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$123+ 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 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
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 July 1, 2025.

Round-trip from

$207
(Priceline)

One-way from

$123
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$376

Good round-trip deal

$388 or less

Good one-way deal

$238 or less
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. 12% potential increase in price ($55 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago Midway to Puerto Rico.
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Price to beat on a one-way flight from Chicago Midway to Puerto Rico.
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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 July 1, 2025.

This Priceline deal was found by Cheapflights users on 6/29. 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.
Thu 8/216:15 amMDW - SJU
1 stop7h 11mFrontier
Wed 8/2712:59 amSJU - MDW
1 stop13h 11mFrontier
Deal found 6/29$207

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 July 1, 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

Thu 8/21

6:15 am-2:26 pm

1 stop7h 11m

San Juan Luis Munoz Marin Intl

Wed 8/27

12:59 am-1:10 pm

1 stop13h 11m

$207

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 9/18

1:59 pm-9:52 am

2 stops18h 53m

$123

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 8/22

9:32 am-4:21 pm

3 stops29h 49m

$162

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/12

8:35 am-10:30 pm

1 stop12h 55m

$174

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 9/2

6:00 am-4:36 pm

1 stop9h 36m

$196

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $254). Flying from Chicago Midway Airport to Puerto Rico in June is currently the most expensive (average of $339). 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 July 1, 2025.

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.

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 July 1, 2025.
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
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,273 reviews
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,291 reviews
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • 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 Frontier ($123), Southwest ($174), and Delta ($196).

  • What are the cheapest flights from Chicago Midway Airport to Puerto Rico?

    Looking for the cheapest flight from Chicago Midway Airport to Puerto Rico? While on average our users pay $331, our data indicates the cheapest price to be $226. The most popular route (Chicago Midway - San Juan Luis Munoz Marin Intl), is priced around $247.

  • 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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $254). Flying from Chicago Midway Airport to Puerto Rico in June is currently the most expensive (average of $339). 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.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
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Midway to Luis Munoz Marin Intl flights
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Midway to Montego Bay flights
O'Hare Intl to Saint Thomas Island flights
Midway to Punta Cana flights
O'Hare Intl to Nassau flights
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Midway to Oranjestad flights
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Midway to Nassau flights
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O'Hare Intl to Bridgetown flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Kingston flights
O'Hare Intl to Port of Spain flights
Midway to Providenciales flights
Midway to Santo Domingo flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to St. John's flights
O'Hare Intl to Road Town flights
Midway to George Town flights
O'Hare Intl to Castries flights
Midway to Santiago de los Caballeros flights
O'Hare Intl to Basseterre flights
O'Hare Intl to St. George's flights
Midway to Simpson Bay flights
O'Hare Intl to Georgetown flights
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O'Hare Intl to Havana flights
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O'Hare Intl to The Valley flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Aguadilla flights
Midway to Castries flights
O'Hare Intl to Gregory Town flights
Midway to Kingston flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Culebra flights
O'Hare Intl to Mayagüez flights
Midway to Gregory Town flights

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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$133Average$280FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$149Average$327FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$299Average$443FlexibilityNo cancel feeOn-time69%
DeltaCheapest$325Average$428FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$354Average$491FlexibilityNo cancel feeOn-time63%

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