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Midway

$110+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
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 November 26, 2025.

Round-trip from

$195
(Kiwi.com)

One-way from

$110
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$341
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. 1% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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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 November 26, 2025.

This CheapOair deal was found by Cheapflights users on 11/23. 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.
Sun 12/213:54 amSJU - MDW
1 stop12h 11mFrontier
Wed 1/73:01 pmMDW - SJU
1 stop19h 34mFrontier
Deal found 11/23$201
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/233:54 amSJU - MDW
1 stop12h 43mFrontier
Wed 12/313:32 pmMDW - SJU
1 stop9h 07mFrontier
Deal found 11/24$205
This CheapOair deal was found by Cheapflights users on 11/24. 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 12/103:55 amSJU - MDW
1 stop20h 03mFrontier
Sun 12/142:59 pmMDW - SJU
1 stop6h 51mFrontier
Deal found 11/24$215
This CheapOair deal was found by Cheapflights users on 11/23. 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 12/183:55 amSJU - MDW
1 stop20h 03mFrontier
Wed 1/73:01 pmMDW - SJU
1 stop19h 34mFrontier
Deal found 11/23$217
This CheapOair deal was found by Cheapflights users on 11/26. 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 12/243:55 amSJU - MDW
1 stop20h 03mFrontier
Tue 12/303:10 pmMDW - SJU
1 stop27h 17mFrontier
Deal found 11/26$229
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:54 amSJU - MDW
1 stop12h 43mMultiple Airlines
Mon 1/56:15 amMDW - SJU
1 stop10h 58mMultiple Airlines
Deal found 11/25$230
This Frontier deal was found by Cheapflights users on 11/25. 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
Mon 1/58:15 amMDW - SJU
1 stop12h 00mFrontier
Deal found 11/25$237
This CheapOair deal was found by Cheapflights users on 11/26. 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 12/43:55 amSJU - MDW
1 stop20h 44mFrontier
Mon 12/86:15 amMDW - SJU
1 stop6h 56mFrontier
Deal found 11/26$238
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/107:10 amSJU - MDW
1 stop31h 51mMultiple Airlines
Sun 12/142:59 pmMDW - SJU
1 stop26h 51mMultiple Airlines
Deal found 11/25$248
This Priceline deal was found by Cheapflights users on 11/25. 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 12/223:55 amSJU - MDW
1 stop20h 03mFrontier
Tue 12/303:10 pmMDW - SJU
1 stop9h 40mFrontier
Deal found 11/25$249
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:16 pmSJU - MDW
1 stop7h 56mMultiple Airlines
Thu 1/16:12 amMDW - SJU
2 stops18h 22mMultiple Airlines
Deal found 11/24$253

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 November 26, 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

Thu 3/5

6:59 pm-3:33 pm

1 stop22h 34m

Chicago Midway

Mon 3/9

8:00 am-12:45 am

1 stop15h 45m

$201

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 12/18

3:55 am-9:58 pm

1 stop20h 03m

Chicago Midway

Wed 1/7

3:01 pm-12:35 pm

1 stop19h 34m

$217

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/16

2:15 pm-10:07 pm

1 stop9h 52m

Chicago Midway

Mon 1/19

6:00 am-2:31 pm

1 stop6h 31m

$225

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 12/7

3:55 am-9:58 pm

1 stop20h 03m

Chicago Midway

Mon 12/15

6:15 am-3:11 pm

1 stop6h 56m

$238

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/12

6:30 am-1:20 pm

2 stops8h 50m

Chicago Midway

Mon 2/16

2:40 pm-11:25 pm

1 stop6h 45m

$252

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 12/24

2:10 pm-10:22 pm

1 stop10h 12m

Chicago Midway

Thu 1/1

9:50 am-9:09 pm

1 stop9h 19m

$270

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 12/24

3:55 am-9:58 pm

1 stop20h 03m

Chicago Midway

Tue 12/30

3:10 pm-3:59 pm

1 stop22h 49m

$280

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/12

6:30 am-1:20 pm

2 stops8h 50m

Chicago Midway

Sun 2/15

6:10 am-9:50 pm

1 stop13h 40m

$292

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 12/31

7:30 am-1:21 pm

1 stop7h 51m

Chicago Midway

Mon 1/5

6:15 am-2:39 am

1 stop18h 24m

$292

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 12/24

7:30 am-1:21 pm

1 stop7h 51m

Chicago Midway

Sat 1/3

2:24 pm-2:39 am

1 stop10h 15m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/26

Showing 1-10 of 23 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, December is the cheapest month in which you can book a flight from Puerto Rico to Chicago Midway Airport (average of $149). 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 November 26, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 40% 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 November 26, 2025.
Read reviews from past customers who have flown Southwest and Frontier 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

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,099 reviews
Southwest
8.0
Very good
4,254 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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, Delta, and Southwest fly from Puerto Rico to Chicago Midway Airport in about 8h 50m. The time it takes to get you to your destination can typically vary by up to 13h 44m. There are 2057 mi between Puerto Rico and Chicago Midway Airport. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Puerto Rico to Chicago Midway Airport one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $111. Users have also found prices from $113 and $113 on Delta and Southwest, respectively.

  • 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 $149). 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
Hammond
Porter
Benton Harbor
Merrillville

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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.
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Aguadilla to Midway flights
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Port Au Prince to Midway flights

Top 2 airlines flying from Puerto Rico to Midway

Discover the top 2 airlines 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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$279FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$419Average$566FlexibilityNo cancel feeOn-time63%

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