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Chicago to Boston 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 Chicago to Boston

Departure Arrival Travel dates Round-trip
CHI BOS Thu, Apr 16 - Wed, Apr 22 $157
CHI BOS Wed, Dec 24 - Tue, Jan 20 $161
CHI BOS Wed, Dec 24 - Tue, Jan 20 $161
CHI BOS Wed, Dec 31 - Tue, Jan 6 $170
CHI BOS Fri, Feb 13 - Sat, Feb 28 $184
CHI BOS Sat, Jan 10 - Sat, Jan 17 $185
CHI BOS Thu, Dec 11 - Sun, Dec 14 $303
CHI BOS Sun, Dec 21 - Sat, Jan 17 $1,286
CHI BOS Thu, Jun 18 - Mon, Jun 22 $1,762
CHI BOS Fri, May 1 - Sun, May 3 $22,455

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
7 8 9 10 11 12 13
14 15 16 17 18 19 20
$161
21 22 23
$161
24
$161
25 26 27
28 29 30 31
$161

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

December

Cheapest weekend flights in December from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Dec 25 Chicago (ORD) Boston (BOS) American Airlines $199
Earn $1.99
Return Sat, Dec 27 Boston (BOS) Chicago (ORD) American Airlines

Lowest roundtrip airfare in December from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Dec 23 Chicago (ORD) Boston (BOS) American Airlines $161
Earn $1.61
Return Wed, Dec 31 Boston (BOS) Chicago (ORD) American Airlines

Best one-week trip in December from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Dec 24 Chicago (ORD) Boston (BOS) American Airlines $161
Earn $1.61
Return Wed, Dec 31 Boston (BOS) Chicago (ORD) American Airlines
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January

Cheapest weekend flights in January from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jan 29 Chicago (ORD) Boston (BOS) United Airlines $181
Earn $1.81
Return Sat, Jan 31 Boston (BOS) Chicago (ORD) United Airlines

Lowest roundtrip airfare in January from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Jan 10 Chicago (ORD) Boston (BOS) American Airlines $168
Earn $1.68
Return Sat, Jan 17 Boston (BOS) Chicago (ORD) American Airlines

Best one-week trip in January from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Jan 10 Chicago (ORD) Boston (BOS) American Airlines $168
Earn $1.68
Return Sat, Jan 17 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 $181
Earn $1.81
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 Tue, Feb 3 Chicago (ORD) Boston (BOS) United Airlines $181
Earn $1.81
Return Thu, Feb 5 Boston (BOS) Chicago (ORD) United Airlines

Best one-week trip in February from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Feb 9 Chicago (ORD) Boston (BOS) Delta Air Lines $198
Earn $1.98
Return Mon, Feb 16 Boston (BOS) Chicago (ORD) Delta Air Lines
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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.

Interesting facts about flights from Chicago to Boston

    • 21 direct flights are operating from Chicago to Boston today.
    • Today's average time for a direct flight is 2h 10m.
    • United Airlines flight 6432 (12:15 AM GMT, Embraer 175) is today's earliest available flight from Chicago to Boston.
    • United Airlines flight 557 (3:13 PM GMT, Boeing 757-200 Passenger) is today's latest available flight from Chicago to Boston.
    • Today's shortest direct flight from Chicago to Boston (American Airlines flight 1570, Boeing 737-800 Passenger) takes 2h 4m.
    • Today's longest direct flight from Chicago to Boston (United Airlines flight 1186, Boeing 737-800 Passenger) takes 2h 21m.
    • Flights from Midway Airport (MDW), O'Hare Airport (ORD) to Boston Logan Airport (BOS) are available for this route.