Flights from Chicago to Boston

Selected fares from Chicago to Boston

Departure Arrival Travel dates Round-trip
CHI BOS Wed, Jun 3 - Wed, Jun 10 $147
CHI BOS Tue, May 26 - Wed, May 27 $155
CHI BOS Wed, May 27 - Wed, Jun 3 $161
CHI BOS Wed, Oct 7 - Wed, Oct 14 $161
CHI BOS Sat, Jun 6 - Wed, Jun 10 $175
CHI BOS Tue, Sep 15 - Tue, Sep 22 $178
CHI BOS Thu, May 28 - Mon, Jun 1 $364
CHI BOS Tue, Sep 1 - Wed, Sep 23 $729

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, Spirit 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, Spirit Airlines, US Airways, United Airlines
    Terminal C jetBlue
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$155
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Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Boston Airport Hotels

Hotel only $169

Hilton Boston Logan Airport

4 stars
4.2 / 5 206 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 $157

Hyatt Boston Harbor

4 stars
4.2 / 5 171 reviews

101 Harborside Dr Map

Valet parking for 1 vehicle up to 8 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 $139

Embassy Suites Boston - at Logan Airport

3 stars
3.9 / 5 97 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 $169

Courtyard by Marriott Boston Logan Airport

3 stars
3.9 / 5 87 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

Hotel only $149

TownePlace Suites Boston Logan Airport/Chelsea

2 stars
3.0 / 5 1 reviews

30 Eastern Avenue Map

...Place Suites Boston Logan Airport/Chelsea offers exceptional service for your extended stay in the Boston area.... The closest Marriott property, located just 1.1 miles from Logan Airport and... More

May

Cheapest weekend flights in May from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, May 28 Chicago (ORD) Boston (BOS) Delta Air Lines $201
Earn $2.01
Return Mon, Jun 1 Boston (BOS) Chicago (ORD) Delta Air Lines

Lowest roundtrip airfare in May from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, May 26 Chicago (ORD) Boston (BOS) US Airways $155
Earn $1.55
Return Wed, May 27 Boston (BOS) Chicago (ORD) US Airways

Best one-week trip in May from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, May 27 Chicago (ORD) Boston (BOS) US Airways $161
Earn $1.61
Return Wed, Jun 3 Boston (BOS) Chicago (ORD) US Airways
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June

Cheapest weekend flights in June from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Jun 6 Chicago (ORD) Boston (BOS) Delta Air Lines $184
Earn $1.84
Return Mon, Jun 8 Boston (BOS) Chicago (ORD) Delta Air Lines

Lowest roundtrip airfare in June from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Jun 3 Chicago (ORD) Boston (BOS) Spirit Airlines $147
Earn $1.47
Return Wed, Jun 10 Boston (BOS) Chicago (ORD) Spirit Airlines

Best one-week trip in June from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Jun 3 Chicago (ORD) Boston (BOS) Spirit Airlines $147
Earn $1.47
Return Wed, Jun 10 Boston (BOS) Chicago (ORD) Spirit Airlines
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July

Cheapest weekend flights in July from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jul 9 Chicago (ORD) Boston (BOS) Spirit Airlines $207
Earn $2.07
Return Mon, Jul 13 Boston (BOS) Chicago (ORD) Spirit Airlines

Lowest roundtrip airfare in July from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Jul 1 Chicago (ORD) Boston (BOS) US Airways $161
Earn $1.61
Return Wed, Jul 8 Boston (BOS) Chicago (ORD) US Airways

Best one-week trip in July from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Jul 1 Chicago (ORD) Boston (BOS) US Airways $161
Earn $1.61
Return Wed, Jul 8 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.

Interesting facts about flights from Chicago to Boston

    • 26 direct flights are operating from Chicago to Boston today.
    • Today's average time for a direct flight is 2h 22m.
    • jetBlue flight 1012 (6:00 AM GMT, Embraer 190) is today's earliest available flight from Chicago to Boston.
    • American Airlines flight 288 (9:40 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 (jetBlue flight 1012, Embraer 190) takes 2h 12m.
    • Today's longest direct flight from Chicago to Boston (American Airlines flight 1557, Boeing 737-800 Passenger) takes 2h 31m.
    • Flights from Midway Airport (MDW), O'Hare Airport (ORD) to Boston Logan Airport (BOS) are available for this route.

Flight schedule for flights from Chicago to Boston on Tue, Apr 28, 2015

Carrier Flight # Departing Arriving Aircraft Flight time
Airport Time Airport Time
Emirates/Emirates EK6750/EK6705 ORD 6:24 PM BOS 12:12 AM 320/E90 4hr 48min
American Airlines/American Airlines AA1167/AA1812 ORD 6:15 PM BOS 12:13 AM 738/321 4hr 58min
American Airlines/US Airways AA1167/US1812 ORD 6:15 PM BOS 12:13 AM 738/321 4hr 58min
US Airways/American Airlines US1167/AA1812 ORD 6:15 PM BOS 12:13 AM 738/321 4hr 58min
US Airways/US Airways US1167/US1812 ORD 6:15 PM BOS 12:13 AM 738/321 4hr 58min
US Airways US288 ORD 9:40 PM BOS 1:01 AM 738 2hr 21min
jetBlue B61012 ORD 6:00 AM BOS 9:12 AM E90 2hr 12min
United Airlines UA4995 ORD 6:30 AM BOS 9:51 AM E75 2hr 21min
American Airlines AA1240 ORD 7:05 AM BOS 10:22 AM 738 2hr 17min
US Airways US1240 ORD 7:05 AM BOS 10:22 AM 738 2hr 17min
American Airlines/American Airlines AA276/AA2136 ORD 6:00 AM BOS 11:18 AM 738/E90 4hr 18min
American Airlines/US Airways AA276/US2136 ORD 6:00 AM BOS 11:18 AM 738/E90 4hr 18min
US Airways/American Airlines US276/AA2136 ORD 6:00 AM BOS 11:18 AM 738/E90 4hr 18min