American Airlines flights from Chicago to Boston

Flying from Chicago to Boston

Looking for flight deals to Boston, Massachusetts? Fly nonstop from Chicago O'Hare (ORD) to Boston Logan (BOS) with American Airlines. Plan your trip today to explore Boston's rich history, vibrant culture and renowned dining.

Finding cheap flights from Chicago

Planning a trip from Chicago? Whether you're going for business or pleasure, booking ahead or last minute, American has cheap flight options for your travel needs.

• Book early: Booking 1 to 3 months ahead can help you find cheap flights from Chicago.
• Be flexible with dates: Tuesdays and Wednesdays are often more affordable travel days.
• Travel off-peak: Late January and early February tend to be quieter times, with lower fares and fewer crowds.

Upgrade your flight with Main Cabin Extra

Make your trip more comfortable with Main Cabin Extra. Enjoy benefits like:

• Extra legroom: More space with seats at the front of the Main Cabin or in exit rows.
• Early boarding: Preferred Group 5 boarding allows easier access to overhead bins.
• Complimentary drinks: Enjoy beer, wine and spirits on flights with full beverage service.

Discover how Main Cabin Extra can enhance your trip.

Tips for a smooth departure from Chicago O'Hare International Airport (ORD)

Heading from Chicago to Boston? Planning ahead can help you prepare for your flight, which generally takes about 2 hours and 30 minutes, though timing can vary.

• Arrive early: Plan to arrive at least 2 hours before domestic flights and 3 hours for international trips.
• Get your boarding pass: Download your boarding pass in the American app or print it before you arrive at the airport.
• Know your terminal: American typically operates from Terminal 3 at ORD. Make sure to check your terminal before your flight.
• Have your ID and travel documents: Travelers need a REAL ID or a valid passport to fly within the U.S. For international travel, a valid passport is required, and some destinations may have additional entry requirements.
• Locate the lounge: Admirals Club® lounge access may be available for qualifying customers.
• Find dining options and amenities: ORD offers dining, shopping and amenities near the gates, plus accessible and family bathrooms.

Learn more about how you can manage travel on the go using the American app.

Arriving in Boston

Boston Logan International Airport (BOS)

Boston Logan International Airport (BOS) is one of the largest airports in New England. Located just 3 miles from downtown, BOS is a key destination served by American Airlines, offering easy access to explore Boston's neighborhoods, historical sites and renowned culinary scene.

• MBTA Blue Line subway, Silver Line bus and water ferry: Affordable options that connect to downtown Boston in about 20 – 30 minutes.
• Taxi / rideshare services: Curbside is available at all terminals, typically taking 15–25 minutes to reach downtown Boston.
• Shuttle service: Many hotels offer free or low-cost shuttle rides to and from the airport. Check with your hotel to learn more about shuttle options for your stay.
• Rental cars: Pick up a rental at the airport and explore Boston on your own schedule — perfect if you're planning to travel beyond downtown.

Check out BOS Airport's official website for more details on transportation.

Discover Boston

Best time to visit Boston

Boston is a year-round destination, with each season offering unique experiences.

• Spring and fall: Perfect for historical tours and outdoor activities.
• Summer: Enjoy harbor cruises and al fresco dining.
• Winter: Experience festive events and cozy indoor attractions.

Top things to see and do in Boston

Boston is a city rich in history and culture, offering a wide array of attractions for visitors to explore. Here are some of the most popular and frequently searched tourist destinations:

• Sporting events: Boston has major sporting events throughout the year at Gillette Stadium, Fenway Park, TD Garden and more.
• Freedom Trail: A 2.5-mile walk through Boston's rich history, including landmarks like Paul Revere's House.
• Boston Common: America's oldest public park, perfect for a stroll or a picnic.
• Museum of Fine Arts Boston: A world-class museum with an impressive collection of art from around the globe.
• New England Aquarium: Family-friendly and filled with marine life from around the world.

Booking your trip to Boston with American Airlines

Fly to Boston with American Airlines and experience one of America's most historic and walkable cities. With flights designed to fit your schedule and budget, American Airlines makes planning your Boston adventure simple. Book today and discover why Boston is a must-visit destination.