Book cheap flights from Boston to Chicago from £35

Last minute flights from Boston to Chicago

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Prices shown below were available within the past 3 days for the period specified and should not be considered the final price offered. Please note that availability and prices are subject to change.

Boston Chicago

BEST

DEAL

Sat, 27 Apr BOS - ORD

Mon, 29 Apr ORD - BOS

£259 £249

Prime price per passenger

Boston Chicago

BEST

DEAL

Sat, 08 Jun BOS - ORD

£37 £35

Prime price per passenger

Boston Chicago

BEST

DEAL

Thu, 02 May BOS - MDW

Sat, 04 May MDW - BOS

£140 £132

Prime price per passenger

Boston Chicago

BEST

DEAL

Tue, 07 May BOS - ORD

Thu, 09 May ORD - BOS

£148 £140

Prime price per passenger

Boston Chicago

BEST

DEAL

Sat, 18 May BOS - MDW

Tue, 21 May MDW - BOS

£275 £269

Prime price per passenger

Route information

Distance: 854 miles

Boston airports

Logan International Airport (BOS) How far from city centre: 3 miles

Lawrence (LWM) How far from city centre: 25 miles

Chicago airports

O'hare International Airport (ORD) How far from city centre: 14 miles

Pal Waukee (PWK) How far from city centre: 22 miles

Midway Airport (MDW) How far from city centre: 4 miles

Dupage County (DPA) How far from city centre: 27 miles

Chicago Nas (NOH) How far from city centre: 22 miles

Merrill C Meigs (CGX) How far from city centre: 7 miles

Searching for Boston to Chicago flights?

Enjoy the best flight deals whether you are looking for the cheapest or earliest!

Are you ready to fly with eDreams? Check the last minute airfares or book the lowest route price departing from Boston to Chicago. Stop spending a lot of money to the flight ticket and start enjoying your holiday. No worries, we got your back! eDreams is on your side for a hassle-free and convenient booking experience. You have the privilege to reach the top airline carriers and the cheapest prices. When do you want to depart from Boston? Adjust your travel dates now and explore the dozens of options to Chicago at great prices. Choose a well-suited flight to Chicago amongst the large selection of options, as everything you are looking for is what eDreams offer. You can even book a hotel and rent a car for the perfect vacation mix. It is much easier to book a flight and hotel together, even cheaper! Go ahead; select the best offer from Chicago to Boston and you're done! Enjoy your holiday, but first, fasten your seatbelt. We are flying!

Frequently asked questions about flights from Boston to Chicago

What are the benefits of booking flexible flight tickets?

Using the flexible flight ticket, you're guaranteed a refund or a rebooking option (without fees) in case of flight cancellations when travelling to United States. At eDreams have you covered!

If I want to book flights from Boston to Chicago at eDreams, how can I find them?

Using our flight search engine, you can find flights from £35 for the route Boston - Chicago. At eDreams, we always aim at providing our customers with the cheapest option, allowing you to adjust according to stopovers, airports, dates and many other filters.

What would be the best time to book a flight from Boston to Chicago?

The most popular months to book from Boston to Chicago are May, June and March.

When would be the best time to travel from Boston to Chicago?

The best time of the year to visit Chicago from Boston really depends on lots of personal preferences, especially the price. Regarding popularity, June is the best month to fly to Chicago from Boston in terms of searches from our customers, followed by August and May. If you would rather avoid the busy season and get away from the crowds January, March and December are the months with fewer searches for Boston - Chicago.

What is the duration of a flight from Boston to Chicago?

Flight duration from Boston to Chicago is around 02:54 hours on average, at an average distance of 1,391 km, for flights for the route (which may have 1 or more stops in other cities in between).

From which airports is it possible to fly from Boston to Chicago?

The main route from Boston to Chicago is: Logan International Airport (BOS) to O hare International Airport (ORD). The following airlines fly this route: