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Midway

$104+ Cheap flights to Midway

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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
Aug 27 — Sep 31
Thu 8/27
Thu 9/3
1 adult, Economy
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Flights to Midway in 2026

Cheapest flights to Midway Airport
Explore the most affordable flight options available to Midway Airport. Find the lowest fares based on data from user searches, with prices last updated on July 28, 2026.

This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/254:10 pm
LGA
-
MDW
Nonstop2h 30m
Southwest
Tue 8/257:05 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 7/27$207
This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:05 pm
LGA
-
MDW
1 stop5h 45m
Southwest
Wed 9/27:05 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 7/27$217
This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:50 pm
LGA
-
MDW
Nonstop2h 30m
Southwest
Sun 9/62:50 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 7/27$218
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
EWR
-
MDW
1 stop4h 59m
Delta
Tue 8/256:05 am
MDW
-
EWR
1 stop5h 13m
Delta
Deal found 7/27$227
This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:45 pm
LGA
-
MDW
1 stop5h 05m
Southwest
Tue 9/87:15 am
MDW
-
LGA
1 stop7h 35m
Southwest
Deal found 7/27$227
This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/99:35 pm
LGA
-
MDW
Nonstop2h 20m
Southwest
Fri 9/115:00 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Deal found 7/27$229
This Southwest deal was found by Cheapflights users on 7/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:00 am
LGA
-
MDW
2 stops10h 05m
Southwest
Tue 9/87:15 am
MDW
-
LGA
1 stop7h 35m
Southwest
Deal found 7/26$232
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:00 pm
EWR
-
MDW
1 stop5h 15m
Delta
Tue 8/255:10 pm
MDW
-
EWR
1 stop6h 00m
Delta
Deal found 7/27$237
This Southwest deal was found by Cheapflights users on 7/24. 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 8/228:20 am
LGA
-
MDW
1 stop6h 45m
Southwest
Mon 8/245:50 pm
MDW
-
LGA
1 stop4h 30m
Southwest
Deal found 7/24$237
This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/229:40 am
LGA
-
MDW
Nonstop2h 25m
Southwest
Sun 8/235:25 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Deal found 7/27$238
This Frontier deal was found by Cheapflights users on 7/24. 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.
Mon 9/75:55 am
EWR
-
MDW
1 stop6h 00m
Frontier
Mon 9/1412:03 pm
MDW
-
EWR
1 stop11h 56m
Frontier
Deal found 7/24$239
This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/99:45 am
LGA
-
MDW
1 stop7h 50m
Southwest
Sun 9/135:25 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Deal found 7/27$239

Find flight deals to Midway Airport

Find the latest flights to Midway in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 2,558,603 searches and data was last updated on July 28, 2026.

Popular in

June

Cheapest in

January

Average price

$310

Round-trip from

$198

One-way from

$104

Good round-trip deal

$202 or less

Good one-way deal

$150 or less
Highest demand for flights based on searches. 17% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
From New York to Chicago
Search Deals
One-way flight from New York to Chicago Midway (MDW)
Search Deals
Price to beat on a round-trip flight from New York to Chicago Midway.
Search Deals
Price to beat on a one-way flight from New York to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Locate flights to Midway that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 2,558,603 searches and data was last updated on July 28, 2026.
Use the filters below to find and compare flights to Chicago Midway Airport that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest round-trip

