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Cheap flights from New York to Chicago from C$ 97

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 22/10. 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 round-trip flights

Spirit Airlines Logo
3:29 p.m. - 5:13 p.m.LGA-ORD
2h 44mdirect
Spirit Airlines Logo
6:58 p.m. - 9:00 a.m.ORD-LGA
13h 02m1 stop
C$ 181Spirit Airlines
Find Deal
Wed, 8 Oct - Wed, 8 Oct
Spirit Airlines Logo
3:29 p.m. - 5:13 p.m.LGA-ORD
2h 44mdirect
Spirit Airlines Logo
11:13 a.m. - 2:08 p.m.ORD-LGA
1h 55mdirect
C$ 183Spirit Airlines
Find Deal
Mon, 20 Oct - Wed, 22 Oct
United Airlines Logo
6:30 p.m. - 8:07 p.m.LGA-ORD
2h 37mdirect
United Airlines Logo
8:00 a.m. - 11:16 a.m.ORD-LGA
2h 16mdirect
C$ 184United Airlines
Find Deal
Tue, 30 Sep - Wed, 1 Oct
American Airlines Logo
2:06 p.m. - 3:58 p.m.LGA-ORD
2h 52mdirect
American Airlines Logo
7:00 a.m. - 10:08 a.m.ORD-LGA
2h 08mdirect
C$ 186American Airlines
Find Deal
Wed, 8 Oct - Wed, 15 Oct
Spirit Airlines Logo
5:55 a.m. - 9:33 p.m.LGA-ORD
16h 38m1 stop
Spirit Airlines Logo
6:58 p.m. - 9:00 a.m.ORD-LGA
13h 02m1 stop
C$ 190Spirit Airlines
Find Deal
Wed, 8 Oct - Wed, 15 Oct
Southwest Logo
6:00 a.m. - 12:45 p.m.LGA-ORD
7h 45m1 stop
Southwest Logo
3:10 p.m. - 9:00 p.m.ORD-LGA
4h 50m1 stop
C$ 193Southwest
Find Deal
Wed, 1 Oct - Wed, 1 Oct
United Airlines Logo
4:28 p.m. - 6:05 p.m.LGA-ORD
2h 37mdirect
United Airlines Logo
6:30 p.m. - 9:54 p.m.ORD-LGA
2h 24mdirect
C$ 195United Airlines
Find Deal
Wed, 8 Oct - Fri, 17 Oct
Southwest Logo
6:05 a.m. - 12:15 p.m.LGA-ORD
7h 10m1 stop
Southwest Logo
1:45 p.m. - 11:15 p.m.ORD-LGA
8h 30m1 stop
C$ 200Southwest
Find Deal
Wed, 5 Nov - Wed, 5 Nov
Delta Logo
2:55 p.m. - 4:34 p.m.LGA-ORD
2h 39mdirect
Delta Logo
6:00 a.m. - 9:07 a.m.ORD-LGA
2h 07mdirect
C$ 205Delta
Find Deal
Sat, 25 Oct - Mon, 27 Oct
Delta Logo
5:40 p.m. - 7:25 p.m.LGA-ORD
2h 45mdirect
Delta Logo
7:00 a.m. - 10:11 a.m.ORD-LGA
2h 11mdirect
C$ 218Delta
Find Deal
Tue, 28 Oct - Tue, 4 Nov

United Airlines flights from New York to Chicago

Our best United Airlines deals on New York to Chicago flight tickets
United Airlines
30 Sep
LGA6:30 p.m.New York LaGuardia
2h 37m
ORD8:07 p.m.Chicago O'Hare Intl
1 Oct
ORD8:00 a.m.Chicago O'Hare Intl
2h 16m
LGA11:16 a.m.New York LaGuardia
C$ 184
Find similar
United Airlines
8 Oct
LGA4:28 p.m.New York LaGuardia
2h 37m
ORD6:05 p.m.Chicago O'Hare Intl
17 Oct
ORD6:30 p.m.Chicago O'Hare Intl
2h 24m
LGA9:54 p.m.New York LaGuardia
C$ 195
Find similar
United Airlines
8 Oct
LGA7:28 a.m.New York LaGuardia
2h 37m
ORD9:05 a.m.Chicago O'Hare Intl
10 Oct
ORD7:00 a.m.Chicago O'Hare Intl
2h 16m
LGA10:16 a.m.New York LaGuardia
C$ 202
Find similar

