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Boston to Chicago Flights

Staying on budget when planning a trip can be a challenge, but Orbitz.com makes it a little easier. You will discover cheap flights from Boston to Chicago as well as discount ground transportation and accommodations. Chicago is home to more than 2.7 million people, making it the third-largest city in the United States.

Boston Information

When you leave Boston, you will depart from the Logan International Airport, which is located on the east side of Boston. It is host to several airlines, including Delta, Spirit, American, JetBlue, US Airways, and AirTran. All these airlines provide air service to Chicago, and their best rates can be found on Orbitz.com. The most convenient public transportation option for getting to the airport is the T Bus, which costs $2 from downtown. Numerous taxi companies are readily available, and their rates range from $25 to $35 from downtown.

Abundant parking spaces are available at the airport, including short-term, long-term, and economy parking. Economy has the cheapest rate of $18 per day, and regular parking will cost about $27 daily. Whether you want a quick snack or a full meal, you will discover a variety of restaurants and menu items inside the terminals. Johnny Rockets, Ozone, Boston Beer Works, and Asian Too are a few of your options, and you'll find pizzas, burgers, and more.

Chicago Information

Chicago is a fun and exciting city to visit and has so much to enjoy. Whether you enjoy sports, classical music, or modern architecture, Chicago is the place to be. Located in northern Illinois, Chicago borders Lake Michigan, which provides a variety of water activities. The city has a rich history and diverse culture visitors will enjoy.

When you plan your flight to Chicago, you have two airports to choose from: Chicago O'Hare International Airport and Chicago Midway International Airport. O'Hare is located about 17 miles northwest of downtown, and Midway is 8 miles from downtown. Ground transportation from both airports is offered by way of train, taxi, and shuttle. The CTA trains provide fast and convenient transportation from the airport for $2.25 or less. Taxi fares average about $40 to downtown from O'Hare and $25 from Midway. Shuttle service is provided by Go Airport Express and Omega Airport Shuttle, and their average rate is $25 from O'Hare and $15 from Midway. Most major car rental companies are located at both airports, and you can arrange for a car in advance when you book your flight with Orbitz.com.

The weather in Chicago ranges from cold in the winter to warm in summer. The coldest month is January, during which the average temperature ranges from nightly lows in the teens to daytime highs of around 31 degrees Fahrenheit. July is the warmest month and has average temperatures in the mid-80s. The months of May through August each receive around 4 inches of rainfall. January and February only receive about 2 inches of precipitation, but it is usually in the form of snow.

Chicago has an extensive list of attractions everyone will enjoy. Theater enthusiasts will enjoy the Chicago Shakespeare Theater located on Navy Pier and the Lookingglass Theatre Company. If you enjoy water sports, check out the many attractions on Lake Michigan. Kid and adults will have a great time watching a ballgame at Wrigley Field or spending a day at the Lincoln Zoo.

Start Planning Your Trip to Chicago

Let Orbitz.com help save you time and money when you are planning your trip from Boston to Chicago. You will discover discounts on flights, ground transportation, and hotel accommodations. Take a break from your everyday life, and start planning a fun trip to the Windy City.

Cheap flights from Boston to Chicago

Prices are for round-trip flights per adult (taxes and fees included)

Cheapest fares highlighted below

Sun Mon Tue Wed Thu Fri Sat
27 28 29 30 31 1 $206 2 $206
3 $208 4 $196 5 $196 6 $186 7 $196 8 $206 9 $196
10 11 $196 12 $186 13 $186 14 $196 15 $206 16 $206
17 $226 18 $196 19 $186 20 $186 21 $196 22 $206 23 $206
24 $216 25 $203 26 $186 27 $186 28 1 2

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 48 hours. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.

February

Cheapest weekend flights in February from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Feb 7 Boston (BOS) Chicago (ORD) US Airways $200
Return Mon, Feb 11 Chicago (ORD) Boston (BOS) US Airways

Lowest roundtrip airfare in February from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Feb 6 Boston (BOS) Chicago (ORD) American Airlines $186
Return Wed, Feb 13 Chicago (ORD) Boston (BOS) American Airlines

Best one-week trip in February from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Feb 6 Boston (BOS) Chicago (ORD) American Airlines $186
Return Wed, Feb 13 Chicago (ORD) Boston (BOS) American Airlines
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March

Cheapest weekend flights in March from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Mar 28 Boston (BOS) Chicago (ORD) United Airlines $206
Return Mon, Apr 1 Chicago (ORD) Boston (BOS) United Airlines

Lowest roundtrip airfare in March from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Mar 27 Boston (BOS) Chicago (ORD) United Airlines $186
Return Tue, Apr 2 Chicago (ORD) Boston (BOS) United Airlines

Best one-week trip in March from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Mar 5 Boston (BOS) Chicago (ORD) American Airlines $186
Return Tue, Mar 12 Chicago (ORD) Boston (BOS) American Airlines
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April

