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 $36, 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 $3,221, however they can be found for as little as $77.

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).

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.

$52+ Flights to Chicago, Illinois

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Flights to Chicago in 2025

Popular in	December
Cheapest in	September
Average price	$206
Round-trip from	$105
One-way from	$52
Good round-trip deal	$183 or less
Good one-way deal	$99 or less

Highest demand for flights based on searches. 3% potential increase in price ($7 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 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

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 April 3, 2025.

Mon 4/288:59 pmEWR - ORD

1 stop13h 25mSpirit Airlines

Sat 5/35:38 pmORD - EWR

Nonstop2h 22mSpirit Airlines

Deal found 4/1$105

Fri 4/254:38 pmLGA - ORD

Nonstop2h 39mSpirit Airlines

Wed 4/305:55 amORD - LGA

Nonstop2h 05mSpirit Airlines

Deal found 4/2$122

Sun 5/258:00 amJFK - ORD

Nonstop2h 51mDelta

Wed 5/286:18 pmORD - JFK

Nonstop2h 42mDelta

Deal found 4/1$137

Wed 5/286:10 amLGA - MDW

Nonstop2h 20mSouthwest

Wed 5/288:20 pmMDW - LGA

Nonstop2h 05mSouthwest

Deal found 4/2$137

Sat 4/197:25 amLGA - ORD

Nonstop2h 49mDelta

Wed 4/236:00 amORD - LGA

Nonstop2h 12mDelta

Deal found 4/2$153

Mon 5/55:30 pmLGA - ORD

1 stop6h 41mMultiple Airlines

Sat 5/101:59 pmORD - LGA

1 stop7h 04mMultiple Airlines

Deal found 4/2$166

Sun 4/208:59 amJFK - ORD

Nonstop3h 06mAmerican Airlines

Tue 4/225:10 pmORD - JFK

Nonstop2h 20mAmerican Airlines

Deal found 4/2$167

Sat 5/248:00 pmJFK - ORD

Nonstop2h 54mJetBlue

Thu 5/296:15 amORD - JFK

Nonstop2h 15mJetBlue

Deal found 4/2$168

Wed 5/287:07 pmEWR - ORD

1 stop5h 51mDelta

Sat 5/314:25 pmORD - EWR

1 stop7h 42mDelta

Deal found 4/2$179

Thu 5/19:55 pmEWR - ORD

Nonstop2h 49mUnited Airlines

Tue 5/610:36 amORD - EWR

Nonstop2h 17mUnited Airlines

Deal found 4/1$193

Sun 4/276:05 amLGA - ORD

1 stop9h 55mSouthwest

Fri 5/27:00 amORD - LGA

1 stop12h 10mSouthwest

Deal found 4/3$194

Wed 5/76:30 amLGA - MDW

1 stop5h 56mFrontier

Thu 5/81:19 pmMDW - LGA

1 stop6h 40mFrontier

Deal found 4/2$196

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 April 3, 2025.

