How long does it take to fly to Chicago Midway Airport?

On average, it takes 2h 28m to fly from New York to Chicago Midway Airport if you fly out of Newark (the most popular airport in New York) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago Midway Airport). If you’re flying out of New York and into Chicago O'Hare Intl Airport, then the flight time is around 2h 39m.

What day of the week experiences the fewest flight delays on this route?

Monday is statistically the day of the week which experiences the fewest number of delays on this flight route. Thursday has historically seen more delays on average compared to the rest of the week.

What is the cheapest airline that flies from New York to Chicago Midway?

Frontier, Southwest, and Delta are the most popular carriers operating from New York to Chicago Midway

What airlines fly to Chicago Midway Airport?

Southwest, Delta and Frontier are the top three most popular airlines that fly to Chicago Midway Airport from New York according to our data. Southwest is the first choice among our users, with 64% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 4 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

Which airline has the best punctuality record on New York to Chicago flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 19% of their flights experiencing any sort of delay.

What is the most punctual flight time for New York to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights at night have, in the past, seen delays more frequently in comparison.

How many flights depart from New York to Chicago Midway Airport on average per week?

The number of flights available between New York and Chicago Midway Airport is 27 per week as of December 2025. The most frequent departure day is Tue, with 30% of weekly flights leaving on this day.

How often are flights from New York to Chicago delayed?

Historically, on average around 20% of flights between New York and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 141 minutes.

How many flights depart from New York to Chicago Midway Airport on average per day?

As of December 2025, 3 flights take off from New York and land in Chicago Midway Airport each day. The most common flight departure time for this route is 9:00PM, with 35% of daily flights taking off at noon.

When did momondo last update prices for flights from New York to Chicago Midway Airport?

Prices for flights from New York to Chicago Midway Airport were last updated today.

How many operators does momondo search for flights from New York to Chicago Midway Airport?

There are 4 operators available for flights from New York to Chicago Midway Airport as of December 2025.

How old do you have to be to fly from New York to Chicago Midway Airport?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from New York to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$58 Cheap Flights from New York to Chicago Midway Airport in 2025/26

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Cheap round-trip flights

Enter your travel dates to find the best prices.

