Cheap flights from Chicago to Boston

Yes, it's possible to combine different modes of transport between Chicago and Boston thanks to our Virtual Interlining technology. Making use of not only flights but also trains and buses between Chicago and Boston can give rise to new adventures. Read more about how Virtual Interlining works on Kiwi.com Stories.

Virtual Interlining provides a revolutionary way of traveling. You can combine different modes of transport like flights, trains, and buses into one itinerary. And this often saves money. Thanks to the world's largest carrier database, the Kiwi.com search function enables anyone to mix and match different modes of transport easily.

Currently, you can fly between Chicago and Boston with Southwest Airlines, American Airlines, United Airlines, Spirit Airlines, Delta Air Lines.

If you don’t have specific dates for your trip between Chicago and Boston, you can enter a date range into the departure and return fields. Most carriers on the Kiwi.com website allow you to search and book up to six months from the day of your search. Order the search results by the best, cheapest, or fastest route, or find the cheapest outbound and return combination in the pricing table.

Traveling between Chicago and Boston, you can choose between direct (nonstop) flights or flights with one or more stops. You can select the number of stops on your journey, including an overnight stopover, and the duration of the stopover. What's more, you can also select where you want to have your stopover. Want to say "Hi" to a friend in another city en route to your destination? Or fancy a quick round of shopping? Go Multi-City or Nomad and add places to your search that you wish to visit.

There are a number of airports in and around Chicago. The main one is O Hare International and other nearby airports include General Mitchell International, Gerald R. Ford International, Dane County Regional, General Wayne A. Downing Peoria International, Quad City International, South Bend International, Fort Wayne International, Central Illinois Regional, Muskegon County, Kalamazoo/Battle Creek International

There are a number of airports in and around Boston. The main one is Logan International and other nearby airports include Logan International, Bradley International, T. F. Green, Albany International, Portland International Jetport, Lebanon Municipal, Portsmouth International Airport at Pease, Barnstable Municipal, Rutland–Southern Vermont Regional, Knox County Regional.

Yes, Chicago has great ground transport connections with the rest of the world. Our price graph doesn't just show prices for flights to and from Chicago, it also shows buses and trains.

This depends on the airline's flight schedule. You can easily select your preferred departure time when you search on our website or mobile app. Choose the time of day you wish to depart from Chicago, such as morning, afternoon, evening, or night, or select the exact hours for departure.

This depends on the airline's flight schedule. You can easily select your preferred arrival time when you search on our website or mobile app. Choose the time of day you wish to arrive at Boston, such as morning, afternoon, evening, or night, or select the exact hours for arrival.

This depends on the airline's flight schedule. You can easily select your preferred departure time when you search on our website or mobile app. Choose the time of day you wish to depart from Chicago, such as morning, afternoon, evening, or night, or select the exact hours for departure.

This depends on the airline's flight schedule. You can easily select your preferred arrival time when you search on our website or mobile app. Choose the time of day you wish to arrive at Boston, such as morning, afternoon, evening, or night, or select the exact hours for arrival.