Cheap flights from New York to Chicago from $73

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 5/27. 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

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Spirit Airlines Logo
8:47 pm - 10:25 pm
LGA
-
ORD
2h 38mnonstop
Spirit Airlines Logo
6:10 am - 7:52 pm
ORD
-
LGA
12h 42m
1 stop
$151Spirit Airlines
Mon, Jun 1 - Thu, Jun 11
Spirit Airlines Logo
4:59 pm - 11:15 pm
LGA
-
ORD
7h 16m
1 stop
Spirit Airlines Logo
1:49 pm - 5:00 pm
ORD
-
LGA
2h 11mnonstop
$152Spirit Airlines
Thu, May 28 - Wed, Jun 3
Frontier Logo
10:00 pm - 7:55 am
LGA
-
ORD
10h 55m
1 stop
Frontier Logo
5:11 pm - 4:11 pm
ORD
-
LGA
22h 00m
1 stop
$160Frontier
Tue, May 26 - Fri, May 29
Frontier Logo
10:00 pm - 7:55 am
LGA
-
ORD
10h 55m
1 stop
Frontier Logo
1:50 pm - 11:14 pm
ORD
-
LGA
8h 24m
1 stop
$161Frontier
Tue, May 26 - Fri, May 29
JetBlue Logo
7:00 am - 8:45 am
JFK
-
ORD
2h 45mnonstop
JetBlue Logo
6:00 am - 9:20 am
ORD
-
JFK
2h 20mnonstop
$161JetBlue
Mon, Jun 15 - Fri, Jun 19
JetBlue Logo
7:00 am - 8:45 am
JFK
-
ORD
2h 45mnonstop
JetBlue Logo
6:00 am - 9:20 am
ORD
-
JFK
2h 20mnonstop
$168JetBlue
Sat, Jun 27 - Sun, Jun 28
Southwest Logo
6:00 am - 7:20 am
LGA
-
MDW
2h 20mnonstop
Southwest Logo
5:20 am - 8:20 am
MDW
-
LGA
2h 00mnonstop
$177Southwest
Fri, Jul 3 - Sun, Jul 5
Southwest Logo
10:55 am - 12:20 pm
LGA
-
MDW
2h 25mnonstop
Southwest Logo
6:40 pm - 9:45 pm
MDW
-
LGA
2h 05mnonstop
$182Southwest
Wed, May 27 - Sat, Jun 27
Delta Logo
6:55 am - 6:33 pm
JFK
-
MDW
12h 38m
1 stop
Delta Logo
9:22 am - 9:50 pm
MDW
-
JFK
11h 28m
1 stop
$283Delta
Tue, May 26 - Tue, Jun 2
Delta Logo
7:15 am - 1:19 pm
JFK
-
MDW
7h 04m
1 stop
Delta Logo
9:22 am - 9:50 pm
MDW
-
JFK
11h 28m
1 stop
$290Delta
Sun, May 24 - Tue, Jun 2

JetBlue flights from New York to Chicago

Our best JetBlue deals on New York to Chicago flight tickets
JetBlue
Jun 15
JFK7:00 amNew York John F Kennedy Intl
2h 45m
ORD8:45 amChicago O'Hare Intl
Jun 19
ORD6:00 amChicago O'Hare Intl
2h 20m
JFK9:20 amNew York John F Kennedy Intl
$161
JetBlue
Jun 27
JFK7:00 amNew York John F Kennedy Intl
2h 45m
ORD8:45 amChicago O'Hare Intl
Jun 28
ORD6:00 amChicago O'Hare Intl
2h 20m
JFK9:20 amNew York John F Kennedy Intl
$168
JetBlue
Jun 13
JFK7:00 amNew York John F Kennedy Intl
2h 45m
ORD8:45 amChicago O'Hare Intl
Jun 16
ORD6:27 pmChicago O'Hare Intl
2h 46m
JFK10:13 pmNew York John F Kennedy Intl
$172

Frontier flights from New York to Chicago

Our best Frontier deals on New York to Chicago flight tickets
Frontier
May 26
LGA10:00 pmNew York LaGuardia
10h 55m
1 stop
ORD7:55 amChicago O'Hare Intl
May 29
ORD5:11 pmChicago O'Hare Intl
22h 00m
1 stop
LGA4:11 pmNew York LaGuardia
$160
Frontier
May 26
LGA10:00 pmNew York LaGuardia
10h 55m
1 stop
ORD7:55 amChicago O'Hare Intl
May 29
ORD1:50 pmChicago O'Hare Intl
8h 24m
1 stop
LGA11:14 pmNew York LaGuardia
$161
Frontier
May 25
EWR10:29 pmNewark
10h 26m
1 stop
ORD7:55 amChicago O'Hare Intl
Jun 3
ORD1:29 pmChicago O'Hare Intl
7h 00m
1 stop
EWR9:29 pmNewark
$167