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 8/26

4:10 pm-5:40 pm

Nonstop2h 30m

Chicago Midway

Wed 9/2

7:05 pm-10:10 pm

Nonstop2h 05m

$207

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 8/25

5:45 pm-9:50 pm

1 stop5h 05m

Chicago Midway

Tue 9/1

2:40 pm-5:45 pm

Nonstop2h 05m

$217

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 9/5

2:40 pm-7:20 pm

1 stop5h 40m

Chicago Midway

Tue 9/8

4:40 pm-11:15 pm

1 stop5h 35m

$227

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 8/29

6:00 am-4:40 pm

2 stops11h 40m

Chicago Midway

Mon 8/31

5:00 am-8:00 am

Nonstop2h 00m

$233

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 8/14

3:00 pm-7:45 pm

1 stop5h 45m

Chicago Midway

Sun 8/16

5:25 am-8:25 am

Nonstop2h 00m

$237

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 9/3

7:25 am-8:45 am

Nonstop2h 20m

Chicago Midway

Sun 9/6

2:45 pm-11:00 pm

1 stop7h 15m

$237

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 11/6

10:30 am-6:00 pm

1 stop8h 30m

Chicago Midway

Sat 11/7

11:50 am-2:50 pm

Nonstop2h 00m

$237

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 8/22

8:20 am-2:05 pm

1 stop6h 45m

Chicago Midway

Mon 8/24

5:50 pm-11:20 pm

1 stop4h 30m

$237
Quickest round-trip

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 8/22

9:40 am-11:05 am

Nonstop2h 25m

Chicago Midway

Sun 8/23

5:25 am-8:25 am

Nonstop2h 00m

$238

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 10/29

6:45 pm-11:05 pm

1 stop5h 20m

Chicago Midway

Sun 11/1

9:35 am-12:40 pm

Nonstop2h 05m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 60 resultsSorted by cheapest first
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Compare providers for flights 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 to Midway in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
Super.comPrice Accuracy-Trust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy1 starTrust 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: Out of all of the providers offering Chicago Midway Airport flight deals, Cheapflights users have found FlightHub to have the most accurate pricing on Cheapflights vs. their site about >95% of the time, users can find the same price on Chicago Midway Airport flight deals on Cheapflights and FlightHub. This is based on searches made for Chicago Midway Airport flights over the past month.
  • Most trusted provider: FlightHub is the most trusted provider by Cheapflights users offering Chicago Midway Airport flight deals. With a user feedback rating of 3 out of 3 stars (3 being the best), FlightHub has received the most positive sentiment from Cheapflights users searching for flights to Chicago Midway Airport. This is based on data collected from Cheapflights searches made over the past month.

Best time to book a flight to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway 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 to Chicago Midway Airport

How long is the flight to Midway?

On average, a flight from New York to Midway takes 8 hours 51 minutes. Flights to Midway from other popular cities in USA will vary in length. Below are a few examples of popular routes and their flight times.

Weekly flight availability to Midway

The most flights from New York to Midway are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

What are the most popular airlines that fly to Midway?

The most popular airlines flying from New York to Midway are Southwest, Frontier and Delta.

Southwest
Southwest
From $77
Frontier
Frontier
From $46
Delta
Delta
From $68
Allegiant Air
Allegiant Air
From $73

What are the cheapest airlines that fly to Midway?

The cheapest airlines flying from New York to Midway are Frontier, United Airlines and Southwest.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Midway ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Midway when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Midway, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

When is the best time to book a flight to Midway?

Booking 33 days in advance of your planned departure date is, on average, the best time to get cheap flights to Midway. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

When is the cheapest time to fly to Midway?

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

Users looking for the lowest fares to Midway should consider flying on Wednesday evenings, when prices are typically cheapest. Budget-minded travelers will want to avoid Sunday afternoons, when prices are usually at their highest.

The best insider tips for flights to Chicago Midway Airport

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 Chicago Midway Airport trip
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on American Airlines and Frontier

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Harriet Baskas

Harriet Baskas

Expert on Delta and United Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Matt Meltzer

Matt Meltzer

Expert on Allegiant Air

Matt Meltzer has been a travel writer for over a decade, covering U.S. domestic locations and hotels for Thrillist, Fifty Grande, Matador Network, Conde Nast Traveler, and other top publications. He's won multiple travel journalism awards from the Society of American Travel Writers and North American Travel Journalists Association, and currently resides in South Florida.

Read more
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

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 July 28, 2026.
Read through reviews of airlines servicing the United States, such as Southwest,United Airlines, andFrontier. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,228 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,228 reviews
Southwest
8.0
Very good
4,228 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
10,045 reviews
Southwest
8.0
Very good
4,228 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,753 reviews
Southwest
8.0
Very good
4,228 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

FAQs about flying to Midway

Chicago Midway International Airport (MDW) is developing into an important hub for domestic air travel in the United States. In 2010, more than 17 million passengers passed through its gates, gaining connections to hundreds of American and international destinations.

Flights to Chicago Midway International Airport are mainly provided by Dallas-based low-cost carrier Southwest Airlines, offering cheap flights to a host of American and Canadian destinations. Most other airlines fly into Chicago’s other major airport, O’Hare.

There’s quite a lot to see and do in Chicago Midway, including a lovely central area known as Midway Boulevard. Full of shops, restaurants and cafes, Midway Boulevard is the perfect place to pull up a chair and people-watch.

  • Can I find cheaper flights to Midway if I am willing to have layovers?

    Yes, flights with layovers are often cheaper than direct flights. Keep an eye out for flight deals to Midway on Cheapflights that require 1 or 2 stops for potential cost savings.

  • What is the best airline to fly to Midway?

    Based on reviews from Cheapflights users, Frontier is rated the highest out of the airlines that fly to Midway.

  • What is the cheapest airport to fly to in Midway?

    Chicago Midway is currently the cheapest airport to fly to in Midway. One-way flights to Chicago Midway typically cost $56, while round-trip flights cost around $98.

  • How much is a round-trip flight to Midway?

    A round-trip flight to Midway will typically cost around $167, however they can be found for as little as $98.

  • Where does the fastest flight to Midway depart from?

    For those looking to save time traveling to Midway, Milwaukee-Mitchell offers the quickest one-way flight (0 hours 45 minutes).

  • Does Chicago Midway have rental cars?

    Yes. Those touching down at Chicago Midway can take advantage of the rental car services offered upon their arrival.

  • Are there hotels close to Chicago Midway?

    Yes. Chicago Midway has hotels nearby for those requiring accommodations. Midway Airport 2 Bedroom With Full Kitchen is the closest property to Chicago Midway (0.0 mi away from Chicago Midway).

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
Valparaiso
Hammond
Saint Joseph
Porter

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