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Puerto Rico

$112+ Cheap flights from Midway (MDW) to Puerto Rico

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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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Cheap flight deals from Midway to Puerto Rico

Keep the following information in mind while searching for Midway to Puerto Rico flight deals. Data was last updated November 4, 2025.

Round-trip from

$211
(Frontier)

One-way from

$112
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$381
From Chicago Midway to Puerto Rico
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One-way flight from Chicago Midway to Puerto Rico
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Highest demand for flights based on searches. 7% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 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 Midway to Puerto Rico

Cheapest flights from Midway to Puerto Rico
Explore the most affordable flight options available from Midway to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2025.

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.
Sun 12/72:59 pmMDW - SJU
1 stop16h 38mFrontier
Thu 12/1110:42 amSJU - MDW
1 stop13h 11mFrontier
Deal found 11/4$214
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 12/42:16 pmMDW - SJU
1 stop18h 16mMultiple Airlines
Tue 12/95:00 pmSJU - MDW
2 stops17h 46mMultiple Airlines
Deal found 11/3$220
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/205:30 pmMDW - SJU
1 stop7h 24mFrontier
Sun 11/232:25 amSJU - MDW
1 stop17h 41mFrontier
Deal found 11/3$223
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 11/191:56 pmMDW - SJU
1 stop9h 10mFrontier
Thu 12/113:55 amSJU - MDW
1 stop20h 44mFrontier
Deal found 11/3$226
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.
Thu 11/275:30 pmMDW - SJU
1 stop7h 24mFrontier
Fri 12/54:31 pmSJU - MDW
1 stop7h 41mFrontier
Deal found 11/4$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.
Thu 12/42:16 pmMDW - SJU
1 stop18h 16mMultiple Airlines
Sun 12/71:22 pmSJU - MDW
1 stop11h 08mMultiple Airlines
Deal found 11/2$229
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.
Wed 12/32:49 pmMDW - SJU
2 stops41h 43mMultiple Airlines
Wed 12/107:10 amSJU - MDW
1 stop31h 51mMultiple Airlines
Deal found 11/3$235
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.
Sat 11/152:05 pmMDW - SJU
1 stop16h 40mFrontier
Sat 11/227:10 amSJU - MDW
1 stop12h 05mFrontier
Deal found 11/4$240
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:15 amMDW - SJU
1 stop7h 04mFrontier
Thu 11/274:05 pmSJU - MDW
1 stop8h 38mFrontier
Deal found 11/2$242
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/53:52 pmMDW - SJU
1 stop8h 58mFrontier
Fri 12/124:31 pmSJU - MDW
1 stop7h 41mFrontier
Deal found 11/3$246

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Puerto Rico 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 Chicago Midway Airport to Puerto Rico that are best for you.

Fly from

Midway

Fly to

Puerto Rico

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/26

3:15 pm-12:35 am

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Thu 1/29

6:10 am-1:55 pm

2 stops9h 45m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 2/2

9:50 am-8:55 pm

2 stops9h 05m

San Juan Luis Munoz Marin Intl

Fri 2/6

4:10 pm-10:25 pm

1 stop8h 15m

$252

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/31

12:50 pm-11:00 pm

2 stops8h 10m

San Juan Luis Munoz Marin Intl

Sat 2/7

6:00 am-1:40 pm

2 stops9h 40m

$357

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/30

1:50 pm-12:35 am

2 stops8h 45m

San Juan Luis Munoz Marin Intl

Sat 2/7

6:00 am-4:55 pm

1 stop12h 55m

$376

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 12/2

1:10 pm-10:05 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Tue 12/9

5:45 am-2:30 pm

1 stop10h 45m

$382

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/10

9:45 am-9:30 pm

2 stops9h 45m

San Juan Luis Munoz Marin Intl

Wed 1/14

9:05 am-2:45 pm

1 stop7h 40m

$386

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/23

2:20 pm-12:35 am

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Mon 1/26

9:05 am-6:35 pm

1 stop11h 30m

$392

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 11/28

12:55 pm-12:35 am

2 stops9h 40m

San Juan Luis Munoz Marin Intl

Tue 12/2

2:05 pm-9:00 pm

1 stop8h 55m

$395

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 12/13

9:50 am-11:00 pm

2 stops11h 10m

San Juan Luis Munoz Marin Intl

Sat 1/31

5:30 am-1:40 pm

2 stops10h 10m

$402

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 2/2

6:00 am-2:30 pm

1 stop6h 30m

$114

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 18 results
1
2

Best time to book a flight from Midway to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Midway 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 Chicago Midway Airport to Puerto Rico

What is the cheapest month to book a flight from Chicago Midway Airport to Puerto Rico?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $133). Flying from Chicago Midway Airport to Puerto Rico in June is currently the most expensive (average of $298). 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 MDW to PR?

Find hourly flight availability from Midway to Puerto Rico. 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 at noon, when flights are generally more expensive, you can save up to 55% on flights from Chicago Midway Airport to Puerto Rico by exploring options for tickets in the evening.

What is the cheapest day to fly from Chicago Midway Airport to Puerto Rico?

Use this chart to determine the cheapest time to fly round-trip from Midway to Puerto Rico. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago Midway Airport to Puerto Rico flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated November 4, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Chicago Midway Airport to Puerto Rico to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Overall

8.0

Food

7.0

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

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Overall

8.0

Food

7.0

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
Delta
7.9
Good
8,002 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Overall

8.0

Food

7.0

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
United Airlines
7.4
Good
8,998 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Overall

8.0

Food

7.0

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
Spirit Airlines
6.3
Okay
8,112 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Overall

8.0

Food

7.0

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

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Overall

8.0

Food

7.0

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 Midway to Puerto Rico. 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 Chicago Midway Airport to Puerto Rico?

    Airlines like Southwest fly from Chicago Midway Airport to Puerto Rico in about 7h 20m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 2057 mi.

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

    The cheapest airlines for a one-way flight from Chicago Midway Airport to Puerto Rico are Delta ($114), Southwest ($114), and Frontier ($122).

  • Can I find deals for flights from Midway to Puerto Rico that include hotel bookings?

    Yes. In addition to deals on Midway to Puerto Rico flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Puerto Rico?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Puerto Rico.

  • Can I find deals for business class flights from Midway to Puerto Rico?

    Yes. Cheapflights offers flight deals from Midway to Puerto Rico 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 Chicago Midway Airport to Puerto Rico?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $133). Flying from Chicago Midway Airport to Puerto Rico in June is currently the most expensive (average of $298). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Midway to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Midway to Puerto Rico

Discover the top 5 airlines that operate flights from Midway to Puerto Rico. 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$144Average$292FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$149Average$327FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$299Average$443FlexibilityNo cancel feeOn-time69%
DeltaCheapest$325Average$405FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$380Average$503FlexibilityNo cancel feeOn-time63%

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