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Boston to Chicago Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Selected fares from Boston to Chicago

Departure Arrival Travel dates Round-trip
BOS CHI Wed, Oct 1 - Tue, Oct 7 $148
BOS CHI Sat, Aug 30 - Sat, Sep 13 $192
BOS CHI Sat, Aug 30 - Sat, Sep 13 $192
BOS CHI Wed, Sep 3 - Thu, Sep 4 $192
BOS CHI Thu, Sep 4 - Mon, Sep 8 $211
BOS CHI Tue, Aug 19 - Tue, Aug 26 $214
BOS CHI Tue, Aug 19 - Tue, Aug 26 $214
BOS CHI Thu, Oct 2 - Sun, Oct 5 $444
BOS CHI Thu, Sep 4 - Tue, Sep 9 $606
BOS CHI Thu, Sep 11 - Mon, Sep 15 $662

Boston and Chicago airports and terminals

Airports in Boston MA, US
map of airports in Boston
  • 1

    Boston Logan Airport (BOS)

    Distance from City Center: 3 miles

    Terminals and carriers for flights from BOS to CHI

    Terminal Carriers
    Terminal B American Airlines, Cathay Pacific, US Airways, United Airlines
    Terminal C US Airways, United Airlines, jetBlue
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Airports in Chicago IL, US
map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

    Terminals and carriers for flights from BOS to ORD

    Terminal Carriers
    Terminal 1 US Airways, United Airlines
    Terminal 2 US Airways, United Airlines
    Terminal 3 American Airlines, Cathay Pacific, US Airways, jetBlue
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Cheap flights from Boston to Chicago

Sun Mon Tue Wed Thu Fri Sat
1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27
$168
28 29 30
$168
31

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Chicago Airport Hotels

Hotel only $139

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 165 reviews

O'Hare International Airport Map

Park & Fly - Includes up to 3 nights valet parking

...This O'Hare airport hotel is located in Terminal 2 and is within walking distance to all O'Hare Airport's domestic terminals.... More

Hotel only $137

Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
4.1 / 5 68 reviews

6500 SOUTH CICERO AVE Map

Exceptional Hotel Near Chicago Midway Airport Searching for hotels near the best sights in downtown Chicago?... More

Hotel only $144

Hilton Garden Inn Chicago/Midway Airport

3 stars
3.6 / 5 22 reviews

6530 S. Cicero Avenue Map

...Advance Purchase Rate online!The Hilton Garden Inn Chicago Midway Airport in Chicago is located on the Midway Hotel Center campus just two blocks south of the Chicago Midway Airport and the... More

Hotel only $135

Hampton Inn Chicago-Midway Airport

2 stars
3.8 / 5 30 reviews

6540 S. Cicero Ave. Map

...And no matter what time your flight got in or is going out, we're here to pick you up or drop you off.... land here and let your vacation take off...welcome to the Hampton Inn Chicago-Midway... More

Hotel only $179

Chicago Marriott Midway

3 stars
3.6 / 5 11 reviews

6520 South Cicero Avenue Map

Rate includes breakfast

...WiFi-equipped guest rooms at our Chicago Midway Airport hotel are recently renovated and offer soundproof windows, 32" flat-screen TVs and room service.... Perfect for business travel and... More

Hotel only $99

Sheraton Chicago O’Hare Airport Hotel

4 stars
4.0 / 5 146 reviews

6501 N. Mannheim Road Map

Save 15% on your stay, Breakfast Included

...Complimentary shuttle service to and from O'Hare Airport is available 24 hours a day.... Our all-suite hotel is conveniently located minutes from O'Hare International Airport, Donald E. Stephens... More

August

Cheapest weekend flights in August from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Aug 22 Boston (BOS) Chicago (ORD) Spirit Airlines $208
Earn $2.08
Return Sat, Aug 23 Chicago (ORD) Boston (BOS) Spirit Airlines

Lowest roundtrip airfare in August from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Aug 27 Boston (BOS) Chicago (ORD) Spirit Airlines $168
Earn $1.68
Return Wed, Sep 3 Chicago (ORD) Boston (BOS) Spirit Airlines

Best one-week trip in August from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Aug 27 Boston (BOS) Chicago (ORD) Spirit Airlines $168
Earn $1.68
Return Wed, Sep 3 Chicago (ORD) Boston (BOS) Spirit Airlines
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September

Cheapest weekend flights in September from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Sep 13 Boston (BOS) Chicago (ORD) Spirit Airlines $168
Earn $1.68
Return Mon, Sep 15 Chicago (ORD) Boston (BOS) Spirit Airlines

Lowest roundtrip airfare in September from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Sep 16 Boston (BOS) Chicago (ORD) Spirit Airlines $148
Earn $1.48
Return Wed, Sep 17 Chicago (ORD) Boston (BOS) Spirit Airlines

Best one-week trip in September from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Sep 24 Boston (BOS) Chicago (ORD) Spirit Airlines $148
Earn $1.48
Return Wed, Oct 1 Chicago (ORD) Boston (BOS) Spirit Airlines
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October

Cheapest weekend flights in October from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 16 Boston (BOS) Chicago (ORD) Spirit Airlines $168
Earn $1.68
Return Mon, Oct 20 Chicago (ORD) Boston (BOS) Spirit Airlines

Lowest roundtrip airfare in October from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Oct 1 Boston (BOS) Chicago (ORD) Spirit Airlines $148
Earn $1.48
Return Tue, Oct 7 Chicago (ORD) Boston (BOS) Spirit Airlines
Back to menu Return to top

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.

Interesting facts about flights from Boston to Chicago

    • 33 direct flights are operating from Boston to Chicago today.
    • Today's average time for a direct flight is 2h 43m.
    • United Airlines flight 1198 (12:35 AM GMT, Boeing 737-700 Passenger) is today's earliest available flight from Boston to Chicago.
    • American Airlines flight 1612 (2:55 PM GMT, Boeing 737-800 Passenger) is today's latest available flight from Boston to Chicago.
    • Today's shortest direct flight from Boston to Chicago (United Airlines flight 1198, Boeing 737-700 Passenger) takes 2h 35m.
    • Today's longest direct flight from Boston to Chicago (American Airlines flight 187, Boeing 737-800 Passenger) takes 2h 50m.
    • Flights from Boston Logan Airport (BOS) to Midway Airport (MDW), O'Hare Airport (ORD) are available for this route.

Aircraft options between Boston and Chicago

Equipment Carrier
Boeing 737-700 Passenger United Airlines, US Airways
Embraer 170 United Airlines, US Airways
Boeing 757-200 Passenger United Airlines, US Airways
Boeing 757-300 Passenger United Airlines
Boeing 737-900 Passenger United Airlines, US Airways
Airbus Industrie A319 United Airlines, US Airways
Boeing 737-800 Passenger American Airlines, US Airways, United Airlines, Cathay Pacific
Embraer 190 jetBlue
Canadair Regional Jet 700 United Airlines, US Airways
Airbus Industrie A320 United Airlines, jetBlue, US Airways
Embraer 175 United Airlines