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$118+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Find 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 October 14, 2025.

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 12/43:00 pmSJU - MDW
1 stop10h 25mFrontier
Thu 12/116:00 amMDW - SJU
2 stops18h 50mFrontier
Deal found 10/12$213
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 10/313:31 pmSJU - MDW
1 stop7h 14mFrontier
Fri 11/73:32 pmMDW - SJU
1 stop9h 22mFrontier
Deal found 10/12$232
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/74:31 pmSJU - MDW
1 stop28h 08mFrontier
Tue 11/116:26 pmMDW - SJU
1 stop31h 07mFrontier
Deal found 10/13$254
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/64:31 pmSJU - MDW
1 stop7h 32mFrontier
Tue 11/116:26 pmMDW - SJU
1 stop31h 07mFrontier
Deal found 10/13$256
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.
Fri 10/243:05 pmSJU - MDW
1 stop9h 41mFrontier
Mon 10/279:45 amMDW - SJU
1 stop12h 44mFrontier
Deal found 10/13$257
This Frontier deal was found by Cheapflights users on 10/11. 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 10/233:19 pmSJU - MDW
1 stop9h 27mFrontier
Thu 11/1310:12 amMDW - SJU
1 stop9h 12mFrontier
Deal found 10/11$268
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/163:00 pmSJU - MDW
1 stop10h 25mFrontier
Tue 1/66:00 amMDW - SJU
1 stop7h 01mFrontier
Deal found 10/13$270
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/164:04 pmSJU - MDW
1 stop24h 08mMultiple Airlines
Tue 10/215:56 pmMDW - SJU
1 stop31h 06mMultiple Airlines
Deal found 10/13$275
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 10/243:05 pmSJU - MDW
1 stop9h 41mFrontier
Sun 10/2611:57 amMDW - SJU
1 stop13h 33mFrontier
Deal found 10/12$278
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/123:59 amSJU - MDW
1 stop7h 13mFrontier
Mon 11/176:15 amMDW - SJU
1 stop7h 04mFrontier
Deal found 10/12$280

Cheap 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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$213
(Frontier)

One-way from

$118
(Kiwi.com)

Popular in

July

Cheapest in

November

Average price

$395
Provider with most accurate pricing for San Juan Luis Munoz Marin Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for San Juan Luis Munoz Marin Intl-Chicago Midway flights.
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From San Juan Luis Munoz Marin Intl to Chicago Midway
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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 ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 October 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

Fri 10/24

3:05 pm-11:46 pm

1 stop9h 41m

Chicago Midway

Sun 10/26

11:57 am-2:30 am

1 stop13h 33m

$278

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 11/3

2:22 pm-12:30 am

1 stop12h 08m

Chicago Midway

Mon 11/10

6:15 am-3:14 pm

1 stop6h 59m

$284

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 10/24

3:05 pm-11:46 pm

1 stop9h 41m

Chicago Midway

Mon 10/27

5:28 pm-2:09 am

1 stop7h 41m

$284

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 12/18

3:59 pm-11:05 pm

1 stop9h 06m

Chicago Midway

Tue 1/6

6:00 am-3:01 pm

1 stop7h 01m

$284

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/5

3:59 pm-11:05 pm

1 stop9h 06m

Chicago Midway

Mon 12/8

2:15 pm-2:50 am

1 stop10h 35m

$284

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 12/6

2:20 pm-5:35 pm

Nonstop5h 15m

Chicago Midway

Sun 12/14

1:50 pm-10:00 pm

1 stop6h 10m

$285

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 11/22

7:10 am-5:15 pm

1 stop12h 05m

Chicago Midway

Wed 11/26

3:47 pm-1:12 am

1 stop7h 25m

$292

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/23

6:22 am-8:21 pm

2 stops14h 59m

Chicago Midway

Sun 10/26

6:20 am-2:09 pm

1 stop6h 49m

$298

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/30

10:39 pm-8:32 am

1 stop10h 53m

Chicago Midway

Sun 11/2

5:20 am-2:19 pm

1 stop6h 59m

$299

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 11/14

3:59 am-10:26 am

1 stop8h 27m

Chicago Midway

Sun 11/16

6:15 am-3:19 pm

1 stop7h 04m

$301

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 16 results
1
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
OneTravelPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 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 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, 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 $154). 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 October 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 62% 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 October 14, 2025.
See what other customers who have flown with Southwest and Frontier 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
4,238 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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 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 41m. 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 are the cheapest airlines flying 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 Frontier. Our recent data shows that you can find tickets from as low as $148 on this airline. An additional option worth looking into is Southwest, starting at $394. Frontier is currently priced 64% below the average price you’ll pay for this route.

  • 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 $154). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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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 2 airlines flying from Luis Munoz Marin Intl to Midway

Discover the top 2 airlines 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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$265FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$394Average$566FlexibilityNo cancel feeOn-time63%

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