Cheap flights from New York to Chicago from £29

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 3/12. 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 return flights

Spirit Airlines Logo
15:13 - 16:51LGA-ORD
2h 38mdirect
Spirit Airlines Logo
11:13 - 14:18ORD-LGA
2h 05mdirect
£67Spirit Airlines
Find Deal
Tue, 9 Sep - Wed, 10 Sep
Spirit Airlines Logo
15:13 - 16:51LGA-ORD
2h 38mdirect
Spirit Airlines Logo
11:13 - 14:18ORD-LGA
2h 05mdirect
£76Spirit Airlines
Find Deal
Thu, 30 Oct - Sun, 2 Nov
Delta Logo
19:29 - 21:47JFK-ORD
3h 18mdirect
Delta Logo
07:00 - 10:23ORD-JFK
2h 23mdirect
£106Delta
Find Deal
Wed, 3 Sep - Wed, 10 Sep
Delta Logo
16:05 - 18:02LGA-ORD
2h 57mdirect
Delta Logo
20:10 - 23:40ORD-LGA
2h 30mdirect
£106Delta
Find Deal
Wed, 3 Sep - Tue, 9 Sep
United Airlines Logo
06:00 - 07:38EWR-ORD
2h 38mdirect
United Airlines Logo
08:45 - 11:59ORD-EWR
2h 14mdirect
£110United Airlines
Find Deal
Wed, 10 Sep - Sat, 13 Sep
American Airlines Logo
19:22 - 21:01EWR-ORD
2h 39mdirect
American Airlines Logo
15:42 - 18:59ORD-EWR
2h 17mdirect
£111American Airlines
Find Deal
Tue, 9 Sep - Wed, 10 Sep
United Airlines Logo
21:44 - 23:25EWR-ORD
2h 41mdirect
United Airlines Logo
07:10 - 10:28ORD-EWR
2h 18mdirect
£114United Airlines
Find Deal
Wed, 27 Aug - Wed, 3 Sep
Southwest Logo
09:40 - 16:25LGA-ORD
7h 45m1 stop
Southwest Logo
14:55 - 22:50ORD-LGA
6h 55m1 stop
£141Southwest
Find Deal
Thu, 4 Sep - Fri, 5 Sep
Southwest Logo
08:15 - 22:00LGA-ORD
14h 45m2 stops
Southwest Logo
14:55 - 22:50ORD-LGA
6h 55m1 stop
£149Southwest
Find Deal
Sat, 6 Sep - Mon, 8 Sep
American Airlines Logo
07:30 - 09:10EWR-ORD
2h 40mdirect
American Airlines Logo
07:05 - 10:19ORD-EWR
2h 14mdirect
£152American Airlines
Find Deal
Thu, 25 Sep - Sun, 28 Sep

JetBlue flights from New York to Chicago

Our best JetBlue deals on New York to Chicago flight tickets
JetBlue
4 Nov
JFK20:00New York John F Kennedy Intl
2h 48m
ORD21:48Chicago O'Hare Intl
8 Nov
ORD06:45Chicago O'Hare Intl
2h 14m
JFK09:59New York John F Kennedy Intl
JetBlue
30 Aug
JFK20:30New York John F Kennedy Intl
2h 58m
ORD22:28Chicago O'Hare Intl
3 Sept
ORD06:10Chicago O'Hare Intl
2h 19m
JFK09:29New York John F Kennedy Intl
JetBlue
10 Sept
JFK10:30New York John F Kennedy Intl
2h 40m
ORD12:10Chicago O'Hare Intl
17 Sept
ORD13:37Chicago O'Hare Intl
2h 22m
JFK16:59New York John F Kennedy Intl

