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Cheap flights from New York to Chicago from C$ 95

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 5/12. 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

Enter your travel dates to find the best prices.
United Airlines Logo
9:15 p.m. - 10:57 p.m.LGA-ORD
2h 42mdirect
United Airlines Logo
3:00 p.m. - 6:07 p.m.ORD-LGA
2h 07mdirect
C$ 164United Airlines
Find Deal
Wed, 5 Nov - Wed, 12 Nov
United Airlines Logo
7:20 a.m. - 9:02 a.m.LGA-ORD
2h 42mdirect
United Airlines Logo
6:30 p.m. - 9:51 p.m.ORD-LGA
2h 21mdirect
C$ 169United Airlines
Find Deal
Sat, 13 Dec - Mon, 22 Dec
United Airlines Logo
4:15 p.m. - 5:57 p.m.LGA-ORD
2h 42mdirect
United Airlines Logo
7:00 a.m. - 10:07 a.m.ORD-LGA
2h 07mdirect
C$ 175United Airlines
Find Deal
Fri, 5 Dec - Mon, 8 Dec
Spirit Airlines Logo
8:45 a.m. - 9:00 p.m.LGA-ORD
13h 15m1 stop
Spirit Airlines Logo
6:05 a.m. - 2:00 p.m.ORD-LGA
6h 55m1 stop
C$ 190Spirit Airlines
Find Deal
Sun, 1 Feb - Tue, 3 Feb
Delta Logo
6:30 a.m. - 8:20 a.m.LGA-ORD
2h 50mdirect
Delta Logo
12:15 p.m. - 3:31 p.m.ORD-LGA
2h 16mdirect
C$ 192Delta
Find Deal
Thu, 15 Jan - Fri, 16 Jan
Delta Logo
4:40 p.m. - 6:27 p.m.LGA-ORD
2h 47mdirect
Delta Logo
12:35 p.m. - 3:43 p.m.ORD-LGA
2h 08mdirect
C$ 193Delta
Find Deal
Fri, 5 Dec - Mon, 8 Dec
Spirit Airlines Logo
6:00 p.m. - 12:27 a.m.LGA-ORD
7h 27m1 stop
Spirit Airlines Logo
4:57 p.m. - 8:00 p.m.ORD-LGA
2h 03mdirect
C$ 203Spirit Airlines
Find Deal
Fri, 7 Nov - Mon, 10 Nov
Multiple Airlines Logo
11:30 a.m. - 4:56 p.m.EWR-ORD
6h 26m1 stop
Multiple Airlines Logo
2:31 p.m. - 5:40 p.m.ORD-EWR
2h 09mdirect
C$ 223Multiple Airlines
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Fri, 7 Nov - Mon, 10 Nov
Frontier Logo
11:30 a.m. - 4:56 p.m.EWR-ORD
6h 26m1 stop
Frontier Logo
11:24 a.m. - 12:34 a.m.ORD-EWR
12h 10m1 stop
C$ 230Frontier
Find Deal
Fri, 7 Nov - Mon, 10 Nov
Frontier Logo
12:30 p.m. - 12:11 a.m.LGA-ORD
12h 41m1 stop
Frontier Logo
11:24 a.m. - 11:27 p.m.ORD-LGA
11h 03m1 stop
C$ 252Frontier
Find Deal
Fri, 7 Nov - Mon, 10 Nov

United Airlines flights from New York to Chicago

Our best United Airlines deals on New York to Chicago flight tickets
United Airlines
5 Nov
LGA11:15 a.m.New York LaGuardia
2h 42m
ORD12:57 p.m.Chicago O'Hare Intl
12 Nov
ORD8:00 p.m.Chicago O'Hare Intl
2h 16m
LGA11:16 p.m.New York LaGuardia
C$ 164
Find similar
United Airlines
13 Dec
LGA7:20 a.m.New York LaGuardia
2h 42m
ORD9:02 a.m.Chicago O'Hare Intl
14 Dec
ORD6:00 a.m.Chicago O'Hare Intl
2h 07m
LGA9:07 a.m.New York LaGuardia
C$ 169
Find similar
United Airlines
5 Dec
LGA4:15 p.m.New York LaGuardia
2h 42m
ORD5:57 p.m.Chicago O'Hare Intl
8 Dec
ORD7:00 a.m.Chicago O'Hare Intl
2h 07m
LGA10:07 a.m.New York LaGuardia
C$ 175
Find similar

