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

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

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

On average, it takes 1h 55m to fly from State of New York to Chicago Midway Airport if you fly out of Buffalo (the most popular airport in State of New York) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago Midway Airport). If you’re flying out of Syracuse and into Chicago O'Hare Intl Airport, then the flight time is around 2h 16m.

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

As of February 2026, 9 flights take off from State of New York and land in Chicago Midway Airport each day. The most common flight departure time for this route is 5:00AM, with 29% of daily flights taking off at noon.

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 State of New York according to our data. Southwest is the first choice among our users, with 71% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

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

The number of flights available between State of New York and Chicago Midway Airport is 66 per week as of February 2026. The most frequent departure day is Thu, with 27% of weekly flights leaving on this day.

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?

The number of operators available for flights from New York to Chicago Midway Airport is 3 as of February 2026.

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

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to 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.

$57 Cheap Flights from State of New York to Chicago Midway Airport in 2026

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Find the cheapest flights from New York State to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:30 am - 1:00 pm

EWR

MDW

2h 30mnonstop

7:30 am - 10:38 am

MDW

EWR

2h 08mnonstop

$91Frontier

Fri, Apr 17 - Tue, Apr 21

11:30 am - 1:00 pm

EWR

MDW

2h 30mnonstop

7:30 am - 10:38 am

MDW

EWR

2h 08mnonstop

$92Frontier

Tue, Apr 14 - Sat, Apr 18

11:30 am - 1:00 pm

EWR

MDW

2h 30mnonstop

7:30 am - 10:38 am

MDW

EWR

2h 08mnonstop

$95Frontier

Tue, May 5 - Sun, May 10

11:30 am - 1:00 pm

EWR

MDW

2h 30mnonstop

7:30 am - 10:38 am

MDW

EWR

2h 08mnonstop

$96Frontier

Sun, Apr 19 - Tue, Apr 21

6:00 am - 7:25 am

LGA

MDW

2h 25mnonstop

5:25 am - 8:25 am

MDW

LGA

2h 00mnonstop

$147Southwest

Fri, Apr 17 - Tue, Apr 21

8:55 am - 10:30 am

LGA

MDW

2h 35mnonstop

8:20 pm - 11:20 pm

MDW

LGA

2h 00mnonstop

$152Southwest

Tue, Mar 31 - Thu, Apr 2

12:16 pm - 5:54 pm

SYR

MDW

6h 38m

1 stop

6:34 pm - 11:09 pm

MDW

SYR

3h 35m

1 stop

$229Delta

Sat, Apr 11 - Sun, Apr 12

5:50 am - 8:47 am

SYR

MDW

3h 57m

1 stop

6:38 pm - 11:10 pm

MDW

SYR

3h 32m

1 stop

$249Delta

Tue, Apr 28 - Sat, May 2

11:31 am - 10:19 pm

SYR

MDW

11h 48m

2 stops

9:16 am - 9:39 am

MDW

SYR

23h 23m

1 stop

$300Multiple Airlines

Mon, Apr 27 - Sun, May 3

6:41 pm - 10:28 am

ALB

MDW

16h 47m

1 stop

7:34 pm - 11:21 am

MDW

ALB

14h 47m

2 stops

$312Multiple Airlines

Thu, Apr 30 - Sat, May 2

Southwest flights from State of New York to Chicago Midway Airport

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

Southwest

Apr 17

LGA9:45 pmNew York LaGuardia

2h 25m

MDW11:10 pmChicago Midway

Apr 21

MDW7:25 pmChicago Midway

2h 05m

LGA10:30 pmNew York LaGuardia

$147

Southwest

Mar 31

LGA8:55 amNew York LaGuardia

2h 35m

MDW10:30 amChicago Midway

Apr 2

MDW8:20 pmChicago Midway

2h 00m

LGA11:20 pmNew York LaGuardia

$152

Southwest

Mar 16

LGA9:55 pmNew York LaGuardia

2h 25m

MDW11:20 pmChicago Midway

Mar 18

MDW8:20 pmChicago Midway

2h 00m

LGA11:20 pmNew York LaGuardia

$157

Frontier flights from State of New York to Chicago Midway Airport

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

Frontier

Apr 17

EWR11:30 amNewark

2h 30m

MDW1:00 pmChicago Midway

Apr 21

MDW7:30 amChicago Midway

2h 08m

EWR10:38 amNewark

$91

Frontier

Apr 14

EWR11:30 amNewark

2h 30m

MDW1:00 pmChicago Midway

Apr 18

MDW7:30 amChicago Midway

2h 08m

EWR10:38 amNewark

$92

Frontier

May 5

EWR11:30 amNewark

2h 30m

MDW1:00 pmChicago Midway

May 10

MDW7:30 amChicago Midway

2h 08m

EWR10:38 amNewark

$95

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

NewarkChicago

EWR - MDW

EWRMDW

Newark

Fri 4/17

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Tue 4/21

7:30 am-10:38 am

Nonstop2h 08m

$91

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 4/14

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Sat 4/18

7:30 am-10:38 am

Nonstop2h 08m

$92

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 5/5

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Sun 5/10

7:30 am-10:38 am

Nonstop2h 08m

$95

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sun 4/19

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Tue 4/21

7:30 am-10:38 am

Nonstop2h 08m

$96

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 4/17

6:00 am-7:25 am

Nonstop2h 25m

Chicago Midway

Tue 4/21

5:25 am-8:25 am

Nonstop2h 00m

$147

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 3/31

8:55 am-10:30 am

Nonstop2h 35m

Chicago Midway

Thu 4/2

8:20 pm-11:20 pm

Nonstop2h 00m

$152

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Sat 4/11

12:16 pm-5:54 pm

1 stop6h 38m

Chicago Midway

Sun 4/12

6:34 pm-11:09 pm

1 stop3h 35m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Tue 4/28

5:50 am-8:47 am

1 stop3h 57m

Chicago Midway

Sat 5/2

