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$95+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
ene. 31 — feb. 71
sáb. 1/31
sáb. 2/7
1 adult, Economy
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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 enero 1, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 12/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/314:16 pmSJU - MDW
1 stop7h 56mFrontier
dom. 1/46:00 amMDW - SJU
1 stop7h 01mFrontier
Deal found 12/30$436
This Frontier deal was found by Cheapflights users on 12/30. 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.
mié. 12/314:16 pmSJU - MDW
1 stop7h 56mFrontier
lun. 1/58:15 amMDW - SJU
1 stop12h 00mFrontier
Deal found 12/30$443
This Cheapflightsfares deal was found by Cheapflights users on 12/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/314:16 pmSJU - MDW
1 stop7h 56mFrontier
dom. 1/116:10 amMDW - SJU
1 stop7h 09mFrontier
Deal found 12/30$446
This CheapOair deal was found by Cheapflights users on 12/30. 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.
mar. 12/304:19 pmSJU - MDW
1 stop7h 53mFrontier
dom. 1/42:16 pmMDW - SJU
1 stop28h 11mFrontier
Deal found 12/30$478
This Priceline deal was found by Cheapflights users on 12/30. 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.
mié. 12/314:16 pmSJU - MDW
1 stop7h 56mFrontier
jue. 1/13:10 pmMDW - SJU
1 stop16h 13mFrontier
Deal found 12/30$524
This Southwest deal was found by Cheapflights users on 12/30. 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.
mié. 12/312:05 pmSJU - MDW
1 stop8h 55mSouthwest
mar. 1/69:50 amMDW - SJU
1 stop11h 20mSouthwest
Deal found 12/30$570
This Southwest deal was found by Cheapflights users on 12/30. 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.
mar. 12/303:25 pmSJU - MDW
2 stops11h 45mSouthwest
dom. 1/48:15 pmMDW - SJU
1 stop12h 50mSouthwest
Deal found 12/30$704
This Southwest deal was found by Cheapflights users on 12/31. 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.
mié. 12/312:05 pmSJU - MDW
1 stop8h 55mSouthwest
jue. 1/19:05 amMDW - SJU
1 stop10h 25mSouthwest
Deal found 12/31$735

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 enero 1, 2026.

Round-trip from

$180
(Priceline)

One-way from

$95
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$280

Good one-way deal

$280 or less
From Puerto Rico to Chicago Midway
Search Deals
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 ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a one-way flight from Puerto Rico to Chicago Midway.
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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 enero 1, 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

mié. 2/25

5:25 pm-2:26 pm

1 stop23h 01m

Chicago Midway

lun. 3/9

6:15 am-10:45 pm

1 stop15h 30m

$196

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

mié. 1/14

3:48 am-10:32 am

1 stop8h 44m

Chicago Midway

dom. 1/18

6:01 pm-3:03 am

1 stop7h 02m

$215

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

lun. 1/26

8:00 am-7:58 pm

1 stop13h 58m

Chicago Midway

lun. 2/2

1:00 pm-3:26 pm

1 stop24h 26m

$231

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 1/29

11:52 am-3:49 pm

2 stops29h 57m

Chicago Midway

dom. 2/1

1:00 pm-11:33 pm

1 stop8h 33m

$248

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

vie. 2/20

11:52 am-2:55 pm

1 stop29h 03m

Chicago Midway

vie. 2/27

7:53 pm-6:58 pm

2 stops21h 05m

$252

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 1/8

10:47 pm-2:06 pm

1 stop17h 19m

Chicago Midway

jue. 1/15

11:27 am-2:48 am

1 stop13h 21m

$252

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

vie. 2/6

5:01 am-7:52 pm

1 stop16h 51m

Chicago Midway

vie. 2/13

7:30 am-11:20 pm

1 stop13h 50m

$277

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

mar. 1/13

5:50 pm-12:02 am

1 stop8h 12m

Chicago Midway

vie. 1/23

5:01 pm-4:25 pm

2 stops21h 24m

$285

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

lun. 1/26

7:00 pm-12:05 pm

2 stops19h 05m

Chicago Midway

lun. 2/2

9:45 am-12:27 pm

1 stop24h 42m

$285

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

vie. 1/9

5:45 am-2:06 pm

1 stop10h 21m

Chicago Midway

vie. 1/9

4:31 pm-2:50 am

1 stop8h 19m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/1

Showing 1-10 of 27 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 $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 enero 1, 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 enero 1, 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
4,253 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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.

  • 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 $326, our data indicates the cheapest price to be $250. The most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway), is priced around $196.

  • 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

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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
Luis Munoz Marin Intl to O'Hare Intl flights
Punta Cana to Midway flights
Luis Munoz Marin Intl to Midway flights
Nassau to O'Hare Intl flights
Santo Domingo to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Santo Domingo to Midway flights
Santiago de los Caballeros to O'Hare Intl flights
Kingston to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Nassau to Midway flights
Aguadilla to O'Hare Intl flights
George Town to O'Hare Intl flights
Simpson Bay to Midway flights
Port of Spain to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Montego Bay to Midway flights
St. John's to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Port Au Prince to O'Hare Intl flights
Port Au Prince to Midway flights
Road Town to O'Hare Intl flights
Roseau to O'Hare Intl flights
Culebra to O'Hare Intl flights
Aguadilla to Midway 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 enero 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$419Average$566FlexibilityNo cancel feeOn-time63%

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