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Midway

$70+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
LGA — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from New York LaGuardia to Chicago Midway are usually found in September or February, booked 75 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

Cheap 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 September 11, 2025.

Round-trip from

$129
(Southwest)

One-way from

$70
(Southwest)

Popular in

June

Cheapest in

September

Average price

$210

Good round-trip deal

$231 or less

Good one-way deal

$169 or less
From New York LaGuardia to Chicago Midway
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One-way flight from New York LaGuardia to Chicago Midway
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Highest demand for flights based on searches. 9% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from New York LaGuardia to Chicago Midway.
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Price to beat on a one-way flight from New York LaGuardia to Chicago Midway.
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Find 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/9. 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 9/306:15 pmLGA - MDW
1 stop5h 10mSouthwest
Wed 10/16:00 amMDW - LGA
Nonstop2h 00mSouthwest
Deal found 9/9$129
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/156:05 amLGA - MDW
Nonstop2h 25mSouthwest
Tue 10/212:25 pmMDW - LGA
Nonstop2h 00mSouthwest
Deal found 9/11$132
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/179:55 pmLGA - MDW
Nonstop2h 25mSouthwest
Tue 11/1812:55 pmMDW - LGA
Nonstop2h 00mSouthwest
Deal found 9/11$133
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:45 amLGA - MDW
1 stop7h 15mSouthwest
Tue 10/285:55 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 9/11$136
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/18:15 amLGA - MDW
Nonstop2h 25mSouthwest
Wed 11/56:00 amMDW - LGA
Nonstop2h 00mSouthwest
Deal found 9/11$138
This Southwest deal was found by Cheapflights users on 9/10. 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.
Thu 11/137:15 amLGA - MDW
Nonstop2h 30mSouthwest
Sat 11/155:40 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 9/10$140
This Southwest deal was found by Cheapflights users on 9/9. 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 10/110:25 amLGA - MDW
1 stop5h 45mSouthwest
Tue 10/710:55 amMDW - LGA
Nonstop2h 00mSouthwest
Deal found 9/9$141
This Southwest deal was found by Cheapflights users on 9/9. 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 11/18:15 amLGA - MDW
Nonstop2h 25mSouthwest
Mon 11/37:15 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 9/9$142
This Gotogate deal was found by Cheapflights users on 9/10. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2511:30 amLGA - MDW
1 stop12h 17mFrontier
Mon 10/276:15 amMDW - LGA
1 stop9h 14mFrontier
Deal found 9/10$144
This Booking.com deal was found by Cheapflights users on 9/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2310:00 pmLGA - MDW
1 stop14h 08mFrontier
Sun 10/2611:57 amMDW - LGA
1 stop27h 00mFrontier
Deal found 9/11$145

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 September 11, 2025.
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

LaGuardia

Fly to

Midway

Route

Depart

Return

Price

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 11/1

8:15 am-9:40 am

Nonstop2h 25m

Chicago Midway

Wed 11/5

6:00 am-9:00 am

Nonstop2h 00m

$138

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 9/30

6:15 pm-10:25 pm

1 stop5h 10m

Chicago Midway

Wed 10/1

8:35 am-2:55 pm

1 stop5h 20m

$139

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 10/21

12:45 pm-7:25 pm

1 stop7h 40m

Chicago Midway

Wed 10/22

5:55 pm-11:10 pm

1 stop4h 15m

$139

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 10/22

9:45 pm-11:10 pm

Nonstop2h 25m

Chicago Midway

Sat 10/25

5:50 pm-8:55 pm

Nonstop2h 05m

$151

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 10/30

6:25 am-7:45 am

Nonstop2h 20m

Chicago Midway

Tue 11/4

8:25 am-11:30 am

Nonstop2h 05m

$154

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 12/3

3:50 pm-8:30 pm

1 stop5h 40m

Chicago Midway

Sun 12/7

8:25 pm-11:25 pm

Nonstop2h 00m

$154

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 11/12

10:50 am-7:30 pm

2 stops9h 40m

Chicago Midway

Tue 11/18

7:05 am-3:35 pm

1 stop7h 30m

$156

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 11/1

8:15 am-9:40 am

Nonstop2h 25m

Chicago Midway

Mon 11/3

2:10 pm-9:55 pm

1 stop6h 45m

$162

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Mon 10/20

9:35 pm-11:05 pm

Nonstop2h 30m

Chicago Midway

Wed 10/22

8:25 am-11:30 am

Nonstop2h 05m

$164

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 10/30

6:25 am-7:45 am

Nonstop2h 20m

Chicago Midway

Mon 11/3

7:15 pm-10:20 pm

Nonstop2h 05m

$168

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 22 results
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The best insider tips for New York LaGuardia Airport to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your New York LaGuardia Airport to Chicago Midway Airport trip
Airports
LGA

Security lines at LGA are efficient with typical waits under 15 minutes. Plan accordingly to ensure a smooth departure experience.

Read more about LGAby Brandon Schultz
MDW

The Orange Line train from MDW to downtown Chicago takes less than 30 minutes, offering a convenient and affordable transit option.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

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

Brandon Schultz

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

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?

Use this chart to determine the optimal time to book a round-trip flight from LaGuardia to Midway. Price data was last updated on August 29, 2025.

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 75 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, April is the cheapest month in which you can book a flight from New York LaGuardia Airport to Chicago Midway Airport (average of $160). Flying from New York LaGuardia Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 September 11, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 26% 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 September 7, 2025.

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. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 September 11, 2025.
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
4,248 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

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 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 $154. Southwest is currently priced 41% 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 $286, our data indicates the cheapest price to be $85. The most popular route (New York LaGuardia - Chicago Midway), is priced around $119.

  • 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, April is the cheapest month in which you can book a flight from New York LaGuardia Airport to Chicago Midway Airport (average of $160). Flying from New York LaGuardia Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Benton Harbor
Porter
Chesterton

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$154Average$259FlexibilityNo cancel feeOn-time63%

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