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Cheap flights from New York to Chicago from $139

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 4/9. 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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Find the cheapest flights from New York to Chicago (NYC-CHI)

Cheap return flights

United Airlines Logo
09:00 - 10:35EWR-ORD
2h 35mdirect
United Airlines Logo
19:35 - 22:59ORD-EWR
2h 24mdirect
$273United Airlines
Find Deal
Wed, 10 Sep - Fri, 12 Sep
United Airlines Logo
20:15 - 21:56EWR-ORD
2h 41mdirect
United Airlines Logo
19:35 - 22:59ORD-EWR
2h 24mdirect
$276United Airlines
Find Deal
Fri, 5 Sep - Sat, 6 Sep
American Airlines Logo
19:22 - 21:01EWR-ORD
2h 39mdirect
American Airlines Logo
20:41 - 23:59ORD-EWR
2h 18mdirect
$277American Airlines
Find Deal
Wed, 10 Sep - Fri, 12 Sep
United Airlines Logo
15:30 - 17:05EWR-ORD
2h 35mdirect
United Airlines Logo
18:02 - 21:30ORD-EWR
2h 28mdirect
$282United Airlines
Find Deal
Sat, 6 Sep - Mon, 8 Sep
United Airlines Logo
07:00 - 08:38EWR-ORD
2h 38mdirect
United Airlines Logo
06:00 - 09:15ORD-EWR
2h 15mdirect
$288United Airlines
Find Deal
Thu, 25 Sep - Fri, 3 Oct
Spirit Airlines Logo
10:05 - 22:48EWR-ORD
13h 43m1 stop
Spirit Airlines Logo
18:44 - 09:00ORD-EWR
13h 16m1 stop
$290Spirit Airlines
Find Deal
Fri, 5 Sep - Sun, 7 Sep
United Airlines Logo
21:44 - 23:25EWR-ORD
2h 41mdirect
United Airlines Logo
06:00 - 09:15ORD-EWR
2h 15mdirect
$291United Airlines
Find Deal
Tue, 23 Sep - Thu, 25 Sep
Delta Logo
09:51 - 13:43EWR-ORD
4h 52m1 stop
Delta Logo
09:10 - 15:59ORD-EWR
5h 49m1 stop
$297Delta
Find Deal
Sat, 13 Sep - Wed, 24 Sep
Delta Logo
13:00 - 16:20EWR-ORD
4h 20m1 stop
Delta Logo
07:10 - 12:05ORD-EWR
3h 55m1 stop
$319Delta
Find Deal
Sat, 20 Sep - Mon, 22 Sep
Spirit Airlines Logo
10:05 - 22:48EWR-ORD
13h 43m1 stop
Spirit Airlines Logo
05:05 - 17:51ORD-EWR
11h 46m1 stop
$325Spirit Airlines
Find Deal
Fri, 12 Sep - Sun, 14 Sep

Delta flights from New York to Chicago

Our best Delta deals on New York to Chicago flight tickets
Delta
13 Sept
EWR09:51Newark
4h 52m
1 stop
ORD13:43Chicago O'Hare Intl
24 Sept
ORD09:10Chicago O'Hare Intl
5h 49m
1 stop
EWR15:59Newark
$297
Find similar
Delta
4 Sept
EWR09:50Newark
3h 55m
1 stop
ORD12:45Chicago O'Hare Intl
5 Sept
ORD17:00Chicago O'Hare Intl
5h 12m
1 stop
EWR23:12Newark
$307
Find similar
Delta
6 Sept
EWR16:59Newark
4h 24m
1 stop
ORD20:23Chicago O'Hare Intl
2 Oct
ORD09:10Chicago O'Hare Intl
5h 49m
1 stop
EWR15:59Newark
$313
Find similar

United Airlines flights from New York to Chicago

Our best United Airlines deals on New York to Chicago flight tickets
United Airlines
10 Sept
EWR09:00Newark
2h 35m
ORD10:35Chicago O'Hare Intl
12 Sept
ORD19:35Chicago O'Hare Intl
2h 24m
EWR22:59Newark
$273
Find similar
United Airlines
3 Sept
EWR18:30Newark
2h 41m
ORD20:11Chicago O'Hare Intl
4 Sept
ORD14:00Chicago O'Hare Intl
2h 15m
EWR17:15Newark
$276
Find similar
United Airlines
6 Sept
EWR15:30Newark
2h 35m
ORD17:05Chicago O'Hare Intl
8 Sept
ORD18:02Chicago O'Hare Intl
2h 28m
EWR21:30Newark
$282
Find similar

momondo Fare Finder

 
Customise your flight search to find flights from New York to Chicago 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 78,305 searches. Data last updated 26 August 2025.
Use the filters below to find and compare flights from New York to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 10/9

09:00-10:35

Nonstop2h 35m

Chicago O'Hare Intl

Fri 12/9

19:35-22:59

Nonstop2h 24m

$273

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 5/9

20:15-21:56

Nonstop2h 41m

Chicago O'Hare Intl

Sat 6/9

19:35-22:59

Nonstop2h 24m

$276

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 10/9

19:22-21:01

Nonstop2h 39m

Chicago O'Hare Intl

Fri 12/9

20:41-23:59

Nonstop2h 18m

$277

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 6/9

15:30-17:05

Nonstop2h 35m

Chicago O'Hare Intl

Mon 8/9

18:02-21:30

Nonstop2h 28m

$282

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 25/9

07:00-08:38

Nonstop2h 38m

Chicago O'Hare Intl

Fri 3/10

06:00-09:15

Nonstop2h 15m

$288

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 5/9

10:05-22:48

1 stop13h 43m

Chicago O'Hare Intl

Sun 7/9

18:44-09:00

1 stop13h 16m

$290

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 23/9

21:44-23:25

Nonstop2h 41m

Chicago O'Hare Intl

Thu 25/9

06:00-09:15

Nonstop2h 15m

$291

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 13/9

09:51-13:43

1 stop4h 52m

Chicago O'Hare Intl

Wed 24/9

09:10-15:59

1 stop5h 49m

$297

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 20/9

13:00-16:20

1 stop4h 20m

Chicago O'Hare Intl

Mon 22/9

07:10-12:05

1 stop3h 55m

$319

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 12/9

10:05-22:48

1 stop13h 43m

Chicago O'Hare Intl

Sun 14/9

05:05-17:51

1 stop11h 46m

$325

Flights are sorted by cheapest return 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

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 typical price of a round-trip flight between New York and Chicago?

What is the cheapest month to fly to Chicago?

If you don’t want to visit Chicago in January, then you should wait until September to fly from New York, when ticket prices are also cheap, with an average price of $280.

What is the cheapest day to depart on your flight to Chicago?

Our data shows that Saturday is the least expensive day to fly to Chicago. Tickets to fly out on this day can be as low as $320. Flights from New York to Chicago on a Wednesday will generally be more expensive and average around $1,551. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Our data shows that the cheapest New York to Chicago flights are usually those with departure times in the evening. Our users have found flights to Chicago in the evening for as low as $223. Flights at midday are often more expensive, with an average ticket price of $1,762.

What is the cheapest New York to Chicago flight route?

Fly from New York John F Kennedy Intl to Chicago O'Hare Intl for the best New York - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from New York when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $385 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from New York for as low as $307 on momondo.

What cabin class options are available on New York to Chicago flights?

There are 4 cabin classes available to choose from on New York to Chicago 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 flights?

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

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

As of August 2025, prices for New York to Chicago flights are approximately 16% cheaper when compared to flights at the same time last year.

When to book flights from New York to Chicago

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

Cheap New York to Chicago (NYC to CHI) flight deals and tips

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

Fastest flight time

2h 23m

Direct flights

Every day

Airports in Chicago

1 airport
The fastest flight from New York to Chicago takes 2h 23m
Direct flights go from New York to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

  • Is flying the fastest way to get from New York to Chicago?

    The quickest way to travel this route is to take a flight from New York to Chicago, doing so can potentially save up to 17h 20m of travel time. While these options may take longer, booking a train from New York to Chicago or a bus from New York to Chicago may suit your needs if travel time is less of a factor in your decision making.

  • Is flying the cheapest way to get from New York to Chicago?

    Planning to book a bus from New York to Chicago can be a safe bet when looking for a low-cost deal to your destination. Currently, a flight and a train are priced higher than the cost of a bus. You can search prices for a flight from New York starting at $273 to Chicago or a train from New York to Chicago starting at $305 if that is your preferred method of transportation.

  • How far is New York to Chicago by plane?

    The straight-line distance from New York to Chicago is 1143.9 km. Typically, this will take 2h 35m by plane in normal conditions.

  • When did momondo last update prices for flights from New York to Chicago?

    Prices for flights from New York to Chicago are refreshed on a daily basis.

  • How old do you have to be to fly from New York to Chicago?

    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.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's licence and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from New York to Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from New York to Chicago?

Finding the right flight to Chicago from New York is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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 for New York to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport