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Midway

$109+ 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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
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 4, 2025.

Round-trip from

$211
(Frontier)

One-way from

$109
(Trip.com)

Popular in

August

Cheapest in

January

Average price

$285
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. 0% potential increase in price ($3 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 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 4, 2025.

This Frontier deal was found by Cheapflights users on 11/4. 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.
Fri 12/54:31 pmSJU - MDW
1 stop7h 41mFrontier
Mon 12/86:15 amMDW - SJU
1 stop6h 56mFrontier
Deal found 11/4$211
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Fri 11/2112:37 pmSJU - MDW
1 stop8h 54mFrontier
Thu 12/42:16 pmMDW - SJU
1 stop18h 16mFrontier
Deal found 11/4$218
This CheapOair deal was found by Cheapflights users on 11/3. 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 12/33:55 amSJU - MDW
1 stop20h 03mFrontier
Sun 12/72:59 pmMDW - SJU
1 stop16h 38mFrontier
Deal found 11/3$226
This Priceline deal was found by Cheapflights users on 11/2. 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.
Sun 11/1610:39 pmSJU - MDW
1 stop11h 53mFrontier
Thu 11/205:30 pmMDW - SJU
1 stop7h 24mFrontier
Deal found 11/2$227
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/2610:40 amSJU - MDW
1 stop8h 17mFrontier
Thu 12/42:16 pmMDW - SJU
1 stop18h 16mFrontier
Deal found 11/2$231
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Thu 12/410:42 amSJU - MDW
1 stop13h 11mFrontier
Tue 12/97:44 amMDW - SJU
1 stop30h 29mFrontier
Deal found 11/3$240
This Priceline deal was found by Cheapflights users on 11/3. 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 11/193:59 amSJU - MDW
1 stop14h 31mFrontier
Mon 11/2412:25 pmMDW - SJU
1 stop25h 50mFrontier
Deal found 11/3$242
This CheapOair deal was found by Cheapflights users on 11/2. 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 11/192:25 amSJU - MDW
1 stop19h 06mFrontier
Thu 11/275:30 pmMDW - SJU
1 stop7h 24mFrontier
Deal found 11/2$243
This Priceline deal was found by Cheapflights users on 11/4. 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 11/143:59 amSJU - MDW
1 stop8h 27mFrontier
Thu 12/42:16 pmMDW - SJU
1 stop18h 16mFrontier
Deal found 11/4$246
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/2610:40 amSJU - MDW
1 stop8h 17mMultiple Airlines
Fri 12/53:52 pmMDW - SJU
1 stop30h 24mMultiple Airlines
Deal found 11/2$254
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Thu 12/1110:42 amSJU - MDW
1 stop13h 11mMultiple Airlines
Mon 12/1512:35 pmMDW - SJU
1 stop10h 00mMultiple Airlines
Deal found 11/3$259
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/143:59 amSJU - MDW
1 stop8h 27mFrontier
Wed 11/191:56 pmMDW - SJU
1 stop9h 10mFrontier
Deal found 11/3$261

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 4, 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

Fri 12/5

4:31 pm-10:12 pm

1 stop7h 41m

Chicago Midway

Mon 12/8

6:15 am-3:11 pm

1 stop6h 56m

$211

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 11/15

2:11 am-7:30 am

1 stop7h 19m

Chicago Midway

Thu 11/20

9:30 am-11:09 pm

1 stop11h 39m

$226

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 1/28

5:40 am-11:15 am

1 stop7h 35m

Chicago Midway

Wed 2/4

8:25 am-5:05 pm

1 stop6h 40m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 1/31

5:30 am-12:10 pm

1 stop8h 40m

Chicago Midway

Thu 2/5

6:10 am-9:50 pm

1 stop13h 40m

$252

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/15

7:00 am-12:55 pm

1 stop7h 55m

Chicago Midway

Sun 1/18

8:25 am-5:05 pm

1 stop6h 40m

$277

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 12/24

4:16 pm-10:12 pm

1 stop7h 56m

Chicago Midway

Sat 1/3

2:24 pm-2:39 am

1 stop10h 15m

$316

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 11/20

7:15 am-4:30 pm

1 stop11h 15m

Chicago Midway

Mon 12/1

5:47 pm-10:49 am

1 stop15h 02m

$319

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/23

7:30 am-12:01 pm

1 stop6h 31m

Chicago Midway

Tue 2/3

10:53 am-8:57 pm

1 stop8h 04m

$336

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 11/24

12:37 pm-6:06 pm

1 stop7h 29m

Chicago Midway

Fri 11/28

8:41 pm-11:27 am

1 stop12h 46m

$348

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 12/17

3:55 am-9:58 pm

1 stop20h 03m

Chicago Midway

Sun 1/4

6:00 am-3:01 pm

1 stop7h 01m

$373

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 24 results
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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 $154). 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 4, 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 4, 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
4,237 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

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
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

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
3,116 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

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 and Southwest fly from Puerto Rico to Chicago Midway Airport in about 7h 35m. The time it takes to get you to your destination can typically vary by up to 06m. There are 2057 mi between Puerto Rico and Chicago Midway Airport. This flight may include one or multiple stops.

  • 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 $154). 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
Merrillville
Lansing
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.
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Simpson Bay to Midway flights
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Aguadilla to Midway flights
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Port Au Prince to O'Hare Intl flights
Port Au Prince to Midway flights
St. John's to O'Hare Intl 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 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$265FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$394Average$566FlexibilityNo cancel feeOn-time63%

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