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Cheap flights from New York State to Chicago from $55

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 12/4. 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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Cheap round-trip flights

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Frontier Logo
1:00 pm - 6:08 pmJFK-MDW
6h 08m1 stop
Frontier Logo
2:59 pm - 12:07 amMDW-JFK
8h 08m1 stop
$109Frontier
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Thu, Dec 4 - Sat, Dec 6
Frontier Logo
6:20 am - 1:59 pmLGA-MDW
8h 39m1 stop
Frontier Logo
12:18 pm - 10:00 pmMDW-LGA
8h 42m1 stop
$109Frontier
Find Deal
Sat, Dec 6 - Mon, Dec 8
Frontier Logo
6:25 am - 1:59 pmJFK-MDW
8h 34m1 stop
Frontier Logo
8:42 pm - 9:01 amMDW-JFK
11h 19m1 stop
$110Frontier
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Sat, Dec 6 - Mon, Dec 8
Frontier Logo
1:39 pm - 10:19 pmBUF-MDW
9h 40m1 stop
Frontier Logo
6:20 am - 12:44 pmMDW-BUF
5h 24m1 stop
$110Frontier
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Mon, Feb 2 - Thu, Feb 5
Multiple Airlines Logo
11:30 am - 1:01 pmEWR-MDW
2h 31mnonstop
Multiple Airlines Logo
2:59 pm - 11:59 pmMDW-EWR
8h 00m1 stop
$122Multiple Airlines
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Thu, Dec 11 - Sat, Dec 13
Multiple Airlines Logo
12:37 pm - 10:12 pmBUF-MDW
10h 35m2 stops
Multiple Airlines Logo
6:12 am - 4:45 pmMDW-BUF
9h 33m1 stop
$203Multiple Airlines
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Fri, Dec 12 - Fri, Dec 19
Delta Logo
6:00 am - 8:54 amSYR-MDW
3h 54m1 stop
Delta Logo
6:35 pm - 11:15 pmMDW-SYR
3h 40m1 stop
$229Delta
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Fri, Jan 23 - Sun, Jan 25
Southwest Logo
5:10 am - 6:30 amALB-MDW
2h 20mnonstop
Southwest Logo
6:00 pm - 8:50 pmMDW-ALB
1h 50mnonstop
$250Southwest
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Tue, Dec 16 - Wed, Dec 24
Delta Logo
6:00 am - 8:54 amALB-MDW
3h 54m1 stop
Delta Logo
6:00 am - 1:13 pmMDW-ALB
6h 13m1 stop
$251Delta
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Mon, Nov 24 - Thu, Nov 27
Southwest Logo
6:40 am - 12:55 pmALB-MDW
7h 15m1 stop
Southwest Logo
6:00 pm - 8:50 pmMDW-ALB
1h 50mnonstop
$260Southwest
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Tue, Dec 16 - Wed, Dec 24

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
Dec 4
LGA9:55 pmNew York LaGuardia
2h 25m
MDW11:20 pmChicago Midway
Dec 8
MDW7:15 pmChicago Midway
2h 05m
LGA10:20 pmNew York LaGuardia
$137
Find similar
Southwest
Jan 29
LGA6:00 amNew York LaGuardia
2h 40m
MDW7:40 amChicago Midway
Feb 2
MDW5:55 pmChicago Midway
2h 05m
LGA9:00 pmNew York LaGuardia
$139
Find similar
Southwest
Dec 5
LGA6:00 amNew York LaGuardia
2h 30m
MDW7:30 amChicago Midway
Dec 8
MDW7:15 pmChicago Midway
2h 05m
LGA10:20 pmNew York LaGuardia
$143
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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
Jan 23
SYR12:02 pmSyracuse Hancock Intl
6h 30m
1 stop
MDW5:32 pmChicago Midway
Jan 26
MDW6:35 pmChicago Midway
3h 40m
1 stop
SYR11:15 pmSyracuse Hancock Intl
$229
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Delta
Nov 24
ALB6:00 amAlbany Intl
3h 54m
1 stop
MDW8:54 amChicago Midway
Nov 27
MDW6:00 amChicago Midway
6h 13m
1 stop
ALB1:13 pmAlbany Intl
$251
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Delta
Dec 17
SYR7:01 pmSyracuse Hancock Intl
5h 46m
1 stop
MDW11:47 pmChicago Midway
Jan 11
MDW5:31 pmChicago Midway
5h 28m
1 stop
SYR11:59 pmSyracuse Hancock Intl
$254
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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 November 13, 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

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 12/4

1:00 pm-6:08 pm

1 stop6h 08m

Chicago Midway

Sat 12/6

2:59 pm-12:07 am

1 stop8h 08m

$109

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 12/6

6:20 am-1:59 pm

1 stop8h 39m

Chicago Midway

Mon 12/8

12:18 pm-10:00 pm

1 stop8h 42m

$109

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 12/6

6:25 am-1:59 pm

1 stop8h 34m

Chicago Midway

Mon 12/8

8:42 pm-9:01 am

1 stop11h 19m

$110

BuffaloChicago

BUF - MDW

BUFMDW

Buffalo

Mon 2/2

1:39 pm-10:19 pm

1 stop9h 40m

Chicago Midway

Thu 2/5

6:20 am-12:44 pm

1 stop5h 24m

$110

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 12/11

11:30 am-1:01 pm

Nonstop2h 31m

Chicago Midway

Sat 12/13

2:59 pm-11:59 pm

1 stop8h 00m

$122

BuffaloChicago

BUF - MDW

BUFMDW

Buffalo

Fri 12/12

12:37 pm-10:12 pm

2 stops10h 35m

Chicago Midway

Fri 12/19

6:12 am-4:45 pm

1 stop9h 33m

$203

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Fri 1/23

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Sun 1/25

6:35 pm-11:15 pm

1 stop3h 40m

$229

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 12/16

5:10 am-6:30 am

Nonstop2h 20m

Chicago Midway

Wed 12/24

6:00 pm-8:50 pm

Nonstop1h 50m

$250

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Mon 11/24

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Thu 11/27

6:00 am-1:13 pm

1 stop6h 13m

$251

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 12/16

6:40 am-12:55 pm

1 stop7h 15m

Chicago Midway

Wed 12/24

6:00 pm-8:50 pm

Nonstop1h 50m

$260

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 $212. 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 $275. 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 $422.

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 $243 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $360. 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?

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

$156

Fastest flight time

1h 40m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from State of New York in the past 72 hours is $156. The best round-trip flight deal from State of New York to Chicago Midway Airport found on momondo in the last 72 hours is $233.
The fastest flight from State of New York to Chicago Midway Airport takes 1h 40m
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
FrontierPriceFrom $80Free CancellationRating
5.8
3,114 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $92Free CancellationRating
6.3
8,139 reviews
Search Spirit Airlines flights
DeltaPriceFrom $134Free CancellationRating
7.9
8,007 reviews
Search Delta flights
SouthwestPriceFrom $156Free CancellationRating
8.0
4,236 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
Portage
Lansing
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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