Spirit Airlines flights from New York to Chicago

Our best Spirit Airlines deals on New York to Chicago flight tickets
Spirit Airlines
9 Sept
LGA15:13New York LaGuardia
2h 38m
ORD16:51Chicago O'Hare Intl
10 Sept
ORD11:13Chicago O'Hare Intl
2h 05m
LGA14:18New York LaGuardia
Spirit Airlines
30 Oct
LGA15:13New York LaGuardia
2h 38m
ORD16:51Chicago O'Hare Intl
2 Nov
ORD11:13Chicago O'Hare Intl
2h 05m
LGA14:18New York LaGuardia
Spirit Airlines
9 Sept
LGA15:13New York LaGuardia
2h 38m
ORD16:51Chicago O'Hare Intl
10 Sept
ORD06:30Chicago O'Hare Intl
12h 59m
1 stop
LGA20:29New York LaGuardia

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 279,928 searches. Data last updated 30 July 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

Tue 9/9

15:13-16:51

Nonstop2h 38m

Chicago O'Hare Intl

Wed 10/9

11:13-14:18

Nonstop2h 05m

£67

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 30/10

15:13-16:51

Nonstop2h 38m

Chicago O'Hare Intl

Sun 2/11

11:13-14:18

Nonstop2h 05m

£76

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 3/9

19:29-21:47

Nonstop3h 18m

Chicago O'Hare Intl

Wed 10/9

07:00-10:23

Nonstop2h 23m

£106

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 3/9

16:05-18:02

Nonstop2h 57m

Chicago O'Hare Intl

Tue 9/9

20:10-23:40

Nonstop2h 30m

£106

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 10/9

06:00-07:38

Nonstop2h 38m

Chicago O'Hare Intl

Sat 13/9

08:45-11:59

Nonstop2h 14m

£110

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 9/9

19:22-21:01

Nonstop2h 39m

Chicago O'Hare Intl

Wed 10/9

15:42-18:59

Nonstop2h 17m

£111

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 27/8

21:44-23:25

Nonstop2h 41m

Chicago O'Hare Intl

Wed 3/9

07:10-10:28

Nonstop2h 18m

£114

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 4/9

09:40-16:25

1 stop7h 45m

Chicago O'Hare Intl

Fri 5/9

14:55-22:50

1 stop6h 55m

£141

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 6/9

08:15-22:00

2 stops14h 45m

Chicago O'Hare Intl

Mon 8/9

14:55-22:50

1 stop6h 55m

£149

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 25/9

07:30-09:10

Nonstop2h 40m

Chicago O'Hare Intl

Sun 28/9

07:05-10:19

Nonstop2h 14m

£152

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?

The cheapest month to fly to Chicago from New York is in September. Flight prices, which tend to average around £133, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Chicago from New York during January instead. Flights to Chicago in January, while not as cheap as those in September, still average around £135.

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 Tuesday when prices can be found for as low as £121. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Thursday, with ticket prices averaging around £238.

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

Flying to Chicago from New York in the morning is the least expensive time of day to depart. momondo users have found prices as low as £182 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £290.

What is the cheapest New York to Chicago flight route?

Fly from Newark 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 £183 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 £142 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 July 2025, prices for New York to Chicago flights are approximately 21% 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

Best price found

£29

Fastest flight time

2h 24m

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 £29. The best return flight deal from New York to Chicago found on momondo in the last 72 hours is £67.
The fastest flight from New York to Chicago takes 2h 24m
Direct flights go from New York to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

  • 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 24m. 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?

    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 £135 to Chicago or a bus from New York to Chicago starting at £117 if that is your preferred method of transportation.

  • How far is New York to Chicago by plane?

    New York and Chicago are 710.8 mi apart from one another. Typically, this will take 2h 24m 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 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?


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
JetBluePriceFrom £51Free CancellationRating
7.2
2,913 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom £85Free CancellationRating
6.3
8,044 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom £95Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
  • JetBlue Flights From New York to Chicago

    JetBlue flight deals from New York to Chicago start from £68 round-trip. Over the 2 JetBlue flights for this route in a normal week, average airfare is usually £136 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From New York to Chicago

    American Airlines (7.2/10 from 10,000 reviews) operates around 43 flights from New York to Chicago in any given week. The average American Airlines airfare for this route is around £217, with deals from around £127 rare but found on momondo. Referenced prices are for round-trip New York to Chicago flight searches in the last 72 hours.


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?

momondo helps you find the best flight between New York and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from New York to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from New York. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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1 adult
Mon 4/8
Mon 11/8

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