 stop20h 03mFrontier
Wed 1/73:01 pmMDW - SJU
1 stop19h 34mFrontier
Deal found 12/18$233
This Expedia deal was found by Cheapflights users on 12/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2510:33 amSJU - MDW
1 stop13h 25mFrontier
Wed 12/313:10 pmMDW - SJU
1 stop9h 40mFrontier
Deal found 12/20$245
This CheapOair deal was found by Cheapflights users on 12/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:00 amSJU - MDW
1 stop17h 58mFrontier
Thu 1/13:10 pmMDW - SJU
1 stop16h 13mFrontier
Deal found 12/19$246
This Frontier deal was found by Cheapflights users on 12/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:54 amSJU - MDW
1 stop12h 43mFrontier
Sun 1/42:16 pmMDW - SJU
1 stop7h 27mFrontier
Deal found 12/19$247
This CheapOair deal was found by Cheapflights users on 12/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:30 amSJU - MDW
1 stop7h 51mFrontier
Sat 1/36:12 amMDW - SJU
1 stop6h 55mFrontier
Deal found 12/19$250
This Trip.com deal was found by Cheapflights users on 12/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:33 pmSJU - MDW
1 stop21h 04mFrontier
Sun 1/42:16 pmMDW - SJU
1 stop10h 34mFrontier
Deal found 12/19$264
This Frontier deal was found by Cheapflights users on 12/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/294:21 pmSJU - MDW
1 stop7h 51mFrontier
Fri 1/23:10 pmMDW - SJU
1 stop9h 40mFrontier
Deal found 12/19$268
This Priceline deal was found by Cheapflights users on 12/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:42 pmBQN - MDW
1 stop29h 16mFrontier
Fri 1/23:10 pmMDW - BQN
1 stop24h 37mFrontier
Deal found 12/20$389

Find flight deals from Puerto Rico to Midway

Keep the following information in mind while searching for Puerto Rico to Midway flight deals. Data was last updated December 21, 2025.

Round-trip from

$177
(CheapOair)

One-way from

$102
(Priceline)

Popular in

December

Cheapest in

February

Average price

$419

Good one-way deal

$326 or less
From Puerto Rico to Chicago Midway
Search Deals
One-way flight from Puerto Rico to Chicago Midway
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a one-way flight from Puerto Rico to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Puerto Rico to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated December 21, 2025.
Use the filters below to find and compare flights from Puerto Rico to Chicago Midway Airport that are best for you.

Fly from

Puerto Rico

Fly to

Midway

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 12/30

7:33 pm-2:37 pm

1 stop21h 04m

Chicago Midway

Sun 1/4

2:16 pm-2:50 am

1 stop10h 34m

$264

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/9

5:45 am-2:06 pm

1 stop10h 21m

Chicago Midway

Fri 1/9

4:31 pm-2:50 am

1 stop8h 19m

$265

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 12/23

3:54 am-2:37 pm

1 stop12h 43m

Chicago Midway

Sat 1/3

6:12 am-3:07 pm

1 stop6h 55m

$290

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 12/25

7:00 am-5:38 pm

1 stop12h 38m

Chicago Midway

Wed 12/31

3:10 pm-2:50 am

1 stop9h 40m

$321

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 12/28

3:54 am-2:05 pm

1 stop12h 11m

Chicago Midway

Fri 1/2

3:10 pm-2:50 am

1 stop9h 40m

$329

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/29

6:10 am-11:35 am

1 stop7h 25m

Chicago Midway

Sun 2/1

9:50 am-10:25 pm

2 stops10h 35m

$330

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/23

8:00 am-10:19 pm

2 stops16h 19m

Chicago Midway

Tue 2/3

1:20 pm-11:59 pm

2 stops32h 39m

$339

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 2/11

3:53 am-2:26 pm

1 stop12h 33m

Chicago Midway

Sun 2/15

7:30 am-2:53 am

1 stop17h 23m

$351

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/16

5:35 am-2:55 pm

2 stops11h 20m

Chicago Midway

Mon 1/19

1:35 pm-12:05 am

2 stops8h 30m

$360

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/16

5:35 am-11:15 am

1 stop7h 40m

Chicago Midway

Tue 1/20

7:35 am-7:05 pm

1 stop9h 30m

$360

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Showing 1-10 of 29 results
1
2
3

Best time to book a flight from Puerto Rico to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Puerto Rico with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Puerto Rico to Chicago Midway Airport

What is the cheapest month to book a flight from Puerto Rico to Chicago Midway Airport?

Currently, December is the cheapest month in which you can book a flight from Puerto Rico to Chicago Midway Airport (average of $137). Flying from Puerto Rico to Chicago Midway Airport in March is currently the most expensive (average of $427). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PR to MDW?

Find hourly flight availability from Puerto Rico to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 21, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 35% on flights from Puerto Rico to Chicago Midway Airport by exploring options for tickets in the morning.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated December 21, 2025.
Read reviews from past customers who have flown Southwest from Puerto Rico to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Puerto Rico to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Puerto Rico to Chicago Midway Airport?

    Airlines like Frontier fly from Puerto Rico to Chicago Midway Airport in about 21h 04m. The time it takes to get you to your destination can typically vary by up to . There are 2057 mi between Puerto Rico and Chicago Midway Airport.

  • What are the cheapest flights from Puerto Rico to Chicago Midway Airport?

    Looking for the cheapest flight from Puerto Rico to Chicago Midway Airport? While on average our users pay $406, our data indicates the cheapest price to be $250. The most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway), is priced around $177.

  • Can I find deals for flights from Puerto Rico to Midway that include hotel bookings?

    Yes. In addition to deals on Puerto Rico to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Puerto Rico to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Puerto Rico to Midway.

  • Can I find deals for business class flights from Puerto Rico to Midway?

    Yes. Cheapflights offers flight deals from Puerto Rico to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Puerto Rico to Chicago Midway Airport?

    Currently, December is the cheapest month in which you can book a flight from Puerto Rico to Chicago Midway Airport (average of $137). Flying from Puerto Rico to Chicago Midway Airport in March is currently the most expensive (average of $427). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Puerto Rico to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Punta Cana to O'Hare Intl flights
Punta Cana to Midway flights
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Midway flights
Santo Domingo to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Nassau to O'Hare Intl flights
Santo Domingo to Midway flights
Saint Thomas Island to O'Hare Intl flights
Kingston to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Nassau to Midway flights
Port of Spain to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Simpson Bay to Midway flights
Christiansted to O'Hare Intl flights
Aguadilla to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Vieques to O'Hare Intl flights
Aguadilla to Midway flights
Culebra to O'Hare Intl flights
Roseau to O'Hare Intl flights
St. John's to O'Hare Intl flights
Road Town to O'Hare Intl flights
George Town to O'Hare Intl flights
Port Au Prince to O'Hare Intl flights
Port Au Prince to Midway flights
Montego Bay to Midway flights

Top airline flying from Puerto Rico to Midway

Discover the top airline that operate flights from Puerto Rico to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$419Average$566FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.