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Midway

$97+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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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 January 27, 2026.

This Priceline deal was found by Cheapflights users on 1/25. 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.
Wed 2/185:25 pm
SJU
-
MDW
1 stop23h 01m
Frontier
Tue 2/246:10 am
MDW
-
SJU
1 stop6h 56m
Frontier
Deal found 1/25$174
This Mytrip deal was found by Cheapflights users on 1/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
SJU
-
MDW
1 stop9h 56m
Frontier
Mon 3/29:22 pm
MDW
-
SJU
1 stop10h 32m
Frontier
Deal found 1/26$182
This CheapOair deal was found by Cheapflights users on 1/27. 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 2/185:25 pm
SJU
-
MDW
1 stop23h 01m
Frontier
Mon 2/239:22 pm
MDW
-
SJU
1 stop10h 32m
Frontier
Deal found 1/27$190
This Orbitz deal was found by Cheapflights users on 1/26. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/168:00 am
SJU
-
MDW
1 stop9h 13m
Frontier
Mon 5/186:00 am
MDW
-
SJU
1 stop7h 08m
Frontier
Deal found 1/26$203
This CheapOair deal was found by Cheapflights users on 1/25. 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 2/185:25 pm
SJU
-
MDW
1 stop23h 01m
Frontier
Mon 3/29:22 pm
MDW
-
SJU
1 stop10h 32m
Frontier
Deal found 1/25$205
This Frontier deal was found by Cheapflights users on 1/26. 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 2/124:11 pm
SJU
-
MDW
1 stop8h 23m
Frontier
Mon 2/169:22 pm
MDW
-
SJU
1 stop10h 32m
Frontier
Deal found 1/26$211
This CheapOair deal was found by Cheapflights users on 1/25. 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 2/255:25 pm
SJU
-
MDW
1 stop23h 01m
Frontier
Sat 2/288:00 am
MDW
-
SJU
1 stop16h 53m
Frontier
Deal found 1/25$215
This Frontier deal was found by Cheapflights users on 1/26. 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 5/13:18 pm
SJU
-
MDW
1 stop8h 01m
Frontier
Mon 5/49:14 am
MDW
-
SJU
1 stop12h 34m
Frontier
Deal found 1/26$217
This Trip.com deal was found by Cheapflights users on 1/25. 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.
Wed 2/44:36 pm
SJU
-
MDW
1 stop29h 16m
Frontier
Mon 2/97:00 pm
MDW
-
SJU
1 stop15h 57m
Frontier
Deal found 1/25$218
This Frontier deal was found by Cheapflights users on 1/27. 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 3/56:00 am
SJU
-
MDW
1 stop9h 56m
Frontier
Mon 3/99:51 pm
MDW
-
SJU
1 stop11h 21m
Frontier
Deal found 1/27$220
This Frontier deal was found by Cheapflights users on 1/25. 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 2/54:22 pm
SJU
-
MDW
1 stop7h 57m
Frontier
Mon 2/91:00 pm
MDW
-
SJU
1 stop8h 59m
Frontier
Deal found 1/25$224
This CheapOair deal was found by Cheapflights users on 1/27. 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 5/73:18 pm
SJU
-
MDW
1 stop8h 01m
Frontier
Sun 5/109:14 am
MDW
-
SJU
1 stop12h 34m
Frontier
Deal found 1/27$229

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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$174
(Priceline)

One-way from

$97
(CheapOair)

Popular in

July

Cheapest in

December

Average price

$501

Good one-way deal

$280 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. 7% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 27, 2026.
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

Wed 2/18

5:25 pm-2:26 pm

1 stop23h 01m

Chicago Midway

Tue 2/24

6:10 am-3:06 pm

1 stop6h 56m

$174

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/26

6:00 am-1:56 pm

1 stop9h 56m

Chicago Midway

Mon 3/2

9:22 pm-9:54 am

1 stop10h 32m

$182

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 2/18

5:25 pm-2:26 pm

1 stop23h 01m

Chicago Midway

Mon 3/2

9:22 pm-9:54 am

1 stop10h 32m

$205

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/5

4:11 pm-10:29 pm

1 stop8h 18m

Chicago Midway

Mon 3/9

9:51 pm-10:12 am

1 stop11h 21m

$220

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 2/11

4:06 pm-11:27 am

1 stop21h 21m

Chicago Midway

Mon 2/16

6:00 am-1:24 am

2 stops41h 24m

$237

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 2/2

8:00 am-7:58 pm

1 stop13h 58m

Chicago Midway

Mon 2/9

1:00 pm-11:59 pm

1 stop8h 59m

$243

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 2/27

4:16 pm-10:37 pm

1 stop8h 21m

Chicago Midway

Sun 3/1

7:30 am-12:54 am

1 stop15h 24m

$252

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/26

6:00 am-1:56 pm

1 stop9h 56m

Chicago Midway

Mon 3/2

2:19 pm-6:58 pm

2 stops26h 39m

$253

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/12

4:11 pm-5:53 pm

1 stop27h 42m

Chicago Midway

Mon 2/16

6:00 am-1:24 am

2 stops41h 24m

$268

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/12

4:11 pm-10:34 pm

1 stop8h 23m

Chicago Midway

Sun 2/15

7:30 am-12:54 am

1 stop15h 24m

$272

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 21 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OneTravelPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Juan Luis Munoz Marin Intl Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, February 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 $204). 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 January 27, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport as you normally would.

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 January 27, 2026.
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
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

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 23h 01m. 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. Southwest is currently priced 2% below the average price you’ll pay for this route.

  • 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 $280. While the most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway) can be booked for $174 on average, our data indicates $393 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, February 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 $204). 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

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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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$419Average$559FlexibilityNo cancel feeOn-time63%

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