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Cheap flights from New York to Chicago from $27

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 9/6. 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 round-trip flights

Spirit Airlines Logo
10:59 am - 7:07 pmLGA-ORD
9h 08m1 stop
Spirit Airlines Logo
4:35 pm - 7:41 pmORD-LGA
2h 06mnonstop
$65Spirit Airlines
Find Deal
Sat, Aug 30 - Sat, Sep 6
Spirit Airlines Logo
8:36 pm - 10:11 pmLGA-ORD
2h 35mnonstop
Spirit Airlines Logo
5:05 am - 3:59 pmORD-LGA
9h 54m1 stop
$69Spirit Airlines
Find Deal
Sat, Sep 6 - Tue, Sep 9
American Airlines Logo
7:30 am - 9:10 amEWR-ORD
2h 40mnonstop
American Airlines Logo
7:05 am - 10:19 amORD-EWR
2h 14mnonstop
$117American Airlines
Find Deal
Wed, Sep 3 - Wed, Sep 10
American Airlines Logo
7:22 pm - 9:01 pmEWR-ORD
2h 39mnonstop
American Airlines Logo
8:41 pm - 11:59 pmORD-EWR
2h 18mnonstop
$120American Airlines
Find Deal
Sat, Sep 13 - Mon, Sep 15
United Airlines Logo
6:00 am - 7:38 amEWR-ORD
2h 38mnonstop
United Airlines Logo
8:45 am - 11:59 amORD-EWR
2h 14mnonstop
$121United Airlines
Find Deal
Fri, Sep 5 - Sat, Sep 6
United Airlines Logo
7:00 am - 8:47 amEWR-ORD
2h 47mnonstop
United Airlines Logo
9:08 pm - 12:13 amORD-EWR
2h 05mnonstop
$132United Airlines
Find Deal
Tue, Dec 2 - Thu, Dec 4
Southwest Logo
11:25 am - 12:50 pmLGA-MDW
2h 25mnonstop
Southwest Logo
7:05 pm - 10:15 pmMDW-LGA
2h 10mnonstop
$132Southwest
Find Deal
Wed, Sep 3 - Wed, Sep 10
Southwest Logo
3:35 pm - 5:05 pmLGA-MDW
2h 30mnonstop
Southwest Logo
2:15 pm - 5:20 pmMDW-LGA
2h 05mnonstop
$134Southwest
Find Deal
Wed, Aug 27 - Wed, Sep 3
Delta Logo
3:29 pm - 5:37 pmJFK-ORD
3h 08mnonstop
Delta Logo
7:00 am - 10:23 amORD-JFK
2h 23mnonstop
$147Delta
Find Deal
Wed, Sep 3 - Wed, Sep 10
Delta Logo
10:50 am - 12:40 pmJFK-ORD
2h 50mnonstop
Delta Logo
6:20 pm - 10:03 pmORD-JFK
2h 43mnonstop
$167Delta
Find Deal
Thu, Sep 4 - Sat, Sep 6

American Airlines flights from New York to Chicago

Our best American Airlines deals on New York to Chicago flight tickets
American Airlines
Sep 3
EWR7:30 amNewark
2h 40m
ORD9:10 amChicago O'Hare Intl
Sep 10
ORD7:05 amChicago O'Hare Intl
2h 14m
EWR10:19 amNewark
$117
Find similar
American Airlines
Sep 13
EWR7:22 pmNewark
2h 39m
ORD9:01 pmChicago O'Hare Intl
Sep 15
ORD8:41 pmChicago O'Hare Intl
2h 18m
EWR11:59 pmNewark
$120
Find similar
American Airlines
Oct 31
EWR6:59 amNewark
2h 43m
ORD8:42 amChicago O'Hare Intl
Nov 4
ORD7:14 pmChicago O'Hare Intl
2h 16m
EWR10:30 pmNewark
$124
Find similar

United Airlines flights from New York to Chicago

Our best United Airlines deals on New York to Chicago flight tickets
United Airlines
Sep 5
EWR6:00 amNewark
2h 38m
ORD7:38 amChicago O'Hare Intl
Sep 6
ORD8:45 amChicago O'Hare Intl
2h 14m
EWR11:59 amNewark
$121
Find similar
United Airlines
Dec 2
EWR7:00 amNewark
2h 47m
ORD8:47 amChicago O'Hare Intl
Dec 4
ORD9:08 pmChicago O'Hare Intl
2h 05m
EWR12:13 amNewark
$132
Find similar
United Airlines
Sep 3
EWR7:00 amNewark
2h 38m
ORD8:38 amChicago O'Hare Intl
Sep 3
ORD6:02 pmChicago O'Hare Intl
2h 28m
EWR9:30 pmNewark
$137
Find similar

momondo Fare Finder

 
Customize 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 832,500 searches. Data last updated August 5, 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

