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Midway

$77+ Cheap flights from LaGuardia, NY (LGA) 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
LGA — MDW
May 28 — Jun 41
Thu 5/28
Thu 6/4
1 adult, Economy
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Cheapflights Tip: The best prices from New York LaGuardia to Chicago Midway are usually found in January or September, booked 22 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

Cheap flight deals from LaGuardia to Midway

Cheapest flights from LaGuardia to Midway
Explore the most affordable flight options available from LaGuardia to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 28, 2026.

This Southwest deal was found by Cheapflights users on 4/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:00 am
LGA
-
MDW
Nonstop2h 25m
Southwest
Sat 5/236:10 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 4/23$143
This Southwest deal was found by Cheapflights users on 4/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/197:25 am
LGA
-
MDW
Nonstop2h 25m
Southwest
Tue 5/197:25 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 4/23$146
This Southwest deal was found by Cheapflights users on 4/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:55 am
LGA
-
MDW
Nonstop2h 25m
Southwest
Tue 5/195:15 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Deal found 4/23$152
This Southwest deal was found by Cheapflights users on 4/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/99:30 pm
LGA
-
MDW
Nonstop2h 25m
Southwest
Fri 6/127:45 pm
MDW
-
LGA
Nonstop2h 10m
Southwest
Deal found 4/23$153
This Southwest deal was found by Cheapflights users on 4/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:55 am
LGA
-
MDW
Nonstop2h 25m
Southwest
Fri 5/297:50 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 4/23$154
This Southwest deal was found by Cheapflights users on 4/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
LGA
-
MDW
Nonstop2h 25m
Southwest
Tue 6/25:15 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Deal found 4/23$155
This Southwest deal was found by Cheapflights users on 4/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:45 pm
LGA
-
MDW
1 stop5h 05m
Southwest
Wed 8/197:10 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 4/23$156
This Southwest deal was found by Cheapflights users on 4/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:55 am
LGA
-
MDW
Nonstop2h 25m
Southwest
Wed 5/277:25 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 4/23$159
This Southwest deal was found by Cheapflights users on 4/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:05 pm
LGA
-
MDW
Nonstop2h 25m
Southwest
Tue 5/269:30 am
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 4/23$161
This Southwest deal was found by Cheapflights users on 4/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/133:55 pm
LGA
-
MDW
Nonstop2h 45m
Southwest
Sat 5/162:25 pm
MDW
-
LGA
Nonstop2h 00m
Southwest
Deal found 4/23$163
This Southwest deal was found by Cheapflights users on 4/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:30 am
LGA
-
MDW
1 stop5h 15m
Southwest
Wed 6/107:45 pm
MDW
-
LGA
Nonstop2h 10m
Southwest
Deal found 4/23$165
This Southwest deal was found by Cheapflights users on 4/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:05 pm
LGA
-
MDW
Nonstop2h 25m
Southwest
Sat 5/305:30 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Deal found 4/23$167

Find flight deals from LaGuardia to Midway

Discover tips and strategies to find the most affordable flight options for your journey from LaGuardia (LGA) 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 April 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$143
(Southwest)

One-way from

$76
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$275

Good round-trip deal

$256 or less

Good one-way deal

$172 or less
Provider with most accurate pricing for New York LaGuardia-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York LaGuardia-Chicago Midway flights.
Search Deals
From New York LaGuardia to Chicago Midway
Search Deals
One-way flight from New York LaGuardia to Chicago Midway
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from New York LaGuardia to Chicago Midway.
Search Deals
Price to beat on a one-way flight from New York LaGuardia to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from LaGuardia 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 April 28, 2026.
Use the filters below to find and compare flights from New York LaGuardia Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 5/27

