Cheap flights to Chicago, IL from $26

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 4/27. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
BOS — CHI
Apr 23 — Apr 301

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 3,192,047 searches and data was last updated on April 18, 2024.

Popular in

June

Cheapest in

February

Average price

$239

Round-trip from

$55

One-way from

$43
High demand for flights, 16% potential price rise
Best time to find cheap flights, 3% potential price drop
Average for round-trip flights in April 2024
From New York to Chicago
One-way flight from New York to Chicago

Cheap flights to Chicago in April & May 2024

Discover affordable flights and deals to Chicago in April and May 2024. In the last 7 days, Cheapflights users made a total of 3,192,047 searches and data was last updated on April 18, 2024.
The lowest-priced flights departing to Chicago in April and May 2024 can be found below. Check back soon for alternative prices as deals update often.
Tue 5/2111:55 pmLAX - ORD
Nonstop4h 05mSpirit Airlines
Wed 5/221:13 pmORD - LAX
1 stop9h 34mSpirit Airlines
Deal found 4/17$68
Tue 5/2110:21 pmDFW - ORD
Nonstop2h 45mFrontier
Sat 5/253:53 pmORD - DFW
Nonstop2h 31mFrontier
Deal found 4/18$68
Thu 5/26:10 amDFW - ORD
Nonstop2h 24mMultiple Airlines
Sat 5/46:25 pmORD - DFW
Nonstop2h 37mMultiple Airlines
Deal found 4/16$69
Tue 5/2110:43 pmLAX - ORD
1 stop5h 47mSpirit Airlines
Wed 5/221:13 pmORD - LAX
1 stop10h 39mSpirit Airlines
Deal found 4/17$70
Thu 5/95:45 amDFW - ORD
Nonstop2h 28mMultiple Airlines
Sat 5/116:25 pmORD - DFW
Nonstop2h 37mMultiple Airlines
Deal found 4/17$70
Thu 5/165:45 amDFW - ORD
Nonstop2h 28mSpirit Airlines
Mon 5/207:00 amORD - DFW
Nonstop2h 29mSpirit Airlines
Deal found 4/17$71
Sat 5/1810:50 pmDFW - ORD
Nonstop2h 28mSpirit Airlines
Mon 5/207:00 amORD - DFW
Nonstop2h 29mSpirit Airlines
Deal found 4/17$72
Thu 5/25:50 amDFW - ORD
1 stop19h 06mFrontier
Tue 5/76:47 pmORD - DFW
Nonstop2h 37mFrontier
Deal found 4/17$73
Tue 4/231:45 pmDFW - ORD
Nonstop2h 28mSpirit Airlines
Tue 4/309:25 pmORD - DFW
1 stop12h 03mSpirit Airlines
Deal found 4/16$74

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 3,192,047 searches and data were last updated on April 18, 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.
Tue 5/2111:55 pmLAX - ORD
Nonstop4h 05mSpirit Airlines
Wed 5/221:13 pmORD - LAX
1 stop9h 34mSpirit Airlines
Deal found 4/17$68
Tue 5/2110:21 pmDFW - ORD
Nonstop2h 45mFrontier
Sat 5/253:53 pmORD - DFW
Nonstop2h 31mFrontier
Deal found 4/18$68
Thu 5/26:10 amDFW - ORD
Nonstop2h 24mMultiple Airlines
Sat 5/46:25 pmORD - DFW
Nonstop2h 37mMultiple Airlines
Deal found 4/16$69
Tue 5/2110:43 pmLAX - ORD
1 stop5h 47mSpirit Airlines
Wed 5/221:13 pmORD - LAX
1 stop10h 39mSpirit Airlines
Deal found 4/17$70
Thu 5/95:45 amDFW - ORD
Nonstop2h 28mMultiple Airlines
Sat 5/116:25 pmORD - DFW
Nonstop2h 37mMultiple Airlines
Deal found 4/17$70
Thu 5/165:45 amDFW - ORD
Nonstop2h 28mSpirit Airlines
Mon 5/207:00 amORD - DFW
Nonstop2h 29mSpirit Airlines
Deal found 4/17$71
Sat 5/1810:50 pmDFW - ORD
Nonstop2h 28mSpirit Airlines
Mon 5/207:00 amORD - DFW
Nonstop2h 29mSpirit Airlines
Deal found 4/17$72
Thu 6/67:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Wed 6/129:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Deal found 4/17$73
Thu 5/25:50 amDFW - ORD
1 stop19h 06mFrontier
Tue 5/76:47 pmORD - DFW
Nonstop2h 37mFrontier
Deal found 4/17$73

