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Cheap flights from New York State to Chicago from $94

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 7/5. 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.
Southwest Logo
7:25 am - 8:50 am
LGA
-
MDW
2h 25mnonstop
Southwest Logo
7:45 pm - 10:55 pm
MDW
-
LGA
2h 10mnonstop
$177Southwest
Tue, Jul 7 - Tue, Jul 28
Southwest Logo
9:30 pm - 10:55 pm
LGA
-
MDW
2h 25mnonstop
Southwest Logo
7:45 pm - 11:00 pm
MDW
-
LGA
2h 15mnonstop
$182Southwest
Fri, Jul 3 - Wed, Jul 8
Southwest Logo
6:00 am - 7:20 am
LGA
-
MDW
2h 20mnonstop
Southwest Logo
7:45 pm - 11:00 pm
MDW
-
LGA
2h 15mnonstop
$187Southwest
Thu, Jul 9 - Mon, Jul 13
Southwest Logo
6:00 am - 7:20 am
LGA
-
MDW
2h 20mnonstop
Southwest Logo
5:15 am - 8:15 am
MDW
-
LGA
2h 00mnonstop
$192Southwest
Wed, Jun 10 - Wed, Jun 17
Delta Logo
12:05 pm - 4:15 pm
EWR
-
MDW
5h 10m
1 stop
Delta Logo
9:19 am - 3:54 pm
MDW
-
EWR
5h 35m
1 stop
$197Delta
Tue, Jul 7 - Wed, Jul 8
Delta Logo
6:00 am - 9:14 am
EWR
-
MDW
4h 14m
1 stop
Delta Logo
9:17 am - 3:59 pm
MDW
-
EWR
5h 42m
1 stop
$202Delta
Tue, Jun 30 - Fri, Jul 3
Delta Logo
6:00 am - 10:09 am
EWR
-
MDW
5h 09m
1 stop
Delta Logo
6:00 am - 12:21 pm
MDW
-
EWR
5h 21m
1 stop
$212Delta
Tue, Jun 9 - Tue, Jul 14
Frontier Logo
5:55 am - 11:07 am
EWR
-
MDW
6h 12m
1 stop
Frontier Logo
12:11 pm - 9:28 pm
MDW
-
EWR
8h 17m
1 stop
$240Frontier
Tue, Jul 21 - Tue, Jul 28
Frontier Logo
5:58 am - 11:09 am
EWR
-
MDW
6h 11m
1 stop
Frontier Logo
12:27 pm - 9:29 pm
MDW
-
EWR
8h 02m
1 stop
$241Frontier
Wed, Jun 17 - Tue, Jun 23
Frontier Logo
2:48 pm - 10:03 pm
BUF
-
MDW
8h 15m
1 stop
Frontier Logo
6:05 am - 10:29 am
MDW
-
BUF
27h 24m
1 stop
$248Frontier
Wed, Jul 22 - Sat, Jul 25

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
Jul 7
LGA6:00 amNew York LaGuardia
2h 20m
MDW7:20 amChicago Midway
Jul 7
MDW7:45 pmChicago Midway
2h 10m
LGA10:55 pmNew York LaGuardia
$177
Southwest
Jul 3
LGA9:30 pmNew York LaGuardia
2h 25m
MDW10:55 pmChicago Midway
Jul 7
MDW7:45 pmChicago Midway
2h 10m
LGA10:55 pmNew York LaGuardia
$182
Southwest
Jul 9
LGA6:00 amNew York LaGuardia
2h 20m
MDW7:20 amChicago Midway
Jul 13
MDW7:45 pmChicago Midway
2h 15m
LGA11:00 pmNew York LaGuardia
$187

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
Sep 18
EWR10:29 pmNewark
13h 29m
1 stop
MDW10:58 amChicago Midway
Sep 22
MDW12:03 pmChicago Midway
8h 25m
1 stop
EWR9:28 pmNewark
$233
Frontier
Jul 21
EWR5:55 amNewark
6h 12m
1 stop
MDW11:07 amChicago Midway
Jul 28
MDW12:11 pmChicago Midway
8h 17m
1 stop
EWR9:28 pmNewark
$240
Frontier
Jun 17
EWR5:58 amNewark
6h 11m
1 stop
MDW11:09 amChicago Midway
Jun 23
MDW12:27 pmChicago Midway
8h 02m
1 stop
EWR9:29 pmNewark
$241

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 May 25, 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

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 7/7

7:25 am-8:50 am

Nonstop2h 25m

Chicago Midway

Tue 7/28

7:45 pm-10:55 pm

Nonstop2h 10m

$177

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 7/3

9:30 pm-10:55 pm

Nonstop2h 25m

Chicago Midway

Wed 7/8

7:45 pm-11:00 pm

Nonstop2h 15m

$182

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 7/9

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Mon 7/13

7:45 pm-11:00 pm

Nonstop2h 15m

$187
Quickest round-trip

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 6/10

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Wed 6/17

5:15 am-8:15 am

Nonstop2h 00m

$192

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 7/7

12:05 pm-4:15 pm

1 stop5h 10m

Chicago Midway

Wed 7/8

9:19 am-3:54 pm

1 stop5h 35m

$197

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 6/30

6:00 am-9:14 am

1 stop4h 14m

Chicago Midway

Fri 7/3

9:17 am-3:59 pm

1 stop5h 42m

$202

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 6/9

6:00 am-10:09 am

1 stop5h 09m

Chicago Midway

Tue 7/14

6:00 am-12:21 pm

1 stop5h 21m

$212

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 7/21

5:55 am-11:07 am

1 stop6h 12m

Chicago Midway

Tue 7/28

12:11 pm-9:28 pm

1 stop8h 17m

$240

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 6/17

5:58 am-11:09 am

1 stop6h 11m

Chicago Midway

Tue 6/23

12:27 pm-9:29 pm

1 stop8h 02m

$241

BuffaloChicago

BUF - MDW

BUFMDW

Buffalo

Wed 7/22

2:48 pm-10:03 pm

1 stop8h 15m

Chicago Midway

Sat 7/25

6:05 am-10:29 am

1 stop27h 24m

$248

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 December is, on average, the cheapest month to fly to Chicago Midway Airport from State of New York, with most prices found around $39. If you are unable to visit Chicago Midway Airport during the month of December, 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 $53.

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 $271. 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 $406.

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 $218 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $368. 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 New York LaGuardia to Chicago Midway for the best New York - Chicago Midway flight prices

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

There is only 1 cabin class available to choose from on State of New York to Chicago Midway Airport 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

$173

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 $173. The best round-trip flight deal from State of New York to Chicago Midway Airport found on momondo in the last 72 hours is $284.
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
5.6
2,933 reviews
Search Frontier flights
United AirlinesPriceFrom $148Free CancellationRating
7.4
9,748 reviews
Search United Airlines flights
DeltaPriceFrom $153Free CancellationRating
7.9
8,425 reviews
Search Delta flights
SouthwestPriceFrom $164Free CancellationRating
8.0
4,266 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
Munster
Schererville
Crown Point
Monticello
Chesterton
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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