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Cheap flights from Boston to Chicago (BOS - CHI)

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The best prices from Boston to Chicago are usually found in September or January, booked 59 days in advance, depart on a Tuesday or Saturday and return on a Tuesday

Cheap flights from Boston to Chicago
+60.0%
+40.0%
+20.0%
Base
Price
$153 - $225
Temperature
34 - 84 °F
Rainfall
1 - 4 inches
Most popular in July High demand for flights, 13% potential price rise
Cheapest in September Best time to find cheap flights, 2% potential price drop
Average price $153 Price for this month
Cheapest price $153 From Boston to Chicago

Cheap flights from Boston to Chicago in September 2019

The best prices found for BOS to ORD flights for September
26 Sep - 1 Oct
$100pp
BOS
Boston Logan Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BOS
Boston Logan Intl
28 Sep - 1 Oct
$100pp
BOS
Boston Logan Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BOS
Boston Logan Intl
25 Sep - 2 Oct
$105pp
BOS
Boston Logan Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BOS
Boston Logan Intl

Boston to Chicago 2019 flight deals

Cheap flights to Chicago from Boston found for this year
30 Oct - 2 Nov
$80pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
19 Oct - 24 Oct
$100pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
26 Oct - 28 Oct
$100pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl

Non-stop flights to Chicago from Boston

Save time with Boston to Chicago direct flight deals
30 Oct - 2 Nov
$80pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
26 Oct - 28 Oct
$100pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
29 Oct - 30 Oct
$100pp
BOS
Boston Logan Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BOS
Boston Logan Intl

Last minute flights from Boston to Chicago

Late deals on round-trip flights to Chicago from Boston, departing today and this week
26 Sep - 1 Oct
$100pp
BOS
Boston Logan Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BOS
Boston Logan Intl
25 Sep - 2 Oct
$105pp
BOS
Boston Logan Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BOS
Boston Logan Intl
21 Sep - 29 Sep
$128pp
BOS
Boston Logan Intl
Major Airline
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Major Airline
Non-Stop
BOS
Boston Logan Intl

Alternative routes for Boston to Chicago

Bangor to Detroit from $252 pp New York to Fort Wayne from $273 pp Albany to Fort Wayne from $408 pp

Destination information for Chicago

Things to know before you go. Useful info for your trip from Boston to Chicago
Flight duration
2h 41m
Average temperature for September in Chicago
77.0 °F
Avg rainfall for September in Chicago
2.4 ″

Airports servicing Boston

Boston (BOS)

Airports servicing Chicago

Chicago Midway (MDW)
Chicago-O'Hare Intl (ORD)
Rockford (RFD)

Popular flight searches

Check out other popular destinations found by fellow travelers
During this time it is forecast that there will be 1 inch less rainfall in Chicago than in Boston .
During the next 10 days, the weather in Chicago is expected to be 2°F warmer than Boston (75°F).
Recently Sun, Mon, Tue, Wed, Thu, Fri and Sat are the days when direct flights are available.
Which airlines fly from Boston to Chicago?
There are currently 26 airlines offering direct flights from Boston to Chicago , including JAL, Icelandair, Delta.
So far this month, there have been 2179 searches for flights from Boston to Chicago.
How many flights depart from Boston to Chicago on average per day?
On average, you can expect to see 202 flights from Boston Logan Intl to Chicago a day.
Early Morning (Midnight to 6am) - 12% of flight departures
Morning (6am - Noon) - 36% of flight departures
Afternoon (Noon - 6pm) - 31% of flight departures
Evening (6pm - Midnight) - 21% of flight departures
How long does the flight from Boston to Chicago take?
A nonstop flight takes up to 3 hours, covering a distance of 536 miles.

Related info for your journey

Useful info, stats and facts about Boston to Chicago flights.
Flight FAQs
From Boston to Chicago
What percent of flights are delayed?
A delay of 1 hr 12.7 mins is common
How many passenger seats are available on a flight on this route?
On average, all flights from Boston offer a total of 2,337 seats to Chicago per day
What is the cheapest airline for this route?
The cheapest airline for this route is American Airlines Inc. on average. American Airlines Inc. operates 214 flight per week
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