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 8/30

10:59 am-7:07 pm

1 stop9h 08m

Chicago O'Hare Intl

Sat 9/6

4:35 pm-7:41 pm

Nonstop2h 06m

$65

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 9/6

8:36 pm-10:11 pm

Nonstop2h 35m

Chicago O'Hare Intl

Tue 9/9

5:05 am-3:59 pm

1 stop9h 54m

$69

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 9/3

7:30 am-9:10 am

Nonstop2h 40m

Chicago O'Hare Intl

Wed 9/10

7:05 am-10:19 am

Nonstop2h 14m

$117

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 9/13

7:22 pm-9:01 pm

Nonstop2h 39m

Chicago O'Hare Intl

Mon 9/15

8:41 pm-11:59 pm

Nonstop2h 18m

$120

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 9/5

6:00 am-7:38 am

Nonstop2h 38m

Chicago O'Hare Intl

Sat 9/6

8:45 am-11:59 am

Nonstop2h 14m

$121

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 12/2

7:00 am-8:47 am

Nonstop2h 47m

Chicago O'Hare Intl

Thu 12/4

9:08 pm-12:13 am

Nonstop2h 05m

$132

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 9/3

11:25 am-12:50 pm

Nonstop2h 25m

Chicago Midway

Wed 9/10

7:05 pm-10:15 pm

Nonstop2h 10m

$132

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 8/27

3:35 pm-5:05 pm

Nonstop2h 30m

Chicago Midway

Wed 9/3

2:15 pm-5:20 pm

Nonstop2h 05m

$134

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 9/3

3:29 pm-5:37 pm

Nonstop3h 08m

Chicago O'Hare Intl

Wed 9/10

7:00 am-10:23 am

Nonstop2h 23m

$147

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 9/4

10:50 am-12:40 pm

Nonstop2h 50m

Chicago O'Hare Intl

Sat 9/6

6:20 pm-10:03 pm

Nonstop2h 43m

$167

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

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?

The month of September is, on average, the cheapest month to fly to Chicago from New York, with most prices found around $178. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from New York to Chicago during January average around $180.

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

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $293. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from New York to Chicago for around $378.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from New York to Chicago during this time can be as low as $249. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $354.

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 $245 when searching weeks out. 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 $190 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 30% 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 round-trip 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

Best Price Found

$27

Fastest flight time

2h 20m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from New York in the past 72 hours is $27. The best round-trip flight deal from New York to Chicago found on momondo in the last 72 hours is $65.
The fastest flight from New York to Chicago takes 2h 20m
Direct flights go from New York to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
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 12m 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?

    The cheapest way is to get a flight from New York to Chicago, which can be as cheap as $65. A train from New York to Chicago is more expensive than a flight, with prices starting at $198. A bus from New York to Chicago is also an option, with an average price of $153.

  • How far is New York to Chicago by plane?

    Chicago is 710.8 mi away from New York. Typically, this will take 2h 20m 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 updated daily.

  • How many operators does momondo search for flights from New York to Chicago?

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

    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.

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

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

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

Best airlines flying from New York to Chicago

Compare and see reviews for airlines that fly from New York to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $66Free CancellationRating
6.3
8,052 reviews
Search Spirit Airlines flights
FrontierPriceFrom $83Free CancellationRating
5.8
3,232 reviews
Search Frontier flights
JetBluePriceFrom $84Free CancellationRating
7.2
2,915 reviews
Search JetBlue flights
DeltaPriceFrom $101Free CancellationRating
8.0
7,990 reviews
Search Delta flights
American AirlinesPriceFrom $138Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $148Free CancellationRating
7.4
8,910 reviews
Search United Airlines flights
SouthwestPriceFrom $153Free CancellationRating
8.0
4,247 reviews
Search Southwest flights

  • Delta Flights From New York to Chicago

    Delta flight deals from New York to Chicago start from $101 round-trip. Over the 69 Delta flights for this route in a normal week, average airfare is usually $351 round-trip - but some users have found much cheaper deals with momondo.

  • Southwest Flights From New York to Chicago

    Another popular option for New York to Chicago flights is Southwest (8.0/10, 4,247 ratings). Southwest flies from New York to Chicago around 14 times per week, with deals starting from $153 round-trip and rising to an average price of around $258.

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
Lansing
Portage
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?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from New York to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from New York to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from New York to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from New York to Chicago.

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 not ready to book a flight from New York to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago trip

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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 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport