What is the cheapest month to fly to Chicago?

Currently, the cheapest month for flights to Chicago is August . The most expensive month for flights is March . The cheapest prices are shown above but prices will vary according to departure times, airlines, class and how early you book.

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).

$61+ Flights to Chicago, Illinois

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Flights to Chicago in 2025

Popular in	December
Cheapest in	September
Average price	$247
Round-trip from	$117
One-way from	$61
Good round-trip deal	$199 or less
Good one-way deal	$119 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 June 2, 2025.

Tue 6/245:00 amEWR - ORD

Nonstop2h 37mSpirit Airlines

Tue 7/19:28 pmORD - EWR

Nonstop2h 18mSpirit Airlines

Deal found 6/2$117

Fri 6/206:30 pmLGA - ORD

Nonstop2h 35mSpirit Airlines

Wed 6/255:51 amORD - LGA

Nonstop2h 09mSpirit Airlines

Deal found 6/1$134

Wed 6/256:05 amLGA - MDW

Nonstop2h 20mSouthwest

Tue 7/17:20 pmMDW - LGA

Nonstop2h 10mSouthwest

Deal found 6/1$141

Fri 7/49:30 pmJFK - ORD

Nonstop2h 55mJetBlue

Sat 7/56:15 amORD - JFK

Nonstop2h 11mJetBlue

Deal found 6/1$142

Sat 8/235:55 amEWR - ORD

1 stop6h 30mMultiple Airlines

Sun 8/245:10 pmORD - EWR

Nonstop2h 18mMultiple Airlines

Deal found 6/1$144

Tue 6/1011:04 amEWR - MDW

1 stop6h 25mFrontier

Tue 6/2411:39 amMDW - EWR

1 stop12h 05mFrontier

Deal found 6/2$147

Sat 6/79:55 pmLGA - ORD

1 stop27h 04mMultiple Airlines

Tue 6/175:51 amORD - LGA

Nonstop2h 09mMultiple Airlines

Deal found 6/2$150

Sat 9/611:00 amJFK - ORD

Nonstop2h 40mAmerican Airlines

Sat 9/61:59 pmORD - JFK

Nonstop2h 18mAmerican Airlines

Deal found 6/1$152

Tue 7/19:30 pmLGA - ORD

Nonstop2h 39mUnited Airlines

Fri 7/48:52 amORD - LGA

1 stop4h 26mUnited Airlines

Deal found 6/1$152

Wed 7/167:00 amEWR - ORD

Nonstop2h 44mAmerican Airlines

Wed 7/238:29 pmORD - EWR

Nonstop2h 30mAmerican Airlines

Deal found 6/2$169

Tue 6/105:59 amEWR - ORD

1 stop8h 38mFrontier

Wed 6/185:38 pmORD - EWR

1 stop6h 06mFrontier

Deal found 6/1$176

Sat 9/139:40 amEWR - MDW

1 stop3h 52mDelta

Tue 9/1610:35 amMDW - EWR

1 stop5h 19mDelta

Deal found 6/1$177

Best flights to Chicago
Discover carefully curated flight deals to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 2, 2025.

Tue 6/245:00 amEWR - ORD

Nonstop2h 37mSpirit Airlines

Tue 7/19:28 pmORD - EWR

Nonstop2h 18mSpirit Airlines

Deal found 6/2$117

Wed 6/256:05 amLGA - MDW

Nonstop2h 20mSouthwest

Tue 7/17:20 pmMDW - LGA

Nonstop2h 10mSouthwest

Deal found 6/1$141

Fri 7/49:30 pmJFK - ORD

Nonstop2h 55mJetBlue

Sat 7/56:15 amORD - JFK

Nonstop2h 11mJetBlue

Deal found 6/2$142

Sat 8/235:55 amEWR - ORD

1 stop6h 30mMultiple Airlines

Sun 8/245:10 pmORD - EWR

Nonstop2h 18mMultiple Airlines

Deal found 6/1$144

Sat 9/611:00 amJFK - ORD

Nonstop2h 40mAmerican Airlines

Sat 9/61:59 pmORD - JFK

Nonstop2h 18mAmerican Airlines

Deal found 6/1$152

Tue 7/19:30 pmLGA - ORD

Nonstop2h 39mUnited Airlines

Fri 7/48:52 amORD - LGA

1 stop4h 26mUnited Airlines

Deal found 6/1$152

Tue 7/2911:04 amEWR - ORD

1 stop6h 34mFrontier

Tue 8/125:38 pmORD - EWR

1 stop6h 00mFrontier

Deal found 6/2$168

Wed 7/161:15 pmEWR - MDW

1 stop6h 25mDelta

Wed 7/239:25 amMDW - EWR

1 stop5h 30mDelta

Deal found 6/1$179

Fri 7/119:55 amEWR - MDW

1 stop5h 09mAllegiant Air

Mon 7/1410:31 amMDW - EWR

1 stop21h 34mAllegiant Air

Deal found 6/1$224

Wed 7/211:45 amEWR - ORD

1 stop6h 30mSun Country Air

Thu 7/106:09 pmORD - EWR

1 stop16h 15mSun Country Air

Deal found 6/2$265

Fri 6/206:30 pmLGA - ORD

Nonstop2h 35mSpirit Airlines

Wed 6/255:51 amORD - LGA

Nonstop2h 09mSpirit Airlines

Deal found 6/1$134

Tue 6/246:30 amLGA - ORD

1 stop11h 04mMultiple Airlines

Wed 6/255:51 amORD - LGA

Nonstop2h 09mMultiple Airlines

Deal found 6/1$150

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated June 2, 2025 and is based on user searches.

Sat 6/79:55 pmLGA - ORD

1 stop27h 04mMultiple Airlines

Tue 6/175:51 amORD - LGA

Nonstop2h 09mMultiple Airlines

Deal found 6/2$150

Tue 6/105:59 amEWR - ORD

1 stop8h 38mMultiple Airlines

Tue 6/179:28 pmORD - EWR

Nonstop2h 18mMultiple Airlines

Deal found 6/1$144

Tue 6/1011:04 amEWR - MDW

1 stop6h 25mFrontier

Tue 6/2411:39 amMDW - EWR

1 stop12h 05mFrontier

Deal found 6/2$147

Tue 6/106:30 amLGA - ORD

1 stop8h 07mFrontier

Tue 6/249:55 amORD - LGA

1 stop10h 04mFrontier

Deal found 6/2$153

Tue 6/106:30 pmLGA - ORD

Nonstop2h 37mSpirit Airlines

Fri 6/205:51 amORD - LGA

Nonstop2h 09mSpirit Airlines

Deal found 6/2$163

Tue 6/105:59 amEWR - ORD

1 stop8h 38mFrontier

Wed 6/185:38 pmORD - EWR

1 stop6h 06mFrontier

Deal found 6/1$176

Tue 6/106:20 amJFK - ORD

1 stop8h 17mFrontier

Wed 6/185:38 pmORD - JFK

1 stop6h 06mFrontier

Deal found 6/2$194

Tue 6/106:30 amLGA - MDW

1 stop10h 59mFrontier

Sat 6/148:00 amMDW - LGA

1 stop11h 59mFrontier

Deal found 6/1$194

Tue 6/109:00 amJFK - MDW

1 stop8h 29mFrontier

Sat 6/149:12 pmMDW - JFK

1 stop12h 17mFrontier

Deal found 6/2$212

Tue 6/1011:04 amEWR - MDW

1 stop6h 25mFrontier

Tue 6/1711:39 amMDW - EWR

1 stop12h 05mFrontier

Deal found 6/1$176

Wed 6/117:00 amEWR - ORD

Nonstop2h 39mUnited Airlines

Wed 7/910:40 amORD - EWR

Nonstop2h 19mUnited Airlines

Deal found 6/1$220

Wed 6/118:10 pmJFK - ORD

Nonstop2h 50mJetBlue

Wed 6/186:15 amORD - JFK

Nonstop2h 11mJetBlue

Deal found 6/2$230

One-way flights to Chicago
Search for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated June 2, 2025.

