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$117+ 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 7/31. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$240
(Priceline)

One-way from

$117
(Trip.com)

Popular in

March

Cheapest in

January

Average price

$296

Good one-way deal

$292 or less
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. 10% potential increase in price ($33 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 July 2025
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Price to beat on a one-way flight from Puerto Rico to Chicago Midway.
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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 July 3, 2025.

This Priceline deal was found by Cheapflights users on 7/3. 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.
Thu 7/1012:59 amSJU - MDW
1 stop23h 52mFrontier
Sun 7/138:35 amMDW - SJU
1 stop23h 29mFrontier
Deal found 7/3$225
This FlightHub deal was found by Cheapflights users on 7/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/162:59 amBQN - MDW
1 stop18h 23mFrontier
Mon 7/218:35 amMDW - BQN
1 stop16h 26mFrontier
Deal found 7/2$330
This Delta deal was found by Cheapflights users on 7/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/412:58 pmSJU - MDW
1 stop9h 15mDelta
Tue 10/76:00 amMDW - SJU
1 stop9h 18mDelta
Deal found 7/3$337
This Southwest deal was found by Cheapflights users on 7/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/225:50 amSJU - MDW
2 stops9h 10mSouthwest
Tue 9/301:00 pmMDW - SJU
2 stops8h 30mSouthwest
Deal found 7/2$362
This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/710:14 pmSJU - MDW
2 stops16h 42mMultiple Airlines
Mon 8/111:11 pmMDW - SJU
2 stops11h 24mMultiple Airlines
Deal found 7/2$375

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 July 3, 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

Wed 12/3

11:05 am-1:10 pm

1 stop28h 05m

Chicago Midway

Mon 12/8

6:00 am-2:54 pm

1 stop6h 54m

$261

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Wed 7/16

2:59 am-8:22 pm

1 stop18h 23m

Chicago Midway

Mon 7/21

8:35 am-2:01 am

1 stop16h 26m

$330

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 10/4

12:58 pm-9:13 pm

1 stop9h 15m

Chicago Midway

Tue 10/7

6:00 am-4:18 pm

1 stop9h 18m

$337

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 9/22

5:50 am-2:00 pm

2 stops9h 10m

Chicago Midway

Tue 9/30

1:00 pm-10:30 pm

2 stops8h 30m

$362

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/7

10:14 pm-1:56 pm

2 stops16h 42m

Chicago Midway

Mon 8/11

1:11 pm-1:35 am

2 stops11h 24m

$375

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 7/31

3:50 pm-11:17 pm

1 stop8h 27m

$117

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Fri 9/5

3:32 am-9:51 am

1 stop7h 19m

$134

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/28

7:25 am-5:05 pm

1 stop10h 40m

$136

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 9/30

7:20 am-4:25 pm

1 stop10h 05m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

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, April is the cheapest month in which you can book a flight from Puerto Rico to Chicago Midway Airport (average of $160). Flying from Puerto Rico to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 July 3, 2025.

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 July 3, 2025.
Read reviews from past customers who have flown Southwest, Delta, 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
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,286 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • 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 $368, our data indicates the cheapest price to be $292. The most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway), is priced around $284.

  • 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, April is the cheapest month in which you can book a flight from Puerto Rico to Chicago Midway Airport (average of $160). Flying from Puerto Rico to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Puerto Rico?

Book flights to Puerto Rico if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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.
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Midway flights
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Kingston to O'Hare Intl flights
Willemstad to O'Hare Intl flights
St. John's to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Simpson Bay to Midway flights
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Port Au Prince to O'Hare Intl flights
Port Au Prince to Midway flights
Road Town to O'Hare Intl flights
Culebra to O'Hare Intl flights
Aguadilla to Midway flights
Vieques 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$130Average$234FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$312Average$454FlexibilityNo cancel feeOn-time63%

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