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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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Popular in

December

Cheapest in

September

Average price

$268

Round-trip from

$117

One-way from

$61

Good round-trip deal

$203 or less

Good one-way deal

$120 or less
Highest demand for flights based on searches. 2% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 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 June 12, 2025.

Tue 7/15:00 amEWR - ORD
Nonstop2h 37mSpirit Airlines
Sat 7/59:28 pmORD - EWR
Nonstop2h 18mSpirit Airlines
Deal found 6/10$117
Sat 10/185:35 pmLGA - ORD
Nonstop2h 42mSpirit Airlines
Tue 10/218:12 pmORD - LGA
Nonstop2h 19mSpirit Airlines
Deal found 6/12$135
Tue 7/158:30 pmJFK - ORD
Nonstop2h 58mJetBlue
Sat 7/196:16 amORD - JFK
Nonstop2h 13mJetBlue
Deal found 6/10$137
Tue 7/87:54 pmEWR - ORD
Nonstop2h 42mUnited Airlines
Tue 7/156:00 amORD - EWR
Nonstop2h 13mUnited Airlines
Deal found 6/10$137
Tue 7/81:17 pmLGA - ORD
Nonstop2h 38mUnited Airlines
Thu 7/108:00 pmORD - LGA
Nonstop2h 22mUnited Airlines
Deal found 6/10$137
Thu 7/109:05 amLGA - MDW
Nonstop2h 25mSouthwest
Sat 7/127:00 pmMDW - LGA
Nonstop2h 10mSouthwest
Deal found 6/10$137
Tue 7/296:00 amLGA - ORD
Nonstop2h 32mDelta
Thu 8/76:00 amORD - LGA
Nonstop2h 12mDelta
Deal found 6/11$140
Fri 10/317:39 pmLGA - ORD
Nonstop2h 46mAmerican Airlines
Sun 11/25:00 amORD - LGA
Nonstop2h 00mAmerican Airlines
Deal found 6/12$143
Wed 9/106:30 amLGA - ORD
1 stop7h 55mMultiple Airlines
Sat 9/138:12 pmORD - LGA
Nonstop2h 19mMultiple Airlines
Deal found 6/10$154
Wed 8/133:29 pmJFK - ORD
Nonstop3h 08mDelta
Sat 8/167:00 amORD - JFK
Nonstop2h 23mDelta
Deal found 6/11$157
Sat 9/1312:00 pmEWR - MDW
1 stop7h 07mDelta
Tue 9/165:25 pmMDW - EWR
1 stop6h 30mDelta
Deal found 6/11$157
Fri 11/77:20 amEWR - ORD
Nonstop2h 45mAmerican Airlines
Mon 11/106:35 pmORD - EWR
Nonstop2h 16mAmerican Airlines
Deal found 6/12$160

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 June 12, 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

Tue 7/1

5:00 am-6:37 am

Nonstop2h 37m

Chicago O'Hare Intl

Sat 7/5

9:28 pm-12:46 am

Nonstop2h 18m

$117

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 10/18

5:35 pm-7:17 pm

Nonstop2h 42m

Chicago O'Hare Intl

Tue 10/21

8:12 pm-11:31 pm

Nonstop2h 19m

$135

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 7/15

8:30 pm-10:28 pm

Nonstop2h 58m

Chicago O'Hare Intl

Wed 7/23

6:16 am-9:29 am

Nonstop2h 13m

$137

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 7/8

7:54 pm-9:36 pm

Nonstop2h 42m

Chicago O'Hare Intl

Tue 7/15

6:00 am-9:13 am

Nonstop2h 13m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 7/8

8:35 pm-10:27 pm

Nonstop2h 52m

Chicago O'Hare Intl

Tue 7/15

6:59 pm-10:30 pm

Nonstop2h 31m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 7/10

9:05 am-10:30 am

Nonstop2h 25m

Chicago Midway

Sat 7/12

7:00 pm-10:10 pm

Nonstop2h 10m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 10/31

7:39 pm-9:25 pm

Nonstop2h 46m

Chicago O'Hare Intl

Mon 11/3

6:00 am-9:00 am

Nonstop2h 00m

$143

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 7/12

6:05 am-7:44 am

Nonstop2h 39m

Chicago O'Hare Intl

Sat 7/19

5:56 pm-11:39 pm

1 stop4h 43m

$152

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 9/10

6:30 am-1:25 pm

1 stop7h 55m

Chicago O'Hare Intl

Sat 9/13

8:12 pm-11:31 pm

Nonstop2h 19m

$154

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 8/13

3:29 pm-5:37 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sat 8/16

7:00 am-10:23 am

Nonstop2h 23m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 June 9, 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 7 hours 46 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 (188 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (74 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 June 12, 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

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

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

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

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

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

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
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

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
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

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
2,925 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

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 $208, however they can be found for as little as $51.

  • 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
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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