Delta flights from New York to Chicago

Our best Delta deals on New York to Chicago flight tickets
Delta
15 Jan
LGA6:30 a.m.New York LaGuardia
2h 50m
ORD8:20 a.m.Chicago O'Hare Intl
16 Jan
ORD12:15 p.m.Chicago O'Hare Intl
2h 16m
LGA3:31 p.m.New York LaGuardia
C$ 192
Find similar
Delta
5 Dec
LGA4:40 p.m.New York LaGuardia
2h 47m
ORD6:27 p.m.Chicago O'Hare Intl
8 Dec
ORD12:35 p.m.Chicago O'Hare Intl
2h 08m
LGA3:43 p.m.New York LaGuardia
C$ 193
Find similar
Delta
6 Dec
LGA5:40 p.m.New York LaGuardia
2h 42m
ORD7:22 p.m.Chicago O'Hare Intl
8 Dec
ORD9:40 a.m.Chicago O'Hare Intl
2h 07m
LGA12:47 p.m.New York LaGuardia
C$ 220
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 96,600 searches. Data last updated 23 October 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

Wed 5/11

9:15 p.m.-10:57 p.m.

Nonstop2h 42m

Chicago O'Hare Intl

Wed 12/11

3:00 p.m.-6:07 p.m.

Nonstop2h 07m

C$ 164

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 13/12

7:20 a.m.-9:02 a.m.

Nonstop2h 42m

Chicago O'Hare Intl

Mon 22/12

6:30 p.m.-9:51 p.m.

Nonstop2h 21m

C$ 169

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 5/12

4:15 p.m.-5:57 p.m.

Nonstop2h 42m

Chicago O'Hare Intl

Mon 8/12

7:00 a.m.-10:07 a.m.

Nonstop2h 07m

C$ 175

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sun 1/2

8:45 a.m.-9:00 p.m.

1 stop13h 15m

Chicago O'Hare Intl

Tue 3/2

6:05 a.m.-2:00 p.m.

1 stop6h 55m

C$ 190

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 15/1

6:30 a.m.-8:20 a.m.

Nonstop2h 50m

Chicago O'Hare Intl

Fri 16/1

12:15 p.m.-3:31 p.m.

Nonstop2h 16m

C$ 192

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 5/12

4:40 p.m.-6:27 p.m.

Nonstop2h 47m

Chicago O'Hare Intl

Mon 8/12

12:35 p.m.-3:43 p.m.

Nonstop2h 08m

C$ 193

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 7/11

6:00 p.m.-12:27 a.m.

1 stop7h 27m

Chicago O'Hare Intl

Mon 10/11

4:57 p.m.-8:00 p.m.

Nonstop2h 03m

C$ 203

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 7/11

11:30 a.m.-4:56 p.m.

1 stop6h 26m

Chicago O'Hare Intl

Mon 10/11

2:31 p.m.-5:40 p.m.

Nonstop2h 09m

C$ 223

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 7/11

11:30 a.m.-4:56 p.m.

1 stop6h 26m

Chicago O'Hare Intl

Mon 10/11

11:24 a.m.-12:34 a.m.

1 stop12h 10m

C$ 230

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 7/11

12:30 p.m.-12:11 a.m.

1 stop12h 41m

Chicago O'Hare Intl

Mon 10/11

11:24 a.m.-11:27 p.m.

1 stop11h 03m

C$ 252

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 February is another great option to travel to Chicago, with average flight prices from New York averaging around C$ 265.

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 Thursday when prices can be found for as low as C$ 372. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around C$ 670. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

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

In the afternoon is the cheapest time of day to fly from New York to Chicago when you can find flight prices for as low as C$ 372. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. In the evening is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 602 per ticket.

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 C$ 353 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 C$ 260 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 October 2025, prices for New York to Chicago flights are approximately 34% 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

C$ 110

Fastest flight time

2h 21m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from New York in the past 72 hours is C$ 110. The best round-trip flight deal from New York to Chicago found on momondo in the last 72 hours is C$ 354.
The fastest flight from New York to Chicago takes 2h 21m
Direct flights go from New York to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
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  • Is flying the fastest way to get from New York to Chicago?

    Based on just travel duration our users have found a flight from New York to Chicago to be the fastest option to their destination at just 2h 21m. If travel time is less of a concern you may want to look into booking some alternative forms of transportation like a train from New York to Chicago or a bus from New York to Chicago.

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

    Expect a flight to be one of the cheapest options available to you for travel. Currently, a flight has deals available from C$ 164. While they may not be the most cost-effective options currently available a train from New York to Chicago or a bus from New York to Chicago can also be options worth looking into if other factors outside of cost are a higher priority.

  • How far is New York to Chicago by plane?

    There are 1143.9 km between New York and Chicago. Typically, this will take 2h 21m 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?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, 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 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 license 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?

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

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from New York to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. momondo enables you to select and highlight flights to Chicago from New York with this policy.

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 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 trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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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