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Cheap flights from New York State to Chicago from $63

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 4/16. 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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0 bags

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Find the cheapest flights from New York State to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
$123Frontier
Thu, Apr 23 - Fri, Apr 24
Frontier Logo
10:29 pm - 6:37 pm
EWR
-
MDW
21h 08m
1 stop
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
$124Frontier
Fri, May 1 - Sun, May 3
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Frontier Logo
8:41 am - 10:32 am
MDW
-
EWR
24h 51m
1 stop
$125Frontier
Thu, Apr 30 - Mon, May 4
Frontier Logo
10:29 pm - 6:37 pm
EWR
-
MDW
21h 08m
1 stop
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
$126Frontier
Fri, Apr 24 - Mon, Apr 27
Southwest Logo
6:40 pm - 7:50 pm
ALB
-
MDW
2h 10mnonstop
Southwest Logo
12:45 pm - 3:40 pm
MDW
-
ALB
1h 55mnonstop
$285Southwest
Wed, May 6 - Wed, May 13
Delta Logo
6:20 am - 8:43 am
SYR
-
MDW
3h 23m
1 stop
Delta Logo
6:36 pm - 11:49 pm
MDW
-
SYR
4h 13m
1 stop
$289Delta
Fri, May 8 - Sun, May 10
Southwest Logo
12:45 pm - 4:45 pm
ALB
-
MDW
5h 00m
1 stop
Southwest Logo
12:45 pm - 3:40 pm
MDW
-
ALB
1h 55mnonstop
$295Southwest
Wed, May 6 - Wed, May 13
Delta Logo
6:00 am - 8:43 am
ALB
-
MDW
3h 43m
1 stop
Delta Logo
6:36 pm - 11:18 pm
MDW
-
ALB
3h 42m
1 stop
$307Delta
Sat, May 16 - Tue, May 19
Multiple Airlines Logo
11:31 am - 10:26 pm
SYR
-
MDW
11h 55m
2 stops
Multiple Airlines Logo
9:16 am - 9:39 am
MDW
-
SYR
23h 23m
1 stop
$324Multiple Airlines
Fri, May 1 - Sun, May 3
Multiple Airlines Logo
11:31 am - 10:26 pm
SYR
-
MDW
11h 55m
2 stops
Multiple Airlines Logo
9:16 am - 9:39 am
MDW
-
SYR
23h 23m
1 stop
$357Multiple Airlines
Fri, Apr 24 - Sun, Apr 26

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 23
EWR11:30 amNewark
2h 30m
MDW1:00 pmChicago Midway
Apr 24
MDW7:30 amChicago Midway
2h 08m
EWR10:38 amNewark
$123
Frontier
May 1
EWR10:29 pmNewark
21h 08m
1 stop
MDW6:37 pmChicago Midway
May 3
MDW7:30 amChicago Midway
2h 08m
EWR10:38 amNewark
$124
Frontier
Apr 30
EWR11:30 amNewark
2h 30m
MDW1:00 pmChicago Midway
May 4
MDW8:41 amChicago Midway
24h 51m
1 stop
EWR10:32 amNewark
$125

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
May 5
LGA8:55 pmNew York LaGuardia
2h 35m
MDW10:30 pmChicago Midway
May 6
MDW10:15 amChicago Midway
5h 25m
1 stop
LGA4:40 pmNew York LaGuardia
$165
Southwest
May 5
LGA3:55 pmNew York LaGuardia
2h 45m
MDW5:40 pmChicago Midway
May 12
MDW9:40 amChicago Midway
8h 45m
2 stops
LGA7:25 pmNew York LaGuardia
$170
Southwest
May 13
LGA7:25 amNew York LaGuardia
2h 25m
MDW8:50 amChicago Midway
May 16
MDW5:30 amChicago Midway
2h 00m
LGA8:30 amNew York LaGuardia
$171

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 April 10, 2026.
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

Cheapest round-trip

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 4/23

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Fri 4/24

7:30 am-10:38 am

Nonstop2h 08m

$123

NewarkChicago

EWR - MDW

EWRMDW

Newark

Fri 5/1

10:29 pm-6:37 pm

1 stop21h 08m

Chicago Midway

Sun 5/3

7:30 am-10:38 am

Nonstop2h 08m

$124

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 4/30

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Mon 5/4

8:41 am-10:32 am

1 stop24h 51m

$125

NewarkChicago

EWR - MDW

EWRMDW

Newark

Fri 4/24

10:29 pm-6:37 pm

1 stop21h 08m

Chicago Midway

Mon 4/27

7:30 am-10:38 am

Nonstop2h 08m

$126
Quickest round-trip

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Wed 5/6

6:40 pm-7:50 pm

Nonstop2h 10m

Chicago Midway

Wed 5/13

12:45 pm-3:40 pm

Nonstop1h 55m

$285

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Fri 5/8

6:20 am-8:43 am

1 stop3h 23m

Chicago Midway

Sun 5/10

6:36 pm-11:49 pm

1 stop4h 13m

$289

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Wed 5/6

12:45 pm-4:45 pm

1 stop5h 00m

Chicago Midway

Wed 5/13

12:45 pm-3:40 pm

Nonstop1h 55m

$295

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 5/16

6:00 am-8:43 am

1 stop3h 43m

Chicago Midway

Tue 5/19

6:36 pm-11:18 pm

1 stop3h 42m

$307

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Fri 5/1

11:31 am-10:26 pm

2 stops11h 55m

Chicago Midway

Sun 5/3

9:16 am-9:39 am

1 stop23h 23m

$324

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Fri 4/24

11:31 am-10:26 pm

2 stops11h 55m

Chicago Midway

Sun 4/26

9:16 am-9:39 am

1 stop23h 23m

$357

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 $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 February is also very affordable. Most momondo users find prices during this month for around $224.

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 $259. 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 $390.

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 $222 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $362. 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 4% 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

$187

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 $187. The best round-trip flight deal from State of New York to Chicago Midway Airport found on momondo in the last 72 hours is $275.
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

Frequently asked questions about flying from New York State to Chicago Midway Airport

  • 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
FrontierPriceFrom $55Free CancellationRating
5.7
2,997 reviews
Search Frontier flights
United AirlinesPriceFrom $148Free CancellationRating
7.4
9,562 reviews
Search United Airlines flights
DeltaPriceFrom $153Free CancellationRating
7.9
8,397 reviews
Search Delta flights
SouthwestPriceFrom $164Free CancellationRating
8.0
4,335 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
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.

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