10:30 pm - 12:02 am

EWR

MDW

2h 32mnonstop

1:20 pm - 9:35 pm

MDW

EWR

7h 15m1 stop

$115Frontier

Sun, Jan 18 - Tue, Jan 20

11:30 am - 10:19 pm

EWR

MDW

11h 49m1 stop

6:30 pm - 9:30 pm

MDW

EWR

2h 00mnonstop

$116Frontier

Thu, Jan 15 - Sun, Jan 18

10:30 pm - 12:02 am

EWR

MDW

2h 32mnonstop

5:01 pm - 1:08 am

MDW

EWR

7h 07m1 stop

$117Frontier

Thu, Jan 15 - Thu, Jan 22

10:30 pm - 12:02 am

EWR

MDW

2h 32mnonstop

1:20 pm - 9:35 pm

MDW

EWR

7h 15m1 stop

$118Frontier

Thu, Jan 15 - Tue, Jan 20

3:30 pm - 11:09 pm

EWR

MDW

8h 39m1 stop

6:30 pm - 9:30 pm

MDW

EWR

2h 00mnonstop

$119Multiple Airlines

Mon, Jan 12 - Thu, Jan 15

10:30 pm - 12:02 am

EWR

MDW

2h 32mnonstop

1:20 pm - 9:35 pm

MDW

EWR

7h 15m1 stop

$121Frontier

Tue, Jan 13 - Tue, Jan 20

6:00 am - 7:40 am

LGA

MDW

2h 40mnonstop

6:05 am - 9:10 am

MDW

LGA

2h 05mnonstop

$139Southwest

Fri, Jan 23 - Mon, Jan 26

6:00 am - 7:40 am

LGA

MDW

2h 40mnonstop

5:55 pm - 9:00 pm

MDW

LGA

2h 05mnonstop

$148Southwest

Wed, Jan 14 - Wed, Jan 21

6:00 am - 7:40 am

LGA

MDW

2h 40mnonstop

6:05 am - 9:10 am

MDW

LGA

2h 05mnonstop

$157Southwest

Fri, Jan 9 - Mon, Jan 12

6:00 am - 7:40 am

LGA

MDW

2h 40mnonstop

8:40 am - 11:50 am

MDW

LGA

2h 10mnonstop

$159Southwest

Thu, Jan 22 - Sun, Jan 25

Frontier flights from New York to Chicago Midway Airport

Our best Frontier deals on New York to Chicago Midway Airport flight tickets

Frontier

Jan 18

EWR10:30 pmNewark

2h 32m

MDW12:02 amChicago Midway

Jan 20

MDW1:20 pmChicago Midway

10h 23m

1 stop

EWR12:43 amNewark

$115

Find similar

Frontier

Jan 15

EWR11:30 amNewark

11h 49m

1 stop

MDW10:19 pmChicago Midway

Jan 18

MDW6:30 pmChicago Midway

2h 00m

EWR9:30 pmNewark

$116

Find similar

Frontier

Jan 15

EWR10:30 pmNewark

2h 32m

MDW12:02 amChicago Midway

Jan 22

MDW5:01 pmChicago Midway

7h 07m

1 stop

EWR1:08 amNewark

$117

Find similar

Southwest flights from New York to Chicago Midway Airport

Our best Southwest deals on New York to Chicago Midway Airport flight tickets

Southwest

Jan 23

LGA6:00 amNew York LaGuardia

2h 40m

MDW7:40 amChicago Midway

Jan 26

MDW6:05 amChicago Midway

2h 05m

LGA9:10 amNew York LaGuardia

$139

Find similar

Southwest

Jan 14

LGA6:00 amNew York LaGuardia

2h 40m

MDW7:40 amChicago Midway

Jan 21

MDW5:55 pmChicago Midway

2h 05m

LGA9:00 pmNew York LaGuardia

$148

Find similar

Southwest

Jan 9

LGA6:00 amNew York LaGuardia

2h 40m

MDW7:40 amChicago Midway

Jan 10

MDW5:35 pmChicago Midway

2h 05m

LGA8:40 pmNew York LaGuardia

$157

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momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sun 1/18

10:30 pm-12:02 am

Nonstop2h 32m

Chicago Midway

Tue 1/20

1:20 pm-9:35 pm

1 stop7h 15m

$115

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 1/15

11:30 am-10:19 pm

1 stop11h 49m

Chicago Midway

Sun 1/18

6:30 pm-9:30 pm

Nonstop2h 00m

$116

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 1/15

10:30 pm-12:02 am

Nonstop2h 32m

Chicago Midway

Thu 1/22

5:01 pm-1:08 am

1 stop7h 07m

$117

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 1/15

10:30 pm-12:02 am

Nonstop2h 32m

Chicago Midway

Tue 1/20

1:20 pm-9:35 pm

1 stop7h 15m

$118

NewarkChicago

EWR - MDW

EWRMDW

Newark

Mon 1/12

3:30 pm-11:09 pm

1 stop8h 39m

Chicago Midway

Thu 1/15

6:30 pm-9:30 pm

Nonstop2h 00m

$119

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 1/13

10:30 pm-12:02 am

Nonstop2h 32m

Chicago Midway

Tue 1/20

1:20 pm-9:35 pm

1 stop7h 15m

$121

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 1/23

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Mon 1/26

6:05 am-9:10 am

Nonstop2h 05m

$139

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 1/14

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Wed 1/21

5:55 pm-9:00 pm

Nonstop2h 05m

$148

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 1/9

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Mon 1/12

6:05 am-9:10 am

Nonstop2h 05m

$157

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 1/22

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Sun 1/25

8:40 am-11:50 am

Nonstop2h 10m

$159

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Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from New York to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Other information

What is the cheapest month to fly to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from New York, with most prices found around $188. If you are unable to visit Chicago Midway Airport during the month of January, then departing from New York during the month February is also very affordable. Most momondo users find prices during this month for around $221.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from New York. The lowest ticket price found for a Tuesday departure recently was $262. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from New York because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $417.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from New York in the evening is the least expensive time of day to depart. momondo users have found prices as low as $227 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $359. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest New York to Chicago Midway flight route?

Fly from Newark to Chicago Midway for the best New York - Chicago Midway flight prices

What cabin class options are available on New York to Chicago Midway flights?

There is only 1 cabin class available to choose from on New York to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on New York to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between New York to Chicago Midway Airport.

How have New York to Chicago Midway Airport flight prices changed over time?

As of December 2025, prices for New York to Chicago Midway Airport flights are approximately 62% more expensive when compared to flights at the same time last year.

When to book flights from New York to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from New York to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap New York to Chicago Midway Airport (NYC to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New York to Chicago Midway Airport

Best Price Found	$70
Fastest flight time	2h 20m
Direct flights	Every day

The best one-way flight to Chicago Midway Airport from New York in the past 72 hours is $70. The best round-trip flight deal from New York to Chicago Midway Airport found on momondo in the last 72 hours is $67.

The fastest flight from New York to Chicago Midway Airport takes 2h 20m

Direct flights go from New York to Chicago Midway Airport every day.

Search flight deals

How far is New York to Chicago Midway by plane?
Chicago Midway is 716.7 mi away from New York. Flights usually cover this in 2h 20m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from New York to Chicago Midway Airport?
Prices for flights from New York to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from New York to Chicago Midway Airport?
There are 4 operators available for flights from New York to Chicago Midway Airport as of December 2025.
How old do you have to be to fly from New York to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from New York to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from New York to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from New York to Chicago Midway Airport is Boeing 737-800, representing 12.01% of all bookings. The subsequent popular models are Airbus A321neo at 10.44%, Boeing 737 MAX 8 at 10.32%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 6.55%.
What is the most popular airline from New York to Chicago Midway Airport?
Based on momondo bookings for flights between New York and Chicago Midway Airport, the leading airline is Southwest, making up 87% of the total bookings. Other popular airlines include United Airlines with 3%, Frontier with 3%, and Delta with 3%.

