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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 Tue, Apr 21 - Sat, Apr 25 $157
CHI BOS Tue, Mar 24 - Tue, Mar 31 $161
CHI BOS Wed, Dec 31 - Sat, Jan 17 $161
CHI BOS Tue, Mar 24 - Tue, Mar 31 $162
CHI BOS Thu, Dec 18 - Sun, Dec 21 $184
CHI BOS Tue, Jan 20 - Sat, Jan 24 $185
CHI BOS Thu, Dec 11 - Sun, Dec 14 $373
CHI BOS Wed, Jan 14 - Tue, Jan 20 $609
CHI BOS Wed, Apr 1 - Sun, Apr 5 $1,771
CHI BOS Wed, Apr 1 - Sun, Apr 5 $1,860
CHI BOS Sat, Dec 20 - Sun, Jan 4 $2,040
CHI BOS Fri, May 15 - Sun, May 17 $2,439
CHI BOS Wed, Dec 31 - Sat, Jan 3 $8,358
CHI BOS Sun, Dec 21 - Fri, Dec 26 $22,135

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
$161
17
$161
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 $119

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 $143

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 Fri, Dec 19 Chicago (ORD) Boston (BOS) Delta Air Lines $184
Earn $1.84
Return Mon, Dec 22 Boston (BOS) Chicago (ORD) Delta Air Lines

Lowest roundtrip airfare in December from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Dec 31 Chicago (ORD) Boston (BOS) American Airlines $161
Earn $1.61
Return Sat, Jan 17 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 Sat, Jan 24 Chicago (ORD) Boston (BOS) American Airlines $181
Earn $1.81
Return Sun, Jan 25 Boston (BOS) Chicago (ORD) American Airlines

Lowest roundtrip airfare in January from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Jan 6 Chicago (ORD) Boston (BOS) United Airlines $161
Earn $1.61
Return Tue, Jan 13 Boston (BOS) Chicago (ORD) United 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) United Airlines $161
Earn $1.61
Return Tue, Jan 13 Boston (BOS) Chicago (ORD) United 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 12 Chicago (ORD) Boston (BOS) American Airlines $211
Earn $2.11
Return Sun, Feb 15 Boston (BOS) Chicago (ORD) American 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) jetBlue $170
Earn $1.70
Return Wed, Feb 4 Boston (BOS) Chicago (ORD) jetBlue

Best one-week trip in February from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Feb 28 Chicago (ORD) Boston (BOS) Spirit Airlines $424
Earn $4.24
Return Sat, Mar 7 Boston (BOS) Chicago (ORD) Spirit 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.

Interesting facts about flights from Chicago to Boston

    • 17 direct flights are operating from Chicago to Boston today.
    • Today's average time for a direct flight is 2h 10m.
    • jetBlue flight 1012 (1:00 AM GMT, Embraer 190) is today's earliest available flight from Chicago to Boston.
    • American Airlines flight 288 (2:05 PM GMT, Boeing 737-800 Passenger) is today's latest available flight from Chicago to Boston.
    • Today's shortest direct flight from Chicago to Boston (American Airlines flight 186, Boeing 737-800 Passenger) takes 2h 5m.
    • Today's longest direct flight from Chicago to Boston (United Airlines flight 254, Airbus Industrie A319) takes 2h 20m.
    • Flights from Midway Airport (MDW), O'Hare Airport (ORD) to Boston Logan Airport (BOS) are available for this route.