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Puerto Rico

$110+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
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 October 14, 2025.

Round-trip from

$200
(Frontier)

One-way from

$110
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$353
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. 8% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 14, 2025.

This Frontier deal was found by Cheapflights users on 10/13. 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.
Wed 11/263:47 pmMDW - SJU
1 stop7h 25mFrontier
Thu 12/117:00 amSJU - MDW
1 stop9h 05mFrontier
Deal found 10/13$200
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
Tue 11/116:26 pmMDW - SJU
1 stop21h 28mFrontier
Tue 11/189:00 amSJU - MDW
1 stop16h 55mFrontier
Deal found 10/14$220
This Frontier deal was found by Cheapflights users on 10/12. 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 10/249:45 amMDW - SJU
1 stop12h 44mFrontier
Fri 10/313:31 pmSJU - MDW
1 stop7h 14mFrontier
Deal found 10/12$225
This Frontier deal was found by Cheapflights users on 10/13. 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.
Sun 12/76:00 amMDW - SJU
1 stop6h 54mFrontier
Thu 12/117:00 amSJU - MDW
1 stop9h 05mFrontier
Deal found 10/13$231
This Frontier deal was found by Cheapflights users on 10/12. 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.
Mon 10/2012:13 pmMDW - SJU
1 stop11h 16mFrontier
Fri 10/313:31 pmSJU - MDW
1 stop7h 14mFrontier
Deal found 10/12$232
This Frontier deal was found by Cheapflights users on 10/12. 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.
Sat 11/811:36 amMDW - SJU
1 stop13h 18mFrontier
Thu 11/134:31 pmSJU - MDW
1 stop7h 32mFrontier
Deal found 10/12$242
This Frontier deal was found by Cheapflights users on 10/12. 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 12/116:00 amMDW - SJU
2 stops18h 50mFrontier
Mon 12/153:59 pmSJU - MDW
1 stop9h 06mFrontier
Deal found 10/12$248
This Frontier deal was found by Cheapflights users on 10/12. 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.
Sun 11/165:40 amMDW - SJU
2 stops17h 52mFrontier
Thu 11/204:05 pmSJU - MDW
1 stop8h 38mFrontier
Deal found 10/12$260
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
Mon 11/106:15 amMDW - SJU
2 stops19h 18mFrontier
Thu 11/139:00 amSJU - MDW
1 stop16h 55mFrontier
Deal found 10/14$262
This Southwest deal was found by Cheapflights users on 10/12. 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.
Wed 12/31:10 pmMDW - SJU
1 stop6h 55mSouthwest
Wed 12/106:40 amSJU - MDW
2 stops8h 20mSouthwest
Deal found 10/12$263
This Frontier deal was found by Cheapflights users on 10/14. 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 12/112:15 pmMDW - SJU
1 stop10h 35mFrontier
Sun 12/143:59 pmSJU - MDW
1 stop9h 06mFrontier
Deal found 10/14$264

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 October 14, 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

Fri 12/5

4:35 pm-12:35 am

1 stop6h 00m

San Juan Luis Munoz Marin Intl

Mon 12/8

11:20 am-6:25 pm

1 stop9h 05m

$263

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 12/11

1:10 pm-10:05 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Sun 12/14

6:40 am-2:10 pm

2 stops9h 30m

$289

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 12/5

4:35 pm-12:35 am

1 stop6h 00m

San Juan Luis Munoz Marin Intl

Sun 12/14

6:40 am-2:10 pm

2 stops9h 30m

$289

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 12/6

9:50 am-11:00 pm

2 stops11h 10m

San Juan Luis Munoz Marin Intl

Sun 12/14

6:40 am-2:10 pm

2 stops9h 30m

$355

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 12/4

12:25 pm-12:35 am

2 stops10h 10m

San Juan Luis Munoz Marin Intl

Tue 12/9

5:45 am-1:05 pm

2 stops9h 20m

$374

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 12/14

1:50 pm-10:00 pm

1 stop6h 10m

San Juan Luis Munoz Marin Intl

Fri 12/19

5:35 am-1:20 pm

2 stops9h 45m

$385

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 11/14

1:25 pm-12:35 am

2 stops9h 10m

San Juan Luis Munoz Marin Intl

Tue 11/18

9:40 am-7:25 pm

1 stop11h 45m

$395

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 11/5

2:10 pm-12:35 am

2 stops8h 25m

San Juan Luis Munoz Marin Intl

Sat 11/8

5:40 am-12:05 pm

1 stop8h 25m

$395

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 11/3

9:20 am-11:20 pm

1 stop12h 00m

San Juan Luis Munoz Marin Intl

Mon 11/10

2:10 pm-11:25 pm

1 stop11h 15m

$395

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 12/9

12:50 pm-11:20 pm

1 stop8h 30m

$132

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 14 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 October 14, 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 October 14, 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
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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
United Airlines
7.4
Good
8,977 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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
Spirit Airlines
6.3
Okay
8,097 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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
3,135 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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 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 6h. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 2057 mi.

  • 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

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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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$142Average$288FlexibilityNo 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$379Average$499FlexibilityNo cancel feeOn-time63%

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