$41+ Cheap flights to Chicago, IL

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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
Oct 15 — Oct 221

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Flights to Chicago in 2024

Find the latest flights to Chicago in 2024, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 2,713,696 searches and data was last updated on October 10, 2024.

Popular in

December

Cheapest in

September

Average price

$246

Round-trip from

$98

One-way from

$41
High demand for flights, 8% potential price rise
Best time to find cheap flights, 2% potential price drop
Average for round-trip flights in October 2024
From New York to Chicago
One-way flight from New York to Chicago

Cheap flights to Chicago in October & November 2024

Discover affordable flights and deals to Chicago in October and November 2024. In the last 7 days, Cheapflights users made a total of 2,713,696 searches and data was last updated on October 10, 2024.
The lowest-priced flights departing to Chicago in October and November 2024 can be found below. Check back soon for alternative prices as deals update often.
Sat 11/25:59 pmLGA - MDW
1 stop6h 55mFrontier
Tue 11/511:33 amMDW - LGA
1 stop8h 26mFrontier
Deal found 10/10$98
Thu 11/1411:00 amJFK - MDW
1 stop27h 53mFrontier
Mon 11/188:20 pmMDW - JFK
1 stop15h 02mFrontier
Deal found 10/10$100
Sat 10/1910:05 pmEWR - ORD
Nonstop2h 34mSpirit Airlines
Sat 10/263:37 pmORD - EWR
Nonstop2h 22mSpirit Airlines
Deal found 10/10$101
Thu 10/246:00 amLGA - ORD
1 stop19h 09mMultiple Airlines
Tue 10/294:44 pmORD - LGA
Nonstop2h 16mMultiple Airlines
Deal found 10/10$102
Tue 11/51:22 pmJFK - ORD
1 stop23h 43mFrontier
Mon 11/188:26 pmORD - JFK
1 stop14h 56mFrontier
Deal found 10/10$103
Tue 10/229:29 pmLGA - ORD
1 stop9h 18mSpirit Airlines
Wed 10/305:25 amORD - LGA
1 stop6h 44mSpirit Airlines
Deal found 10/10$103
Thu 10/246:00 amLGA - ORD
1 stop19h 09mFrontier
Mon 10/286:24 pmORD - LGA
1 stop25h 35mFrontier
Deal found 10/9$105
Thu 10/3111:30 amJFK - ORD
Nonstop2h 46mDelta
Sat 11/26:25 pmORD - JFK
Nonstop2h 34mDelta
Deal found 10/9$127
Thu 10/316:00 amLGA - ORD
Nonstop2h 35mDelta
Sat 11/25:45 pmORD - LGA
Nonstop2h 18mDelta
Deal found 10/9$127

Chicago 2024 flight deals

Explore flight deals for Chicago in 2024, offering the best prices and options to suit your preferences. In the last 7 days, Cheapflights users made a total of 2,713,696 searches and data were last updated on October 10, 2024.
Browse some of the best deals on flights to Chicago in 2024. More deals are always being added, so be sure to check back regularly.
Sat 11/25:59 pmLGA - MDW
1 stop6h 55mFrontier
Tue 11/511:33 amMDW - LGA
1 stop8h 26mFrontier
Deal found 10/10$98
Thu 11/1411:00 amJFK - MDW
1 stop27h 53mFrontier
Mon 11/188:20 pmMDW - JFK
1 stop15h 02mFrontier
Deal found 10/10$100
Sat 10/1910:05 pmEWR - ORD
Nonstop2h 34mSpirit Airlines
Thu 10/243:37 pmORD - EWR
Nonstop2h 22mSpirit Airlines
Deal found 10/9$101
Thu 10/246:00 amLGA - ORD
1 stop19h 09mMultiple Airlines
Tue 10/294:44 pmORD - LGA
Nonstop2h 16mMultiple Airlines
Deal found 10/10$102
Tue 11/51:22 pmJFK - ORD
1 stop23h 43mFrontier
Mon 11/188:26 pmORD - JFK
1 stop14h 56mFrontier
Deal found 10/10$103
Sat 11/238:29 pmLGA - ORD
Nonstop2h 37mSpirit Airlines
Tue 12/34:29 pmORD - LGA
Nonstop1h 55mSpirit Airlines
Deal found 10/9$103
Sat 11/210:00 pmLGA - ORD
1 stop12h 37mFrontier
Mon 11/410:45 pmORD - LGA
1 stop10h 15mFrontier
Deal found 10/10$104
Thu 10/3111:30 amJFK - ORD
Nonstop2h 46mDelta
Sat 11/26:25 pmORD - JFK
Nonstop2h 34mDelta
Deal found 10/9$127
Thu 10/318:55 amLGA - ORD
Nonstop2h 45mDelta
Mon 11/48:30 amORD - LGA
Nonstop2h 20mDelta
Deal found 10/9$127

