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Puerto Rico

$100+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Feb 10 — Feb 171
Tue 2/10
Tue 2/17
1 adult, Economy
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Cheap 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 January 11, 2026.

This Frontier deal was found by Cheapflights users on 1/11. 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 3/99:51 pmMDW - SJU
1 stop11h 06mFrontier
Wed 3/116:30 amSJU - MDW
1 stop12h 43mFrontier
Deal found 1/11$198
This CheapOair deal was found by Cheapflights users on 1/10. 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.
Thu 2/51:00 pmMDW - SJU
1 stop19h 24mFrontier
Wed 2/115:25 pmSJU - MDW
1 stop23h 01mFrontier
Deal found 1/10$200
This Expedia deal was found by Cheapflights users on 1/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/91:00 pmMDW - SJU
1 stop21h 57mFrontier
Sun 3/83:08 amSJU - MDW
1 stop18h 45mFrontier
Deal found 1/10$201
This Frontier deal was found by Cheapflights users on 1/11. 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 2/218:00 amMDW - SJU
1 stop8h 59mFrontier
Thu 2/266:00 amSJU - MDW
1 stop9h 56mFrontier
Deal found 1/11$203
This Priceline deal was found by Cheapflights users on 1/10. 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.
Fri 2/207:30 amMDW - SJU
1 stop15h 13mFrontier
Wed 2/255:25 pmSJU - MDW
1 stop23h 01mFrontier
Deal found 1/10$205
This Priceline deal was found by Cheapflights users on 1/11. 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.
Fri 2/207:30 amMDW - SJU
1 stop17h 23mFrontier
Tue 3/246:30 amSJU - MDW
1 stop12h 43mFrontier
Deal found 1/11$206
This CheapOair deal was found by Cheapflights users on 1/10. 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.
Sat 4/48:00 amMDW - SJU
1 stop15h 45mFrontier
Fri 4/106:00 amSJU - MDW
1 stop16h 58mFrontier
Deal found 1/10$207
This Frontier deal was found by Cheapflights users on 1/9. 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 2/226:00 amMDW - SJU
1 stop7h 08mFrontier
Thu 2/264:11 pmSJU - MDW
1 stop8h 18mFrontier
Deal found 1/9$209
This CheapOair deal was found by Cheapflights users on 1/10. 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.
Sun 2/11:00 pmMDW - SJU
1 stop27h 40mFrontier
Thu 2/58:00 amSJU - MDW
1 stop13h 52mFrontier
Deal found 1/10$210
This Frontier deal was found by Cheapflights users on 1/11. 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 3/261:24 pmMDW - SJU
1 stop11h 34mFrontier
Mon 3/303:08 amSJU - MDW
1 stop13h 25mFrontier
Deal found 1/11$211

Find 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 January 11, 2026.

Round-trip from

$198
(Priceline)

One-way from

$100
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$359
From Chicago Midway to Puerto Rico
Search Deals
One-way flight from Chicago Midway to Puerto Rico
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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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 January 11, 2026.
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

Sun 1/25

1:35 pm-12:05 am

2 stops8h 30m

San Juan Luis Munoz Marin Intl

Wed 1/28

6:10 am-1:55 pm

2 stops9h 45m

$266

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/26

7:35 am-8:55 pm

1 stop11h 20m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:10 am-1:55 pm

2 stops9h 45m

$266

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 1/21

7:35 am-8:55 pm

1 stop11h 20m

San Juan Luis Munoz Marin Intl

Wed 1/28

6:10 am-1:55 pm

2 stops9h 45m

$266

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/19

5:30 am-3:20 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Thu 1/22

5:40 am-12:30 pm

2 stops8h 50m

$266

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/24

12:15 pm-11:00 pm

1 stop8h 45m

San Juan Luis Munoz Marin Intl

Wed 1/28

9:05 am-2:45 pm

1 stop7h 40m

$266

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/25

2:05 pm-10:15 pm

1 stop6h 10m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:10 am-11:35 am

1 stop7h 25m

$296

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/31

12:15 pm-11:00 pm

1 stop8h 45m

San Juan Luis Munoz Marin Intl

Tue 2/3

5:40 am-12:30 pm

2 stops8h 50m

$315

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/30

8:35 am-8:55 pm

1 stop10h 20m

San Juan Luis Munoz Marin Intl

Tue 2/3

6:10 am-1:55 pm

2 stops9h 45m

$315

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/29

3:15 pm-12:35 am

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Mon 2/2

9:05 am-6:35 pm

1 stop11h 30m

$361

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/24

10:46 am-11:45 pm

1 stop10h 59m

San Juan Luis Munoz Marin Intl

Tue 1/27

3:55 pm-10:22 pm

1 stop8h 27m

$376

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/9

Showing 1-10 of 19 results
1
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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 $137). 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 January 11, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Puerto Rico as you normally would.

How often are flights from Chicago to Puerto Rico delayed?

About 23% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 97 minutes.

What is the most punctual flight time for Chicago to Puerto Rico flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Tuesday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Puerto Rico flights?

Over the last year, Southwest have had the lowest number of delays on this route, with just 23% of flights being delayed.

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 January 11, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and Frontier 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
4,254 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

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
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

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
Delta
7.9
Good
8,035 reviews
Southwest
8.0
Very good
4,254 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

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
Frontier
5.7
Fair
3,057 reviews
Southwest
8.0
Very good
4,254 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

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 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 8h 30m. 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 $137). 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 3 airlines flying from Midway to Puerto Rico

Discover the top 3 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 January 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$294FlexibilityNo cancel feeOn-time62%
DeltaCheapest$325Average$405FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$381Average$489FlexibilityNo cancel feeOn-time63%

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