10:55 am-12:20 pm

Nonstop2h 25m

Chicago Midway

Sun 5/31

5:20 am-8:20 am

Nonstop2h 00m

$173

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 7/24

9:30 pm-10:55 pm

Nonstop2h 25m

Chicago Midway

Wed 7/29

5:15 am-8:15 am

Nonstop2h 00m

$177

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 7/15

5:40 pm-7:30 pm

Nonstop2h 50m

Chicago Midway

Sun 7/19

5:20 am-8:20 am

Nonstop2h 00m

$177

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 7/23

7:25 am-8:50 am

Nonstop2h 25m

Chicago Midway

Sun 7/26

5:20 am-8:20 am

Nonstop2h 00m

$197

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Mon 6/22

9:30 pm-10:55 pm

Nonstop2h 25m

Chicago Midway

Fri 6/26

5:15 am-8:15 am

Nonstop2h 00m

$217
Quickest round-trip

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 7/2

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Sun 7/5

5:20 am-8:20 am

Nonstop2h 00m

$217

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 5/28

12:00 pm-5:50 pm

1 stop6h 50m

Chicago Midway

Sun 5/31

5:20 am-8:20 am

Nonstop2h 00m

$244

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 6/16

4:35 pm-12:05 am

1 stop8h 30m

Chicago Midway

Sun 6/21

5:20 am-8:20 am

Nonstop2h 00m

$247

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sun 5/10

9:05 am-3:20 pm

1 stop7h 15m

Chicago Midway

Wed 5/13

8:15 am-2:25 pm

1 stop5h 10m

$267

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 5/13

1:30 pm-8:35 pm

1 stop8h 05m

Chicago Midway

Sun 5/17

5:20 am-8:20 am

Nonstop2h 00m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

Compare providers for flights from LaGuardia 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 LaGuardia to Midway in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 New York LaGuardia 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 New York LaGuardia Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New York LaGuardia Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New York LaGuardia 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 New York LaGuardia 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 LaGuardia to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from LaGuardia 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 New York LaGuardia Airport to Chicago Midway Airport

How far ahead should I book a flight from New York LaGuardia Airport to Chicago Midway Airport?

The price you pay for your flight from New York LaGuardia Airport to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 21 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from New York LaGuardia Airport to Chicago Midway Airport?

Currently, January is the cheapest month in which you can book a flight from New York LaGuardia Airport to Chicago Midway Airport (average of $185). Flying from New York LaGuardia Airport to Chicago Midway Airport in December is currently the most expensive (average of $410). 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 LGA to MDW?

Find hourly flight availability from LaGuardia 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 April 28, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 19% on flights from New York LaGuardia Airport to Chicago Midway Airport by exploring options for tickets in the evening.

What is the cheapest day to fly from New York LaGuardia Airport to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from LaGuardia to Midway. Price data was last updated on April 25, 2026.

Travelers seeking maximum savings on their New York LaGuardia Airport to Chicago Midway Airport flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from New York LaGuardia Airport to Chicago Midway Airport?

The best insider tips for New York LaGuardia Airport to Chicago Midway Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your New York LaGuardia Airport to Chicago Midway Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Brandon Schultz

Brandon Schultz

Expert on LGA

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

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 April 28, 2026.
Get a feel of what it's like to fly with Southwest from New York LaGuardia Airport to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,314 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,314 reviews
Southwest
8.0
Very good
4,314 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from LaGuardia 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 New York LaGuardia Airport to Chicago Midway Airport?

    Southwest can get you from New York LaGuardia Airport to Chicago Midway Airport in just under 2h 25m. Your travel time will be generally consistent. New York LaGuardia Airport and Chicago Midway Airport are separated by a distance of 722 mi. All flights are typically nonstop.

  • What is the cheapest airline to fly from New York LaGuardia Airport to Chicago Midway Airport round-trip?

    Flying on Southwest is currently your cheapest option to Chicago Midway Airport, with prices starting at $164. Southwest is currently priced 42% below the average price you’ll pay for this route.

  • What are the cheapest flights from New York LaGuardia Airport to Chicago Midway Airport?

    Looking for the cheapest flight from New York LaGuardia Airport to Chicago Midway Airport? While on average our users pay $284, our data indicates the cheapest price to be $98. The most popular route (New York LaGuardia - Chicago Midway), is priced around $177.

  • Can I find deals for flights from LaGuardia to Midway that include hotel bookings?

    Yes. In addition to deals on LaGuardia to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from LaGuardia to Midway?

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

  • Can I find deals for business class flights from LaGuardia to Midway?

    Yes. Cheapflights offers flight deals from LaGuardia 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 New York LaGuardia Airport to Chicago Midway Airport?

    Currently, January is the cheapest month in which you can book a flight from New York LaGuardia Airport to Chicago Midway Airport (average of $185). Flying from New York LaGuardia Airport to Chicago Midway Airport in December is currently the most expensive (average of $410). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Top airline flying from LaGuardia to Midway

Discover the top airline that operate flights from LaGuardia 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 April 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$164Average$295FlexibilityNo cancel feeOn-time63%

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