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Midway

$97+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Feb 13 — Feb 201
Fri 2/13
Fri 2/20
1 adult, Economy
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Cheap 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 January 14, 2026.

Round-trip from

$182
(Frontier)

One-way from

$97
(Priceline)

Popular in

December

Cheapest in

May

Average price

$302
From Puerto Rico to Chicago Midway
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One-way flight from Puerto Rico to Chicago Midway
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Highest demand for flights based on searches. 5% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find 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 January 14, 2026.

This Frontier deal was found by Cheapflights users on 1/11. 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.
Thu 2/266:00 am
SJU
-
MDW
1 stop9h 56m
Frontier
Mon 3/29:22 pm
MDW
-
SJU
1 stop10h 32m
Frontier
Deal found 1/11$182
This CheapOair deal was found by Cheapflights users on 1/12. 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.
Thu 2/194:11 pm
SJU
-
MDW
1 stop8h 26m
Frontier
Thu 2/266:15 am
MDW
-
SJU
1 stop28h 24m
Frontier
Deal found 1/12$183
This Booking.com deal was found by Cheapflights users on 1/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/273:53 am
SJU
-
MDW
1 stop13h 02m
Frontier
Sat 3/74:46 pm
MDW
-
SJU
1 stop9h 12m
Frontier
Deal found 1/14$201
This Priceline deal was found by Cheapflights users on 1/13. 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 2/44:36 pm
SJU
-
MDW
1 stop29h 16m
Frontier
Mon 2/97:00 pm
MDW
-
SJU
1 stop15h 57m
Frontier
Deal found 1/13$203
This CheapOair deal was found by Cheapflights users on 1/12. 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.
Thu 2/58:00 am
SJU
-
MDW
1 stop13h 52m
Frontier
Mon 2/91:00 pm
MDW
-
SJU
1 stop21h 57m
Frontier
Deal found 1/12$209
This CheapOair deal was found by Cheapflights users on 1/12. 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.
Thu 2/194:11 pm
SJU
-
MDW
1 stop8h 26m
Frontier
Sun 2/226:15 am
MDW
-
SJU
1 stop28h 24m
Frontier
Deal found 1/12$210
This Priceline deal was found by Cheapflights users on 1/13. 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.
Fri 2/64:22 pm
SJU
-
MDW
1 stop7h 57m
Frontier
Mon 2/97:00 pm
MDW
-
SJU
1 stop15h 57m
Frontier
Deal found 1/13$217
This CheapOair deal was found by Cheapflights users on 1/14. 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.
Fri 2/2012:27 pm
SJU
-
MDW
1 stop28h 28m
Frontier
Mon 2/239:22 pm
MDW
-
SJU
1 stop27h 31m
Frontier
Deal found 1/14$218
This Frontier deal was found by Cheapflights users on 1/12. 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.
Thu 3/56:00 am
SJU
-
MDW
1 stop9h 56m
Frontier
Mon 3/99:51 pm
MDW
-
SJU
1 stop11h 06m
Frontier
Deal found 1/12$220
This CheapOair deal was found by Cheapflights users on 1/12. 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.
Thu 2/266:00 am
SJU
-
MDW
1 stop9h 56m
Frontier
Sun 3/16:15 am
MDW
-
SJU
1 stop17h 54m
Frontier
Deal found 1/12$222
This Trip.com deal was found by Cheapflights users on 1/13. 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.
Fri 1/3011:34 am
SJU
-
MDW
1 stop10h 18m
Frontier
Mon 2/21:00 pm
MDW
-
SJU
1 stop8h 59m
Frontier
Deal found 1/13$227
This Frontier deal was found by Cheapflights users on 1/13. 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.
Wed 3/116:30 am
SJU
-
MDW
1 stop12h 43m
Frontier
Tue 3/1711:19 am
MDW
-
SJU
1 stop10h 26m
Frontier
Deal found 1/13$228

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 January 14, 2026.
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

Wed 2/18

5:25 pm-2:26 pm

1 stop23h 01m

Chicago Midway

Sat 2/21

8:00 am-1:27 pm

1 stop27h 27m

$183

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 2/27

3:53 am-2:55 pm

1 stop13h 02m

Chicago Midway

Sat 3/7

4:46 pm-3:58 am

1 stop9h 12m

$201

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 4/10

11:30 am-9:58 pm

1 stop11h 28m

Chicago Midway

Mon 4/13

8:00 am-12:45 am

1 stop15h 45m

$210

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 2/6

4:22 pm-10:19 pm

1 stop7h 57m

Chicago Midway

Mon 2/9

7:00 pm-12:57 pm

1 stop15h 57m

$217

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/5

4:11 pm-10:29 pm

1 stop8h 18m

Chicago Midway

Mon 3/9

6:15 am-2:09 pm

1 stop6h 54m

$220

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 2/18

5:25 pm-2:26 pm

1 stop23h 01m

Chicago Midway

Fri 2/20

7:30 am-12:57 pm

1 stop27h 27m

$258

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Sun 2/22

3:58 am-8:27 pm

1 stop18h 29m

Chicago Midway

Thu 2/26

7:30 am-2:57 am

1 stop17h 27m

$264

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/29

5:40 am-12:30 pm

2 stops8h 50m

Chicago Midway

Sat 1/31

2:45 pm-12:10 am

1 stop7h 25m

$266

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/23

9:05 am-6:35 pm

1 stop11h 30m

Chicago Midway

Mon 1/26

3:15 pm-12:35 am

1 stop7h 20m

$266

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 2/17

3:53 am-7:07 pm

2 stops17h 14m

Chicago Midway

Fri 2/20

6:48 pm-2:22 pm

1 stop17h 34m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Showing 1-10 of 29 results
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2
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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, February is the cheapest month in which you can book a flight from Puerto Rico to Chicago Midway Airport (average of $204). 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 January 14, 2026.

When flying from Puerto Rico to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 January 14, 2026.
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
4,258 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

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
4,258 reviews
Southwest
8.0
Very good
4,258 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

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 23h 01m. 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.

  • 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, February is the cheapest month in which you can book a flight from Puerto Rico to Chicago Midway Airport (average of $204). 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

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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
Nassau to O'Hare Intl flights
Santo Domingo to Midway flights
Santiago de los Caballeros to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Kingston to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Nassau to Midway flights
Aguadilla to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Port of Spain to O'Hare Intl flights
St. John's to O'Hare Intl flights
Simpson Bay to Midway flights
Oranjestad to O'Hare Intl flights
George Town to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Montego Bay to Midway flights
Road Town to O'Hare Intl flights
Port Au Prince to O'Hare Intl flights
Port Au Prince to Midway flights
Roseau to O'Hare Intl flights
Culebra to O'Hare Intl flights
Aguadilla to Midway flights
Bridgetown to O'Hare Intl flights
Vieques to O'Hare Intl 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 January 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$419Average$559FlexibilityNo cancel feeOn-time63%

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