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$61+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
6月 12 — 6月 191
周四 6/12
周四 6/19
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 6月 7, 2025.

Popular in

December

Cheapest in

September

Average price

$247

Round-trip from

$117

One-way from

$61

Good round-trip deal

$198 or less

Good one-way deal

$112 or less
Highest demand for flights based on searches. 2% potential increase in price ($5 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in June 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 6月 7, 2025.

周五 6/275:00 amEWR - ORD
Nonstop2h 37mSpirit Airlines
周三 7/29:28 pmORD - EWR
Nonstop2h 18mSpirit Airlines
Deal found 6/5$117
周三 6/1811:04 amEWR - ORD
1 stop6h 30mMultiple Airlines
周二 6/249:28 pmORD - EWR
Nonstop2h 18mMultiple Airlines
Deal found 6/5$132
周二 6/246:30 pmLGA - ORD
Nonstop2h 35mSpirit Airlines
周三 7/25:51 amORD - LGA
Nonstop2h 09mSpirit Airlines
Deal found 6/4$135
周二 9/169:35 amLGA - MDW
2 stops8h 10mSouthwest
周三 9/178:35 amMDW - LGA
Nonstop2h 10mSouthwest
Deal found 6/5$139
周二 7/19:30 pmJFK - ORD
Nonstop2h 55mJetBlue
周二 7/86:16 amORD - JFK
Nonstop2h 13mJetBlue
Deal found 6/6$141
周三 6/1811:30 amLGA - ORD
1 stop6h 04mMultiple Airlines
周三 6/255:51 amORD - LGA
Nonstop2h 09mMultiple Airlines
Deal found 6/7$141
周四 6/125:59 amEWR - MDW
1 stop8h 50mFrontier
周日 6/152:55 pmMDW - EWR
1 stop8h 49mFrontier
Deal found 6/5$143
周二 8/128:00 amEWR - ORD
Nonstop2h 39mUnited Airlines
周四 8/149:25 pmORD - EWR
Nonstop2h 21mUnited Airlines
Deal found 6/6$143
周三 8/64:00 pmLGA - ORD
Nonstop2h 59mDelta
周三 8/139:25 amORD - LGA
Nonstop2h 15mDelta
Deal found 6/5$143
周三 9/1711:00 amJFK - ORD
Nonstop2h 40mAmerican Airlines
周三 9/171:59 pmORD - JFK
Nonstop2h 18mAmerican Airlines
Deal found 6/5$152
周四 8/286:59 amEWR - ORD
Nonstop2h 38mAmerican Airlines
周三 9/38:39 pmORD - EWR
Nonstop2h 20mAmerican Airlines
Deal found 6/5$160
周二 8/197:15 amLGA - ORD
1 stop7h 55mSouthwest
周四 8/212:55 pmORD - LGA
1 stop6h 55mSouthwest
Deal found 6/5$162

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 6月 7, 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 - ORD

EWRORD

Newark

周五 6/27

5:00 am-6:37 am

Nonstop2h 37m

Chicago O'Hare Intl

周三 7/2

9:28 pm-12:46 am

Nonstop2h 18m

$117

NewarkChicago

EWR - ORD

EWRORD

Newark

周三 6/18

11:04 am-4:34 pm

1 stop6h 30m

Chicago O'Hare Intl

周二 6/24

9:28 pm-12:46 am

Nonstop2h 18m

$132

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

周二 6/24

6:30 pm-8:05 pm

Nonstop2h 35m

Chicago O'Hare Intl

周三 7/2

5:51 am-9:00 am

Nonstop2h 09m

$135

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

周二 7/1

9:30 pm-11:25 pm

Nonstop2h 55m

Chicago O'Hare Intl

周二 7/8

6:16 am-9:29 am

Nonstop2h 13m

$141

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

周三 8/20

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

周三 8/20

7:05 pm-10:15 pm

Nonstop2h 10m

$141

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

周三 6/18

11:30 am-4:34 pm

1 stop6h 04m

Chicago O'Hare Intl

周三 6/25

5:51 am-9:00 am

Nonstop2h 09m

$141

NewarkChicago

EWR - MDW

EWRMDW

Newark

周四 6/12

5:59 am-1:49 pm

1 stop8h 50m

Chicago Midway

周日 6/15

2:55 pm-12:44 am

1 stop8h 49m

$143

NewarkChicago

EWR - ORD

EWRORD

Newark

周二 8/12

8:00 am-9:39 am

Nonstop2h 39m

Chicago O'Hare Intl

周四 8/14

9:25 pm-12:46 am

Nonstop2h 21m

$143

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

周三 8/6

4:00 pm-5:59 pm

Nonstop2h 59m

Chicago O'Hare Intl

周三 8/13

9:25 am-12:40 pm

Nonstop2h 15m

$143

NewarkChicago

EWR - ORD

EWRORD

Newark

周四 8/28

6:59 am-8:37 am

Nonstop2h 38m

Chicago O'Hare Intl

周三 9/3

8:39 pm-11:59 pm

Nonstop2h 20m

$160

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/6

Showing 1-10 of 60 results
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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 May 23, 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 35 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 6 hours 54 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 Saturday (158 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (85 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 $147
Spirit Airlines
Spirit Airlines
From $66
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 6月 7, 2025.
See what other customers who have flown with Alaska Airlines, Southwest 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,956 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,778 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,924 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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, 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 $30, while round-trip flights cost around $48.

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

    A round-trip flight to Chicago will typically cost around $296, however they can be found for as little as $64.

  • 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
Valparaiso
Chesterton

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