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$78+ 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
1 adult, Economy
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Find cheap flights to Chicago with Cheapflights

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Flights to Chicago in 2026

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 May 10, 2026.

This SmartFares deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/167:30 pm
JFK
-
ORD
Nonstop3h 00m
JetBlue
Tue 6/306:27 pm
ORD
-
JFK
Nonstop2h 46m
JetBlue
Deal found 5/7$169
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1710:00 pm
LGA
-
MDW
1 stop14h 12m
Frontier
Wed 8/1912:04 pm
MDW
-
LGA
1 stop10h 23m
Frontier
Deal found 5/6$169
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/110:00 pm
LGA
-
MDW
1 stop14h 12m
Frontier
Sat 6/611:59 am
MDW
-
LGA
1 stop6h 30m
Frontier
Deal found 5/6$171
This Cheapflightsfares deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:05 am
JFK
-
ORD
Nonstop2h 43m
JetBlue
Tue 7/286:27 pm
ORD
-
JFK
Nonstop2h 36m
JetBlue
Deal found 5/6$172
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2610:00 pm
LGA
-
ORD
1 stop10h 55m
Frontier
Tue 6/21:29 pm
ORD
-
LGA
1 stop6h 27m
Frontier
Deal found 5/5$173
This Super.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:25 am
JFK
-
ORD
Nonstop2h 43m
JetBlue
Mon 8/316:00 am
ORD
-
JFK
Nonstop2h 17m
JetBlue
Deal found 5/6$175
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/41:00 pm
JFK
-
MDW
1 stop10h 02m
Frontier
Mon 6/812:04 pm
MDW
-
JFK
1 stop22h 55m
Frontier
Deal found 5/6$175
This Flysmarter deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:05 am
JFK
-
ORD
Nonstop2h 43m
JetBlue
Fri 7/105:27 pm
ORD
-
JFK
Nonstop2h 33m
JetBlue
Deal found 5/6$176
This eDestinos deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1710:00 pm
LGA
-
ORD
1 stop11h 03m
Frontier
Wed 8/191:50 pm
ORD
-
LGA
1 stop27h 03m
Frontier
Deal found 5/6$176
This JetBlue deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/42:29 pm
JFK
-
ORD
Nonstop2h 47m
JetBlue
Tue 7/79:39 am
ORD
-
JFK
Nonstop2h 16m
JetBlue
Deal found 5/6$177
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/57:15 am
EWR
-
ORD
Nonstop2h 45m
United Airlines
Mon 8/109:30 pm
ORD
-
EWR
Nonstop2h 23m
United Airlines
Deal found 5/6$177
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/309:25 pm
LGA
-
ORD
Nonstop2h 33m
United Airlines
Wed 7/16:00 am
ORD
-
LGA
Nonstop2h 11m
United Airlines
Deal found 5/7$177

Find flight deals to Chicago

Find the latest flights to Chicago in 2026, 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 May 10, 2026.

Popular in

May

Cheapest in

January

Average price

$288

Round-trip from

$169

One-way from

$78

Good round-trip deal

$98 or less

Good one-way deal

$102 or less
Highest demand for flights based on searches. 12% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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

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 May 10, 2026.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest round-trip

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 7/8

8:45 pm-10:36 pm

Nonstop2h 51m

Chicago O'Hare Intl

Tue 7/14

6:00 am-9:09 am

Nonstop2h 09m

$177

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 6/20

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Wed 6/24

5:50 pm-8:55 pm

Nonstop2h 05m

$177

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 7/10

9:30 pm-10:55 pm

Nonstop2h 25m

Chicago Midway

Wed 7/15

7:45 pm-10:55 pm

Nonstop2h 10m

$182

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 8/11

6:00 am-7:32 am

Nonstop2h 32m

Chicago O'Hare Intl

Tue 8/11

7:05 pm-10:34 pm

Nonstop2h 29m

$187
Quickest round-trip

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 6/16

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Tue 6/30

5:15 am-8:15 am

Nonstop2h 00m

$192

NewarkChicago

EWR - ORD

EWRORD

Newark

Sun 5/24

6:00 am-7:42 am

Nonstop2h 42m

Chicago O'Hare Intl

Tue 5/26

5:00 am-8:13 am

Nonstop2h 13m

$197

NewarkChicago

EWR - MDW

EWRMDW

Newark

Fri 6/12

6:00 am-10:09 am

1 stop5h 09m

Chicago Midway

Sat 6/27

9:54 am-4:55 pm

1 stop6h 01m

$202

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 5/30

6:00 am-9:36 am

1 stop4h 36m

Chicago O'Hare Intl

Tue 6/2

7:50 pm-11:20 pm

Nonstop2h 30m

$207

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 5/23

7:55 pm-9:56 pm

Nonstop3h 01m

Chicago O'Hare Intl

Tue 5/26

6:31 pm-10:00 pm

Nonstop2h 29m

$207

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 7/17

12:00 pm-7:35 pm

1 stop8h 35m

Chicago Midway

Mon 7/20

1:00 pm-6:55 pm

1 stop4h 55m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/7

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
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6

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
eDreamsPrice Accuracy2 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
Super.comPrice Accuracy-Trust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapTicketsDealPrice Accuracy1 starTrust 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 37 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?

Use this chart to determine the cheapest time to fly round-trip from New York to Chicago. Price data was last updated on May 2, 2026.

Users looking for the lowest fares to Chicago should consider flying on Wednesday evenings, when prices are typically cheapest. Budget-minded travelers will want to avoid Thursday at noon, 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 Tuesday, which is when the least amount of flights are scheduled (143 on average).

What are the most popular airlines that fly to Chicago?

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

United Airlines
United Airlines
From $94
American Airlines
American Airlines
From $91
Frontier
Frontier
From $18
Southwest
Southwest
From $77

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from New York to Chicago are Frontier, Spirit Airlines and Delta.

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).

The best insider tips for flights to Chicago

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago trip
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on American Airlines and Frontier

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Robert Schrader

Robert Schrader

Expert on Alaska Airlines

One of the web's original travel bloggers, Robert launched his first site Leave Your Daily Hell in 2009. Since then, he's expanded into destination niche sites (one each for Japan, Thailand and Taiwan), in addition to having written for the inflight magazines of Singapore Airlines and Korean Air. Overall, he's visited nearly 100 countries, and flies business as often as possible.

Read more
Harriet Baskas

Harriet Baskas

Expert on Delta and United Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

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 May 10, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines to the United States. 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
8.0
Very good
4,304 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,304 reviews
Southwest
8.0
Very good
4,304 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,454 reviews
Southwest
8.0
Very good
4,304 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,694 reviews
Southwest
8.0
Very good
4,304 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,667 reviews
Southwest
8.0
Very good
4,304 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.3
Okay
8,636 reviews
Southwest
8.0
Very good
4,304 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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, Frontier 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 $34, while round-trip flights cost around $41.

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

    A round-trip flight to Chicago will typically cost around $98, however they can be found for as little as $83.

  • Where does the fastest flight to Chicago depart from?

    For those looking to save time traveling to Chicago, Milwaukee-Mitchell offers the quickest one-way flight (0 hours 45 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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