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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
jul. 8 — jul. 151
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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 julio 3, 2025.

Popular in

December

Cheapest in

September

Average price

$236

Round-trip from

$132

One-way from

$69

Good round-trip deal

$260 or less

Good one-way deal

$142 or less
Highest demand for flights based on searches. 1% potential increase in price ($3 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Average for round-trip flights in July 2025
From New York to Chicago
One-way flight from New York to Chicago Midway (MDW)
Price to beat on a round-trip flight from New York to Chicago Midway.
Price to beat on a one-way flight from New York to Chicago Midway.

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 julio 3, 2025.

sáb. 8/307:30 amLGA - MDW
Nonstop2h 20mSouthwest
mié. 9/35:55 pmMDW - LGA
Nonstop2h 15mSouthwest
Deal found 7/2$137
vie. 9/1911:15 amEWR - MDW
1 stop5h 43mFrontier
lun. 9/225:04 pmMDW - EWR
1 stop6h 30mFrontier
Deal found 7/3$141
mar. 9/96:30 amLGA - MDW
1 stop10h 28mFrontier
sáb. 9/1311:23 amMDW - LGA
1 stop7h 39mFrontier
Deal found 6/30$144
vie. 10/249:00 amJFK - MDW
1 stop10h 18mFrontier
dom. 10/2610:03 pmMDW - JFK
1 stop11h 22mFrontier
Deal found 7/2$146
sáb. 9/139:51 amEWR - MDW
1 stop3h 37mDelta
mié. 9/171:08 pmMDW - EWR
1 stop5h 16mDelta
Deal found 7/2$167

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 julio 3, 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

sáb. 8/30

7:30 am-8:50 am

Nonstop2h 20m

Chicago Midway

mar. 9/2

6:00 am-9:00 am

Nonstop2h 00m

$137

NewarkChicago

EWR - MDW

EWRMDW

Newark

vie. 9/19

11:15 am-3:58 pm

1 stop5h 43m

Chicago Midway

lun. 9/22

5:04 pm-12:34 am

1 stop6h 30m

$141

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

mar. 9/9

6:30 am-3:58 pm

1 stop10h 28m

Chicago Midway

sáb. 9/13

11:23 am-8:02 pm

1 stop7h 39m

$144

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

vie. 10/24

9:00 am-6:18 pm

1 stop10h 18m

Chicago Midway

dom. 10/26

10:03 pm-10:25 am

1 stop11h 22m

$146

NewarkChicago

EWR - MDW

EWRMDW

Newark

sáb. 9/13

9:51 am-12:28 pm

1 stop3h 37m

Chicago Midway

mar. 9/16

1:08 pm-7:24 pm

1 stop5h 16m

$167

NewarkChicago

EWR - MDW

EWRMDW

Newark

jue. 9/25

11:15 am-3:58 pm

1 stop5h 43m

$69

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

lun. 8/4

6:59 am-3:06 pm

1 stop9h 07m

$77

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

lun. 10/27

11:30 am-6:18 pm

1 stop7h 48m

$78

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

mar. 8/19

9:00 am-10:25 am

Nonstop2h 25m

$79

NewarkChicago

EWR - MDW

EWRMDW

Newark

sáb. 9/6

3:29 pm-9:12 pm

1 stop6h 43m

$84

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 14 results
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The best insider tips for flights to Chicago Midway Airport

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 Chicago Midway Airport trip
Airlines
American Airlines

Main Cabin Extra seats on AA offer 34”-35” pitch, more than standard economy.


AA's Flagship Business class includes lie-flat beds and 16” HD screens.

Frontier

Frontier's UpFront Plus guarantees an empty middle seat for extra comfort.


Frontier offers no in-flight entertainment; bring a book or pre-load devices.

Read more about Frontierby Marisa Garcia
Delta

Delta Comfort+ offers extra legroom and complimentary alcoholic drinks.


Delta offers free Wi-Fi on most domestic flights for SkyMiles members.

Read more about Deltaby Harriet Baskas
United Airlines

Basic Economy on United prohibits carry-ons; exceptions for MileagePlus members or select routes.


United Economy Plus offers extra legroom seats at the front of the economy cabin.

Spirit Airlines

Spirit's Big Front Seats offer 11 inches more legroom and larger tray tables.


Spirit's Saver$ Club offers discounts on luggage, seats, and boarding shortcuts.

Allegiant Air

Allegiant offers nonstop flights between smaller cities, avoiding large hubs.


Allegiant's base fare includes only a small personal item; extras cost more.

Airports
MDW

The Orange Line train is the easiest and cheapest way to reach downtown Chicago from MDW, taking less than 30 minutes.

Read more about MDWby Ramsey Qubein
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on American Airlines and Frontier

Marisa Garcia

Marisa Garcia

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 Baskas

Harriet Baskas

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
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Matt Meltzer

Matt Meltzer

Expert on Allegiant Air

Matt Meltzer

Matt Meltzer

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

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

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 June 27, 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 7 hours 49 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.

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 julio 3, 2025.
Read through reviews of airlines servicing the United States, such as Southwest, Delta, and Allegiant Air. 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.

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
8.0
Very good

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $48, while round-trip flights cost around $53.

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

    A round-trip flight to Midway will typically cost around $97, however they can be found for as little as $53.

  • 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
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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