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Cheap flights from New York State 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 State to Chicago departing on 10/7. 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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Find the cheapest flights from New York State to Chicago

Cheap round-trip flights

Frontier Logo
10:00 pm - 11:25 pmEWR-MDW
2h 25mnonstop
Frontier Logo
5:56 pm - 9:00 pmMDW-EWR
2h 04mnonstop
$97Frontier
Find Deal
Tue, Oct 7 - Tue, Oct 14
Frontier Logo
10:00 pm - 11:25 pmEWR-MDW
2h 25mnonstop
Frontier Logo
5:56 pm - 9:00 pmMDW-EWR
2h 04mnonstop
$107Frontier
Find Deal
Thu, Oct 9 - Tue, Oct 14
Frontier Logo
10:00 pm - 11:25 pmEWR-MDW
2h 25mnonstop
Frontier Logo
5:56 pm - 9:00 pmMDW-EWR
2h 04mnonstop
$114Frontier
Find Deal
Sun, Oct 12 - Tue, Oct 14
Frontier Logo
10:00 pm - 11:25 pmEWR-MDW
2h 25mnonstop
Frontier Logo
5:56 pm - 9:00 pmMDW-EWR
2h 04mnonstop
$117Frontier
Find Deal
Thu, Oct 30 - Sun, Nov 2
Frontier Logo
10:00 pm - 11:25 pmEWR-MDW
2h 25mnonstop
Frontier Logo
5:56 pm - 9:00 pmMDW-EWR
2h 04mnonstop
$118Frontier
Find Deal
Tue, Oct 14 - Thu, Oct 16
Southwest Logo
3:35 pm - 5:05 pmLGA-MDW
2h 30mnonstop
Southwest Logo
10:40 am - 1:45 pmMDW-LGA
2h 05mnonstop
$119Southwest
Find Deal
Tue, Sep 2 - Wed, Sep 3
Southwest Logo
11:25 am - 12:50 pmLGA-MDW
2h 25mnonstop
Southwest Logo
2:35 pm - 5:40 pmMDW-LGA
2h 05mnonstop
$122Southwest
Find Deal
Wed, Sep 3 - Sat, Sep 6
Delta Logo
6:15 am - 10:30 amEWR-MDW
5h 15m1 stop
Delta Logo
1:08 pm - 7:23 pmMDW-EWR
5h 15m1 stop
$179Delta
Find Deal
Sat, Oct 25 - Tue, Oct 28
Delta Logo
12:27 pm - 5:37 pmEWR-MDW
6h 10m1 stop
Delta Logo
6:00 am - 12:11 pmMDW-EWR
5h 11m1 stop
$183Delta
Find Deal
Wed, Sep 3 - Wed, Sep 10
Logo
5:15 am - 3:58 pmEWR-MDW
11h 43m1 stop
Logo
6:20 am - 9:01 pmMDW-EWR
13h 41m2 stops
$201
Find Deal
Tue, Sep 9 - Thu, Sep 11

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
Oct 7
EWR10:00 pmNewark
2h 25m
MDW11:25 pmChicago Midway
Oct 14
MDW5:56 pmChicago Midway
2h 04m
EWR9:00 pmNewark
$97
Find similar
Frontier
Oct 9
EWR10:00 pmNewark
2h 25m
MDW11:25 pmChicago Midway
Oct 14
MDW5:56 pmChicago Midway
2h 04m
EWR9:00 pmNewark
$107
Find similar
Frontier
Oct 12
EWR10:00 pmNewark
2h 25m
MDW11:25 pmChicago Midway
Oct 14
MDW5:56 pmChicago Midway
2h 04m
EWR9:00 pmNewark
$114
Find similar

Delta flights from State of New York to Chicago Midway Airport

Our best Delta deals on State of New York to Chicago Midway Airport flight tickets
Delta
Oct 25
EWR6:15 amNewark
5h 15m
1 stop
MDW10:30 amChicago Midway
Oct 28
MDW1:08 pmChicago Midway
5h 15m
1 stop
EWR7:23 pmNewark
$179
Find similar
Delta
Sep 3
EWR12:27 pmNewark
6h 10m
1 stop
MDW5:37 pmChicago Midway
Sep 10
MDW6:00 amChicago Midway
5h 11m
1 stop
EWR12:11 pmNewark
$183
Find similar
Delta
Aug 31
EWR6:15 amNewark
6h 19m
1 stop
MDW11:34 amChicago Midway
Sep 10
MDW6:00 amChicago Midway
5h 11m
1 stop
EWR12:11 pmNewark
$189
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from State of New York to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 7, 2025.
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

Tue 10/7

10:00 pm-11:25 pm

Nonstop2h 25m

Chicago Midway

Tue 10/14

5:56 pm-9:00 pm

Nonstop2h 04m

$97

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 10/9

10:00 pm-11:25 pm

Nonstop2h 25m

Chicago Midway

Tue 10/14

5:56 pm-9:00 pm

Nonstop2h 04m

$107

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sun 10/12

10:00 pm-11:25 pm

Nonstop2h 25m

Chicago Midway

Tue 10/14

5:56 pm-9:00 pm

Nonstop2h 04m

$114

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 10/30

10:00 pm-11:25 pm

Nonstop2h 25m

Chicago Midway

Sun 11/2

5:56 pm-9:00 pm

Nonstop2h 04m

$117

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 10/14

10:00 pm-11:25 pm

Nonstop2h 25m

Chicago Midway

Thu 10/16

5:56 pm-9:00 pm

Nonstop2h 04m

$118

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 9/2

3:35 pm-5:05 pm

Nonstop2h 30m

Chicago Midway

Wed 9/3

10:40 am-1:45 pm

Nonstop2h 05m

$119

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 9/3

11:25 am-12:50 pm

Nonstop2h 25m

Chicago Midway

Sat 9/6

2:35 pm-5:40 pm

Nonstop2h 05m

$122

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 10/25

6:15 am-10:30 am

1 stop5h 15m

Chicago Midway

Tue 10/28

1:08 pm-7:23 pm

1 stop5h 15m

$179

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 9/3

12:27 pm-5:37 pm

1 stop6h 10m

Chicago Midway

Wed 9/10

6:00 am-12:11 pm

1 stop5h 11m

$183

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 9/9

5:15 am-3:58 pm

1 stop11h 43m

Chicago Midway

Thu 9/11

6:20 am-9:01 pm

2 stops13h 41m

$201

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

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 $208. If you are unable to visit Chicago Midway Airport during the month of January, then departing from State of 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, Wednesday is the cheapest day to fly to Chicago Midway Airport from State of New York. The lowest ticket price found for a Wednesday departure recently was $269. 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 $405.

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 $256 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $343. 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 are 1 cabin classes 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?

No. A direct flight is the cheapest option for a flight between State of New York 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

$58

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 $58. The best round-trip flight deal from State of New York to Chicago Midway Airport found on momondo in the last 72 hours is $97.
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?

  • 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?

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
Spirit AirlinesPriceFrom $92Free CancellationRating
6.3
8,055 reviews
Search Spirit Airlines flights
DeltaPriceFrom $134Free CancellationRating
8.0
7,985 reviews
Search Delta flights
SouthwestPriceFrom $153Free CancellationRating
8.0
4,244 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
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?

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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