Tue 6/175:00 amEWR - ORD

Nonstop2h 37mSpirit Airlines

Deal found 6/1$61

Wed 7/22:05 pmLGA - MDW

Nonstop2h 25mSouthwest

Deal found 6/1$73

Thu 6/197:55 pmLGA - ORD

1 stop13h 55mSpirit Airlines

Deal found 6/1$75

Sat 8/238:30 pmJFK - ORD

Nonstop2h 58mJetBlue

Deal found 6/2$79

Wed 6/185:59 amEWR - MDW

1 stop5h 42mFrontier

Deal found 6/1$88

Tue 6/105:59 amEWR - ORD

1 stop8h 38mFrontier

Deal found 6/2$88

Tue 8/127:35 pmJFK - ORD

Nonstop3h 18mDelta

Deal found 6/1$89

Wed 6/187:00 amLGA - ORD

Nonstop2h 37mUnited Airlines

Deal found 6/1$89

Tue 6/106:20 amJFK - ORD

1 stop8h 17mFrontier

Deal found 6/1$97

Tue 6/106:30 amLGA - ORD

1 stop8h 07mFrontier

Deal found 6/1$97

Tue 6/1011:30 amLGA - MDW

1 stop5h 59mFrontier

Deal found 6/1$97

Sun 8/109:55 amEWR - MDW

1 stop27h 26mAllegiant Air

Deal found 6/1$98

Cheapflights Fare Finder

Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Route

Depart

Return

Price

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 6/24

5:00 am-6:37 am

Nonstop2h 37m

Chicago O'Hare Intl

Tue 7/1

9:28 pm-12:46 am

Nonstop2h 18m

$117

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 6/20

6:30 pm-8:05 pm

Nonstop2h 35m

Chicago O'Hare Intl

Wed 6/25

5:51 am-9:00 am

Nonstop2h 09m

$134

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 6/25

6:05 am-7:25 am

Nonstop2h 20m

Chicago Midway

Tue 7/1

7:20 pm-10:30 pm

Nonstop2h 10m

$141

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Fri 7/4

9:30 pm-11:25 pm

Nonstop2h 55m

Chicago O'Hare Intl

Sat 7/5

6:15 am-9:26 am

Nonstop2h 11m

$142

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 8/23

5:55 am-11:25 am

1 stop6h 30m

Chicago O'Hare Intl

Sun 8/24

5:10 pm-8:28 pm

Nonstop2h 18m

$144

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 6/24

6:30 am-4:34 pm

1 stop11h 04m

Chicago O'Hare Intl

Wed 6/25

5:51 am-9:00 am

Nonstop2h 09m

$150

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 9/6

11:00 am-12:40 pm

Nonstop2h 40m

Chicago O'Hare Intl

Sat 9/6

1:59 pm-5:17 pm

Nonstop2h 18m

$152

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 7/1

9:30 pm-11:09 pm

Nonstop2h 39m

Chicago O'Hare Intl

Fri 7/4

8:52 am-2:18 pm

1 stop4h 26m

$152

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 7/16

7:00 am-8:44 am

Nonstop2h 44m

Chicago O'Hare Intl

Wed 7/23

8:29 pm-11:59 pm

Nonstop2h 30m

$169

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 6/14

11:01 am-10:28 pm

1 stop12h 27m

Chicago Midway

Tue 6/17

11:39 am-12:44 am

1 stop12h 05m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/2

Showing 1-10 of 60 results

...

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?

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 44 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?

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 Sunday (187 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (92 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.

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

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

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

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

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

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

4,289 reviews

Alaska Airlines

8.0

Very good

10,000 reviews

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

7,955 reviews

Alaska Airlines

8.0

Very good

10,000 reviews

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

8,767 reviews

Alaska Airlines

8.0

Very good

10,000 reviews

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

2,927 reviews

Alaska Airlines

8.0

Very good

10,000 reviews

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

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Porter

Lansing

Valparaiso

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Flights to Chicago from $117 - Compare and Save

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/24. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

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 2, 2025.

Popular in

Cheapest in

Average price

Round-trip from

One-way from

Good round-trip deal

Good one-way deal

Find flight deals to Chicago

Cheapest flights to ChicagoExplore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on June 2, 2025.

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 2, 2025.

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 2, 2025.

Use the filters below to find and compare flights to Chicago that are best for you.

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.

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.

How long is the flight to Chicago?

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.

Weekly flight availability to Chicago

What are the most popular airlines that fly to Chicago?

What are the cheapest airlines that fly to Chicago?

Rainfall in Chicago by month

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

Temperature in Chicago by month

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

Reviews of airlines servicing Chicago

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.

FAQs about flying to Chicago

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

What is the best airline to fly to Chicago?

What is the cheapest airport to fly to in Chicago?

How much is a round-trip flight to Chicago?

Where does the fastest flight to Chicago depart from?

Which airport is closest to Aragon Ballroom?

Does Chicago O'Hare Intl have rental cars?

Are there hotels close to Chicago O'Hare Intl?

Traveling to a place near Chicago?

Browse thousands of different options on Cheapflights for your next trip

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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 2, 2025.