Flights from Chicago to Boston

Selected fares from Chicago to Boston

Departure Arrival Travel dates Round-trip
CHI BOS Tue, Sep 22 - Tue, Sep 29 $147
CHI BOS Wed, Sep 2 - Wed, Sep 9 $147
CHI BOS Wed, Aug 12 - Wed, Aug 26 $175
CHI BOS Tue, Jul 28 - Wed, Jul 29 $175
CHI BOS Tue, Aug 4 - Wed, Aug 5 $175
CHI BOS Tue, Nov 17 - Fri, Nov 20 $200
CHI BOS Fri, Aug 7 - Mon, Aug 17 $488
CHI BOS Sat, Aug 15 - Fri, Aug 21 $714
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
$147
19
$147
20 21 22
23 24 25
$147
26
$147
27 28 29
30 31

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Save more with Boston Flight + Hotel packages

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 International 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
Back to menu Return to top

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
Back to menu Return to top

  

Earn up to 5% on hotels and 1% on flights - It's free!

By clicking, I agree to the terms and conditions.

Featured Boston Airport Hotels

From $199

Hilton Boston Logan Airport

4 stars
4.2 / 5 218 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

From $179

Hyatt Boston Harbor

4 stars
4.2 / 5 189 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

From $179

Embassy Suites Boston - at Logan Airport

3 stars
3.9 / 5 105 reviews

207 Porter Street Map

Free cooked-to-order breakfast, Evening Reception

The AAA three diamond-rated Embassy Suites Boston at Logan Airport offers a convenient location, especially for quick trips in and out of Boston.... More

From $149

Courtyard by Marriott Boston Logan Airport

3 stars
3.9 / 5 95 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

Hilton Garden Inn Boston Logan Airport

3 stars
Not yet reviewed

100 Boardman Street Map

The Hilton Garden Inn Boston Logan Airport (BOS) is conveniently located 1 mile from Logan Airport, just minutes from downtown Boston.... More

August

Cheapest weekend flights in August from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Aug 29 Chicago (ORD) Boston (BOS) Spirit Airlines $177
Earn $1.77
Return Mon, Aug 31 Boston (BOS) Chicago (ORD) Spirit Airlines

Lowest roundtrip airfare in August from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Aug 25 Chicago (ORD) Boston (BOS) Spirit Airlines $147
Earn $1.47
Return Wed, Aug 26 Boston (BOS) Chicago (ORD) Spirit Airlines

Best one-week trip in August from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Aug 19 Chicago (ORD) Boston (BOS) Spirit Airlines $147
Earn $1.47
Return Wed, Aug 26 Boston (BOS) Chicago (ORD) Spirit Airlines
Back to menu Return to top

September

Cheapest weekend flights in September from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Sep 19 Chicago (ORD) Boston (BOS) Spirit Airlines $162
Earn $1.62
Return Sun, Sep 20 Boston (BOS) Chicago (ORD) Spirit Airlines

Lowest roundtrip airfare in September from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Sep 19 Chicago (ORD) Boston (BOS) Spirit Airlines $147
Earn $1.47
Return Sat, Sep 26 Boston (BOS) Chicago (ORD) Spirit Airlines

Best one-week trip in September from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Sep 19 Chicago (ORD) Boston (BOS) Spirit Airlines $147
Earn $1.47
Return Sat, Sep 26 Boston (BOS) Chicago (ORD) Spirit Airlines
Back to menu Return to top

October

Cheapest weekend flights in October from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Oct 3 Chicago (ORD) Boston (BOS) Spirit Airlines $162
Earn $1.62
Return Mon, Oct 5 Boston (BOS) Chicago (ORD) Spirit Airlines

Lowest roundtrip airfare in October from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Oct 3 Chicago (ORD) Boston (BOS) Spirit Airlines $147
Earn $1.47
Return Tue, Oct 6 Boston (BOS) Chicago (ORD) Spirit Airlines

Best one-week trip in October from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Oct 21 Chicago (ORD) Boston (BOS) Spirit Airlines $147
Earn $1.47
Return Wed, Oct 28 Boston (BOS) Chicago (ORD) Spirit Airlines
Back to menu Return to top

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

    • 30 direct flights are operating from Chicago to Boston today.
    • Today's average time for a direct flight is 2h 25m.
    • United Airlines flight 1705 (6:02 AM GMT, Boeing 737-900 Passenger) is today's earliest available flight from Chicago to Boston.
    • American Airlines flight 1557 (9:46 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, Airbus Industrie A320) takes 2h 15m.
    • Today's longest direct flight from Chicago to Boston (American Airlines flight 1205, Boeing 737-800 Passenger) takes 2h 34m.
    • Flights from Midway Airport (MDW), O'Hare International Airport (ORD) to Boston Logan Airport (BOS) are available for this route.