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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 Tue, May 12 - Thu, May 14 $157
BOS CHI Sat, Dec 13 - Wed, Dec 17 $161
BOS CHI Wed, Jan 28 - Tue, Feb 3 $161
BOS CHI Sat, Dec 13 - Wed, Dec 17 $162
BOS CHI Wed, Dec 10 - Sat, Dec 13 $169
BOS CHI Wed, Dec 10 - Tue, Dec 16 $194
BOS CHI Thu, Dec 4 - Sun, Dec 7 $261
BOS CHI Tue, Dec 9 - Wed, Dec 10 $600
BOS CHI Wed, Jan 14 - Sat, Jan 17 $1,517
BOS CHI Sat, Nov 8 - Tue, Nov 11 $3,952
BOS CHI Wed, Jan 14 - Sat, Jan 17 $5,070
BOS CHI Wed, Jan 14 - Sat, Jan 17 $6,802
BOS CHI Tue, Dec 23 - Fri, Dec 26 $16,994

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
$161
23 24 25 26 27 28 29
30

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Chicago Airport Hotels

Hotel only $99

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 126 reviews

O'Hare International Airport Map

Rate Includes Breakfast

...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 43 reviews

6500 South Cicero Avenue 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
3.7 / 5 15 reviews

6530 S. Cicero Avenue Map

Complimentary wired and Wi-Fi Internet Access

...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 $127

Hampton Inn Chicago-Midway Airport

2 stars
3.8 / 5 17 reviews

6540 S. Cicero Ave. Map

Free On The HouseT hot breakfast, Wi-Fi

...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
3.7 / 5 7 reviews

6520 South Cicero Avenue Map

Rate includes breakfast

Perfect for business travel and weekend getaways, the renovated Marriott Chicago Midway is just two blocks from MDW airport and offers a free 24-hr shuttle.... More

Hotel only $92

Sheraton Chicago O’Hare Airport Hotel

4 stars
4.0 / 5 112 reviews

6501 N. Mannheim Road Map

Save 40% on your stay

...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

November

Cheapest weekend flights in November from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Nov 15 Boston (BOS) Chicago (ORD) American Airlines $201
Earn $2.01
Return Sun, Nov 16 Chicago (ORD) Boston (BOS) American Airlines

Lowest roundtrip airfare in November from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Nov 22 Boston (BOS) Chicago (ORD) American Airlines $161
Earn $1.61
Return Tue, Dec 2 Chicago (ORD) Boston (BOS) American Airlines

Best one-week trip in November from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Nov 15 Boston (BOS) Chicago (ORD) American Airlines $181
Earn $1.81
Return Sat, Nov 22 Chicago (ORD) Boston (BOS) American Airlines
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December

Cheapest weekend flights in December from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Dec 5 Boston (BOS) Chicago (ORD) United Airlines $181
Earn $1.81
Return Sat, Dec 6 Chicago (ORD) Boston (BOS) United Airlines

Lowest roundtrip airfare in December from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Dec 13 Boston (BOS) Chicago (ORD) United Airlines $161
Earn $1.61
Return Wed, Dec 17 Chicago (ORD) Boston (BOS) United Airlines

Best one-week trip in December from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Dec 13 Boston (BOS) Chicago (ORD) American Airlines $198
Earn $1.98
Return Sat, Dec 20 Chicago (ORD) Boston (BOS) American Airlines
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January

Cheapest weekend flights in January from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Jan 17 Boston (BOS) Chicago (ORD) American Airlines $181
Earn $1.81
Return Mon, Jan 19 Chicago (ORD) Boston (BOS) American Airlines

Lowest roundtrip airfare in January from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Jan 6 Boston (BOS) Chicago (ORD) United Airlines $161
Earn $1.61
Return Wed, Jan 7 Chicago (ORD) Boston (BOS) United Airlines

Best one-week trip in January from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Jan 28 Boston (BOS) Chicago (ORD) United Airlines $161
Earn $1.61
Return Wed, Feb 4 Chicago (ORD) Boston (BOS) United Airlines
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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

    • 30 direct flights are operating from Boston to Chicago today.
    • Today's average time for a direct flight is 2h 48m.
    • American Airlines flight 1083 (1:00 AM GMT, Boeing 737-800 Passenger) is today's earliest available flight from Boston to Chicago.
    • American Airlines flight 1624 (1:15 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 (American Airlines flight 26, Boeing 737-800 Passenger) takes 2h 40m.
    • Today's longest direct flight from Boston to Chicago (United Airlines flight 325, Airbus Industrie A320) takes 2h 59m.
    • Flights from Boston Logan Airport (BOS) to Midway Airport (MDW), O'Hare Airport (ORD) are available for this route.