Mon 4/288:59 pmEWR - ORD

1 stop13h 25mSpirit Airlines

Sat 5/35:38 pmORD - EWR

Nonstop2h 22mSpirit Airlines

Deal found 4/1$105

Sun 5/258:00 amJFK - ORD

Nonstop2h 51mDelta

Wed 5/286:18 pmORD - JFK

Nonstop2h 42mDelta

Deal found 4/1$137

Wed 5/286:10 amLGA - MDW

Nonstop2h 20mSouthwest

Wed 5/288:20 pmMDW - LGA

Nonstop2h 05mSouthwest

Deal found 4/2$137

Mon 5/55:30 pmLGA - ORD

1 stop6h 41mMultiple Airlines

Sat 5/101:59 pmORD - LGA

1 stop7h 04mMultiple Airlines

Deal found 4/2$166

Sun 4/208:59 amJFK - ORD

Nonstop3h 06mAmerican Airlines

Tue 4/225:10 pmORD - JFK

Nonstop2h 20mAmerican Airlines

Deal found 4/2$167

Sat 5/248:00 pmJFK - ORD

Nonstop2h 54mJetBlue

Thu 5/296:15 amORD - JFK

Nonstop2h 15mJetBlue

Deal found 4/2$168

Wed 7/3010:55 amEWR - ORD

1 stop4h 21mUnited Airlines

Sat 8/27:10 amORD - EWR

Nonstop2h 18mUnited Airlines

Deal found 4/2$187

Wed 5/76:30 amLGA - MDW

1 stop5h 56mFrontier

Thu 5/81:19 pmMDW - LGA

1 stop6h 40mFrontier

Deal found 4/2$196

Fri 4/254:38 pmLGA - ORD

Nonstop2h 39mSpirit Airlines

Wed 4/305:55 amORD - LGA

Nonstop2h 05mSpirit Airlines

Deal found 4/2$122

Fri 5/309:55 amEWR - MDW

1 stop9h 15mAllegiant Air

Mon 6/28:04 pmMDW - EWR

1 stop12h 01mAllegiant Air

Deal found 4/2$252

Sat 4/1911:21 amJFK - ORD

1 stop10h 33mSun Country Air

Mon 4/217:05 pmORD - JFK

1 stop14h 18mSun Country Air

Deal found 4/2$285

Sat 4/197:25 amLGA - ORD

Nonstop2h 49mDelta

Wed 4/236:00 amORD - LGA

Nonstop2h 12mDelta

Deal found 4/2$153

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated April 3, 2025 and is based on user searches.

Mon 4/75:40 pmLGA - MDW

1 stop7h 10mFrontier

Tue 4/87:50 amMDW - LGA

1 stop13h 10mFrontier

Deal found 3/31$238

Tue 4/84:40 pmLGA - ORD

Nonstop2h 46mSpirit Airlines

Thu 4/105:55 amORD - LGA

Nonstop2h 05mSpirit Airlines

Deal found 4/1$212

Tue 4/88:29 amJFK - ORD

1 stop7h 36mAmerican Airlines

Sat 4/265:10 pmORD - JFK

Nonstop2h 20mAmerican Airlines

Deal found 4/2$226

Tue 4/810:00 pmEWR - ORD

1 stop10h 45mMultiple Airlines

Sat 4/126:36 pmORD - EWR

Nonstop2h 23mMultiple Airlines

Deal found 4/2$229

Wed 4/95:30 amEWR - ORD

Nonstop2h 33mSpirit Airlines

Sat 4/126:36 pmORD - EWR

Nonstop2h 23mSpirit Airlines

Deal found 4/1$135

Wed 4/910:38 amJFK - ORD

Nonstop2h 43mJetBlue

Sat 4/261:26 pmORD - JFK

Nonstop2h 18mJetBlue

Deal found 4/2$216

Wed 4/96:00 amLGA - ORD

Nonstop2h 40mDelta

Tue 4/296:00 amORD - LGA

Nonstop2h 12mDelta

Deal found 4/2$216

Wed 4/98:00 amJFK - ORD

Nonstop3h 00mDelta

Tue 4/2210:37 amORD - JFK

Nonstop2h 23mDelta

Deal found 4/2$220

Wed 4/96:59 amJFK - MDW

1 stop23h 24mFrontier

Thu 4/244:00 pmMDW - JFK

1 stop17h 26mFrontier

Deal found 3/31$220

Wed 4/911:00 amJFK - ORD

1 stop29h 06mFrontier

Fri 4/255:36 pmORD - JFK

1 stop5h 57mFrontier

Deal found 4/2$230

Sun 4/1310:59 pmLGA - ORD

1 stop13h 18mMultiple Airlines

Wed 4/165:55 amORD - LGA

Nonstop2h 05mMultiple Airlines

Deal found 4/2$175

Sun 4/1310:59 pmLGA - ORD

1 stop13h 18mFrontier

Wed 4/168:50 amORD - LGA

1 stop6h 39mFrontier

Deal found 4/2$238

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 April 3, 2025.

