Flights from Boston to Chicago

March 2016
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Leaving Tue, Mar 8

Returning options:

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Leaving Tue, Mar 15

Returning options:

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Leaving Tue, Mar 22

Returning options:

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= Cheapest round-trip flights

* Prices are round trip per person (conditions apply)

Selected fares from Boston to Chicago

Departure
Arrival
Travel dates
Round-trip

Departure:

BOS

Arrival:

CHI

Travel dates

Tue, Feb 23 - Wed, Mar 2

Round-trip

Departure:

BOS

Arrival:

CHI

Travel dates

Wed, Apr 13 - Thu, Apr 14

Round-trip

Departure:

BOS

Arrival:

CHI

Travel dates

Tue, May 10 - Fri, May 13

Round-trip

Departure:

BOS

Arrival:

CHI

Travel dates

Tue, Mar 8 - Thu, Mar 10

Round-trip

Departure:

BOS

Arrival:

CHI

Travel dates

Sat, Apr 30 - Wed, May 4

Round-trip

Departure:

BOS

Arrival:

CHI

Travel dates

Fri, Mar 11 - Mon, Mar 14

Round-trip

Departure:

BOS

Arrival:

CHI

Travel dates

Sun, Jun 5 - Fri, Jun 10

Round-trip

Save more with Chicago Flight + Hotel packages

Boston and Chicago airports and terminals

Airports in Boston MA, US

Boston

Airports in Chicago IL, US

Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

    Carriers

  • 2

    O'Hare International Airport (ORD)

    Distance from City Center: 15.1 miles

    Terminals and carriers for flights from BOS to ORD

    Terminal

    Carriers

    Terminal 1
    United Airlines
    Terminal 2
    United Airlines
    Terminal 3
    American Airlines, Spirit Airlines, US Airways, jetBlue

  

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Featured Chicago Airport Hotels

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O'Hare International Airport Map
3.9 / 5 128 reviews
  • Rate Includes Breakfast
  • Rate Includes Breakfast
From
$79

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

From
$79
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6500 South Cicero Avenue Map
4.1 / 5 43 reviews
From
$120

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

From
$120
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6530 S. Cicero Avenue Map
3.7 / 5 15 reviews
  • Complimentary wired and Wi-Fi Internet Access
  • Complimentary wired and Wi-Fi Internet Access
From
$118

...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

From
$118
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6540 S. Cicero Ave. Map
3.8 / 5 17 reviews
  • Free On The HouseT hot breakfast, Wi-Fi
  • Free On The HouseT hot breakfast, Wi-Fi
From
$118

...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

From
$118
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6520 South Cicero Avenue Map
3.7 / 5 7 reviews
  • Rate includes breakfast
  • Rate includes breakfast
From
$159

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

From
$159

March

Cheapest weekend flights in March from Boston to Chicago

Leave
Thu, Mar 24
Boston
(BOS)
Chicago
(ORD)
American Airlines
American Airlines
Return
Sun, Mar 27
Chicago
(ORD)
Boston
(BOS)
American Airlines
American Airlines
Earn $1.85

Lowest roundtrip airfare in March from Boston to Chicago

Leave
Tue, Mar 22
Boston
(BOS)
Chicago
(ORD)
jetBlue
jetBlue
Return
Tue, Mar 29
Chicago
(ORD)
Boston
(BOS)
jetBlue
jetBlue
Earn $1.03

Best one-week trip in March from Boston to Chicago

Leave
Tue, Mar 22
Boston
(BOS)
Chicago
(ORD)
jetBlue
jetBlue
Return
Tue, Mar 29
Chicago
(ORD)
Boston
(BOS)
jetBlue
jetBlue
Earn $1.03

April

Cheapest weekend flights in April from Boston to Chicago

Leave
Fri, Apr 8
Boston
(BOS)
Chicago
(ORD)
American Airlines
American Airlines
Return
Mon, Apr 11
Chicago
(ORD)
Boston
(BOS)
American Airlines
American Airlines
Earn $2.15

Lowest roundtrip airfare in April from Boston to Chicago

Leave
Tue, Apr 26
Boston
(BOS)
Chicago
(ORD)
jetBlue
jetBlue
Return
Tue, May 3
Chicago
(ORD)
Boston
(BOS)
jetBlue
jetBlue
Earn $1.03

Best one-week trip in April from Boston to Chicago

Leave
Tue, Apr 26
Boston
(BOS)
Chicago
(ORD)
jetBlue
jetBlue
Return
Tue, May 3
Chicago
(ORD)
Boston
(BOS)
jetBlue
jetBlue
Earn $1.03

May

Cheapest weekend flights in May from Boston to Chicago

Leave
Thu, May 26
Boston
(BOS)
Chicago
(ORD)
Delta Air Lines
Delta Air Lines
Return
Sat, May 28
Chicago
(ORD)
Boston
(BOS)
Delta Air Lines
Delta Air Lines
Earn $2.04

Lowest roundtrip airfare in May from Boston to Chicago

Leave
Sun, May 1
Boston
(BOS)
Chicago
(ORD)
jetBlue
jetBlue
Return
Wed, May 4
Chicago
(ORD)
Boston
(BOS)
jetBlue
jetBlue
Earn $1.47

Best one-week trip in May from Boston to Chicago

Leave
Tue, May 3
Boston
(BOS)
Chicago
(ORD)
jetBlue
jetBlue
Return
Tue, May 10
Chicago
(ORD)
Boston
(BOS)
jetBlue
jetBlue
Earn $1.65

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

    • 10 direct flights are operating from Boston to Chicago today.
    • Today's average time for a direct flight is 3h 0m.
    • United Airlines flight 203 (5:55 AM GMT, Airbus Industrie A320) is today's earliest available flight from Boston to Chicago.
    • American Airlines flight 40 (6:56 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 203, Airbus Industrie A320) takes 2h 54m.
    • Today's longest direct flight from Boston to Chicago (American Airlines flight 40, Boeing 737-800 Passenger) takes 3h 12m.
    • Flights from Boston Logan Airport (BOS) to Midway Airport (MDW), O'Hare International Airport (ORD) are available for this route.