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 3,192,047 searches and data was last updated on April 18, 2024.
Browse through available last-minute flights traveling to Chicago. Double check the price, date, and time of your last-minute flight.
Sat 4/275:39 pmDFW - ORD
Nonstop2h 26mMultiple Airlines
Tue 4/306:47 pmORD - DFW
Nonstop2h 37mMultiple Airlines
Deal found 4/17$56
Sat 4/275:39 pmDFW - ORD
Nonstop2h 26mSpirit Airlines
Sun 4/285:45 amORD - DFW
Nonstop2h 38mSpirit Airlines
Deal found 4/16$57
Wed 4/2410:29 pmDFW - ORD
Nonstop2h 23mFrontier
Sat 4/276:25 pmORD - DFW
Nonstop2h 37mFrontier
Deal found 4/17$58
Wed 4/2410:29 pmDFW - ORD
Nonstop2h 23mFrontier
Tue 4/306:47 pmORD - DFW
Nonstop2h 37mFrontier
Deal found 4/17$60
Sat 4/2710:29 pmDFW - ORD
Nonstop2h 23mFrontier
Tue 4/306:47 pmORD - DFW
Nonstop2h 37mFrontier
Deal found 4/17$61
Tue 4/231:45 pmDFW - ORD
Nonstop2h 28mMultiple Airlines
Tue 4/306:47 pmORD - DFW
Nonstop2h 37mMultiple Airlines
Deal found 4/16$62
Wed 4/2410:29 pmDFW - ORD
Nonstop2h 23mFrontier
Wed 5/16:47 pmORD - DFW
Nonstop2h 37mFrontier
Deal found 4/17$63
Wed 4/248:52 amDFW - ORD
Nonstop2h 28mMultiple Airlines
Tue 4/306:47 pmORD - DFW
Nonstop2h 37mMultiple Airlines
Deal found 4/17$66
Sat 4/2710:29 pmDFW - ORD
Nonstop2h 23mMultiple Airlines
Mon 4/297:23 amORD - DFW
Nonstop2h 38mMultiple Airlines
Deal found 4/17$69

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 3,192,047 searches and data was last updated on April 18, 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.
Sat 4/275:39 pmDFW - ORD
Nonstop2h 26mSpirit Airlines
Deal found 4/17$26
Sat 4/2710:29 pmDFW - ORD
Nonstop2h 23mFrontier
Deal found 4/17$29
Wed 5/2912:12 pmDFW - ORD
Nonstop2h 45mFrontier
Deal found 4/18$32
Tue 4/3010:29 pmDFW - ORD
Nonstop2h 23mFrontier
Deal found 4/16$34
Tue 5/2110:43 pmLAX - ORD
1 stop5h 47mSpirit Airlines
Deal found 4/17$35
Tue 4/231:45 pmDFW - ORD
Nonstop2h 28mSpirit Airlines
Deal found 4/16$35
Thu 6/67:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/17$36
Sun 4/286:10 amDFW - ORD
Nonstop2h 24mSpirit Airlines
Deal found 4/17$36
Wed 6/127:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/17$37

Direct flights to Chicago

Wed 5/18:37 amLGA - ORD
Nonstop2h 37mSpirit Airlines
Wed 5/811:14 amORD - LGA
Nonstop2h 11mSpirit Airlines
Deal found 4/17$55
Tue 5/78:37 amLGA - ORD
Nonstop2h 37mSpirit Airlines
Tue 5/75:09 pmORD - LGA
Nonstop2h 15mSpirit Airlines
Deal found 4/17$57
Wed 5/158:35 amLGA - ORD
Nonstop2h 39mSpirit Airlines
Wed 5/2211:14 amORD - LGA
Nonstop2h 11mSpirit Airlines
Deal found 4/17$59
Wed 5/18:37 amLGA - ORD
Nonstop2h 37mSpirit Airlines
Wed 5/155:19 pmORD - LGA
Nonstop2h 09mSpirit Airlines
Deal found 4/17$60
Tue 5/148:09 pmLGA - ORD
Nonstop2h 37mSpirit Airlines
Wed 5/2211:14 amORD - LGA
Nonstop2h 11mSpirit Airlines
Deal found 4/17$61
Tue 5/2110:21 pmDFW - ORD
Nonstop2h 45mFrontier
Sat 5/253:53 pmORD - DFW
Nonstop2h 31mFrontier
Deal found 4/18$68
Thu 5/26:10 amDFW - ORD
Nonstop2h 24mMultiple Airlines
Sat 5/46:25 pmORD - DFW
Nonstop2h 37mMultiple Airlines
Deal found 4/16$69
Sat 5/48:03 pmLGA - ORD
Nonstop2h 40mSpirit Airlines
Wed 5/811:14 amORD - LGA
Nonstop2h 11mSpirit Airlines
Deal found 4/17$70
Thu 5/95:45 amDFW - ORD
Nonstop2h 28mMultiple Airlines
Sat 5/116:25 pmORD - DFW
Nonstop2h 37mMultiple Airlines
Deal found 4/17$70