6:38 pm-11:10 pm

1 stop3h 32m

$249

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Mon 4/27

11:31 am-10:19 pm

2 stops11h 48m

Chicago Midway

Sun 5/3

9:16 am-9:39 am

1 stop23h 23m

$300

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 4/30

6:41 pm-10:28 am

1 stop16h 47m

Chicago Midway

Sat 5/2

7:34 pm-11:21 am

2 stops14h 47m

$312

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from State of 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

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 State of New York, with most prices found around $149. If you are unable to visit Chicago Midway Airport during the month of January, then departing from State of New York during the month July is also very affordable. Most momondo users find prices during this month for around $253.

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 State of New York. The lowest ticket price found for a Tuesday departure recently was $257. 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 State of New York because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $401.

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

Flying to Chicago Midway Airport from State of New York in the evening is the least expensive time of day to depart. momondo users have found prices as low as $224 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $358. 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 State of New York to Chicago Midway Airport flights?

You could potentially save up to 1% on your flight if you consider stops on a State of New York to Chicago Midway Airport flight.

Cheap State of New York to Chicago Midway Airport flight deals and tips

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

Best Price Found	$162
Fastest flight time	1h 35m
Direct flights	Every day

The best one-way flight to Chicago Midway Airport from State of New York in the past 72 hours is $162. The best round-trip flight deal from State of New York to Chicago Midway Airport found on momondo in the last 72 hours is $239.

The fastest flight from State of New York to Chicago Midway Airport takes 1h 35m

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

Search flight deals

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?
The number of operators available for flights from New York to Chicago Midway Airport is 3 as of February 2026.
How old do you have to be to fly from New York to Chicago Midway Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to 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 State of New York to Chicago Midway Airport?
Based on momondo bookings for flights between State of New York and Chicago Midway Airport, the leading plane model is Boeing 737 MAX 8, making up 13.59% of the total bookings. Other popular models include Airbus A320-100/200 with 9.47%, Boeing 737-800 with 9.13%, and Airbus A321neo with 7.67%.

Best airlines flying from State of New York to Chicago Midway Airport

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

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $56	Free Cancellation	Rating 5.7 3,046 reviews	Search Frontier flights
Delta	PriceFrom $153	Free Cancellation	Rating 7.9 8,215 reviews	Search Delta flights
Southwest	PriceFrom $158	Free Cancellation	Rating 8.0 4,295 reviews	Search Southwest flights

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Munster

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Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

It is quick and easy to find New York to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. momondo allows you to filter the results for New York to Chicago flights to just show those with 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?

Of course. momondo tracks the price of New York to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Chicago Midway Airport trip

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Cheap flights from New York State to Chicago from $57

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 State to Chicago departing on 3/8. 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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Southwest flights from State of New York to Chicago Midway Airport

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

Frontier flights from State of New York to Chicago Midway Airport

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

momondo Fare Finder

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

See travel insights to Chicago from

How to get the cheapest flight ticket from State of 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?

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

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

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

What airlines fly to Chicago Midway Airport?

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

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

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

Cheap State of New York to Chicago Midway Airport flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Best airlines flying from State of New York to Chicago Midway Airport

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

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

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Get notified when prices go down

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List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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