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$54+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Find cheap flights to Chicago with Cheapflights

1. Tell us where you want to go

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Flights to Chicago in 2025

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 December 23, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Mon 1/266:57 pmORD - LGA
1 stop13h 03mSpirit Airlines
Deal found 12/22$88
This Cheapflightsfares deal was found by Cheapflights users on 12/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Mon 1/126:57 pmORD - LGA
1 stop13h 03mSpirit Airlines
Deal found 12/22$96
This Super.com deal was found by Cheapflights users on 12/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Wed 1/74:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 12/22$99
This Cheapflightsfares deal was found by Cheapflights users on 12/21. 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 12/318:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Sun 1/258:43 pmORD - LGA
1 stop12h 17mSpirit Airlines
Deal found 12/21$104
This Frontier deal was found by Cheapflights users on 12/21. 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.
Wed 12/3111:00 amJFK - ORD
Nonstop2h 57mFrontier
Mon 1/56:40 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/21$105
This Cheapflightsfares deal was found by Cheapflights users on 12/21. 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 12/318:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Sat 1/37:20 amORD - LGA
Nonstop2h 01mSpirit Airlines
Deal found 12/21$108
This Cheapflightsfares deal was found by Cheapflights users on 12/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Tue 1/69:34 amORD - EWR
Nonstop2h 16mSpirit Airlines
Deal found 12/22$109
This Cheapflightsfares deal was found by Cheapflights users on 12/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Mon 1/54:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 12/22$115
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:00 amJFK - ORD
Nonstop2h 57mFrontier
Sat 1/36:40 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/22$116
This Cheapflightsfares deal was found by Cheapflights users on 12/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Mon 1/268:43 pmORD - EWR
1 stop13h 59mSpirit Airlines
Deal found 12/22$121
This Priceline deal was found by Cheapflights users on 12/21. 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.
Wed 12/3111:00 amJFK - ORD
Nonstop2h 57mMultiple Airlines
Sun 1/257:45 amORD - JFK
1 stop6h 13mMultiple Airlines
Deal found 12/21$122
This Cheapflightsfares deal was found by Cheapflights users on 12/21. 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 12/316:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Sun 1/49:34 amORD - EWR
Nonstop2h 16mSpirit Airlines
Deal found 12/21$124

Find flight deals to Chicago

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 December 23, 2025.

Popular in

August

Cheapest in

January

Average price

$276

Round-trip from

$85

One-way from

$54

Good round-trip deal

$73 or less

Good one-way deal

$73 or less
Highest demand for flights based on searches. 8% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
From New York to Chicago
Search Deals
One-way flight from New York to Chicago
Search Deals
Price to beat on a round-trip flight from New York to Chicago.
Search Deals
Price to beat on a one-way flight from New York to Chicago.
Search Deals

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 December 23, 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

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 1/14

11:30 am-10:19 pm

1 stop11h 49m

Chicago Midway

Sun 1/18

6:30 pm-9:30 pm

Nonstop2h 00m

$110

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 2/18

9:15 pm-11:10 pm

Nonstop2h 55m

Chicago O'Hare Intl

Tue 2/24

6:04 am-9:20 am

Nonstop2h 16m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 2/2

3:52 pm-5:45 pm

Nonstop2h 53m

Chicago O'Hare Intl

Sat 2/7

10:29 am-1:54 pm

Nonstop2h 25m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 2/18

9:15 pm-11:10 pm

Nonstop2h 55m

Chicago O'Hare Intl

Mon 2/23

6:04 am-9:20 am

Nonstop2h 16m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sun 1/18

7:50 am-9:49 am

Nonstop2h 59m

Chicago O'Hare Intl

Tue 1/20

10:29 am-1:54 pm

Nonstop2h 25m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 2/23

9:15 pm-11:10 pm

Nonstop2h 55m

Chicago O'Hare Intl

Wed 2/25

12:41 pm-4:02 pm

Nonstop2h 21m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 2/2

3:52 pm-5:45 pm

Nonstop2h 53m

Chicago O'Hare Intl

Tue 2/10

10:29 am-1:54 pm

Nonstop2h 25m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 2/7

5:30 pm-7:45 pm

Nonstop3h 15m

Chicago O'Hare Intl

Thu 2/12

6:04 am-9:20 am

Nonstop2h 16m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 1/17

3:55 pm-5:48 pm

Nonstop2h 53m

Chicago O'Hare Intl

Tue 2/3

1:57 pm-5:30 pm

Nonstop2h 33m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 2/5

5:25 pm-7:31 pm

Nonstop3h 06m

Chicago O'Hare Intl

Thu 2/12

6:04 am-9:20 am

Nonstop2h 16m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
OvagoPrice Accuracy2 starsTrust Score*2 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust 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 CheapOair 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 CheapOair. This is based on searches made for Chicago flights over the past month.
  • Most trusted provider: CheapOair 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), CheapOair 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.

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 December 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 81 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 37 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 20, 2025.

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 Tuesday (166 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (58 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 $97
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 Frontier, Spirit Airlines 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).

The best insider tips for flights to Chicago

AI-powered summary based on content written by travel experts. AI can make mistakes.
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

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 December 23, 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
4,253 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,014 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,105 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,054 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,196 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 $51.

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

    A round-trip flight to Chicago will typically cost around $87, however they can be found for as little as $59.

  • 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).

  • 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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