Cheapest weekend flights in April from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Apr 27 Boston (BOS) Chicago (ORD) Spirit Airlines $198
Return Mon, Apr 29 Chicago (ORD) Boston (BOS) Spirit Airlines

Lowest roundtrip airfare in April from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Apr 10 Boston (BOS) Chicago (ORD) United Airlines $196
Return Wed, Apr 17 Chicago (ORD) Boston (BOS) United Airlines

Best one-week trip in April from Boston to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Apr 10 Boston (BOS) Chicago (ORD) United Airlines $196
Return Wed, Apr 17 Chicago (ORD) Boston (BOS) United Airlines
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Flight facts

    • 19 direct flights are operating from Boston to Chicago today.
    • Today's average time for a direct flight is 2h 50m.
    • American Airlines flight 1715 (12:00 AM GMT, Boeing 737-800 Passenger) is today's earliest available flight from Boston to Chicago.
    • American Airlines flight 1081 (1:55 PM GMT, Boeing 737-800 Passenger) is today's latest available flight from Boston to Chicago.
    • Today's shortest direct flight from Boston to Chicago (American Airlines flight 1081, Boeing 737-800 Passenger) takes 2h 45m.
    • Today's longest direct flight from Boston to Chicago (American Airlines flight 289, Boeing 737-800 Passenger) takes 3h 0m.

Lowest round trip fares by airline from Boston to Chicago

Airline Departure Arrival Travel dates Round-trip
airline logo United Airlines BOS CHI Wed, Jun 5 - Wed, Jun 19 $185
airline logo American Airlines BOS CHI Tue, Jun 25 - Tue, Jul 9 $185
airline logo US Airways BOS CHI Tue, Jan 29 - Tue, Feb 5 $185
airline logo JetBlue Airways BOS CHI Tue, Jun 25 - Tue, Jul 9 $185
airline logo Spirit Airlines BOS CHI Fri, May 31 - Tue, Jun 4 $197
Delta Airlines Delta Air Lines BOS CHI Tue, Jan 29 - Tue, Feb 5 $207
airline logo AirTran Airways BOS CHI Wed, Jan 16 - Wed, Jan 23 $207
airline logo Virgin America BOS CHI Mon, Jan 28 - Mon, Feb 4 $591
airline logo Alaska Airlines BOS CHI Sat, Feb 23 - Sat, Mar 2 $650
Daily

Daily flight schedule for Fri, Jan 4, 2013

Carrier Flight # Departing Arriving Aircraft Flight time
Airport Time Airport Time
United Airlines UA3460 BOS 5:30 AM ORD 7:25 AM E70 2hr 55min
US Airways US7884 BOS 5:30 AM ORD 7:25 AM E70 2hr 55min
American Airlines AA1715 BOS 6:00 AM ORD 7:55 AM 738 2hr 55min
United Airlines UA457 BOS 7:00 AM ORD 8:51 AM 320 2hr 51min
US Airways US6865 BOS 7:00 AM ORD 8:51 AM 320 2hr 51min
American Airlines AA289 BOS 7:00 AM ORD 9:00 AM 738 3hr 0min
United Airlines UA1181 BOS 8:05 AM ORD 9:51 AM 738 2hr 46min
American Airlines AA1323 BOS 8:30 AM ORD 10:25 AM 738 2hr 55min
United Airlines UA655 BOS 8:55 AM ORD 10:40 AM 752 2hr 45min
US Airways US6144 BOS 8:55 AM ORD 10:40 AM 752 2hr 45min
American Airlines AA1689 BOS 10:15 AM ORD 12:05 PM 738 2hr 50min
United Airlines UA921 BOS 10:36 AM ORD 12:26 PM 319 2hr 50min
US Airways US6453 BOS 10:36 AM ORD 12:26 PM 319 2hr 50min
American Airlines AA1551 BOS 12:00 PM ORD 1:45 PM 738 2hr 45min
American Airlines AA187 BOS 2:10 PM ORD 4:00 PM 738 2hr 50min
United Airlines UA3462 BOS 2:24 PM ORD 4:18 PM E70 2hr 54min
US Airways US7122 BOS 2:24 PM ORD 4:18 PM E70 2hr 54min
JetBlue Airways B6925 BOS 5:05 PM ORD 7:00 PM E90 2hr 55min
United Airlines UA437 BOS 5:39 PM ORD 7:25 PM 752 2hr 46min
American Airlines AA1049 BOS 5:50 PM ORD 7:45 PM 738 2hr 55min
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Weekly

Number of direct flights this week

Carrier Thu 3 Fri 4 Sat 5 Sun 6 Mon 7 Tue 8 Wed 9
airline logo United Airlines 6 8 4 7 7 5 8
airline logo US Airways 4 6 2 4 7 5 5
airline logo American Airlines 8 8 6 7 8 8 7
airline logo JetBlue Airways 1 1 1 1 2 2 2
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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

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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

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