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 832,500 searches. Data last updated May 5, 2026.
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

Cheapest round-trip

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 6/1

8:47 pm-10:25 pm

Nonstop2h 38m

Chicago O'Hare Intl

Thu 6/11

6:10 am-7:52 pm

1 stop12h 42m

$151

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 5/28

4:59 pm-11:15 pm

1 stop7h 16m

Chicago O'Hare Intl

Wed 6/3

1:49 pm-5:00 pm

Nonstop2h 11m

$152

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 5/26

10:00 pm-7:55 am

1 stop10h 55m

Chicago O'Hare Intl

Fri 5/29

5:11 pm-4:11 pm

1 stop22h 00m

$160

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 5/26

10:00 pm-7:55 am

1 stop10h 55m

Chicago O'Hare Intl

Fri 5/29

1:50 pm-11:14 pm

1 stop8h 24m

$161

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 6/15

7:00 am-8:45 am

Nonstop2h 45m

Chicago O'Hare Intl

Fri 6/19

6:00 am-9:20 am

Nonstop2h 20m

$161

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 6/27

7:00 am-8:45 am

Nonstop2h 45m

Chicago O'Hare Intl

Sun 6/28

6:00 am-9:20 am

Nonstop2h 20m

$168
Quickest round-trip

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 7/3

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Sun 7/5

5:20 am-8:20 am

Nonstop2h 00m

$177

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 5/27

10:55 am-12:20 pm

Nonstop2h 25m

Chicago Midway

Sat 6/27

6:40 pm-9:45 pm

Nonstop2h 05m

$182

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 5/26

6:55 am-6:33 pm

1 stop12h 38m

Chicago Midway

Tue 6/2

9:22 am-9:50 pm

1 stop11h 28m

$283

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sun 5/24

7:15 am-1:19 pm

1 stop7h 04m

Chicago Midway

Tue 6/2

9:22 am-9:50 pm

1 stop11h 28m

$290

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 typical price of a round-trip flight between New York and Chicago?

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from New York, with most prices found around $199. If you’re not able to fly to Chicago in January, then November is your next best option. Flight prices from New York to Chicago during November average around $217.

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 $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 $367.

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 $273. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $361.

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 from New York 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 $239 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 $162 on momondo.

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 May 2026, prices for New York to Chicago flights are approximately 41% more expensive 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

$103

Fastest flight time

2h 15m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from New York in the past 72 hours is $103. The best round-trip flight deal from New York to Chicago found on momondo in the last 72 hours is $88.
The fastest flight from New York to Chicago takes 2h 15m
Direct flights go from New York to Chicago every day.
There are 3 airports in Chicago. From New York there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Frequently asked questions about flying from New York to Chicago

  • 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 12m 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 $151. A train from New York to Chicago is more expensive than a flight, with prices starting at $218. A bus from New York to Chicago is also an option, with an average price of $185.

  • 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
FrontierPriceFrom $47Free CancellationRating
5.6
2,966 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $61Free CancellationRating
6.3
8,634 reviews
Search Spirit Airlines flights
DeltaPriceFrom $74Free CancellationRating
7.9
8,459 reviews
Search Delta flights
JetBluePriceFrom $88Free CancellationRating
7.1
2,977 reviews
Search JetBlue flights
United AirlinesPriceFrom $139Free CancellationRating
7.4
9,683 reviews
Search United Airlines flights
American AirlinesPriceFrom $157Free CancellationRating
7.1
11,668 reviews
Search American Airlines flights
SouthwestPriceFrom $164Free CancellationRating
7.9
4,305 reviews
Search Southwest flights
  • Delta Flights From New York to Chicago

    Delta flight deals from New York to Chicago start from $74 round-trip. Over the 44 Delta flights for this route in a normal week, average airfare is usually $328 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 (7.9/10, 4,306 ratings). Southwest flies from New York to Chicago around 34 times per week, with deals starting from $164 round-trip and rising to an average price of around $302.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
Porter
Griffith
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.

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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 6/4
Thu 6/11

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