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Fares from $18 One Way, $35 Round Trip from Boston to Chicago

Prices starting at $35 for return flights and $18 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

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More About Flying To Chicago from Boston

Flights from Boston to Chicago - Frequently Asked Questions

Are there non-stop flights from Boston to Chicago?

Get ready to click "book" because there are 5 airlines that operate nonstop services from Boston, MA Airport (BOS-Logan Intl.) to Chicago, IL Airport (ORD-O'Hare Intl.). Head to Chicago in comfort aboard one of these respected carriers:

  • United Airlines
  • American Airlines
  • JetBlue Airways
  • Delta Air Lines
  • Spirit Airlines
What is the shortest flight from Boston to Chicago?

If the weather is good and everything goes to plan, you could be jetting into Chicago, IL Airport (ORD-O'Hare Intl.) from Boston, MA Airport (BOS-Logan Intl.) in only 2 hours and 40 minutes. With such a brief flight time, think about bringing just carry-on luggage.

What airlines fly from Boston to Chicago most frequently?

Here are the four carriers that fly the most frequently between Boston and Chicago. Discover which one best meets your needs: United Airlines - (UA) with 152 flights every month American Airlines - (AA) with 127 flights every month JetBlue Airways - (B6) with 101 flights every month Delta Air Lines - (DL) with 79 flights every month

Route Information for Flights from Boston to Chicago

Origin Airport IATA CodeBOS
Destination Airport IATA CodeCHI
Distance863 mi
Direct Flight AirlinesAmerican Airlines, Alaska Airlines, JetBlue Airways, Emirates, SAS, Hawaiian Airlines, ANA, Air New Zealand, United Airlines, El Al, Spirit Airlines
Earliest Flight Arrival11:42AM UTC
Latest Flight Arrival12:15AM UTC

Flights Review

Mar 23, 2020

Please put Sterilray.com technology on you planes to disinfect the air and seats. Better than chemicals and more efficient.

Feb 17, 2020

early arrive!

Feb 12, 2020

good price but I gave up some usual comforts, like checked bag and earlier check in. still, was worth it for a short flight when price matters.

Feb 12, 2020

Diverse flight crew was appreciated. And the flight attendants were normal (friendly) people. Not overly made up and glamorized. They all seemed relaxed and polite with each other. It felt very comfortable to travel with this crew.

Feb 12, 2020

Free WiFi only works for movies/entertainment, NOT email, internet, games etc. on your devices.

Feb 2, 2020

I greatly appreciated boarding early because I served in the military! Thank you!

Dec 30, 2019

Got seated with my husband on return flight home.

Dec 28, 2019

I wasn't happy with the fact we were told backpacks couldn't be put in overheads because they needed the space for large carry-on. The under-the-seat place for my backpack was very small and I had severe leg pain because I couldn't stretch out my leg at all.

Dec 21, 2019

Easy on time flight

Dec 18, 2019

Because of weather, we had a delay. Staff handled all this beautifully. The only negative was that we had four different gates, and gate 4 is half way across the airport from 21. We went from 20 to 21 to 4 to 21.

Flights from Boston to Chicago

Staying on budget when planning a trip can be a challenge, but Orbitz.com makes it a little easier. You will discover cheap flights from Boston to Chicago as well as discount ground transportation and accommodations. Chicago is home to more than 2.7 million people, making it the third-largest city in the United States.

Boston Information

When you leave Boston, you will depart from the Logan International Airport, which is located on the east side of Boston. It is host to several airlines, including Delta, Spirit, American, JetBlue, US Airways, and AirTran. All these airlines provide air service to Chicago, and their best rates can be found on Orbitz.com. The most convenient public transportation option for getting to the airport is the T Bus, which costs $2 from downtown. Numerous taxi companies are readily available, and their rates range from $25 to $35 from downtown.

Abundant parking spaces are available at the airport, including short-term, long-term, and economy parking. Economy has the cheapest rate of $18 per day, and regular parking will cost about $27 daily. Whether you want a quick snack or a full meal, you will discover a variety of restaurants and menu items inside the terminals. Johnny Rockets, Ozone, Boston Beer Works, and Asian Too are a few of your options, and you'll find pizzas, burgers, and more.

Chicago Information

Chicago is a fun and exciting city to visit and has so much to enjoy. Whether you enjoy sports, classical music, or modern architecture, Chicago is the place to be. Located in northern Illinois, Chicago borders Lake Michigan, which provides a variety of water activities. The city has a rich history and diverse culture visitors will enjoy.

When you plan your flight to Chicago, you have two airports to choose from: Chicago O'Hare International Airport and Chicago Midway International Airport. O'Hare is located about 17 miles northwest of downtown, and Midway is 8 miles from downtown. Ground transportation from both airports is offered by way of train, taxi, and shuttle. The CTA trains provide fast and convenient transportation from the airport for $2.25 or less. Taxi fares average about $40 to downtown from O'Hare and $25 from Midway. Shuttle service is provided by Go Airport Express and Omega Airport Shuttle, and their average rate is $25 from O'Hare and $15 from Midway. Most major car rental companies are located at both airports, and you can arrange for a car in advance when you book your flight with Orbitz.com.

The weather in Chicago ranges from cold in the winter to warm in summer. The coldest month is January, during which the average temperature ranges from nightly lows in the teens to daytime highs of around 31 degrees Fahrenheit. July is the warmest month and has average temperatures in the mid-80s. The months of May through August each receive around 4 inches of rainfall. January and February only receive about 2 inches of precipitation, but it is usually in the form of snow.

Chicago has an extensive list of attractions everyone will enjoy. Theater enthusiasts will enjoy the Chicago Shakespeare Theater located on Navy Pier and the Lookingglass Theatre Company. If you enjoy water sports, check out the many attractions on Lake Michigan. Kid and adults will have a great time watching a ballgame at Wrigley Field or spending a day at the Lincoln Zoo.

Start Planning Your Trip to Chicago

Let Orbitz.com help save you time and money when you are planning your trip from Boston to Chicago. You will discover discounts on flights, ground transportation, and hotel accommodations. Take a break from your everyday life, and start planning a fun trip to the Windy City.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.