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Midway

$69+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
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Flights to Midway in 2025

Find the latest flights to Midway in 2025, 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 April 29, 2025.

Popular in

December

Cheapest in

September

Average price

$237

Round-trip from

$118

One-way from

$69

Good round-trip deal

$242 or less

Good one-way deal

$126 or less
Highest demand for flights based on searches. 2% potential increase in price ($6 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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From New York to Chicago
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One-way flight from New York to Chicago Midway (MDW)
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Price to beat on a round-trip flight from New York to Chicago Midway.
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Price to beat on a one-way flight from New York to Chicago Midway.
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Find flight deals to Midway Airport

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 April 29, 2025.

Wed 5/216:10 amLGA - MDW
Nonstop2h 20mSouthwest
Wed 5/288:20 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 4/26$153
Wed 5/286:05 amEWR - MDW
1 stop8h 10mDelta
Wed 6/44:15 pmMDW - EWR
1 stop7h 52mDelta
Deal found 4/28$168
Wed 5/146:00 amJFK - MDW
1 stop6h 26mFrontier
Wed 5/212:12 pmMDW - JFK
1 stop9h 08mFrontier
Deal found 4/28$198
Wed 5/146:30 amLGA - MDW
1 stop5h 56mFrontier
Sat 5/1710:48 amMDW - LGA
1 stop11h 15mFrontier
Deal found 4/27$198
Thu 5/295:59 amEWR - MDW
1 stop16h 57mFrontier
Tue 6/36:40 amMDW - EWR
1 stop26h 34mFrontier
Deal found 4/28$203
Thu 6/1212:55 pmEWR - MDW
1 stop20h 27mAllegiant Air
Mon 6/168:36 pmMDW - EWR
1 stop11h 29mAllegiant Air
Deal found 4/27$235
Fri 5/306:45 amEWR - MDW
2 stops13h 29mMultiple Airlines
Mon 6/28:04 pmMDW - EWR
1 stop12h 01mMultiple Airlines
Deal found 4/28$280
Sun 5/256:00 amJFK - MDW
1 stop6h 53mDelta
Wed 5/286:25 pmMDW - JFK
1 stop3h 49mDelta
Deal found 4/27$293

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 April 29, 2025.
Use the filters below to find and compare flights to Chicago Midway Airport that are best for you.

Fly from

New York

Route

Depart

Return

Price

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 5/21

6:10 am-7:30 am

Nonstop2h 20m

Chicago Midway

Wed 5/28

8:20 pm-11:25 pm

Nonstop2h 05m

$153

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 5/28

6:05 am-1:15 pm

1 stop8h 10m

Chicago Midway

Wed 6/4

4:15 pm-1:07 am

1 stop7h 52m

$168

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 5/14

6:00 am-11:26 am

1 stop6h 26m

Chicago Midway

Wed 5/21

2:12 pm-12:20 am

1 stop9h 08m

$198

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 5/14

6:30 am-11:26 am

1 stop5h 56m

Chicago Midway

Tue 5/20

10:34 am-10:20 pm

1 stop10h 46m

$198

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 5/29

5:59 am-9:56 pm

1 stop16h 57m

Chicago Midway

Tue 6/3

6:40 am-10:14 am

1 stop26h 34m

$203

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 6/12

12:55 pm-8:22 am

1 stop20h 27m

Chicago Midway

Mon 6/16

8:36 pm-9:05 am

1 stop11h 29m

$235

NewarkChicago

EWR - MDW

EWRMDW

Newark

Fri 5/30

6:45 am-7:14 pm

2 stops13h 29m

Chicago Midway

Mon 6/2

8:04 pm-9:05 am

1 stop12h 01m

$280

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 5/24

2:20 pm-9:13 pm

1 stop7h 53m

Chicago Midway

Sat 5/31

12:48 pm-10:00 pm

1 stop8h 12m

$291

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 5/28

6:10 am-7:30 am

Nonstop2h 20m

$69

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sun 5/25

5:59 am-8:40 am

1 stop3h 41m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 19 results
1
2

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy-Trust 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: 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: eDreams 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), eDreams 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

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

Use this chart to determine the optimal time to book a round-trip flight from New York to Midway. Price data was last updated on April 25, 2025.

Booking 81 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.

How long is the flight to Midway?

On average, a flight from New York to Midway takes 9 hours 53 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.

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 December 16, 2024.

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

Weekly flight availability to Midway

The most flights from New York to Midway are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

What are the most popular airlines that fly to Midway?

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

Southwest

Southwest

From $148

Delta

Delta

From $203

Spirit Airlines

Spirit Airlines

From $37

What are the cheapest airlines that fly to Midway?

The cheapest airlines flying from New York to Midway are Spirit Airlines, Southwest and Delta.

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).

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 29, 2025.
To help decide which airline to fly to Chicago, see what other customers have to say about Southwest, Delta and Allegiant Air. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,292 reviews

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,292 reviews
Southwest
8.0
Very good
4,292 reviews

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,929 reviews
Southwest
8.0
Very good
4,292 reviews

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,292 reviews

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,285 reviews
Southwest
8.0
Very good
4,292 reviews

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $44, while round-trip flights cost around $51.

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

    A round-trip flight to Midway will typically cost around $172, however they can be found for as little as $51.

  • Where does the fastest flight to Midway depart from?

    For those looking to save time traveling to Midway, Grand Rapids Gerald R. Ford Intl offers the quickest one-way flight (1 hour 0 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
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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