Flights to Chicago departing soon

Discover available last-minute flight options to Chicago, providing immediate availability and potentially lower prices. In the last 7 days, Cheapflights users made a total of 2,713,696 searches and data was last updated on October 10, 2024.
Browse through available last-minute flights traveling to Chicago. Double check the price, date, and time of your last-minute flight.
Wed 10/169:59 pmEWR - ORD
Nonstop2h 38mSpirit Airlines
Wed 11/137:00 amORD - EWR
Nonstop2h 13mSpirit Airlines
Deal found 10/9$77
Wed 10/168:34 amLGA - ORD
Nonstop2h 40mSpirit Airlines
Tue 10/225:25 amORD - LGA
1 stop5h 36mSpirit Airlines
Deal found 10/9$105
Wed 10/1610:00 pmLGA - ORD
1 stop13h 29mFrontier
Sat 10/199:17 amORD - LGA
1 stop11h 49mFrontier
Deal found 10/9$108
Thu 10/1710:00 pmLGA - ORD
1 stop13h 24mMultiple Airlines
Tue 10/224:44 pmORD - LGA
Nonstop2h 16mMultiple Airlines
Deal found 10/9$116
Wed 10/1610:59 pmLGA - MDW
1 stop13h 57mFrontier
Wed 11/1311:59 amMDW - LGA
1 stop8h 00mFrontier
Deal found 10/9$171
Thu 10/178:05 amJFK - ORD
Nonstop2h 49mDelta
Wed 11/137:05 amORD - JFK
Nonstop2h 25mDelta
Deal found 10/9$179
Tue 10/156:30 amLGA - MDW
Nonstop2h 20mSouthwest
Thu 11/146:00 amMDW - LGA
Nonstop2h 05mSouthwest
Deal found 10/8$180
Wed 10/168:59 amJFK - ORD
1 stop9h 38mFrontier
Wed 10/236:42 pmORD - JFK
1 stop12h 18mFrontier
Deal found 10/9$198
Thu 10/176:00 amEWR - MDW
1 stop3h 55mDelta
Tue 11/195:42 pmMDW - EWR
1 stop4h 35mDelta
Deal found 10/9$198

One-way flights to Chicago

Explore one-way flight options to Chicago for greater flexibility in your travel plans. Find up-to-date pricing and availability for one-way flights. In the last 7 days, Cheapflights users made a total of 2,713,696 searches and data was last updated on October 10, 2024.
These are some of the best available deals on flights to Chicago. Users seeking round-trip flights to Chicago should update the search form at the top of the page accordingly.
Tue 10/299:59 pmEWR - ORD
Nonstop2h 38mSpirit Airlines
Deal found 10/9$41
Sat 11/93:00 pmJFK - ORD
1 stop7h 45mFrontier
Deal found 10/10$50
Wed 12/49:55 amLGA - ORD
1 stop10h 06mSpirit Airlines
Deal found 10/10$50
Wed 10/3010:59 amLGA - ORD
1 stop7h 38mFrontier
Deal found 10/9$51
Sat 11/25:59 pmLGA - MDW
1 stop6h 55mFrontier
Deal found 10/9$51
Thu 10/3111:01 amJFK - MDW
1 stop7h 58mFrontier
Deal found 10/10$54
Tue 11/1210:00 pmEWR - MDW
1 stop14h 04mFrontier
Deal found 10/9$63
Sun 11/37:14 amJFK - ORD
Nonstop2h 49mJetBlue
Deal found 10/9$64
Fri 11/19:55 pmLGA - MDW
Nonstop2h 20mSouthwest
Deal found 10/9$64

Find flights to Chicago within your budget

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 2,713,696 searches and data was last updated on October 10, 2024.

Fly from

Any airport

Budget

$98 - $163

Route

Depart

Return

Price

New York LaGuardiaChicago Midway

LGA - MDW

LGAMDW

New York LaGuardia

Sat 11/2

1 stop6h 55m

Chicago Midway

Tue 11/5

1 stop8h 26m

$98

New York John F Kennedy IntlChicago Midway

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 11/14

1 stop27h 53m

Chicago Midway

Mon 11/18

1 stop15h 02m

$100

NewarkChicago O'Hare Intl

EWR - ORD

EWRORD

Newark

Sat 10/19

Nonstop2h 34m

Chicago O'Hare Intl

Sat 10/26

Nonstop2h 22m

$101

New York LaGuardiaChicago O'Hare Intl

LGA - ORD

LGAORD

New York LaGuardia

Thu 10/24

1 stop19h 09m

Chicago O'Hare Intl

Tue 10/29

Nonstop2h 16m

$102

New York John F Kennedy IntlChicago O'Hare Intl

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 10/31

Nonstop2h 49m

Chicago O'Hare Intl

Mon 11/4

Nonstop2h 11m

$127

New York LaGuardiaChicago O'Hare Intl

LGA - ORD

LGAORD

New York LaGuardia

Thu 10/31

Nonstop2h 35m

Chicago O'Hare Intl

Sat 11/2

Nonstop2h 18m

$127

New York LaGuardiaChicago Midway

LGA - MDW

LGAMDW

New York LaGuardia

Fri 11/1

Nonstop2h 20m

Chicago Midway

Mon 11/4

Nonstop2h 05m

$128

NewarkChicago O'Hare Intl

EWR - ORD

EWRORD

Newark

Wed 12/4

Nonstop2h 45m

Chicago O'Hare Intl

Sat 12/7

Nonstop2h 05m

$147

New York LaGuardiaChicago O'Hare Intl

LGA - ORD

LGAORD

New York LaGuardia

Wed 10/30

Nonstop2h 39m

Chicago O'Hare Intl

Fri 2/28

Nonstop2h 16m

$163

Flights are sorted by cheapest first

Deals found on 10/10

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.

Travel insights for flights to Chicago

Get recent, data-driven insights about flights to Chicago including ideal travel times, pricing trends, and more.

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 October 4, 2024.

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 50 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 28 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 October 6, 2024.

Users looking for the lowest fares to Chicago should consider flying on Wednesday afternoons, 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 (195 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 cheapest airlines that fly to Chicago?

The cheapest airlines flying from New York to Chicago are Spirit Airlines, JetBlue 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).

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 October 10, 2024.
See what other customers who have flown with Spirit Airlines, Alaska Airlines 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.
8.2
Very good
5,203 reviews

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

8.2
Very good
5,203 reviews
8.2
Very good
5,203 reviews

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

8.0
Very good
8,963 reviews
8.2
Very good
5,203 reviews

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

8.0
Very good
9,392 reviews
8.2
Very good
5,203 reviews

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

7.8
Good
300 reviews
8.2
Very good
5,203 reviews

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

7.8
Good
391 reviews
8.2
Very good
5,203 reviews

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Chicago Travel Guide

Chicago is a skyscraper metropolis. The Windy City is a feat of modern architecture and home to what was once the world’s tallest building, Sears Tower, Chicago may not be a traditional tourist destination but you will find that the Second City is well worth a visit. As the hub of the Midwest, Chicago is not to be overlooked. Its picturesque skyline is reflected in the waters of Lake Michigan. World-class museums of art and science, fine public art, huge parks and sandy beaches and a multicultural vibe (thanks to the Poles, the Italians, the Greeks and the Irish among many other groups) make it an unbeatable destination for a holiday. First stop should be the lakefront, from Lakeview to Oak Street Beach, the entire area is bustling for things for you to do and to see. Whatever your passion, Chicago will match it.

Getting to and around the city of Chicago

Flights to Chicago land at O’Hare International Airport (ORD) located in the city’s northwest corner, about 17 miles away from the CBD or Chicago Loop. Trains and buses provide efficient transportation to city center and suburbs. The Blue Line of the Chicago subway (known as the ‘L’ to locals) connects O’Hare directly to the city, and commuter rail services are easily accessible by a short shuttle ride. Taxi and car hire services are also available from the airport.

Tips for your stay in Chicago

  • Chicago is a big and busy city, and you’ll want to stay aware of your surroundings to keep yourself and your family and friends safe. Keep purses and valuables close to your person, or better yet, leave them in an in-room safe before you head out for the day.
  • Security at Chicago’s attraction is generally a given, and your bags and belongings will be searched, making this another good reason to travel lightly as you tour the city’s treasures.
  • Traffic throughout the Chicago area is heavy, with rush hour lasting basically throughout the day. Consider budgeting a taxi into your visit or use the subway to get around town.
  • There’s a lot to see when you visit Chicago, and you’ll want to plan your days accordingly. Consider investing in a Go Chicago pass, which lets you add the attractions to one convenient card that saves you money on admissions.

Finding Flights from Chicago

Chicago O’Hare International airport is among the country’s busiest airports and, along with Midway International airport, sees millions of passengers off each year. Both airports are served by many of the world’s largest airlines, including American, United, Delta, KLM, Lufthansa and Emirates, offering flights across the country and around the world. Searching Cheapflights for your next flight out of Chicago puts you in touch with great fares.

