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Cheap flights from New York to Chicago from $132

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 19/10. 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 return flights

United Airlines Logo
10:30 - 12:05EWR-ORD
2h 35mdirect
United Airlines Logo
12:00 - 15:17ORD-EWR
2h 17mdirect
$250United Airlines
Find Deal
Wed, 1 Oct - Sat, 4 Oct
Spirit Airlines Logo
06:20 - 18:38EWR-ORD
13h 18m1 stop
Spirit Airlines Logo
19:43 - 09:00ORD-EWR
12h 17m1 stop
$253Spirit Airlines
Find Deal
Mon, 6 Oct - Wed, 8 Oct
United Airlines Logo
21:49 - 23:30EWR-ORD
2h 41mdirect
United Airlines Logo
06:00 - 09:15ORD-EWR
2h 15mdirect
$255United Airlines
Find Deal
Mon, 13 Oct - Mon, 20 Oct
United Airlines Logo
21:49 - 23:30EWR-ORD
2h 41mdirect
United Airlines Logo
06:00 - 09:15ORD-EWR
2h 15mdirect
$261United Airlines
Find Deal
Fri, 17 Oct - Mon, 20 Oct
United Airlines Logo
07:00 - 08:38EWR-ORD
2h 38mdirect
United Airlines Logo
21:23 - 00:45ORD-EWR
2h 22mdirect
$262United Airlines
Find Deal
Tue, 7 Oct - Fri, 10 Oct
Delta Logo
12:50 - 16:18EWR-ORD
4h 28m1 stop
Delta Logo
09:30 - 16:53ORD-EWR
6h 23m1 stop
$265Delta
Find Deal
Tue, 9 Dec - Tue, 10 Feb
United Airlines Logo
21:49 - 23:30EWR-ORD
2h 41mdirect
United Airlines Logo
06:00 - 09:15ORD-EWR
2h 15mdirect
$267United Airlines
Find Deal
Fri, 17 Oct - Mon, 20 Oct
Delta Logo
13:29 - 18:49EWR-ORD
6h 20m1 stop
Delta Logo
16:21 - 23:07ORD-EWR
5h 46m1 stop
$268Delta
Find Deal
Sat, 8 Nov - Mon, 10 Nov
United Airlines Logo
07:00 - 08:38EWR-ORD
2h 38mdirect
United Airlines Logo
06:00 - 09:15ORD-EWR
2h 15mdirect
$270United Airlines
Find Deal
Thu, 16 Oct - Thu, 23 Oct
American Airlines Logo
19:22 - 21:01EWR-ORD
2h 39mdirect
American Airlines Logo
19:42 - 22:59ORD-EWR
2h 17mdirect
$340American Airlines
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Tue, 30 Sep - Fri, 3 Oct

Spirit Airlines flights from New York to Chicago

Our best Spirit Airlines deals on New York to Chicago flight tickets
Spirit Airlines
6 Oct
EWR06:20Newark
13h 18m
1 stop
ORD18:38Chicago O'Hare Intl
8 Oct
ORD19:43Chicago O'Hare Intl
12h 17m
1 stop
EWR09:00Newark
$253
Find similar
Spirit Airlines
2 Oct
EWR06:10Newark
12h 29m
1 stop
ORD17:39Chicago O'Hare Intl
5 Oct
ORD18:58Chicago O'Hare Intl
13h 05m
1 stop
EWR09:03Newark
$274
Find similar
Spirit Airlines
7 Oct
EWR20:19Newark
14h 49m
2 stops
ORD10:08Chicago O'Hare Intl
8 Oct
ORD19:43Chicago O'Hare Intl
12h 17m
1 stop
EWR09:00Newark
$291
Find similar

United Airlines flights from New York to Chicago

Our best United Airlines deals on New York to Chicago flight tickets
United Airlines
1 Oct
EWR10:30Newark
2h 35m
ORD12:05Chicago O'Hare Intl
4 Oct
ORD12:00Chicago O'Hare Intl
2h 17m
EWR15:17Newark
$250
Find similar
United Airlines
13 Oct
EWR21:49Newark
2h 41m
ORD23:30Chicago O'Hare Intl
20 Oct
ORD06:00Chicago O'Hare Intl
2h 15m
EWR09:15Newark
$255
Find similar
United Airlines
17 Oct
EWR21:49Newark
2h 41m
ORD23:30Chicago O'Hare Intl
20 Oct
ORD06:00Chicago O'Hare Intl
2h 15m
EWR09:15Newark
$261
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 17 September 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 1/10

10:30-12:05

Nonstop2h 35m

Chicago O'Hare Intl

Sat 4/10

12:00-15:17

Nonstop2h 17m

$250

NewarkChicago

EWR - ORD

EWRORD

Newark

Mon 6/10

06:20-18:38

1 stop13h 18m

Chicago O'Hare Intl

Wed 8/10

19:43-09:00

1 stop12h 17m

$253

NewarkChicago

EWR - ORD

EWRORD

Newark

Mon 13/10

21:49-23:30

Nonstop2h 41m

Chicago O'Hare Intl

Mon 20/10

06:00-09:15

Nonstop2h 15m

$255

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 17/10

21:49-23:30

Nonstop2h 41m

Chicago O'Hare Intl

Mon 20/10

06:00-09:15

Nonstop2h 15m

$261

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 7/10

07:00-08:38

Nonstop2h 38m

Chicago O'Hare Intl

Fri 10/10

21:23-00:45

Nonstop2h 22m

$262

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 9/12

12:50-16:18

1 stop4h 28m

Chicago O'Hare Intl

Tue 10/2

09:30-16:53

1 stop6h 23m

$265

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 17/10

21:49-23:30

Nonstop2h 41m

Chicago O'Hare Intl

Mon 20/10

06:00-09:15

Nonstop2h 15m

$267

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 8/11

13:29-18:49

1 stop6h 20m

Chicago O'Hare Intl

Mon 10/11

16:21-23:07

1 stop5h 46m

$268

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 16/10

07:00-08:38

Nonstop2h 38m

Chicago O'Hare Intl

Thu 23/10

06:00-09:15

Nonstop2h 15m

$270

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 30/9

19:22-21:01

Nonstop2h 39m

Chicago O'Hare Intl

Fri 3/10

19:42-22:59

Nonstop2h 17m

$340

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 cheapest month to fly to Chicago?

If you don’t want to visit Chicago in January, then you should wait until February to fly from New York, when ticket prices are also cheap, with an average price of $283.

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 $311. Flights from New York to Chicago on a Wednesday will generally be more expensive and average around $1,508. 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 $217. Flights at midday are often more expensive, with an average ticket price of $1,713.

What is the cheapest New York to Chicago flight route?

Fly from Newark to Chicago Midway 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 $378 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 $300 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 September 2025, prices for New York to Chicago flights are approximately 31% 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 13m 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 flight from New York to Chicago can be a safe bet when looking for a low-cost deal to your destination. Currently, a train and a bus are priced higher than the cost of a flight. You can search prices for a train from New York starting at $270 to Chicago or a bus from New York to Chicago starting at $267 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 27m 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