HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$102+ Cheap flights from Luis Munoz Marin Intl (SJU) 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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Jan 13 — Jan 201
Tue 1/13
Tue 1/20
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Luis Munoz Marin Intl to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Luis Munoz Marin Intl to Midway

Cheapest flights from Luis Munoz Marin Intl to Midway
Explore the most affordable flight options available from Luis Munoz Marin Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 14, 2025.

This Priceline deal was found by Cheapflights users on 12/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amSJU - MDW
1 stop17h 58mFrontier
Mon 1/56:15 amMDW - SJU
1 stop18h 24mFrontier
Deal found 12/13$192
This CheapOair deal was found by Cheapflights users on 12/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/239:37 pmSJU - MDW
1 stop26h 21mFrontier
Mon 1/56:15 amMDW - SJU
1 stop18h 24mFrontier
Deal found 12/11$193
This Priceline deal was found by Cheapflights users on 12/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:33 pmSJU - MDW
1 stop20h 32mFrontier
Mon 1/56:15 amMDW - SJU
1 stop18h 24mFrontier
Deal found 12/13$217
This Frontier deal was found by Cheapflights users on 12/12. 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.
Tue 12/3010:33 amSJU - MDW
1 stop13h 25mFrontier
Wed 3/46:00 amMDW - SJU
1 stop7h 02mFrontier
Deal found 12/12$233
This CheapOair deal was found by Cheapflights users on 12/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3010:33 amSJU - MDW
1 stop13h 25mFrontier
Mon 1/56:15 amMDW - SJU
1 stop18h 24mFrontier
Deal found 12/12$234
This Frontier deal was found by Cheapflights users on 12/12. 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.
Tue 12/233:54 amSJU - MDW
1 stop12h 43mFrontier
Sat 1/32:24 pmMDW - SJU
1 stop10h 15mFrontier
Deal found 12/12$249
This CheapOair deal was found by Cheapflights users on 12/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amSJU - MDW
1 stop17h 58mFrontier
Wed 12/313:10 pmMDW - SJU
1 stop16h 13mFrontier
Deal found 12/13$250
This CheapOair deal was found by Cheapflights users on 12/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/283:55 amSJU - MDW
1 stop20h 03mFrontier
Thu 1/1511:27 amMDW - SJU
1 stop19h 58mFrontier
Deal found 12/14$255
This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/204:02 pmSJU - MDW
1 stop8h 10mFrontier
Mon 12/226:15 amMDW - SJU
1 stop24h 24mFrontier
Deal found 12/11$260
This Expedia deal was found by Cheapflights users on 12/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/193:54 amSJU - MDW
1 stop7h 25mFrontier
Mon 12/296:15 amMDW - SJU
1 stop24h 24mFrontier
Deal found 12/12$264
This CheapOair deal was found by Cheapflights users on 12/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/283:55 amSJU - MDW
1 stop20h 03mFrontier
Fri 1/28:15 amMDW - SJU
1 stop12h 29mFrontier
Deal found 12/12$267

Find flight deals from Luis Munoz Marin Intl to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Luis Munoz Marin Intl (SJU) 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 December 14, 2025.

Most accurate provider

OneTravel
3 stars

Most trusted provider

OneTravel
3 stars

Round-trip from

$180
(Frontier)

One-way from

$102
(Frontier)

Popular in

July

Cheapest in

December

Average price

$297

Good one-way deal

$256 or less
Provider with most accurate pricing for San Juan Luis Munoz Marin Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Juan Luis Munoz Marin Intl-Chicago Midway flights.
Search Deals
From San Juan Luis Munoz Marin Intl to Chicago Midway
Search Deals
One-way flight from San Juan Luis Munoz Marin Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($55 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 December 2025
Search Deals
Price to beat on a one-way flight from San Juan Luis Munoz Marin Intl to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Luis Munoz Marin Intl 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 December 14, 2025.
Use the filters below to find and compare flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Luis Munoz Marin Intl

Fly to

Midway

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/5

6:00 am-1:56 pm

1 stop9h 56m

Chicago Midway

Mon 3/9

6:00 am-3:06 pm

1 stop8h 06m

$180

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/16

6:00 am-6:54 pm

1 stop14h 54m

Chicago Midway

Sun 1/18

8:19 pm-12:42 pm

1 stop14h 23m

$184

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/9

5:45 am-2:06 pm

1 stop10h 21m

Chicago Midway

Mon 1/12

4:31 pm-2:50 am

1 stop8h 19m

$203

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/16

11:52 am-6:54 pm

1 stop9h 02m

Chicago Midway

Sun 1/18

6:30 pm-3:27 pm

2 stops18h 57m

$220

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/9

5:45 am-2:06 pm

1 stop10h 21m

Chicago Midway

Fri 1/9

4:31 pm-2:50 am

1 stop8h 19m

$265

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 12/28

3:55 am-9:58 pm

1 stop20h 03m

Chicago Midway

Fri 1/2

8:15 am-10:44 pm

1 stop12h 29m

$269

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/26

9:49 am-9:19 am

1 stop25h 30m

Chicago Midway

Fri 1/9

4:31 pm-2:50 am

1 stop8h 19m

$273

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/30

4:22 pm-10:19 pm

1 stop7h 57m

Chicago Midway

Wed 2/4

1:20 pm-6:58 pm

2 stops27h 38m

$277

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 12/24

4:16 pm-10:12 pm

1 stop7h 56m

Chicago Midway

Sat 1/3

2:24 pm-2:39 am

1 stop10h 15m

$279

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 2/13

4:16 pm-10:34 pm

1 stop8h 18m

Chicago Midway

Sat 2/14

8:00 am-7:07 pm

1 stop9h 07m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/12

Showing 1-10 of 18 results
1
2

Compare providers for flights from Luis Munoz Marin Intl to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Luis Munoz Marin Intl to Midway in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
OneTravelPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on San Juan Luis Munoz Marin Intl Airport-Chicago Midway Airport flights, users find the pricing of OneTravel to be most consistent on Cheapflights vs. OneTravel Users can find the same prices on San Juan Luis Munoz Marin Intl Airport-Chicago Midway Airport flight deals on Cheapflights vs. OneTravel >95% of the time. Price accuracy is based on data collected from San Juan Luis Munoz Marin Intl Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Juan Luis Munoz Marin Intl Airport-Chicago Midway Airport flights, Cheapflights users trust OneTravel the most. OneTravel has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Juan Luis Munoz Marin Intl Airport-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Luis Munoz Marin Intl to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Luis Munoz Marin Intl 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 San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport

What is the cheapest month to book a flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

Currently, December is the cheapest month in which you can book a flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport (average of $137). Flying from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport in March is currently the most expensive (average of $427). 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 SJU to MDW?

Find hourly flight availability from Luis Munoz Marin Intl 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 December 14, 2025.

A simple way to save on the total cost of your ticket is to fly from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport in the evening. If you’re flexible enough to do this you can expect to save up to 72% on your trip compared to booking a flight in the afternoon.

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 December 14, 2025.
See what other customers who have flown with Southwest from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,251 reviews

Crew

8.6

Overall

7.9

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

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
7.9
Good
4,251 reviews
Southwest
7.9
Good
4,251 reviews

Crew

8.6

Overall

7.9

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

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 Luis Munoz Marin Intl to Midway. 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 San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

    Frontier can get you from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport in just under 9h 56m. Your travel time can differ by up to . San Juan Luis Munoz Marin Intl Airport and Chicago Midway Airport are separated by a distance of 2057 mi.

  • What is the cheapest airline to fly from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport round-trip?

    Our cheapest airline available from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport is Southwest. Our recent data shows that you can find tickets from as low as $419 on this airline.

  • What are the cheapest flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $250. While the most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway) can be booked for $117 on average, our data indicates $406 when flying from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport.

  • Can I find deals for flights from Luis Munoz Marin Intl to Midway that include hotel bookings?

    Yes. In addition to deals on Luis Munoz Marin Intl to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Luis Munoz Marin Intl to Midway?

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

  • Can I find deals for business class flights from Luis Munoz Marin Intl to Midway?

    Yes. Cheapflights offers flight deals from Luis Munoz Marin Intl 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 San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

    Currently, December is the cheapest month in which you can book a flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport (average of $137). Flying from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport in March is currently the most expensive (average of $427). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Luis Munoz Marin Intl 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

Top airline flying from Luis Munoz Marin Intl to Midway

Discover the top airline that operate flights from Luis Munoz Marin Intl 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 December 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$419Average$559FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.