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$68+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Puerto Rico to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Puerto Rico (PR0) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$140
(FlightHub)

One-way from

$68
(Mytrip)

Good one-way deal

$347 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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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 January 21, 2025.

This FlightHub deal was found by Cheapflights users on 1/21. 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.
Sat 2/89:15 pmSJU - MDW
1 stop14h 47mFrontier
Mon 2/1011:33 amMDW - SJU
1 stop12h 46mFrontier
Deal found 1/21$140
This Trip.com deal was found by Cheapflights users on 1/20. 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.
Thu 1/303:51 amBQN - MDW
1 stop12h 51mFrontier
Sun 2/210:58 amMDW - BQN
1 stop13h 48mFrontier
Deal found 1/20$254
This Southwest deal was found by Cheapflights users on 1/20. 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.
Thu 2/206:05 amSJU - MDW
1 stop10h 40mSouthwest
Mon 2/241:25 pmMDW - SJU
2 stops9h 25mSouthwest
Deal found 1/20$310
This Delta deal was found by Cheapflights users on 1/21. 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.
Tue 3/47:30 amSJU - MDW
1 stop10h 50mDelta
Tue 3/119:54 amMDW - SJU
1 stop9h 16mDelta
Deal found 1/21$325

Find flights from Puerto Rico to Midway within your budget

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 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 3/4

7:59 pm-3:13 pm

1 stop21h 14m

Chicago Midway

Tue 3/11

7:25 am-9:44 am

1 stop25h 19m

$144

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/20

6:05 am-2:45 pm

1 stop10h 40m

Chicago Midway

Mon 2/24

1:25 pm-12:50 am

2 stops9h 25m

$310

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 3/4

7:30 am-4:20 pm

1 stop10h 50m

Chicago Midway

Tue 3/11

12:51 pm-8:10 pm

1 stop6h 19m

$325

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Thu 2/13

3:56 am-7:19 pm

1 stop17h 23m

Chicago Midway

Mon 2/17

12:43 pm-3:01 am

1 stop12h 18m

$455

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 2/1

6:14 am-8:31 am

3 stops28h 17m

Chicago Midway

Wed 2/5

1:05 pm-12:59 am

3 stops33h 54m

$681

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 4/7

5:01 am-7:46 pm

1 stop15h 45m

$68

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/20

6:05 am-2:45 pm

1 stop10h 40m

$118

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/6

6:15 am-11:59 am

1 stop7h 44m

$163

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 5/21

8:30 pm-7:13 pm

2 stops23h 43m

$242

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 4/6

1:35 pm-10:20 am

2 stops21h 45m

$389

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 11 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.

Travel insights for flights from Puerto Rico to Midway

Get recent, data-driven insights about flights from Puerto Rico to Midway including ideal travel times, pricing trends, and more.

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 January 21, 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 21, 2025.
To help decide which airline to fly from Puerto Rico to Chicago, see what other customers have to say about Southwest, Frontier and Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Air Transat
7.8
Good
381 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,443 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 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 $68. Users have also found prices from $118 and $163 on Southwest and Delta, respectively.

  • 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 $432, our data indicates the cheapest price to be $238. The most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway), is priced around $157.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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
Nassau to O'Hare Intl flights
Santo Domingo to O'Hare Intl flights
Punta Cana to O'Hare Intl flights
Roseau to O'Hare Intl flights
Santo Domingo to Midway flights
Port of Spain to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Punta Cana to Midway flights
Nassau to Midway flights
Santiago de los Caballeros to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
George Town to O'Hare Intl flights
Montego Bay to Midway flights
Kingston to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Aguadilla to O'Hare Intl flights
Aguadilla to Midway flights
Willemstad to O'Hare Intl flights
Simpson Bay to Midway flights
Port Au Prince to Midway flights
Port Au Prince to O'Hare Intl flights
Road Town to O'Hare Intl flights
Culebra to O'Hare Intl flights
Christiansted to O'Hare Intl flights
St. John's to O'Hare Intl flights
Vieques to O'Hare Intl flights

Top 3 airlines flying from Puerto Rico to Midway

Discover the top 3 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$322FlexibilityNo cancel feeOn-time62%
DeltaCheapest$249Average$509FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$267Average$384FlexibilityNo cancel feeOn-time63%
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