Keeping with the airports’ busy daily schedules, arriving early for your flight is a must. Leave time to make it through the baggage claim and security and arrive at your gate before the boarding call. International travelers should be aware that security can take longer and plan with that in mind.

CTA trains serve both O’Hare and Midway and are the most cost-effective way to get to the airport if you haven’t rented a car. The Blue Line gets you from downtown Chicago to O’Hare, while the Orange Line will get you from downtown to Midway. Make sure to leave enough time for delays.

  • What’s the weather like in Chicago?

    One of the biggest challenges for visitors to Chicago can be the weather. Fiercely hot in the summer, the city is bitterly cold and windy in the winter. In the winter, wear layers and don’t expose skin to the wind; in summer, be sure to drink plenty of water.

  • When is the best time to fly to Chicago?

    Peak Season: Summer runs from June through August and is a hugely popular time in the city, despite the heat and humidity from the lake. This is also the Chicago’s peak festival season, which sees major events taking place in the parks and neighborhoods every weekend. Prices for flights to Chicago and crowd numbers can see an increase when the city hosts its most popular festivals. Foodies should book a flight to Chicago during mid-July for the Taste of Chicago festival. This outdoor food event takes place at the lakefront and showcases a variety of cuisines and local flavors accompanied by live music. August is host to another popular event – the Chicago Air and Water Show. With free admission and lakefront location, the show attracts huge numbers of fans of aviation and adventure seekers. September can be the most enjoyable and mild month of the year but there’s less going on during this period. Off-peak Season: January to March is when Chicago is least busy, making cheap flights to Chicago and hotel deals more attainable. However, true to its reputation as the “Windy City”, cold temperatures and brisk winds will make you want to stay inside for most of your visit. How long is the flight to Chicago? Chicago is home to two major airports, O’Hare International and Midway International, and welcomes travelers from around the country on many major airlines. How long your flight will take depends upon your departure city with flights from Seattle, WA, and Los Angeles, CA, taking approximately four hours. Air travel from New York, NY, lasts approximately 2.5 hours, and you’ll spend a little less than three hours in the air if you’re flying in from Houston, TX.

  • Which airlines fly to Chicago?

    Multiple airlines serve the two airports with Delta, Southwest and Volaris being among those that fly to Midway International and JetBlue, United and Spirit included in airlines that fly to O’Hare. International travelers can fly on a multitude of airlines into Chicago, including Lufthansa, Qatar Airways and Emirates.

  • What should you pack for a flight to Chicago?

    Because Chicago experiences all four seasons to their fullest, you’ll want to pack according to the time you choose to visit. Late spring and summer are typically warm, calling for shorts and light tops. Bring your walking shoes to walk along the shores of Lake Michigan. Fall offers beautiful color and crisp days that can turn rather chilly as evening descends. Pack clothing that is easily layered so that you can adjust as the temperature does. Winter in the Chicago area can be pretty brutal, with windy days, snow and below-freezing temperatures. Before you zip your suitcase, make sure you’ve brought along extra socks, gloves, a hat and scarf to ward off the worst of the winter weather.

  • What are some things to do in Chicago?

    There’s never a shortage of things to do no matter what time of year you choose to visit Chicago. Visitors at Christmastime don’t want to miss a stroll down the Miracle Mile with its high-end shops and upscale dining experiences. Top the evening off with a visit to 360 Chicago at the top of the John Hancock building. The thrilling attraction offers breathtaking views of the city along with Tilt, a one-of-a-kind observation cube that moves you out over the streets from 1,000 feet up. Chicago’s lakefront offers beautiful views of Lake Michigan along with immersive educational experiences that are made for the entire family to enjoy. Begin your day at the Museum of Science and Industry and take a ride down into a replica coal mine or explore a German U-boat. The hands-on museum offers a little bit of something for everyone. Spend the afternoon in the Lincoln Park Zoo, which is free to the public and offers a range of animals to enthrall your youngsters, from reptiles to gorillas. If baseball is your passion, no trip to Chicago is complete without a trip to Wrigley Field for a game in the spring or summer. The park has been hosting fans of the Cubs and their opponents for over 100 years.

  • What does ORD mean?

    This is defined as Chicago O'Hare Intl Airport (ORD). Codes like ORD are often used to just call airports uniquely. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight destination and their unique identifiers/IATA codes.

  • 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 $29, while round-trip flights cost around $46.

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

    A round-trip flight to Chicago will typically cost around $243, however they can be found for as little as $46.

  • Where does the fastest flight to Chicago depart from?