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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)
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) |
|
$200 |
| Return Mon, Feb 11 | Chicago (ORD) | Boston (BOS) |
|
Lowest roundtrip airfare in February from Boston to Chicago
| Travel dates | Departure | Arrival | Stops: | Round-trip |
|---|---|---|---|---|
| Leave Wed, Feb 6 | Boston (BOS) | Chicago (ORD) |
|
$186 |
| Return Wed, Feb 13 | Chicago (ORD) | Boston (BOS) |
|
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) |
|
$186 |
| Return Wed, Feb 13 | Chicago (ORD) | Boston (BOS) |
|
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) |
|
$206 |
| Return Mon, Apr 1 | Chicago (ORD) | Boston (BOS) |
|
Lowest roundtrip airfare in March from Boston to Chicago
| Travel dates | Departure | Arrival | Stops: | Round-trip |
|---|---|---|---|---|
| Leave Wed, Mar 27 | Boston (BOS) | Chicago (ORD) |
|
$186 |
| Return Tue, Apr 2 | Chicago (ORD) | Boston (BOS) |
|
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) |
|
$186 |
| Return Tue, Mar 12 | Chicago (ORD) | Boston (BOS) |
|
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) |
|
$198 |
| Return Mon, Apr 29 | Chicago (ORD) | Boston (BOS) |
|
Lowest roundtrip airfare in April from Boston to Chicago
| Travel dates | Departure | Arrival | Stops: | Round-trip |
|---|---|---|---|---|
| Leave Wed, Apr 10 | Boston (BOS) | Chicago (ORD) |
|
$196 |
| Return Wed, Apr 17 | Chicago (ORD) | Boston (BOS) |
|
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) |
|
$196 |
| Return Wed, Apr 17 | Chicago (ORD) | Boston (BOS) |
|
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 |
|---|---|---|---|---|
|
| BOS | CHI | Wed, Jun 5 - Wed, Jun 19 | $185 |
|
| BOS | CHI | Tue, Jun 25 - Tue, Jul 9 | $185 |
|
| BOS | CHI | Tue, Jan 29 - Tue, Feb 5 | $185 |
|
| BOS | CHI | Tue, Jun 25 - Tue, Jul 9 | $185 |
|
| BOS | CHI | Fri, May 31 - Tue, Jun 4 | $197 |
|
| BOS | CHI | Tue, Jan 29 - Tue, Feb 5 | $207 |
|
| BOS | CHI | Wed, Jan 16 - Wed, Jan 23 | $207 |
|
| BOS | CHI | Mon, Jan 28 - Mon, Feb 4 | $591 |
|
| 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 |
Weekly
Number of direct flights this week
| Carrier | Thu 3 | Fri 4 | Sat 5 | Sun 6 | Mon 7 | Tue 8 | Wed 9 |
|---|---|---|---|---|---|---|---|
|
|
6 | 8 | 4 | 7 | 7 | 5 | 8 |
|
|
4 | 6 | 2 | 4 | 7 | 5 | 5 |
|
|
8 | 8 | 6 | 7 | 8 | 8 | 7 |
|
|
1 | 1 | 1 | 1 | 2 | 2 | 2 |
Airports in Boston, MA, US
-
1
Boston Logan Airport (BOS)
Distance from City Center: 3 miles
Airports in Chicago, IL, US
-
1
Midway Airport (MDW)
Distance from City Center: 9.5 miles
-
2
O'Hare Airport (ORD)
Distance from City Center: 15.1 miles