What is the cheapest month to fly to Midway?

April is currently the cheapest month to fly to Midway . At this moment in time November is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

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 $38, while round-trip flights cost around $48.

How much is a round-trip flight to Midway?

A round-trip flight to Midway will typically cost around $129, however they can be found for as little as $48.

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).

$79+ Flights to Midway | Cheapflights

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Flights to Midway in 2025

Popular in	December
Cheapest in	September
Average price	$268
Round-trip from	$117
One-way from	$79
Good round-trip deal	$235 or less
Good one-way deal	$120 or less

Highest demand for flights based on searches. 2% potential increase in price ($4 potential increase over avg. RT price).

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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).

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Average for round-trip flights in June 2025

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From New York to Chicago

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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.

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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 June 12, 2025.

Thu 7/109:05 amLGA - MDW

Nonstop2h 25mSouthwest

Sat 7/127:00 pmMDW - LGA

Nonstop2h 10mSouthwest

Deal found 6/10$137

Sat 9/1312:00 pmEWR - MDW

1 stop7h 07mDelta

Tue 9/165:25 pmMDW - EWR

1 stop6h 30mDelta

Deal found 6/11$157

Tue 6/175:59 amEWR - MDW

1 stop5h 42mFrontier

Wed 6/1811:39 amMDW - EWR

1 stop12h 05mFrontier

Deal found 6/9$176

Sat 9/201:01 pmJFK - MDW

1 stop11h 08mFrontier

Tue 9/238:00 amMDW - JFK

1 stop22h 28mFrontier

Deal found 6/10$182

Sat 8/2311:30 amLGA - MDW

1 stop12h 41mFrontier

Mon 8/256:15 amMDW - LGA

1 stop27h 20mFrontier

Deal found 6/12$216

Fri 8/19:55 amEWR - MDW

1 stop5h 01mAllegiant Air

Mon 8/41:11 pmMDW - EWR

1 stop18h 54mAllegiant Air

Deal found 6/11$232

Mon 11/2410:00 amJFK - MDW

1 stop9h 36mDelta

Tue 12/29:30 amMDW - JFK

1 stop7h 42mDelta

Deal found 6/12$238

Thu 7/1010:12 amEWR - MDW

2 stops24h 29mMultiple Airlines

Wed 7/164:27 pmMDW - EWR

1 stop18h 38mMultiple Airlines

Deal found 6/10$291

Thu 7/2411:13 amSWF - MDW

2 stops27h 51mAllegiant Air

Sun 7/2711:37 amMDW - SWF

1 stop21h 52mAllegiant Air

Deal found 6/10$401

Thu 7/37:52 pmSWF - MDW

2 stops19h 12mMultiple Airlines

Sun 7/611:37 amMDW - SWF

1 stop21h 52mMultiple Airlines

Deal found 6/11$574

Best flights to Midway Airport
Discover carefully curated flight deals to Midway Airport that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 12, 2025.

