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$70+ Cheap flights to Chicago

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
Oct 25 — Nov 11
Sat 10/25
Sat 11/1
1 adult, Economy
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Flights to Chicago in 2025

Find the latest flights to Chicago in 2025, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 2,558,603 searches and data was last updated on September 25, 2025.

Popular in

August

Cheapest in

January

Average price

$218

Round-trip from

$125

One-way from

$70

Good round-trip deal

$116 or less

Good one-way deal

$53 or less
Highest demand for flights based on searches. 7% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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From New York to Chicago
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One-way flight from New York to Chicago
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Price to beat on a round-trip flight from New York to Chicago.
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Price to beat on a one-way flight from New York to Chicago.
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Find flight deals to Chicago

Cheapest flights to Chicago
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on September 25, 2025.

This Mytrip deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1811:00 amJFK - ORD
Nonstop2h 45mFrontier
Mon 11/2411:48 amORD - JFK
Nonstop2h 20mFrontier
Deal found 9/23$125
This SmartFares deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/253:21 pmLGA - ORD
Nonstop2h 44mSpirit Airlines
Mon 10/274:03 pmORD - LGA
Nonstop1h 57mSpirit Airlines
Deal found 9/24$125
This Frontier deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/811:00 amJFK - ORD
Nonstop2h 45mFrontier
Sat 11/156:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 9/24$126
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/114:32 pmLGA - ORD
1 stop15h 42mMultiple Airlines
Sat 10/1811:55 amORD - LGA
1 stop10h 30mMultiple Airlines
Deal found 9/24$126
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/811:59 amLGA - ORD
1 stop12h 46mSpirit Airlines
Mon 10/2011:13 amORD - LGA
Nonstop1h 55mSpirit Airlines
Deal found 9/23$127
This Cheapflightsfares deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2711:00 amJFK - ORD
Nonstop2h 45mFrontier
Thu 10/306:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 9/24$128
This Mytrip deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/253:21 pmLGA - ORD
Nonstop2h 44mMultiple Airlines
Mon 10/278:15 amORD - LGA
1 stop6h 42mMultiple Airlines
Deal found 9/24$128
This Mytrip deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/96:59 amJFK - ORD
1 stop25h 35mFrontier
Wed 10/156:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 9/22$129
This Cheapflightsfares deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/811:59 amLGA - ORD
1 stop12h 46mSpirit Airlines
Thu 10/911:13 amORD - LGA
Nonstop1h 55mSpirit Airlines
Deal found 9/23$129
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2411:00 amJFK - ORD
Nonstop2h 45mFrontier
Sat 10/256:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 9/24$130
This Cheapflightsfares deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/85:55 amLGA - ORD
1 stop12h 58mSpirit Airlines
Wed 10/86:58 pmORD - LGA
1 stop13h 02mSpirit Airlines
Deal found 9/24$130
This Priceline deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2511:00 amJFK - ORD
Nonstop2h 45mFrontier
Mon 10/275:50 pmORD - JFK
1 stop5h 43mFrontier
Deal found 9/23$131

Cheapflights Fare Finder

 
Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 2,558,603 searches and data was last updated on September 25, 2025.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

New York

Route

Depart

Return

Price

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 10/16

1:01 pm-8:21 pm

1 stop8h 20m

Chicago Midway

Thu 10/23

9:26 pm-7:28 am

1 stop9h 02m

$156

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 10/15

8:00 am-9:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Tue 10/21

10:36 am-1:59 pm

Nonstop2h 23m

$157

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 10/22

6:05 am-7:30 am

Nonstop2h 25m

Chicago Midway

Sat 10/25

5:50 pm-8:55 pm

Nonstop2h 05m

$157

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 10/21

8:00 am-9:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Wed 10/29

7:00 am-10:25 am

Nonstop2h 25m

$157

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 10/21

8:00 am-9:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Tue 10/28

7:00 am-10:25 am

Nonstop2h 25m

$157

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 10/21

7:30 am-9:07 am

Nonstop2h 37m

Chicago O'Hare Intl

Wed 10/29

6:00 am-9:07 am

Nonstop2h 07m

$157

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 10/25

8:15 am-9:40 am

Nonstop2h 25m

Chicago Midway

Mon 10/27

8:35 am-11:40 am

Nonstop2h 05m

$158

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 10/25

7:30 am-9:07 am

Nonstop2h 37m

Chicago O'Hare Intl

Mon 10/27

7:00 am-10:11 am

Nonstop2h 11m

$158

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 10/30

4:30 pm-5:55 pm

Nonstop2h 25m

Chicago Midway

Sun 11/2

5:10 am-8:15 am

Nonstop2h 05m

$159

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 10/24

8:45 pm-10:26 pm

Nonstop2h 41m

Chicago O'Hare Intl

Mon 10/27

6:00 am-9:07 am

Nonstop2h 07m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/25

Showing 1-10 of 60 results
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Compare providers for flights to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals to Chicago in September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
PricelinePrice Accuracy1 starTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: Out of all of the providers offering Chicago flight deals, Cheapflights users have found FlightHub to have the most accurate pricing on Cheapflights vs. their site about >95% of the time, users can find the same price on Chicago flight deals on Cheapflights and FlightHub. This is based on searches made for Chicago flights over the past month.
  • Most trusted provider: FlightHub is the most trusted provider by Cheapflights users offering Chicago flight deals. With a user feedback rating of 3 out of 3 stars (3 being the best), FlightHub has received the most positive sentiment from Cheapflights users searching for flights to Chicago. This is based on data collected from Cheapflights searches made over the past month.