Thu 4/175:30 amEWR - ORD

Nonstop2h 33mSpirit Airlines

Deal found 4/3$52

Sat 4/1910:38 amJFK - ORD

Nonstop2h 43mJetBlue

Deal found 4/2$69

Wed 5/287:15 amLGA - ORD

Nonstop2h 41mDelta

Deal found 4/2$69

Mon 5/266:30 amLGA - MDW

Nonstop2h 20mSouthwest

Deal found 4/2$69

Tue 4/229:20 pmLGA - ORD

2 stops25h 06mSpirit Airlines

Deal found 4/2$71

Wed 6/251:58 pmEWR - RFD

1 stop19h 33mMultiple Airlines

Deal found 4/2$78

Sun 4/207:00 amLGA - ORD

Nonstop2h 34mAmerican Airlines

Deal found 4/2$79

Sun 4/276:29 amLGA - ORD

Nonstop2h 35mUnited Airlines

Deal found 4/3$85

Wed 6/188:00 amJFK - ORD

Nonstop2h 55mDelta

Deal found 4/2$89

Tue 4/226:15 amJFK - ORD

1 stop26h 51mFrontier

Deal found 4/2$93

Tue 4/225:30 pmLGA - MDW

1 stop17h 35mFrontier

Deal found 4/2$93

Fri 5/99:00 amJFK - MDW

1 stop5h 34mFrontier

Deal found 4/2$94

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

Mon 4/28

8:59 pm-9:24 am

1 stop13h 25m

Chicago O'Hare Intl

Sat 5/3

5:38 pm-9:00 pm

Nonstop2h 22m

$105

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 4/25

4:38 pm-6:17 pm

Nonstop2h 39m

Chicago O'Hare Intl

Wed 4/30

5:55 am-9:00 am

Nonstop2h 05m

$122

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sun 5/25

8:00 am-9:51 am

Nonstop2h 51m

Chicago O'Hare Intl

Wed 5/28

6:18 pm-10:00 pm

Nonstop2h 42m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 5/28

6:10 am-7:30 am

Nonstop2h 20m

Chicago Midway

Wed 5/28

8:20 pm-11:25 pm

Nonstop2h 05m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 4/19

7:25 am-9:14 am

Nonstop2h 49m

Chicago O'Hare Intl

Wed 4/23

6:00 am-9:12 am

Nonstop2h 12m

$153

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 5/5

5:30 pm-11:11 pm

1 stop6h 41m

Chicago O'Hare Intl

Sat 5/10

1:59 pm-10:03 pm

1 stop7h 04m

$166

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sun 4/20

8:59 am-11:05 am

Nonstop3h 06m

Chicago O'Hare Intl

Tue 4/22

5:10 pm-8:30 pm

Nonstop2h 20m

$167

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 5/24

8:00 pm-9:54 pm

Nonstop2h 54m

Chicago O'Hare Intl

Thu 5/29

6:15 am-9:30 am

Nonstop2h 15m

$168

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 4/16

1:15 pm-2:55 pm

Nonstop2h 40m

Chicago O'Hare Intl

Tue 4/22

6:30 pm-9:48 pm

Nonstop2h 18m

$173

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 5/28

7:07 pm-11:58 pm

1 stop5h 51m

Chicago O'Hare Intl

Sat 5/31

4:25 pm-1:07 am

1 stop7h 42m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 60 results

...

Compare providers for flights to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals to Chicago in April.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
Cheapflightsfares	Price Accuracy3 stars	Trust Score*2 stars
CheapOair	Price Accuracy1 star	Trust Score*3 stars
Priceline	Price Accuracy1 star	Trust Score*3 stars
FareScan	Price Accuracy-	Trust Score*3 stars
Kiwi.com	Price Accuracy3 stars	Trust Score*2 stars
Justfly.com	Price Accuracy3 stars	Trust Score*3 stars
Mytrip	Price Accuracy3 stars	Trust 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.

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 61 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 15 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 Wednesday (178 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (31 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

From $137

United Airlines

From $149

Spirit Airlines

From $65

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

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

9,825 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines

8.0

Very good

9,825 reviews

Alaska Airlines

8.0

Very good

9,825 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Southwest

8.0

Very good

4,274 reviews

Alaska Airlines

8.0

Very good

9,825 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta

8.0

Very good

7,897 reviews

Alaska Airlines

8.0

Very good

9,825 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Porter Airlines

7.9

Good

279 reviews

Alaska Airlines

8.0

Very good

9,825 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines

7.4

Good

8,619 reviews

Alaska Airlines

8.0

Very good

9,825 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $36, 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 $3,221, however they can be found for as little as $77.
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

Merrillville

New Buffalo

Hammond

Benton Harbor

Porter

Lansing

Valparaiso

Chesterton

Browse thousands of different options on Cheapflights for your next trip

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$52+ 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 4/17. 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 April 3, 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 April 3, 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 April 3, 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 April 3, 2025.

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

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 April.

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 March 28, 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Find the best flight deals to Chicago

Some of the lowest fares we’ve come across for flights to Chicago.

100% Free

Book with Flexibility

Travel Smart

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 April 3, 2025.