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Chicago to Boston Flights

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 Chicago to Boston

Departure Arrival Travel dates Round-trip
CHI BOS Thu, Jan 29 - Thu, Feb 5 $133
CHI BOS Mon, Jan 12 - Wed, Jan 14 $133
CHI BOS Mon, Jan 12 - Wed, Jan 14 $133
CHI BOS Wed, Apr 22 - Tue, Apr 28 $137
CHI BOS Tue, Feb 3 - Wed, Feb 4 $169
CHI BOS Fri, Jan 23 - Fri, Jan 30 $184
CHI BOS Thu, Jan 22 - Sun, Jan 25 $551
CHI BOS Thu, Jan 22 - Sun, Jan 25 $577
CHI BOS Sun, Jun 7 - Sun, Jun 14 $887

Chicago and Boston airports and terminals

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 ORD to BOS

    Terminal Carriers
    Terminal 1 All Nippon Airways, US Airways, United Airlines
    Terminal 2 US Airways, United Airlines
    Terminal 3 American Airlines, US Airways, jetBlue
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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 CHI to BOS

    Terminal Carriers
    Terminal B American Airlines, US Airways, United Airlines
    Terminal C All Nippon Airways, US Airways, United Airlines, jetBlue
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Cheap flights from Chicago to Boston

Sun Mon Tue Wed Thu Fri Sat
1 2 3
4 5 6
$133
7
$133
8
$133
9 10
$133
11 12
$133
13
$133
14
$133
15
$133
16 17
$133
18 19 20
$133
21
$133
22
$133
23 24
25 26 27 28 29
$133
30 31
$133

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Boston Airport Hotels

Hotel only $139

Hilton Boston Logan Airport

4 stars
4.2 / 5 196 reviews

One Hotel Drive Map

Includes parking for up to 7 nights

The Hilton Boston Logan Airport beckons weary vacationers with its illuminated 85-foot-tall spire, connected to the Logan Airport (BOS) by covered skywalk, but with soundproofed rooms to keep... More

Hotel only $131

Hyatt Boston Harbor

4 stars
4.2 / 5 148 reviews

101 Harborside Dr Map

Valet Parking For 1 vehicle up to 4 nights

...With a location close to Boston's Logan International Airport, the HYATT Boston Harbor is popular with both holidaymakers and business visitors.... More

Hotel only $118

Embassy Suites Boston - at Logan Airport

3 stars
3.9 / 5 85 reviews

207 Porter Street Map

Free cooked-to-order breakfast, Evening Reception

Airport-adjacent hotel with indoor pool and easy access to Boston The AAA three diamond-rated Embassy Suites Boston at Logan Airport offers a convenient location, especially for quick trips in and... More

Hotel only $127

Courtyard by Marriott Boston Logan Airport

3 stars
3.9 / 5 86 reviews

225 William F. McClellan Highway Map

Rate includes breakfast

...Contemporary hotel with free airport shuttle a mile from Logan Airport.... Courtyard by Marriott Boston Logan Airport surprises guests with modern, luxurious accommodations at affordable rates.... More

TownePlace Suites Boston Logan Airport/Chelsea

2 stars
Not yet reviewed

30 Eastern Avenue Map

...The closest Marriott property, located 1.3 miles, to Logan Airport and minutes from the Seaport district and Downtown Boston.... Place Suites Boston Logan Airport/Chelsea offers exceptional... More

Hotel only $119

Suburban Extended Stay Logan Airport

2 stars
3.5 / 5 80 reviews

312 Shirley Street Map

...Limited airport shuttle by advance request only.... More

January

Cheapest weekend flights in January from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Jan 31 Chicago (ORD) Boston (BOS) American Airlines $133
Earn $1.33
Return Mon, Feb 2 Boston (BOS) Chicago (ORD) American Airlines

Lowest roundtrip airfare in January from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Jan 7 Chicago (ORD) Boston (BOS) American Airlines $133
Earn $1.33
Return Sat, Jan 10 Boston (BOS) Chicago (ORD) American Airlines

Best one-week trip in January from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Jan 6 Chicago (ORD) Boston (BOS) American Airlines $133
Earn $1.33
Return Tue, Jan 13 Boston (BOS) Chicago (ORD) American Airlines
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February

Cheapest weekend flights in February from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Feb 5 Chicago (ORD) Boston (BOS) United Airlines $133
Earn $1.33
Return Sat, Feb 7 Boston (BOS) Chicago (ORD) United Airlines

Lowest roundtrip airfare in February from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Feb 4 Chicago (ORD) Boston (BOS) American Airlines $133
Earn $1.33
Return Mon, Feb 9 Boston (BOS) Chicago (ORD) American Airlines

Best one-week trip in February from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Feb 2 Chicago (ORD) Boston (BOS) United Airlines $147
Earn $1.47
Return Mon, Feb 9 Boston (BOS) Chicago (ORD) United Airlines
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March

Cheapest weekend flights in March from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Mar 6 Chicago (ORD) Boston (BOS) American Airlines $201
Earn $2.01
Return Sun, Mar 8 Boston (BOS) Chicago (ORD) American Airlines

