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Flights from Boston to Chicago

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  • Cheap flights with 660+ top airlines
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  • Fly to Chicago from $71

View last minute flights to Chicago

Latest deals from all Boston airports.

Departure Fri, 08 Nov Return Sun, 10 Nov
BOS Boston
MDW Chicago
return from $234
Departure Wed, 23 Oct Return Sat, 26 Oct
BOS Boston
ORD Chicago
return from $71
Departure Fri, 08 Nov Return Sun, 10 Nov
BOS Boston
MDW Chicago
return from $234
Departure Fri, 08 Nov Return Sun, 10 Nov
BOS Boston
ORD Chicago
return from $148
Route information
Find out relevant information on Boston and Chicago to help you prepare for your trip.
( Boston airports
  • ? Logan International Airport (BOS)
    How far from city center: 3 miles
  • ? Lawrence (LWM)
    How far from city center: 25 miles
) Chicago airports
  • ? O'hare International Airport (ORD)
    How far from city center: 14 miles
  • ? Midway Airport (MDW)
    How far from city center: 4 miles
  • ? Pal Waukee (PWK)
    How far from city center: 22 miles
  • ? Dupage County (DPA)
    How far from city center: 27 miles
  • ? Chicago Nas (NOH)
    How far from city center: 22 miles
  • ? Merrill C Meigs (CGX)
    How far from city center: 7 miles
L Distance: 854 miles

Are you searching for flights from Boston to Chicago?

Thinking of a break in Chicago for some well-deserved holidays, to see a loved one or just for business purposes?

Whatever your need is, eDreams will make the job done! Enter your date preferences and let us show you the greatest deals from Boston. If you are looking for a spot of inspiration or are flexible on your travel dates, then take a look at when the cheapest days to fly to Chicago are. If your trip was a last minute afterthought then take a look at our last minute flight prices, there is sure to be something to tempt you. Finally, to make sure that you have everything prepared for your holidays in Chicago, book a hotel and rental car with your flight. Your journey starts here with eDreams!

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