Southwest flights from New York to Chicago

Our best Southwest deals on New York to Chicago flight tickets
Southwest
1 Oct
LGA6:00 a.m.New York LaGuardia
7h 45m
1 stop
ORD12:45 p.m.Chicago O'Hare Intl
1 Oct
ORD3:10 p.m.Chicago O'Hare Intl
4h 50m
1 stop
LGA9:00 p.m.New York LaGuardia
C$ 193
Find similar
Southwest
5 Nov
LGA6:05 a.m.New York LaGuardia
7h 10m
1 stop
ORD12:15 p.m.Chicago O'Hare Intl
5 Nov
ORD1:45 p.m.Chicago O'Hare Intl
8h 30m
1 stop
LGA11:15 p.m.New York LaGuardia
C$ 200
Find similar
Southwest
21 Oct
LGA7:20 a.m.New York LaGuardia
9h 00m
1 stop
ORD3:20 p.m.Chicago O'Hare Intl
25 Oct
ORD7:30 a.m.Chicago O'Hare Intl
7h 10m
1 stop
LGA3:40 p.m.New York LaGuardia
C$ 204
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 11 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

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 8/10

3:29 p.m.-5:13 p.m.

Nonstop2h 44m

Chicago O'Hare Intl

Wed 8/10

6:58 p.m.-9:00 a.m.

1 stop13h 02m

C$ 181

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 20/10

3:29 p.m.-5:13 p.m.

Nonstop2h 44m

Chicago O'Hare Intl

Wed 22/10

11:13 a.m.-2:08 p.m.

Nonstop1h 55m

C$ 183

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 30/9

6:30 p.m.-8:07 p.m.

Nonstop2h 37m

Chicago O'Hare Intl

Wed 1/10

8:00 a.m.-11:16 a.m.

Nonstop2h 16m

C$ 184

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 8/10

2:06 p.m.-3:58 p.m.

Nonstop2h 52m

Chicago O'Hare Intl

Wed 15/10

7:00 a.m.-10:08 a.m.

Nonstop2h 08m

C$ 186

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 8/10

5:55 a.m.-9:33 p.m.

1 stop16h 38m

Chicago O'Hare Intl

Wed 15/10

6:58 p.m.-9:00 a.m.

1 stop13h 02m

C$ 190

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 1/10

6:00 a.m.-12:45 p.m.

1 stop7h 45m

Chicago O'Hare Intl

Wed 1/10

3:10 p.m.-9:00 p.m.

1 stop4h 50m

C$ 193

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 8/10

4:28 p.m.-6:05 p.m.

Nonstop2h 37m

Chicago O'Hare Intl

Fri 17/10

6:30 p.m.-9:54 p.m.

Nonstop2h 24m

C$ 195

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 5/11

6:05 a.m.-12:15 p.m.

1 stop7h 10m

Chicago O'Hare Intl

Wed 5/11

1:45 p.m.-11:15 p.m.

1 stop8h 30m

C$ 200

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 25/10

2:55 p.m.-4:34 p.m.

Nonstop2h 39m

Chicago O'Hare Intl

Mon 27/10

6:00 a.m.-9:07 a.m.

Nonstop2h 07m

C$ 205

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 28/10

5:40 p.m.-7:25 p.m.

Nonstop2h 45m

Chicago O'Hare Intl

Tue 4/11

7:00 a.m.-10:11 a.m.

Nonstop2h 11m

C$ 218

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 another great option to travel to Chicago, with average flight prices from New York averaging around C$ 256.

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 Saturday when prices can be found for as low as C$ 370. 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 Sunday because tickets tend to average around C$ 587. 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$ 368. 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$ 548 per ticket.

What is the cheapest New York to Chicago flight route?

Fly from New York LaGuardia 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$ 348 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$ 278 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?

You could potentially save up to 34% on your flight if you consider stops on a New York to Chicago flight.

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

As of September 2025, prices for New York to Chicago flights are approximately 41% 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$ 400

Fastest flight time

2h 25m

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$ 400. The best round-trip flight deal from New York to Chicago found on momondo in the last 72 hours is C$ 242.
The fastest flight from New York to Chicago takes 2h 25m
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?

    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 27m. 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$ 181. 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 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?

    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