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Cheap flights from New York to Chicago from €38

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Spirit Airlines flights from New York to Chicago

Our best Spirit Airlines deals on New York to Chicago flight tickets
Spirit Airlines
13 Sept
LGA15:12New York LaGuardia
2h 38m
ORD16:50Chicago O'Hare Intl
20 Sept
ORD16:35Chicago O'Hare Intl
2h 06m
LGA19:41New York LaGuardia
€42
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Spirit Airlines
6 Sept
LGA15:12New York LaGuardia
2h 38m
ORD16:50Chicago O'Hare Intl
16 Sept
ORD11:13Chicago O'Hare Intl
2h 05m
LGA14:18New York LaGuardia
€43
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Spirit Airlines
13 Sept
LGA20:36New York LaGuardia
2h 35m
ORD22:11Chicago O'Hare Intl
20 Sept
ORD16:35Chicago O'Hare Intl
2h 06m
LGA19:41New York LaGuardia
€53
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American Airlines flights from New York to Chicago

Our best American Airlines deals on New York to Chicago flight tickets
American Airlines
6 Sept
EWR14:27Newark
2h 37m
ORD16:04Chicago O'Hare Intl
16 Sept
ORD07:05Chicago O'Hare Intl
2h 14m
EWR10:19Newark
€150
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American Airlines
13 Sept
EWR07:30Newark
2h 40m
ORD09:10Chicago O'Hare Intl
15 Sept
ORD20:41Chicago O'Hare Intl
2h 18m
EWR23:59Newark
€161
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American Airlines
6 Sept
EWR07:30Newark
2h 40m
ORD09:10Chicago O'Hare Intl
8 Sept
ORD20:41Chicago O'Hare Intl
2h 18m
EWR23:59Newark
€162
Find similar

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 cheapest month to fly to Chicago from New York is in September. Flight prices, which tend to average around €154, are often lower during this time because this is during the off-season. If you don’t want to visit Chicago in September, then you should wait until January to fly from New York, when ticket prices are also cheap, with an average price of €155.

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

On average, the least expensive day to fly to Chicago from New York is on a Friday. momondo users have found tickets for Friday departures for as low as €192. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Tuesday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Tuesday is €527.

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

In the evening is the cheapest time of day to fly from New York to Chicago when you can find flight prices for as low as €106. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying at midday when prices are €527 on average. Flights to Chicago from New York at midday are generally more expensive because this time of day is more convenient for travellers’ schedules.

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 €213 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 €169 on momondo.

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

There are 1 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 August 2025, prices for New York to Chicago flights are approximately 17% 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

  • Is flying the fastest way to get from New York to Chicago?

    We’ve found that taking a flight from New York to Chicago with {10} is more time-efficient when based simply on travel duration. A train from New York to Chicago or a bus from New York to Chicago can take you longer than a 2h 23m flight.

  • Is flying the cheapest way to get from New York to Chicago?

    A flight from New York to Chicago is currently going to be the least expensive option currently available. You can also find deals for a train from New York to Chicago starting at €185, or consider a bus from New York to Chicago starting at €138. Both of these alternative options are worth considering when looking to reach your destination.

  • How far is New York to Chicago by plane?

    Chicago is 1143.9 km away from New York. Flights usually cover this in 2h 23m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from New York to Chicago?

    Prices for flights from New York to Chicago were last updated today.

  • 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 stopovers. 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 licence, 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?

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?

momondo does allow users to show only those flights to Chicago from New York which offer a flexible booking policy as well as other useful filters and features.

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.

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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