Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from New York to Chicago from £44

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 30/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Deals available from 900+ travel sites.

'This year, momondo is the #1 place for airfares on the internet.'
Voted winner of Europe's Best Travel App 2023
Save money when you book flights with momondo
Big names, great deals
Big names, great deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customise your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from New York to Chicago

Cheap return flights

These are some of the best return flight deals from New York to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from New York to Chicago.

Cheap last-minute flights

Planning a quick getaway from New York to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without stopovers.

Cheap bus & train deals from New York to Chicago

Find recent round-trip train or bus tickets from New York to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
08:35 - 10:07LGA-ORD
2h 32mdirect
16:45 - 20:00ORD-LGA
2h 15mdirect
£66Spirit Airlines
Find Deal
Wed, 8 Jan - Wed, 8 Jan
08:35 - 10:07LGA-ORD
2h 32mdirect
20:14 - 07:35ORD-LGA
10h 21m1 stop
£93Spirit Airlines
Find Deal
Wed, 8 Jan - Wed, 8 Jan
15:25 - 17:01EWR-ORD
2h 36mdirect
09:10 - 12:28ORD-EWR
2h 18mdirect
£113United Airlines
Find Deal
Wed, 15 Jan - Sun, 19 Jan
08:00 - 09:55JFK-ORD
2h 55mdirect
07:05 - 10:31ORD-JFK
2h 26mdirect
£114Delta
Find Deal
Mon, 13 Jan - Thu, 16 Jan
20:45 - 22:36LGA-ORD
2h 51mdirect
08:35 - 12:00ORD-LGA
2h 25mdirect
£114Delta
Find Deal
Mon, 13 Jan - Thu, 16 Jan
15:25 - 17:01EWR-ORD
2h 36mdirect
15:15 - 18:31ORD-EWR
2h 16mdirect
£116United Airlines
Find Deal
Wed, 8 Jan - Wed, 15 Jan
07:00 - 08:46EWR-ORD
2h 46mdirect
18:20 - 21:32ORD-EWR
2h 12mdirect
£117American Airlines
Find Deal
Wed, 8 Jan - Wed, 8 Jan
14:55 - 16:45JFK-ORD
2h 50mdirect
11:44 - 14:59ORD-JFK
2h 15mdirect
£120JetBlue
Find Deal
Sat, 22 Feb - Tue, 4 Mar
09:15 - 10:59JFK-ORD
2h 44mdirect
11:35 - 14:50ORD-JFK
2h 15mdirect
£123JetBlue
Find Deal
Thu, 27 Feb - Sat, 1 Mar
07:00 - 08:46EWR-ORD
2h 46mdirect
18:20 - 21:32ORD-EWR
2h 12mdirect
£159American Airlines
Find Deal
Wed, 22 Jan - Sat, 25 Jan
11:00 - 22:27JFK-ORD
12h 27m1 stop
£44Frontier
Find Deal
Thu, 30 Jan
10:59 - 22:27LGA-ORD
12h 28m1 stop
£47Frontier
Find Deal
Thu, 30 Jan
07:59 - 09:34EWR-ORD
2h 35mdirect
£51Spirit Airlines
Find Deal
Thu, 30 Jan
20:45 - 22:36LGA-ORD
2h 51mdirect
£58Delta
Find Deal
Mon, 13 Jan
13:07 - 14:48EWR-ORD
2h 41mdirect
£58United Airlines
Find Deal
Tue, 21 Jan
20:45 - 22:36LGA-ORD
2h 51mdirect
£58Delta
Find Deal
Fri, 31 Jan
10:03 - 11:46EWR-ORD
