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Cheap flights from New York to Chicago from $31

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 5/28. 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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0 bags

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Find the cheapest flights from New York to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from New York to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.
Spirit Airlines Logo
5:55 am - 7:27 amEWR-ORD
2h 32mnonstop
Spirit Airlines Logo
9:08 pm - 12:29 amORD-EWR
2h 21mnonstop
$75Spirit Airlines
Find Deal
Wed, May 28 - Sat, May 31
Spirit Airlines Logo
5:55 am - 7:27 amEWR-ORD
2h 32mnonstop
Spirit Airlines Logo
9:08 pm - 12:29 amORD-EWR
2h 21mnonstop
$78Spirit Airlines
Find Deal
Wed, May 28 - Sat, May 31
United Airlines Logo
10:25 am - 12:05 pmLGA-ORD
2h 40mnonstop
United Airlines Logo
8:00 pm - 11:18 pmORD-LGA
2h 18mnonstop
$137United Airlines
Find Deal
Tue, May 13 - Tue, May 13
Southwest Logo
6:10 am - 7:30 amLGA-MDW
2h 20mnonstop
Southwest Logo
8:20 pm - 11:25 pmMDW-LGA
2h 05mnonstop
$137Southwest
Find Deal
Tue, May 13 - Wed, May 14
American Airlines Logo
9:00 am - 11:09 amJFK-ORD
3h 09mnonstop
American Airlines Logo
4:44 pm - 8:00 pmORD-JFK
2h 16mnonstop
$138American Airlines
Find Deal
Tue, May 13 - Wed, May 14
United Airlines Logo
8:30 pm - 10:12 pmEWR-ORD
2h 42mnonstop
United Airlines Logo
6:00 am - 9:13 amORD-EWR
2h 13mnonstop
$147United Airlines
Find Deal
Sat, May 24 - Sun, May 25
Delta Logo
11:00 am - 12:48 pmJFK-ORD
2h 48mnonstop
Delta Logo
10:31 am - 1:50 pmORD-JFK
2h 19mnonstop
$147Delta
Find Deal
Tue, May 13 - Wed, May 21
Delta Logo
7:30 pm - 9:33 pmJFK-ORD
3h 03mnonstop
Delta Logo
6:18 pm - 10:00 pmORD-JFK
2h 42mnonstop
$157Delta
Find Deal
Wed, May 28 - Sat, May 31
Southwest Logo
9:45 pm - 11:00 pmLGA-MDW
2h 15mnonstop
Southwest Logo
8:20 pm - 11:25 pmMDW-LGA
2h 05mnonstop
$157Southwest
Find Deal
Wed, May 28 - Wed, Jun 4
American Airlines Logo
5:45 am - 7:27 amLGA-ORD
2h 42mnonstop
American Airlines Logo
5:10 pm - 8:14 pmORD-LGA
2h 04mnonstop
$178American Airlines
Find Deal
Sat, Jun 21 - Wed, Jun 25

Spirit Airlines flights from New York to Chicago

Our best Spirit Airlines deals on New York to Chicago flight tickets
Spirit Airlines
May 28
EWR5:55 amNewark
2h 32m
ORD7:27 amChicago O'Hare Intl
May 31
ORD9:08 pmChicago O'Hare Intl
2h 21m
EWR12:29 amNewark
Spirit Airlines
May 28
EWR5:55 amNewark
2h 32m
ORD7:27 amChicago O'Hare Intl
May 31
ORD9:08 pmChicago O'Hare Intl
2h 21m
EWR12:29 amNewark
Spirit Airlines
May 31
EWR5:55 amNewark
2h 32m
ORD7:27 amChicago O'Hare Intl
Jun 4
ORD9:08 pmChicago O'Hare Intl
2h 21m
EWR12:29 amNewark

American Airlines flights from New York to Chicago

Our best American Airlines deals on New York to Chicago flight tickets
American Airlines
May 13
JFK9:00 amNew York John F Kennedy Intl
3h 09m
ORD11:09 amChicago O'Hare Intl
May 14
ORD4:44 pmChicago O'Hare Intl
2h 16m
JFK8:00 pmNew York John F Kennedy Intl
American Airlines
Jun 21
LGA5:45 amNew York LaGuardia
2h 42m
ORD7:27 amChicago O'Hare Intl
Jun 25
ORD5:10 pmChicago O'Hare Intl
2h 04m
LGA8:14 pmNew York LaGuardia
American Airlines
May 27
JFK9:00 amNew York John F Kennedy Intl
3h 09m
ORD11:09 amChicago O'Hare Intl
May 29
ORD4:44 pmChicago O'Hare Intl
2h 16m
JFK8:00 pmNew 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 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 $176. 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 $179.

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 $291. 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 $376.

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 $236. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $341.

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 5 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $243 when searching 5 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 $202 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.

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

As of April 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

$31

Fastest flight time

2h 15m

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 $31. The best round-trip flight deal from New York to Chicago found on momondo in the last 72 hours is $75.
The fastest flight from New York to Chicago takes 2h 15m
Direct flights go from New York to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • 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 40m 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 $75. A train from New York to Chicago is more expensive than a flight, with prices starting at $180. A bus from New York to Chicago is also an option, with an average price of $155.

  • How far is New York to Chicago by plane?

    Chicago is 710.8 mi away from New York. Typically, this will take 2h 15m 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 $37Free CancellationRating
6.3
7,961 reviews
Search Spirit Airlines flights
DeltaPriceFrom $68Free CancellationRating
8.0
7,929 reviews
Search Delta flights
JetBluePriceFrom $85Free CancellationRating
7.3
2,922 reviews
Search JetBlue flights
FrontierPriceFrom $98Free CancellationRating
5.9
3,287 reviews
Search Frontier flights
American AirlinesPriceFrom $140Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $148Free CancellationRating
7.4
8,696 reviews
Search United Airlines flights
SouthwestPriceFrom $148Free CancellationRating
8.0
4,295 reviews
Search Southwest flights
  • Delta Flights From New York to Chicago

    Delta flight deals from New York to Chicago start from $68 round-trip. Over the 59 Delta flights for this route in a normal week, average airfare is usually $330 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, 4,295 ratings). Southwest flies from New York to Chicago around 37 times per week, with deals starting from $148 round-trip and rising to an average price of around $248.


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
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
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.


Choose the best way to get from New York to Chicago

Buses

19h 55m
$74 one-way$155 round-trip
Nonstop · from $1551 stop · from $74

Distance to downtown

G1N10.6 mi

Find Buses

New York to Chicago Buses

Trains

19h 32m
$90 one-way$180 round-trip
Nonstop · from $180

Distance to downtown

ZUN0.7 mi

Flights

2h 15m
$31 one-way$75 round-trip
Nonstop · from $751 stop · from $95

Distance to downtown

ORD15.9 mi

An easier way to manage your Chicago trip

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1 adult
From?
To?
Sun 5/4
Sun 5/11

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