Flights from Chicago to Boston

Selected fares from Chicago to Boston

Departure Arrival Travel dates Round-trip
CHI BOS Tue, Apr 21 - Tue, Apr 28 $127
CHI BOS Tue, May 5 - Wed, May 6 $141
CHI BOS Tue, Apr 28 - Wed, Apr 29 $141
CHI BOS Tue, Apr 28 - Wed, Apr 29 $141
CHI BOS Wed, Apr 29 - Sat, May 2 $147
CHI BOS Thu, Oct 29 - Mon, Nov 2 $178
CHI BOS Thu, Apr 23 - Sun, Apr 26 $416
CHI BOS Tue, Apr 21 - Tue, Apr 28 $538

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 United Airlines
    Terminal 2 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 jetBlue
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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

April

Cheapest weekend flights in April from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Apr 30 Chicago (ORD) Boston (BOS) United Airlines $147
Earn $1.47
Return Sat, May 2 Boston (BOS) Chicago (ORD) United Airlines

Lowest roundtrip airfare in April from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Apr 28 Chicago (ORD) Boston (BOS) Spirit Airlines $127
Earn $1.27
Return Wed, Apr 29 Boston (BOS) Chicago (ORD) Spirit Airlines

Best one-week trip in April from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Apr 21 Chicago (ORD) Boston (BOS) Spirit Airlines $127
Earn $1.27
Return Tue, Apr 28 Boston (BOS) Chicago (ORD) Spirit Airlines
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May

Cheapest weekend flights in May from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, May 7 Chicago (ORD) Boston (BOS) US Airways $147
Earn $1.47
Return Mon, May 11 Boston (BOS) Chicago (ORD) US Airways

Lowest roundtrip airfare in May from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, May 19 Chicago (ORD) Boston (BOS) Spirit Airlines $127
Earn $1.27
Return Wed, May 20 Boston (BOS) Chicago (ORD) Spirit Airlines

Best one-week trip in May from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, May 13 Chicago (ORD) Boston (BOS) Spirit Airlines $127
Earn $1.27
Return Wed, May 20 Boston (BOS) Chicago (ORD) Spirit Airlines
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June

Cheapest weekend flights in June from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Jun 5 Chicago (ORD) Boston (BOS) Spirit Airlines $157
Earn $1.57
Return Mon, Jun 8 Boston (BOS) Chicago (ORD) Spirit Airlines

Lowest roundtrip airfare in June from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jun 4 Chicago (ORD) Boston (BOS) United Airlines $147
Earn $1.47
Return Fri, Jun 5 Boston (BOS) Chicago (ORD) United Airlines

Best one-week trip in June from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Jun 2 Chicago (ORD) Boston (BOS) US Airways $154
Earn $1.54
Return Tue, Jun 9 Boston (BOS) Chicago (ORD) US Airways
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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 Wed, Mar 4, 2015

Carrier Flight # Departing Arriving Aircraft Flight time
Airport Time Airport Time
Emirates/Emirates EK6750/EK6705 ORD 6:35 PM BOS 12:02 AM 320/320 4hr 27min
American Airlines/American Airlines AA1713/AA1812 ORD 6:10 PM BOS 12:15 AM 321/321 5hr 5min
American Airlines/US Airways AA1713/US1812 ORD 6:10 PM BOS 12:15 AM 321/321 5hr 5min
United Airlines/American Airlines UA4232/AA1812 ORD 6:00 PM BOS 12:15 AM ERJ/321 5hr 15min
United Airlines/US Airways UA4232/US1812 ORD 6:00 PM BOS 12:15 AM ERJ/321 5hr 15min
US Airways/American Airlines US1167/AA1812 ORD 5:59 PM BOS 12:15 AM 738/321 5hr 16min
US Airways/US Airways US1167/US1812 ORD 5:59 PM BOS 12:15 AM 738/321 5hr 16min
US Airways/American Airlines US1713/AA1812 ORD 6:10 PM BOS 12:15 AM 321/321 5hr 5min
US Airways/US Airways US1713/US1812 ORD 6:10 PM BOS 12:15 AM 321/321 5hr 5min
United Airlines UA961 ORD 9:00 PM BOS 12:18 AM 320 2hr 18min
jetBlue B61012 ORD 6:00 AM BOS 9:09 AM E90 2hr 9min
United Airlines UA5526 ORD 6:00 AM BOS 9:17 AM E75 2hr 17min
US Airways US2430 ORD 6:15 AM BOS 9:25 AM 738 2hr 10min