2h 43mdirect
£62United Airlines
Find Deal
Tue, 15 Apr
08:38 - 11:25LGA-ORD
3h 47m1 stop
£103American Airlines
Find Deal
Wed, 1 Jan
06:16 - 11:03JFK-ORD
5h 47m1 stop
£106American Airlines
Find Deal
Wed, 1 Jan
05:45 - 17:11EWR-ORD
12h 26m2 stops
£112Spirit Airlines
Find Deal
Thu, 30 Jan
18:29 - 20:13EWR-ORD
2h 44mdirect
06:00 - 09:11ORD-EWR
2h 11mdirect
£300United Airlines
Find Deal
Mon, 23 Dec - Tue, 14 Jan
20:10 - 21:52EWR-ORD
2h 42mdirect
21:45 - 00:57ORD-EWR
2h 12mdirect
£308United Airlines
Find Deal
Mon, 23 Dec - Thu, 2 Jan
21:28 - 23:00EWR-ORD
2h 32mdirect
21:45 - 00:57ORD-EWR
2h 12mdirect
£309United Airlines
Find Deal
Mon, 23 Dec - Thu, 2 Jan
19:29 - 21:30JFK-ORD
3h 01mdirect
18:30 - 22:06ORD-JFK
2h 36mdirect
£337Delta
Find Deal
Mon, 23 Dec - Wed, 15 Jan
07:30 - 09:26JFK-ORD
2h 56mdirect
07:00 - 12:50ORD-JFK
4h 50m1 stop
£360JetBlue
Find Deal
Mon, 23 Dec - Tue, 14 Jan
21:05 - 22:43LGA-ORD
2h 38mdirect
20:14 - 07:30ORD-LGA
10h 16m1 stop
£379Spirit Airlines
Find Deal
Mon, 23 Dec - Sat, 28 Dec
07:30 - 09:26JFK-ORD
2h 56mdirect
10:11 - 13:29ORD-JFK
2h 18mdirect
£388JetBlue
Find Deal
Sun, 22 Dec - Sun, 5 Jan
19:29 - 21:30JFK-ORD
3h 01mdirect
18:20 - 22:01ORD-JFK
2h 41mdirect
£395Delta
Find Deal
Mon, 23 Dec - Fri, 3 Jan
14:52 - 21:53EWR-ORD
8h 01m1 stop
12:09 - 22:34ORD-EWR
9h 25m1 stop
£405Spirit Airlines
Find Deal
Mon, 23 Dec - Thu, 26 Dec
12:00 - 15:30JFK-ORD
4h 30m1 stop
16:28 - 19:40ORD-JFK
2h 12mdirect
£614American Airlines
Find Deal
Mon, 23 Dec - Fri, 27 Dec
08:35 - 10:07LGA-ORD
2h 32mdirect
16:45 - 20:00ORD-LGA
2h 15mdirect
£61Spirit Airlines
Find Deal
Wed, 8 Jan - Wed, 8 Jan
08:35 - 10:07LGA-ORD
2h 32mdirect
16:45 - 20:00ORD-LGA
2h 15mdirect
£66Spirit Airlines
Find Deal
Wed, 8 Jan - Wed, 8 Jan
15:25 - 17:01EWR-ORD
2h 36mdirect
09:10 - 12:28ORD-EWR
2h 18mdirect
£113United Airlines
Find Deal
Wed, 15 Jan - Sun, 19 Jan
08:00 - 09:55JFK-ORD
2h 55mdirect
07:05 - 10:31ORD-JFK
2h 26mdirect
£114Delta
Find Deal
Mon, 13 Jan - Thu, 16 Jan
20:45 - 22:36LGA-ORD
2h 51mdirect
08:35 - 12:00ORD-LGA
2h 25mdirect
£114Delta
Find Deal
Mon, 13 Jan - Thu, 16 Jan
15:25 - 17:01EWR-ORD
2h 36mdirect
15:15 - 18:31ORD-EWR
2h 16mdirect
£116United Airlines
Find Deal
Wed, 8 Jan - Wed, 15 Jan
07:00 - 08:46EWR-ORD
2h 46mdirect
18:20 - 21:32ORD-EWR
2h 12mdirect
£117American Airlines
Find Deal
Wed, 8 Jan - Wed, 8 Jan
14:55 - 16:45JFK-ORD
2h 50mdirect
11:44 - 14:59ORD-JFK
2h 15mdirect
£120JetBlue
Find Deal
Sat, 22 Feb - Tue, 4 Mar
09:15 - 10:59JFK-ORD
2h 44mdirect
11:35 - 14:50ORD-JFK
2h 15mdirect
£123JetBlue
Find Deal
Thu, 27 Feb - Sat, 1 Mar
07:00 - 08:46EWR-ORD
2h 46mdirect
18:20 - 21:32ORD-EWR
2h 12mdirect
£159American Airlines
Find Deal
Wed, 22 Jan - Sat, 25 Jan