Thu 7/109:05 amLGA - MDW

Nonstop2h 25mSouthwest

Sat 7/127:00 pmMDW - LGA

Nonstop2h 10mSouthwest

Deal found 6/10$137

Wed 7/96:00 amEWR - MDW

1 stop3h 44mDelta

Wed 7/95:05 pmMDW - EWR

1 stop6h 54mDelta

Deal found 6/11$157

Tue 6/175:59 amEWR - MDW

1 stop5h 42mFrontier

Wed 6/1811:39 amMDW - EWR

1 stop12h 05mFrontier

Deal found 6/9$176

Sun 7/139:55 amEWR - MDW

1 stop24h 46mAllegiant Air

Fri 7/1810:31 amMDW - EWR

1 stop21h 34mAllegiant Air

Deal found 6/9$224

Thu 7/1010:12 amEWR - MDW

2 stops24h 29mMultiple Airlines

Wed 7/164:27 pmMDW - EWR

1 stop18h 38mMultiple Airlines

Deal found 6/10$291

Sat 9/201:01 pmJFK - MDW

1 stop11h 08mFrontier

Tue 9/238:00 amMDW - JFK

1 stop22h 28mFrontier

Deal found 6/10$182

Sat 8/2311:30 amLGA - MDW

1 stop12h 41mFrontier

Tue 8/268:00 amMDW - LGA

1 stop25h 35mFrontier

Deal found 6/12$206

Mon 11/2410:00 amJFK - MDW

1 stop9h 36mDelta

Tue 12/29:30 amMDW - JFK

1 stop7h 42mDelta

Deal found 6/12$238

Thu 7/2411:13 amSWF - MDW

2 stops27h 51mAllegiant Air

Sun 7/2711:37 amMDW - SWF

1 stop21h 52mAllegiant Air

Deal found 6/10$401

Thu 7/37:52 pmSWF - MDW

2 stops19h 12mMultiple Airlines

Sun 7/611:37 amMDW - SWF

1 stop21h 52mMultiple Airlines

Deal found 6/11$574

Last-minute flights to Midway Airport
Discover last-minute flight deals to Midway Airport. Data last updated June 12, 2025 and is based on user searches.

Tue 6/175:59 amEWR - MDW

1 stop5h 42mFrontier

Wed 6/1811:39 amMDW - EWR

1 stop12h 05mFrontier

Deal found 6/9$176

Tue 6/176:05 amLGA - MDW

Nonstop2h 20mSouthwest

Tue 6/247:20 pmMDW - LGA

Nonstop2h 10mSouthwest

Deal found 6/10$190

Tue 6/174:35 pmEWR - MDW

2 stops24h 02mMultiple Airlines

Fri 6/201:41 pmMDW - EWR

1 stop18h 24mMultiple Airlines

Deal found 6/10$376

Thu 6/1910:55 pmLGA - MDW

1 stop13h 45mFrontier

Sun 6/227:40 amMDW - LGA

1 stop12h 19mFrontier

Deal found 6/9$260

Thu 6/1911:11 amSWF - MDW

2 stops27h 52mAllegiant Air

Sun 6/2211:45 amMDW - SWF

1 stop21h 46mAllegiant Air

Deal found 6/11$623

Fri 6/206:59 amJFK - MDW

1 stop14h 18mFrontier

Sat 6/289:12 pmMDW - JFK

1 stop12h 17mFrontier

Deal found 6/11$318

Fri 6/209:55 amEWR - MDW

1 stop5h 08mAllegiant Air

Mon 6/239:12 amMDW - EWR

1 stop24h 53mAllegiant Air

Deal found 6/11$383

Sat 6/216:00 amEWR - MDW

1 stop3h 41mDelta

Sat 6/286:20 pmMDW - EWR

1 stop3h 40mDelta

Deal found 6/11$240

Sat 6/218:30 amJFK - MDW

1 stop8h 11mDelta

Sat 6/286:20 pmMDW - JFK

1 stop4h 20mDelta

Deal found 6/11$297

Thu 7/310:55 pmLGA - MDW

1 stop13h 45mFrontier

Wed 7/911:39 amMDW - LGA

1 stop10h 53mFrontier

Deal found 6/9$228

Thu 7/37:52 pmSWF - MDW

2 stops19h 12mMultiple Airlines

Sun 7/611:37 amMDW - SWF

1 stop21h 52mMultiple Airlines

Deal found 6/11$574

Wed 7/96:00 amEWR - MDW

1 stop3h 44mDelta

Wed 7/95:05 pmMDW - EWR

1 stop6h 54mDelta

Deal found 6/11$157

One-way flights to Midway Airport
Search for one-way flight options to Midway Airport. Find affordable one-way fares based on user searches. Data last updated June 12, 2025.