Lowest roundtrip airfare in March from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Mar 11 Chicago (ORD) Boston (BOS) United Airlines $161
Earn $1.61
Return Wed, Mar 18 Boston (BOS) Chicago (ORD) United Airlines

Best one-week trip in March from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Mar 11 Chicago (ORD) Boston (BOS) United Airlines $161
Earn $1.61
Return Wed, Mar 18 Boston (BOS) Chicago (ORD) United Airlines
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Flights from Chicago to Boston

Taking a flight from Chicago to Boston is a simple way to learn about the country's history. Boston is home to the Freedom Trail and dozens of other sites and monuments devoted to important moments in history. Use Orbitz.com to find low-cost tickets for tourist attractions, hotels, rental cars, and flights.

Chicago, Illinois

Chicago is the largest city in Illinois, and its O'Hare International Airport is big enough to handle the needs of any passenger. American Airlines, United Airlines, and JetBlue Airways offer nonstop flights to Boston through this airport. If you live in the area and decide to park your car at the airport, you will find multiple parking areas. The daily parking lots are the best bargain, as prices range from $31 per day for weekend parking to $33 per day for weekday parking. Valet parking starts at $48 per day, and the economy lots, which are farther from the airport, charge $19 per day.

Transportation to the airport is available by taxi, shuttle, and city bus. PACE, CTA, and METRA all have stops at the airport, and shuttles and taxis make regular runs, as well. A variety of restaurants at the airport serve hungry passengers, and these restaurants include Eli's Cheesecake, Auntie Anne's, McDonald's, Starbucks, and Chili's To Go.

Boston, Massachusetts

Some of the oldest buildings in the country are in Boston, but the city also boasts numerous restaurants, museums, and outdoor attractions. When you plan your trip to Boston, you might enjoy a combination of these attractions, as well as a trip to watch the Red Sox play.

Discover Boston

Travelers arriving in Boston at Logan Airport have a variety of transportation options available. The Massachusetts Bay Transportation Authority provides service throughout the Boston metropolitan area by train and bus, while some travelers might prefer taxis. There are nine rental car agencies on-site, including Thrifty, Advantage, Hertz, and Enterprise for those who prefer driving around the city.

One of the best times for a trip to Boston is in August because the highs are around 80 degrees Fahrenheit and the city experiences less rainfall. Winter can bring temperatures in the mid-20s and low 30s, while fall temperatures reach the high 50s. The warm weather in the summer gives you more time to spend outside.

The Freedom Trail is one of the things you cannot miss on your trip, and you can find several local companies offering historic walking tours. Some of the other top historic sites in the city are Old North Church, Beacon Hill, and the Boston Public Library. You can also take a tour of the Samuel Adams Brewery, which still makes beer the way it did decades ago, and you can watch a live performance by the Boston Symphony Orchestra. The Museum of Fine Arts and Boston Public Garden also delight travelers.

Planning a Beantown Trip

Planning your trip to Boston is easy. Orbitz.com has a wide selection of flights from Chicago to Boston available, and the prices are as low as the sales that the airlines run. Orbitz also lets you find discounts on all of your other travel arrangements, including your rental car and hotel room.

Flight schedule for flights from Chicago to Boston on Sat, Dec 20, 2014

Carrier Flight # Departing Arriving Aircraft Flight time
Airport Time Airport Time
American Airlines/American Airlines AA1142/AA1812 ORD 5:55 PM BOS 12:10 AM 738/319 5hr 15min
American Airlines/US Airways AA1142/US1812 ORD 5:55 PM BOS 12:10 AM 738/319 5hr 15min
American Airlines/American Airlines AA1916/AA1812 ORD 6:25 PM BOS 12:10 AM 319/319 4hr 45min
American Airlines/US Airways AA1916/US1812 ORD 6:25 PM BOS 12:10 AM 319/319 4hr 45min
US Airways/American Airlines US1142/AA1812 ORD 5:55 PM BOS 12:10 AM 738/319 5hr 15min
US Airways/US Airways US1142/US1812 ORD 5:55 PM BOS 12:10 AM 738/319 5hr 15min
US Airways/American Airlines US1916/AA1812 ORD 6:25 PM BOS 12:10 AM 319/319 4hr 45min
US Airways/US Airways US1916/US1812 ORD 6:25 PM BOS 12:10 AM 319/319 4hr 45min
American Airlines AA1496 ORD 8:05 AM BOS 11:10 AM 738 2hr 5min
US Airways US1496 ORD 8:05 AM BOS 11:10 AM 738 2hr 5min
American Airlines/American Airlines AA40/AA2110 ORD 6:20 AM BOS 11:55 AM 738/E90 4hr 35min
American Airlines/US Airways AA40/US2110 ORD 6:20 AM BOS 11:55 AM 738/E90 4hr 35min
US Airways/American Airlines US40/AA2110 ORD 6:20 AM BOS 11:55 AM 738/E90 4hr 35min