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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, Oct 21 - Sat, Oct 25 $155
CHI BOS Sat, Oct 11 - Tue, Oct 14 $157
CHI BOS Wed, Oct 22 - Tue, Oct 28 $157
CHI BOS Tue, Oct 21 - Sat, Oct 25 $157
CHI BOS Wed, Oct 22 - Tue, Oct 28 $174
CHI BOS Wed, Sep 24 - Wed, Oct 1 $214
CHI BOS Wed, Oct 22 - Tue, Oct 28 $216
CHI BOS Mon, Sep 22 - Thu, Oct 2 $465
CHI BOS Tue, Sep 30 - Tue, Oct 7 $610
CHI BOS Tue, Nov 25 - Mon, Dec 1 $1,441
CHI BOS Fri, Oct 24 - Mon, Oct 27 $1,607
CHI BOS Fri, Oct 24 - Mon, Oct 27 $2,099
CHI BOS Tue, Nov 25 - Mon, Dec 1 $2,142
CHI BOS Mon, Nov 24 - Tue, Dec 2 $7,838
CHI BOS Tue, Nov 25 - Mon, Dec 1 $8,748

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
$155
4 5 6
$155
7 8 9
$155
10
$155
11 12 13
14 15 16
$155
17
$155
18 19 20
$155
21 22 23
$155
24
$155
25 26 27
$155
28 29 30
$155

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Boston Airport Hotels

Hotel only $199

Hilton Boston Logan Airport

4 stars
4.2 / 5 308 reviews

One Hotel Drive Map

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 $189

Hyatt Boston Harbor

4 stars
4.2 / 5 175 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 $236

Embassy Suites Boston - at Logan Airport

3 stars
3.9 / 5 131 reviews

207 Porter Street Map

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 $189

Courtyard by Marriott Boston Logan Airport

3 stars
3.9 / 5 118 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 $142

Suburban Extended Stay Logan Airport

2 stars
3.5 / 5 106 reviews

312 Shirley Street Map

...Limited airport shuttle by advance request only.... More

Hotel only $219

The Westin Boston Waterfront

4 stars
4.1 / 5 176 reviews

425 Summer Street Map

Save 40% on your stay

...Take the T train to city financial district, The Loop, or hop aboard an on-call water taxi at Fan Pier or Liberty Wharf when you're headed the three miles to Logan International Airport (BOS),... More

September

Cheapest weekend flights in September from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Sep 11 Chicago (ORD) Boston (BOS) Spirit Airlines $165
Earn $1.65
Return Sat, Sep 13 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 6 Chicago (ORD) Boston (BOS) Spirit Airlines $155
Earn $1.55
Return Tue, Sep 9 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 20 Chicago (ORD) Boston (BOS) Spirit Airlines $155
Earn $1.55
Return Sat, Sep 27 Boston (BOS) Chicago (ORD) Spirit Airlines
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October

Cheapest weekend flights in October from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 16 Chicago (ORD) Boston (BOS) Spirit Airlines $175
Earn $1.75
Return Sat, Oct 18 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 18 Chicago (ORD) Boston (BOS) Spirit Airlines $155
Earn $1.55
Return Wed, Oct 22 Boston (BOS) Chicago (ORD) Spirit Airlines

Best one-week trip in October from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Oct 11 Chicago (ORD) Boston (BOS) Spirit Airlines $175
Earn $1.75
Return Sat, Oct 18 Boston (BOS) Chicago (ORD) Spirit Airlines
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November

Cheapest weekend flights in November from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Nov 6 Chicago (ORD) Boston (BOS) jetBlue $237
Earn $2.37
Return Sun, Nov 9 Boston (BOS) Chicago (ORD) jetBlue

Lowest roundtrip airfare in November from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Nov 18 Chicago (ORD) Boston (BOS) jetBlue $157
Earn $1.57
Return Sat, Nov 22 Boston (BOS) Chicago (ORD) jetBlue

Best one-week trip in November from Chicago to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Nov 1 Chicago (ORD) Boston (BOS) United Airlines $164
Earn $1.64
Return Sat, Nov 8 Boston (BOS) Chicago (ORD) United 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 15m.
    • jetBlue flight 1012 (5:30 AM GMT, Airbus Industrie A320) is today's earliest available flight from Chicago to Boston.
    • American Airlines flight 2221 (5:05 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 1494, Boeing 737-800 Passenger) takes 2h 9m.
    • Today's longest direct flight from Chicago to Boston (United Airlines flight 1186, Boeing 737-800 Passenger) takes 2h 24m.
    • Flights from Midway Airport (MDW), O'Hare Airport (ORD) to Boston Logan Airport (BOS) are available for this route.

Aircraft options between Chicago and Boston

Equipment Carrier
Embraer 170 United Airlines, US Airways
Boeing 737-700 Passenger United Airlines, US Airways, All Nippon Airways
Boeing 757-200 Passenger United Airlines, US Airways
Boeing 737-900 Passenger United Airlines, US Airways
Airbus Industrie A319 United Airlines, US Airways, All Nippon Airways
Boeing 737-800 Passenger American Airlines, US Airways, United Airlines, All Nippon Airways
Canadair Regional Jet 700 US Airways, United Airlines
Embraer 190 jetBlue
Airbus Industrie A320 United Airlines, jetBlue, US Airways
Embraer 175 United Airlines