American Airlines flights from New York to Chicago

Our best American Airlines deals on New York to Chicago flight tickets
American Airlines
8 Jan
EWR07:00Newark
2h 46m
ORD08:46Chicago O'Hare Intl
8 Jan
ORD18:20Chicago O'Hare Intl
2h 12m
EWR21:32Newark
American Airlines
22 Jan
EWR07:00Newark
2h 46m
ORD08:46Chicago O'Hare Intl
25 Jan
ORD18:20Chicago O'Hare Intl
2h 12m
EWR21:32Newark
American Airlines
8 Jan
JFK09:00New York John F Kennedy Intl
2h 47m
ORD10:47Chicago O'Hare Intl
8 Jan
ORD16:22Chicago O'Hare Intl
2h 18m
JFK19:40New York John F Kennedy Intl

JetBlue flights from New York to Chicago

Our best JetBlue deals on New York to Chicago flight tickets
JetBlue
22 Feb
JFK14:55New York John F Kennedy Intl
2h 50m
ORD16:45Chicago O'Hare Intl
4 Mar
ORD11:44Chicago O'Hare Intl
2h 15m
JFK14:59New York John F Kennedy Intl
JetBlue
27 Feb
JFK09:15New York John F Kennedy Intl
2h 44m
ORD10:59Chicago O'Hare Intl
1 Mar
ORD11:35Chicago O'Hare Intl
2h 15m
JFK14:50New York John F Kennedy Intl
JetBlue
9 Jan
JFK15:28New York John F Kennedy Intl
2h 50m
ORD17:18Chicago O'Hare Intl
23 Jan
ORD17:05Chicago O'Hare Intl
2h 26m
JFK20:31New York John F Kennedy Intl

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 £139, 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 £155.

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 £90. 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 Monday, with ticket prices averaging around £221.

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

Flying to Chicago from New York in the evening is the least expensive time of day to depart. momondo users have found prices as low as £107 when looking at flights departing in the evening. Flights at midday are often more expensive, with an average ticket price of £199.

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?

The ideal time to book your flight to Chicago is 33 days in advance, when prices tend to average £193. However, in the past 72 hours, people saw flights from New York for as low as £104.

What cabin class options are available on New York to Chicago flights?

There are 3 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 13% 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 December 2024, prices for New York to Chicago flights are approximately 2% 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

£44

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 £44. The best return flight deal from New York to Chicago found on momondo in the last 72 hours is £66.
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 £134 to Chicago or a bus from New York to Chicago starting at £131 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 £54Free CancellationRating
7.4
3,274 reviews
Search JetBlue flights
American AirlinesPriceFrom £100Free 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 6 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 60 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.


Choose the best way to get from New York to Chicago

Buses

21h 55m
£81 one-way£131 return
Direct · from £131

Distance to city centre

F990.8 mi

Find Buses

New York to Chicago Buses

Trains

19h 32m
£67 one-way£134 return
Direct · from £134

Distance to city centre

ZUN0.7 mi

Find Trains

New York to Chicago Trains

Flights

2h 31m
£44 one-way£66 return
Direct · from £661 stop · from £93

Distance to city centre

ORD15.9 mi

An easier way to manage your Chicago trip

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

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Tue 24/12
Tue 31/12
Email me momondo's favourite deals

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