Flights from Boston to Chicago

Our cheapest offers for flights from Boston to Chicago

Here you can compare cheap flights from Boston (BOS) to Chicago (CHI) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Chicago. Prices and availability may change at any time.

Tips and tricks to help you find cheap flights from Boston to Chicago

Favorite airline: Sun Country Airlines
Sun Country Airlines is the most popular airline for flights from Boston to Chicago.
Sun Country Airlines
30 %
American Airlines
19 %
United Airlines
16 %
Tip: book 6 months before departure
Save up to 29 % by booking flights 6 months before departure.
179 days before departure
Cheapest weekday: Friday
Choosing the right day of the week is worthwhile as prices of flights on this route are cheapest on Friday.
Direct flights are the cheapest connection
Direct flights on this route are $18.00 cheaper on average than flights with a stopover.
non stop flight
1 stop
02h 59min
05h 45min
Favourite connection: via Minneapolis
Flights with a stopover in Minneapolis are the most popular connection for this route.
1 stopover Minneapolis - St. Paul International Airport, MN
08h 25min, from $286
33 %
Direct flights
02h 59min, from $199
32 %
1 stopover Orlando International Airport, FL
10h 02min, from $298
13 %

Flight information: Boston - Chicago

Roundtrip from $278.39
Flight duration min. 02:45 / max. 06:55
Return flight duration min. 02:08/ max. 11:15
Distance 1371 km
Flights per week 162
Departure airport Boston Logan International Airport, MA (BOS)
Arrival airport Chicago-IL all Airports (ORD, MDW, RFD) (CHI)
Destination country United States
Alternative routes to United States
Alternative flights to Chicago
Flight destinations with a similar price
Flight destinations with a similar price