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Cheap flights from New York to Chicago from $33

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 to Chicago departing on 10/23. 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

Frontier Logo
10:00 pm - 11:25 pmEWR-MDW
2h 25mnonstop
Frontier Logo
5:56 pm - 9:00 pmMDW-EWR
2h 04mnonstop
$67Frontier
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
$85Frontier
Find Deal
Thu, Oct 23 - Tue, Oct 28
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
Southwest Logo
6:00 am - 7:20 amLGA-MDW
2h 20mnonstop
Southwest Logo
7:05 pm - 10:15 pmMDW-LGA
2h 10mnonstop
$137Southwest
Find Deal
Wed, Sep 3 - Wed, Sep 3
Southwest Logo
9:00 am - 10:25 amLGA-MDW
2h 25mnonstop
Southwest Logo
6:55 am - 9:55 amMDW-LGA
2h 00mnonstop
$142Southwest
Find Deal
Wed, Sep 3 - Sat, Sep 6
Southwest Logo
7:30 am - 8:50 amLGA-MDW
2h 20mnonstop
Southwest Logo
6:00 am - 9:00 amMDW-LGA
2h 00mnonstop
$147Southwest
Find Deal
Sat, Sep 13 - Tue, Sep 16
Southwest Logo
6:00 am - 7:20 amLGA-MDW
2h 20mnonstop
Southwest Logo
6:00 am - 9:00 amMDW-LGA
2h 00mnonstop
$152Southwest
Find Deal
Sun, Aug 31 - Wed, Sep 3
Delta Logo
9:50 am - 12:28 pmEWR-MDW
3h 38m1 stop
Delta Logo
6:17 pm - 11:30 pmMDW-EWR
4h 13m1 stop
$162Delta
Find Deal
Wed, Sep 3 - Sat, Sep 6
Delta Logo
3:30 pm - 9:10 pmEWR-MDW
6h 40m1 stop
Delta Logo
6:00 am - 12:10 pmMDW-EWR
5h 10m1 stop
$167Delta
Find Deal
Sat, Sep 20 - Wed, Sep 24
Delta Logo
9:51 am - 12:28 pmEWR-MDW
3h 37m1 stop
Delta Logo
6:15 pm - 11:31 pmMDW-EWR
4h 16m1 stop
$173Delta
Find Deal
Sat, Sep 13 - Tue, Sep 16

Frontier flights from New York to Chicago Midway Airport

Our best Frontier deals on 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
$67
Find similar
Frontier
Oct 23
EWR10:00 pmNewark
2h 25m
MDW11:25 pmChicago Midway
Oct 28
MDW5:56 pmChicago Midway
2h 04m
EWR9:00 pmNewark
$85
Find similar
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

Delta flights from New York to Chicago Midway Airport

Our best Delta deals on New York to Chicago Midway Airport flight tickets
Delta
Sep 3
EWR9:50 amNewark
3h 38m
1 stop
MDW12:28 pmChicago Midway
Sep 6
MDW6:17 pmChicago Midway
4h 13m
1 stop
EWR11:30 pmNewark
$162
Find similar
Delta
Sep 20
EWR3:30 pmNewark
6h 40m
1 stop
MDW9:10 pmChicago Midway
Sep 24
MDW6:00 amChicago Midway
5h 10m
1 stop
EWR12:10 pmNewark
$167
Find similar
Delta
Sep 13
EWR9:51 amNewark
3h 37m
1 stop
MDW12:28 pmChicago Midway
Sep 16
MDW6:15 pmChicago Midway
4h 16m
1 stop
EWR11:31 pmNewark
$173
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from 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 July 31, 2025.
Use the filters below to find and compare flights from New York 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

$67

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 10/23

10:00 pm-11:25 pm

Nonstop2h 25m

Chicago Midway

Tue 10/28

5:56 pm-9:00 pm

Nonstop2h 04m

$85

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

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 9/3

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Wed 9/3

7:05 pm-10:15 pm

Nonstop2h 10m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 9/3

9:00 am-10:25 am

Nonstop2h 25m

Chicago Midway

Sat 9/6

6:55 am-9:55 am

Nonstop2h 00m

$142

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 9/13

7:30 am-8:50 am

Nonstop2h 20m

Chicago Midway

Tue 9/16

6:00 am-9:00 am

Nonstop2h 00m

$147

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sun 8/31

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Wed 9/3

6:00 am-9:00 am

Nonstop2h 00m

$152

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 9/3

9:50 am-12:28 pm

1 stop3h 38m

Chicago Midway

Sat 9/6

6:17 pm-11:30 pm

1 stop4h 13m

$162

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 9/20

3:30 pm-9:10 pm

1 stop6h 40m

Chicago Midway

Wed 9/24

6:00 am-12:10 pm

1 stop5h 10m

$167

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 9/13

9:51 am-12:28 pm

1 stop3h 37m

Chicago Midway

Tue 9/16

6:15 pm-11:31 pm

1 stop4h 16m

$173

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 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 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 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 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 New York because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $407.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from 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 $344. 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 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 New York to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between New York to Chicago Midway Airport.

How have New York to Chicago Midway Airport flight prices changed over time?

As of July 2025, prices for New York to Chicago Midway Airport flights are approximately 8% more expensive when compared to flights at the same time last year.

When to book flights from New York to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from New York to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap New York to Chicago Midway Airport (NYC to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New York to Chicago Midway Airport

Best Price Found

$33

Fastest flight time

2h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from New York in the past 72 hours is $33. The best round-trip flight deal from New York to Chicago Midway Airport found on momondo in the last 72 hours is $67.
The fastest flight from New York to Chicago Midway Airport takes 2h 20m
Direct flights go from New York to Chicago Midway Airport every day.
Search flight deals

  • How far is New York to Chicago Midway by plane?

    Chicago Midway is 716.7 mi away from New York. Flights usually cover this in 2h 20m, depending on flying conditions and air traffic around both airports.

  • 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 for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for 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 New York to Chicago Midway Airport?

  • What is the most popular airline from New York to Chicago Midway Airport?

Best airlines flying from New York to Chicago Midway Airport

Compare and see reviews for airlines that fly from New York to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $92Free CancellationRating
6.3
8,048 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $152Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
DeltaPriceFrom $192Free CancellationRating
8.0
7,981 reviews
Search Delta flights

  • Southwest Flights From New York to Chicago Midway Airport

    Across 21 Southwest flights from New York to Chicago Midway Airport this week, the average price was $253, with the best Southwest deals starting from $152 round-trip. 4,246 users have rated Southwest on momondo, with an average score of 8.0/10.

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?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from New York.

Can I find flights from New York to Chicago with flexible booking policies on momondo?

All flight searches from New York to Chicago on momondo can be filtered to show those which offer 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?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from New York and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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