Selected fares from Boston to Chicago

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.

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Hotels in Chicago

See all 671 Hotels in Chicago
Club Quarters Hotel, Central Loop
Club Quarters Hotel, Central Loop
111 West Adams Street, Chicago
4.0 out of 5.0
4.1 out of 5 (566 reviews)

Club Quarters is a club-like hotel in the center of the Loop, Chicago’s central business district. A short walk to Symphony Center, the Art Institute, Board ...

$103

$103
Sofitel Chicago Magnificent Mile
Sofitel Chicago Magnificent Mile
20 E Chestnut St, Chicago
4.5 out of 5.0
4.6 out of 5 (140 reviews)

Located 1 block from Rush Street nightclubs, Oak Street shopping, and the Magnificent Mile, this 32-story Gold Coast hotel is 2 blocks from the John Hancock ...

$235

$235
The Palmer House Hilton
The Palmer House Hilton
17 E Monroe St, Chicago
4.0 out of 5.0
4.1 out of 5 (735 reviews)

This 1925 Beaux Arts-style Chicago hotel is steps from Millennium Park, 2 blocks from Macy's and the Art Institute, and 1 mile from Lake Michigan, Magnificent ...

$192

$192
Congress Plaza Hotel
Congress Plaza Hotel
520 South Michigan Avenue, Chicago
3.0 out of 5.0
3.4 out of 5 (1,246 reviews)

Built in 1893, this downtown Chicago hotel offers a convenient location across from Grant Park and close to Lake Michigan.

$152

$152
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park
200 North Columbus Drive, Chicago
4.5 out of 5.0
4.1 out of 5 (239 reviews)

The 45-story Fairmont Chicago hotel is adjacent to Millennium Park, a half-block from Michigan Avenue, and 3 blocks from Lake Michigan; Navy Pier, Art Institute, ...

$223

$223
Embassy Suites Chicago Downtown Magnificent Mile
Embassy Suites Chicago Downtown Magnificent Mile
511 North Columbus Drive, Chicago
4.0 out of 5.0
4.2 out of 5 (313 reviews)

The Embassy Suites Chicago Downtown Lakefront offers a newly renovated fresh look and is located two blocks from Navy Pier, Magnificent Mile shopping, and within ...

$189

$189
Hyatt Regency Chicago
Hyatt Regency Chicago
151 East Wacker Dr, Chicago
4.0 out of 5.0
4.1 out of 5 (756 reviews)

This Magnificent Mile hotel is located among Chicago's world-class shopping, restaurants and attractions. The Navy Pier, Millennium Park and Art Institute are ...

$169

$169
Millennium Knickerbocker
Millennium Knickerbocker
163 East Walton Place, Chicago
4.0 out of 5.0
4.1 out of 5 (229 reviews)

This 1927 landmark Chicago hotel is a half block from Michigan Avenue/Magnificent Mile shopping, two blocks from Oak Street shopping and Water Tower Place. Lake ...

$149

$149
Hilton Chicago O'Hare Airport
Hilton Chicago O'Hare Airport
Ohare International Airport, Chicago
4.0 out of 5.0
4.0 out of 5 (157 reviews)

The only hotel on airport property, the Hilton Chicago O'Hare Airport is located 2 miles from the Donald E. Stephens Convention Center and the Rosemont Theatre, ...

$164

$164
MileNorth Hotel
MileNorth Hotel
166 E Superior Street, Chicago
4.0 out of 5.0
4.3 out of 5 (464 reviews)

Situated in Chicago, this boutique hotel is steps from Northwestern Memorial Hospital and Chicago Water Tower. John Hancock Center and Tribune Tower are also ...

$125

$125

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 48 hours. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.