Average price of flights to Chicago by month

Plan your trip to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight to Chicago is currently $33 while a round-trip flight costs $63. Price data was last updated on April 14, 2024.

Currently, February is the cheapest month in which you can book a flight to Chicago (average of $245). Flying to Chicago in June will prove the most costly (average of $357). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

January

$248

February

$245

March

$280

April

$276

May

$283

June

$357

July

$336

August

$276

September

$258

October

$248

November

$270

December

$248

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.

Temperature and rainfall in Chicago by month

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

CHI

Temperature

23 - 73.4 °F

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).

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 to Chicago. Price data was last updated on January 28, 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 78 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Search Deals

When is the cheapest time to fly to Chicago?

Use this chart to determine the cheapest time to fly round-trip to Chicago. Price data was last updated on April 14, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Users looking for the lowest fares to Chicago should consider flying on Saturday evenings, when prices are typically cheapest. Budget-minded travelers will want to avoid Sunday at noon, when prices are usually at their highest.
Search Deals

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 April 18, 2024.
See what other customers who have flown with Frontier, Spirit Airlines and JetBlue 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.
Southwest
8.2
Very good
6,215 reviews

Comfort

8.1

Entertainment

7.9

Overall

8.2

Crew

8.7

Boarding

8.3

Food

7.4

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.2
Very good
6,215 reviews
Southwest
8.2
Very good
6,215 reviews

Comfort

8.1

Entertainment

7.9

Overall

8.2

Crew

8.7

Boarding

8.3

Food

7.4

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

8.1
Very good
9,106 reviews
Southwest
8.2
Very good
6,215 reviews

Comfort

8.1

Entertainment

7.9

Overall

8.2

Crew

8.7

Boarding

8.3

Food

7.4

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

8.1
Very good
11,104 reviews
Southwest
8.2
Very good
6,215 reviews

Comfort

8.1

Entertainment

7.9

Overall

8.2

Crew

8.7

Boarding

8.3

Food

7.4

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

7.7
Good
4,678 reviews
Southwest
8.2
Very good
6,215 reviews

Comfort

8.1

Entertainment

7.9

Overall

8.2

Crew

8.7

Boarding

8.3

Food

7.4

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

7.3
Good
439 reviews
Southwest
8.2
Very good
6,215 reviews

Comfort

8.1

Entertainment

7.9

Overall

8.2

Crew

8.7

Boarding

8.3

Food

7.4

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

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.

If you’re looking to learn more about Chicago’s airports before you book your flight, check out our Chicago Airport Guides for more detailed information on airlines, terminals and other important must-know travel information.

  • 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.

  • 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 Airport is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago Midway Airport typically cost $24, while round-trip flights cost around $39.

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

    A round-trip flight to Chicago will typically cost around $630, however they can be found for as little as $50.

  • Where does the fastest flight to Chicago depart from?

    For those looking to save time traveling to Chicago, Madison offers the quickest one-way flight (0 hours 58 minutes).

  • Which airport is closest to Allstate Arena?

    If being close to Chicago is important to you, you’ll want to land at Chicago O'Hare Intl Airport.

  • Does Chicago O'Hare Intl Airport have rental cars?

    Yes. Those touching down at Chicago O'Hare Intl Airport can take advantage of the rental car services offered upon their arrival.

  • Are there hotels close to Chicago O'Hare Intl Airport?

    Yes. Chicago O'Hare Intl Airport has hotels nearby for those requiring accommodations. Hilton Chicago O'Hare Airport is the closest property to Chicago O'Hare Intl Airport (0.0 mi away from Chicago O'Hare Intl Airport).

See more FAQs

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Find flights to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Classfrom $155/person
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