Cheap Flights from Boston Logan International (BOS) to Chicago (CHI)

Top tips for finding a cheap flight from Boston to Chicago

Finding cheap tickets from Boston to Chicago is easy with a little flexibility. Use our Whole Month search feature to scan through the calendar for the cheapest dates. You can also set up a Price Alert for your route and let us monitor the fares for you, sending notifications when prices change. If you’d rather skip layovers, select the Direct Flights search to view non-stop options that’ll save you time.

Booking your tickets early often leads to savings, but we can also find you some last-minute deals. In general, January is the best time to schedule your trip from Boston to Chicago, with the lowest average fares across the board. Keep these strategies in mind to find the best itinerary.

Handy information about Boston airport

Boston Logan International Airport serves as the primary gateway for travelers in and out of Boston. This airport features four terminals, each catering to both domestic and international flights.

Terminal A offers a range of airlines and includes gates from A1 to A22, with ground transportation options that include taxis, rental cars, shuttles, and ridesharing services. Terminal B is divided into four concourses (B1 to B4) and hosts a variety of carriers with similar transportation amenities. Terminal C serves a selection of airlines and provides extensive transport links. Terminal E is the primary terminal for international travelers. All terminals provide an array of ground transport options to cater to passenger needs. For the most up-to-date information regarding flights and services, consult the official Boston Logan International Airport website or contact your airline directly.

Chicago airport: good to know

Chicago caters to a broad range of air travel needs through its diverse array of airports. Chicago O'Hare International Airport, one of the world's largest airports, boasts four terminals, providing numerous ground transport options including the CTA "L" train, connecting passengers to virtually anywhere in the city. It serves a wide range of domestic and international destinations, with a dedicated terminal for international travelers.

Complementing O'Hare, Chicago Midway International Airport operates from one terminal with three concourses and ensures connectivity with various ground transportation modes, focusing primarily on domestic flights and a few international routes. For more personalized travel, both Chicago Executive and DuPage Airports offer a terminal each for private and corporate aircraft, alongside convenient transport services. Lastly, Chicago Rockford, despite its single terminal structure, supports domestic travel, particularly catering to budget-conscious passengers. Each airport, strategically located, makes accessible the vast metropolitan landscape and aligns with different travel preferences, maintaining Chicago's reputation as a significant transportation hub. Improve your travel experience when flying from Boston to Chicago by finding out what airport facilities are available.

Best time to fly from Boston to Chicago

The best time to fly from Boston to Chicago is during the spring or fall months when the weather is mild and more enjoyable for sightseeing. In spring, from March to May, temperatures in Chicago range between a comfortable 43°F and 63°F. Alternatively, fall temperatures from September to November are equally pleasant, averaging 45°F to 68°F. These periods avoid the cold and potential snow disruptions of winter and the occasional heatwaves of the summer months, making them ideal for your travel plans.

Reasons to visit Chicago

When planning your trip to Chicago, check out these activities and attractions the city has to offer. Tap into the energy of Lollapalooza, a celebrated music festival that draws fans and top artists alike for an unforgettable experience. Rise above the city streets at the Willis Tower Skydeck to capture expansive views from one of the tallest buildings in the world. Find a moment of tranquility as you stroll through Millennium Park and gaze upon the renowned public art and architecture. Not to be missed, The Art Institute of Chicago houses a vast collection that spans thousands of years, offering insights into humanity's creative legacy.

Add hotel bookings and car hire to your Boston to Chicago flight

Planning your trip to Chicago is easy and convenient with Skyscanner. Find the perfect vehicle for your stay from trusted rental car brands like Budget, Europcar, and Thrifty. Accommodation choices are plentiful; choose from well-known hotels such as The Palmer House Hilton, Hyatt Regency Chicago, or InterContinental Chicago Magnificent Mile, an IHG Hotel. Skyscanner helps you organize both your travel and comfortable stay in the Windy City.