Best airlines flying from New York to Chicago Midway Airport

Compare and see reviews for airlines that fly from New York to Chicago Midway Airport with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $59	Free Cancellation	Rating 5.8 3,081 reviews	Search Frontier flights
United Airlines	PriceFrom $118	Free Cancellation	Rating 7.4 9,091 reviews	Search United Airlines flights
Southwest	PriceFrom $153	Free Cancellation	Rating 7.9 4,250 reviews	Search Southwest flights
Delta	PriceFrom $192	Free Cancellation	Rating 7.9 8,007 reviews	Search Delta flights

Southwest Flights From New York to Chicago Midway Airport
Across 24 Southwest flights from New York to Chicago Midway Airport this week, the average price was $272, with the best Southwest deals starting from $153 round-trip. 4,250 users have rated Southwest on momondo, with an average score of 7.9/10.
Frontier Flights From New York to Chicago Midway Airport
$59 is the best Frontier flight deal from New York to Chicago Midway Airport found on momondo over the last 72 hours. The average Frontier ticket price found was closer to $209, however, with flight time and availability significantly affecting the price. Frontier (5.8/10 from 3,081 user reviews) flies into Chicago Midway Airport from New York 3 times in an average week so prices can vary.

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Hammond

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Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from New York to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from New York.

Can I find flights from New York to Chicago with flexible booking policies on momondo?

All flight searches from New York to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from New York to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from New York.

I’m not ready to book a flight from New York to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from New York and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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Cheap flights from New York to Chicago from $58

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from New York to Chicago departing on 3/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Frontier flights from New York to Chicago Midway Airport

Our best Frontier deals on New York to Chicago Midway Airport flight tickets

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Our best Southwest deals on New York to Chicago Midway Airport flight tickets

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

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How to get the cheapest flight ticket from New York to Chicago Midway Airport

What is the cheapest month to fly to Chicago Midway Airport?

What is the cheapest day to depart on your flight to Chicago Midway Airport?

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

What is the cheapest New York to Chicago Midway flight route?

Fly from Newark to Chicago Midway for the best New York - Chicago Midway flight prices

What cabin class options are available on New York to Chicago Midway flights?

There is only 1 cabin class available to choose from on New York to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on New York to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between New York to Chicago Midway Airport.

How have New York to Chicago Midway Airport flight prices changed over time?

As of December 2025, prices for New York to Chicago Midway Airport flights are approximately 62% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from New York to Chicago Midway?

Frontier, Southwest, and Delta are the most popular carriers operating from New York to Chicago Midway

What airlines fly to Chicago Midway Airport?

How often are flights from New York to Chicago delayed?

Historically, on average around 20% of flights between New York and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 141 minutes.

What is the most punctual flight time for New York to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights at night have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Monday is statistically the day of the week which experiences the fewest number of delays on this flight route. Thursday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on New York to Chicago flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 19% of their flights experiencing any sort of delay.

How many flights depart from New York to Chicago Midway Airport on average per day?

As of December 2025, 3 flights take off from New York and land in Chicago Midway Airport each day. The most common flight departure time for this route is 9:00PM, with 35% of daily flights taking off at noon.

How many flights depart from New York to Chicago Midway Airport on average per week?

The number of flights available between New York and Chicago Midway Airport is 27 per week as of December 2025. The most frequent departure day is Tue, with 30% of weekly flights leaving on this day.

How long does it take to fly to Chicago Midway Airport?

When to book flights from New York to Chicago Midway Airport

Cheap New York to Chicago Midway Airport (NYC to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New York to Chicago Midway Airport

Best Price Found

Fastest flight time

Direct flights

How far is New York to Chicago Midway by plane?

When did momondo last update prices for flights from New York to Chicago Midway Airport?

How many operators does momondo search for flights from New York to Chicago Midway Airport?

How old do you have to be to fly from New York to Chicago Midway Airport?

What documentation or ID do you need to fly to Chicago Midway Airport?

What is the most popular plane model from New York to Chicago Midway Airport?

What is the most popular airline from New York to Chicago Midway Airport?

Best airlines flying from New York to Chicago Midway Airport

Compare and see reviews for airlines that fly from New York to Chicago Midway Airport with momondo

Southwest Flights From New York to Chicago Midway Airport

Frontier Flights From New York to Chicago Midway Airport

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from New York to Chicago?

Can I find flights from New York to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from New York to Chicago?

I’m not ready to book a flight from New York to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Chicago

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo