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$43+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
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 February 22, 2025.

Popular in

December

Cheapest in

September

Average price

$207

Round-trip from

$89

One-way from

$43

Good round-trip deal

$182 or less

Good one-way deal

$95 or less
Highest demand for flights based on searches. 3% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 22, 2025.

Fri 5/169:33 pmEWR - ORD
Nonstop2h 37mSpirit Airlines
Mon 5/195:10 pmORD - EWR
Nonstop2h 18mSpirit Airlines
Deal found 2/21$89
Tue 3/1110:58 amLGA - ORD
1 stop13h 58mSpirit Airlines
Thu 3/1312:31 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 2/21$95
Tue 3/2511:01 amJFK - MDW
1 stop5h 52mFrontier
Tue 4/14:40 pmMDW - JFK
1 stop7h 03mFrontier
Deal found 2/21$98
Fri 3/76:00 amEWR - ORD
Nonstop2h 44mMultiple Airlines
Sat 3/82:25 pmORD - EWR
1 stop5h 44mMultiple Airlines
Deal found 2/21$99
Tue 3/181:01 pmJFK - ORD
1 stop21h 04mFrontier
Tue 4/19:22 amORD - JFK
1 stop23h 38mFrontier
Deal found 2/20$100
Thu 5/15:30 pmLGA - ORD
1 stop6h 41mMultiple Airlines
Mon 5/55:55 amORD - LGA
Nonstop2h 05mMultiple Airlines
Deal found 2/21$100
Wed 3/510:00 pmLGA - MDW
1 stop14h 31mFrontier
Tue 3/117:50 amMDW - LGA
1 stop12h 09mFrontier
Deal found 2/21$100
Mon 5/1210:00 pmEWR - MDW
1 stop11h 19mFrontier
Sat 5/1710:48 amMDW - EWR
1 stop9h 18mFrontier
Deal found 2/21$104
Mon 3/310:00 pmLGA - ORD
1 stop12h 51mFrontier
Tue 3/42:25 pmORD - LGA
1 stop7h 35mFrontier
Deal found 2/22$117
Tue 2/2510:10 pmEWR - ORD
1 stop10h 18mFrontier
Wed 3/59:08 amORD - EWR
1 stop11h 02mFrontier
Deal found 2/21$123
Mon 4/288:00 amJFK - ORD
Nonstop2h 55mDelta
Wed 4/307:20 amORD - JFK
Nonstop2h 19mDelta
Deal found 2/21$145
Thu 5/110:35 amJFK - ORD
Nonstop2h 42mJetBlue
Sun 5/46:20 amORD - JFK
Nonstop2h 13mJetBlue
Deal found 2/22$147

Find flights to Chicago within your budget

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 February 22, 2025.

Fly from

New York

Route

Depart

Return

Price

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 5/16

9:33 pm-11:10 pm

Nonstop2h 37m

Chicago O'Hare Intl

Sun 5/18

5:10 pm-8:28 pm

Nonstop2h 18m

$89

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 3/11

10:58 am-11:56 pm

1 stop13h 58m

Chicago O'Hare Intl

Thu 3/13

12:31 pm-3:35 pm

Nonstop2h 04m

$95

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 3/25

11:01 am-3:53 pm

1 stop5h 52m

Chicago Midway

Tue 4/1

4:40 pm-12:43 am

1 stop7h 03m

$98

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 3/7

6:00 am-7:44 am

Nonstop2h 44m

Chicago O'Hare Intl

Sat 3/8

2:25 pm-9:09 pm

1 stop5h 44m

$99

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 3/18

1:01 pm-9:05 am

1 stop21h 04m

Chicago O'Hare Intl

Tue 4/1

9:22 am-10:00 am

1 stop23h 38m

$100

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 5/1

5:30 pm-11:11 pm

1 stop6h 41m

Chicago O'Hare Intl

Mon 5/5

5:55 am-9:00 am

Nonstop2h 05m

$100

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 3/5

10:00 pm-11:31 am

1 stop14h 31m

Chicago Midway

Tue 3/11

7:50 am-8:59 pm

1 stop12h 09m

$100

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 4/1

10:00 pm-10:40 am

1 stop13h 40m

Chicago O'Hare Intl

Sat 4/5

7:20 am-10:32 am

1 stop26h 12m

$103

NewarkChicago

EWR - MDW

EWRMDW

Newark

Mon 5/12

10:00 pm-8:19 am

1 stop11h 19m

Chicago Midway

Sat 5/17

10:48 am-9:06 pm

1 stop9h 18m

$104

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 2/25

10:10 pm-7:28 am

1 stop10h 18m

Chicago O'Hare Intl

Wed 3/5

9:08 am-9:10 pm

1 stop11h 02m

$123

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
CheapOairPrice Accuracy1 starTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
FareScanPrice Accuracy-Trust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*2 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
GotogatePrice 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 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.

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.

Travel insights for flights to Chicago

Get recent, data-driven insights about flights to Chicago including ideal travel times, pricing trends, and more.

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 February 14, 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 84 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 3 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 afternoons, 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 (173 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (121 on average).

What are the most popular airlines that fly to Chicago?

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

American Airlines

American Airlines

From $137

United Airlines

United Airlines

From $149

Spirit Airlines

Spirit Airlines

From $65

Delta

Delta

From $68

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from New York to Chicago are Spirit Airlines, Delta 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 February 22, 2025.
See what other customers who have flown with Southwest, Alaska Airlines and Delta to Chicago have to say. 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
8.1
Very good
4,396 reviews

Overall

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,396 reviews
Southwest
8.1
Very good
4,396 reviews

Overall

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,702 reviews
Southwest
8.1
Very good
4,396 reviews

Overall

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,396 reviews

Overall

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,068 reviews
Southwest
8.1
Very good
4,396 reviews

Overall

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,396 reviews

Overall

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

  • 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, Spirit Airlines 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 $22, while round-trip flights cost around $38.

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

    A round-trip flight to Chicago will typically cost around $1,074, however they can be found for as little as $58.

  • 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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