The best insider tips for flights to Chicago

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago trip
Airlines
American Airlines

American Airlines' Main Cabin Extra provides more legroom than standard economy.


American Airlines' Flagship Business offers lie-flat seats on select transcontinental flights.

Read more about American Airlinesby Marisa Garcia
Alaska Airlines

Alaska Airlines offers 32” legroom in Main Cabin, ideal for short domestic flights.


Saver Fare allows a carry-on, but no seat selection in advance.

Read more about Alaska Airlinesby Robert Schrader
Frontier

Frontier's UpFront Plus offers a guaranteed empty middle seat for extra comfort.


Frontier charges for carry-on bags; add them during booking for lower fees.

Read more about Frontierby Marisa Garcia
Delta

Delta offers free Wi-Fi on most domestic flights for SkyMiles members.


Delta Comfort Plus provides extra legroom and early boarding on domestic flights.

Read more about Deltaby Harriet Baskas
United Airlines

United's Basic Economy allows a personal item but no carry-on bags.


United Economy Plus offers extra legroom and priority boarding on domestic routes.

Read more about United Airlinesby Harriet Baskas
Spirit Airlines

Spirit's Big Front Seats offer 11 inches more legroom, ideal for comfort.


Spirit's Saver$ Club offers discounts on luggage and seats.

Read more about Spirit Airlinesby Daniel Scheffler
Airports
ORD

Take the 'L' train from ORD to downtown Chicago for a reliable and traffic-free journey.

Read more about ORDby Ramsey Qubein
MDW

The Orange Line train connects MDW to downtown Chicago in under 30 minutes, offering a convenient and affordable travel option.

Read more about MDWby Ramsey Qubein
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on American Airlines and Frontier

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Robert Schrader

Robert Schrader

Expert on Alaska Airlines

Robert Schrader

Robert Schrader

One of the web's original travel bloggers, Robert launched his first site Leave Your Daily Hell in 2009. Since then, he's expanded into destination niche sites (one each for Japan, Thailand and Taiwan), in addition to having written for the inflight magazines of Singapore Airlines and Korean Air. Overall, he's visited nearly 100 countries, and flies business as often as possible.

Read more
Harriet Baskas

Harriet Baskas

Expert on Delta and United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Best time to book a flight to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight to Chicago

When is the best time to book a flight to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from New York to Chicago. Price data was last updated on September 19, 2025.

The price you pay for your flight to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 64 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

How long is the flight to Chicago?

On average, a flight from New York to Chicago takes 8 hours 11 minutes. Flights to Chicago from other popular cities in USA will vary in length. Below are a few examples of popular routes and their flight times.

When is the cheapest time to fly to Chicago?

Use this chart to determine the cheapest time to fly round-trip from New York to Chicago. Price data was last updated on December 16, 2024.

Users looking for the lowest fares to Chicago should consider flying on Tuesday mornings, when prices are typically cheapest. Budget-minded travelers will want to avoid Sunday at noon, when prices are usually at their highest.

Weekly flight availability to Chicago

The most flights from New York to Chicago are scheduled on a Thursday (186 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (80 on average).

What are the most popular airlines that fly to Chicago?

The most popular airlines flying from New York to Chicago are United Airlines, American Airlines and Spirit Airlines.

American Airlines
American Airlines
From $91
United Airlines
United Airlines
From $93
Frontier
Frontier
From $37
Southwest
Southwest
From $79

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from New York to Chicago are Spirit Airlines, Frontier and JetBlue.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 25, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines to the United States. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,926 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,045 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

FAQs about flying to Chicago

  • Can I find cheaper flights to Chicago if I am willing to have layovers?

    Yes, flights with layovers are often cheaper than direct flights. Keep an eye out for flight deals to Chicago on Cheapflights that require 1 or 2 stops for potential cost savings.

  • What is the best airline to fly to Chicago?

    Based on reviews from Cheapflights users, Frontier is rated the highest out of the airlines that fly to Chicago.

  • What is the cheapest airport to fly to in Chicago?

    Chicago Midway is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago Midway typically cost $25, while round-trip flights cost around $46.

  • How much is a round-trip flight to Chicago?

    A round-trip flight to Chicago will typically cost around $1,022, however they can be found for as little as $75.

  • Where does the fastest flight to Chicago depart from?

    For those looking to save time traveling to Chicago, Muskegon offers the quickest one-way flight (0 hours 50 minutes).

  • Which airport is closest to Aragon Ballroom?

    If being close to Aragon Ballroom is important to you, you’ll want to land at Chicago O'Hare Intl Airport.

  • Does Chicago O'Hare Intl have rental cars?

    Yes. Those touching down at Chicago O'Hare Intl can take advantage of the rental car services offered upon their arrival.

  • Are there hotels close to Chicago O'Hare Intl?

    Yes. Chicago O'Hare Intl has hotels nearby for those requiring accommodations. Hilton Chicago O'Hare Airport is the closest property to Chicago O'Hare Intl (0.0 mi away from Chicago O'Hare Intl).

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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