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Cheap flights from New York State to Chicago from $54

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 1/13. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
9:45 pm - 11:15 pm
LGA
-
MDW
2h 30mnonstop
Southwest Logo
5:55 pm - 9:00 pm
MDW
-
LGA
2h 05mnonstop
$97Southwest
Fri, Jan 30 - Mon, Feb 2
Southwest Logo
11:55 am - 1:30 pm
LGA
-
MDW
2h 35mnonstop
Southwest Logo
7:15 pm - 10:20 pm
MDW
-
LGA
2h 05mnonstop
$107Southwest
Sat, Feb 7 - Sun, Feb 8
Frontier Logo
11:30 am - 10:19 pm
EWR
-
MDW
11h 49m1 stop
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
$110Frontier
Thu, Jan 15 - Sun, Jan 18
Frontier Logo
11:30 am - 10:19 pm
EWR
-
MDW
11h 49m1 stop
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
$111Frontier
Thu, Jan 15 - Sun, Jan 18
Frontier Logo
11:30 am - 10:19 pm
EWR
-
MDW
11h 49m1 stop
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
$112Frontier
Thu, Jan 15 - Sun, Jan 18
Frontier Logo
11:30 am - 1:01 pm
EWR
-
MDW
2h 31mnonstop
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
$113Frontier
Thu, Jan 1 - Tue, Jan 13
Multiple Airlines Logo
10:30 pm - 12:02 am
EWR
-
MDW
2h 32mnonstop
Multiple Airlines Logo
1:20 pm - 11:30 pm
MDW
-
EWR
9h 10m1 stop
$122Multiple Airlines
Sun, Jan 18 - Tue, Jan 27
Delta Logo
5:50 am - 8:52 am
SYR
-
MDW
4h 02m1 stop
Delta Logo
6:35 pm - 11:13 pm
MDW
-
SYR
3h 38m1 stop
$229Delta
Fri, Jan 23 - Mon, Jan 26
Delta Logo
6:03 am - 8:52 am
BUF
-
MDW
3h 49m1 stop
Delta Logo
6:14 pm - 10:57 pm
MDW
-
BUF
3h 43m1 stop
$243Delta
Sat, Jan 17 - Sun, Jan 18
Multiple Airlines Logo
12:43 pm - 9:27 am
ROC
-
MDW
21h 44m1 stop
Multiple Airlines Logo
7:30 am - 5:40 pm
MDW
-
ROC
9h 10m2 stops
$303Multiple Airlines
Wed, Feb 25 - Fri, Feb 27

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
Jan 30
LGA6:00 amNew York LaGuardia
2h 40m
MDW7:40 amChicago Midway
Feb 2
MDW6:05 amChicago Midway
2h 05m
LGA9:10 amNew York LaGuardia
$97
Find similar
Southwest
Feb 7
LGA11:55 amNew York LaGuardia
2h 35m
MDW1:30 pmChicago Midway
Feb 8
MDW7:15 pmChicago Midway
2h 05m
LGA10:20 pmNew York LaGuardia
$107
Find similar
Southwest
Jan 16
LGA2:05 pmNew York LaGuardia
2h 40m
MDW3:45 pmChicago Midway
Jan 20
MDW7:15 pmChicago Midway
2h 05m
LGA10:20 pmNew York LaGuardia
$117
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
Jan 30
EWR7:00 amNewark
5h 59m
1 stop
MDW11:59 amChicago Midway
Feb 2
MDW10:46 amChicago Midway
5h 43m
1 stop
EWR5:29 pmNewark
$177
Find similar
Delta
Feb 10
EWR7:00 amNewark
5h 59m
1 stop
MDW11:59 amChicago Midway
Feb 17
MDW6:20 pmChicago Midway
3h 46m
1 stop
EWR11:06 pmNewark
$178
Find similar
Delta
Jan 15
EWR9:39 amNewark
4h 09m
1 stop
MDW12:48 pmChicago Midway
Jan 18
MDW6:45 amChicago Midway
5h 13m
1 stop
EWR12:58 pmNewark
$187
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 December 27, 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

LGA - MDW

LGAMDW

New York LaGuardia

Fri 1/30

9:45 pm-11:15 pm

Nonstop2h 30m

Chicago Midway

Mon 2/2

5:55 pm-9:00 pm

Nonstop2h 05m

$97

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 2/7

11:55 am-1:30 pm

Nonstop2h 35m

Chicago Midway

Sun 2/8

7:15 pm-10:20 pm

Nonstop2h 05m

$107

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

$110

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

$111

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

$112

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 1/1

11:30 am-1:01 pm

Nonstop2h 31m

Chicago Midway

Tue 1/13

6:30 pm-9:30 pm

Nonstop2h 00m

$113

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sun 1/18

10:30 pm-12:02 am

Nonstop2h 32m

Chicago Midway

Tue 1/27

1:20 pm-11:30 pm

1 stop9h 10m

$122

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Fri 1/23

5:50 am-8:52 am

1 stop4h 02m

Chicago Midway

Mon 1/26

6:35 pm-11:13 pm

1 stop3h 38m

$229

BuffaloChicago

BUF - MDW

BUFMDW

Buffalo

Sat 1/17

6:03 am-8:52 am

1 stop3h 49m

Chicago Midway

Sun 1/18

6:14 pm-10:57 pm

1 stop3h 43m

$243

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 2/25

12:43 pm-9:27 am

1 stop21h 44m

Chicago Midway

Fri 2/27

7:30 am-5:40 pm

2 stops9h 10m

$303

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 $188. 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, 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 $409.

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 $226 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $357. 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 13% 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

$188

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 $188. The best round-trip flight deal from State of New York to Chicago Midway Airport found on momondo in the last 72 hours is $247.
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 $58Free CancellationRating
5.7
3,065 reviews
Search Frontier flights
United AirlinesPriceFrom $118Free CancellationRating
7.4
9,113 reviews
Search United Airlines flights
DeltaPriceFrom $134Free CancellationRating
7.9
8,019 reviews
Search Delta flights
SouthwestPriceFrom $152Free CancellationRating
8.0
4,256 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
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.

An easier way to manage your Chicago Midway Airport trip

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