Sat 8/233:29 pmEWR - MDW

1 stop6h 43mDelta

Deal found 6/11$79

Wed 8/2710:25 amLGA - MDW

1 stop5h 45mSouthwest

Deal found 6/10$79

Tue 6/175:59 amEWR - MDW

1 stop5h 42mFrontier

Deal found 6/10$93

Thu 8/219:55 amEWR - MDW

1 stop23h 47mAllegiant Air

Deal found 6/11$95

Tue 8/191:00 pmJFK - MDW

1 stop26h 01mFrontier

Deal found 6/9$98

Wed 8/206:30 amLGA - MDW

1 stop8h 31mFrontier

Deal found 6/9$103

Wed 7/91:00 pmJFK - MDW

1 stop6h 40mDelta

Deal found 6/10$146

Tue 7/151:12 pmEWR - MDW

2 stops27h 25mMultiple Airlines

Deal found 6/11$153

Fri 7/46:00 amLGA - MDW

2 stops10h 41mDelta

Deal found 6/12$159

Thu 9/46:30 amLGA - MDW

2 stops35h 13mMultiple Airlines

Deal found 6/11$176

Sun 7/2711:13 amSWF - MDW

2 stops23h 28mAllegiant Air

Deal found 6/11$195

Fri 6/2711:00 amEWR - MDW

1 stop8h 41mSpirit Airlines

Deal found 6/12$209

Cheapflights Fare Finder

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

Fly from

Route

Depart

Return

Price

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 7/10

9:05 am-10:30 am

Nonstop2h 25m

Chicago Midway

Sat 7/12

7:00 pm-10:10 pm

Nonstop2h 10m

$137

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 7/9

6:00 am-8:44 am

1 stop3h 44m

Chicago Midway

Wed 7/9

5:05 pm-12:59 am

1 stop6h 54m

$157

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 6/17

5:59 am-10:41 am

1 stop5h 42m

Chicago Midway

Wed 6/18

11:39 am-12:44 am

1 stop12h 05m

$176

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 9/9

1:01 pm-10:58 pm

1 stop10h 57m

Chicago Midway

Tue 9/16

8:00 am-12:40 am

1 stop15h 40m

$184

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 9/10

6:30 am-10:58 pm

1 stop17h 28m

Chicago Midway

Wed 9/24

8:00 am-11:32 pm

1 stop14h 32m

$206

NewarkChicago

EWR - MDW

EWRMDW

Newark

Fri 8/1

9:55 am-1:56 pm

1 stop5h 01m

Chicago Midway

Mon 8/4

1:11 pm-9:05 am

1 stop18h 54m

$232

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 8/19

12:29 pm-5:47 pm

1 stop6h 18m

Chicago Midway

Tue 8/26

9:30 am-8:12 pm

1 stop9h 42m

$260

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 7/10

10:12 am-9:41 am

2 stops24h 29m

Chicago Midway

Wed 7/16

4:27 pm-12:05 pm

1 stop18h 38m

$291

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 7/24

11:13 am-2:04 pm

2 stops27h 51m

Chicago Midway

Sun 7/27

11:37 am-10:29 am

1 stop21h 52m

$401

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 7/3

7:52 pm-2:04 pm

2 stops19h 12m

Chicago Midway

Sun 7/6

11:37 am-10:29 am

1 stop21h 52m

$574

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 24 results

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?

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 48 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?

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 most popular airlines that fly to Midway?

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

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

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

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

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

4,287 reviews

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.

Southwest

8.0

Very good

4,287 reviews

Southwest

8.0

Very good

4,287 reviews

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.

Delta

8.0

Very good

7,950 reviews

Southwest

8.0

Very good

4,287 reviews

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.

Allegiant Air

7.3

Good

725 reviews

Southwest

8.0

Very good

4,287 reviews

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.

Spirit Airlines

6.3

Okay

8,052 reviews

Southwest

8.0

Very good

4,287 reviews

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.

Frontier

5.9

Fair

3,295 reviews

Southwest

8.0

Very good

4,287 reviews

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 $38, while round-trip flights cost around $48.
How much is a round-trip flight to Midway?
A round-trip flight to Midway will typically cost around $129, however they can be found for as little as $48.
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

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$79+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights to Midway with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

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 June 12, 2025.

Popular in

Cheapest in

Average price

Round-trip from

One-way from

Good round-trip deal

Good one-way deal

Find flight deals to Midway Airport

Cheapest flights to Midway AirportExplore the most affordable flight options available to Midway Airport. Find the lowest fares based on data from user searches, with prices last updated on June 12, 2025.

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 June 12, 2025.

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 June 12, 2025.

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

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.

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 9, 2025.

How long is the flight to Midway?

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.

What are the most popular airlines that fly to Midway?

What are the cheapest airlines that fly to Midway?

Rainfall in Midway by month

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

Temperature in Midway by month

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

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 June 12, 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.

FAQs about flying to Midway

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

What is the best airline to fly to Midway?

What is the cheapest airport to fly to in Midway?

How much is a round-trip flight to Midway?

Where does the fastest flight to Midway depart from?

Does Chicago Midway have rental cars?

Are there hotels close to Chicago Midway?

Traveling to a place near Chicago Midway Airport?

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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 June 12, 2025.