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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 28 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

BOS
Boston
CHI
Chicago
 Add details to search for flights
Cheap flights from Boston to Chicago
+75.0%
+50.0%
+25.0%
Base
Price
129 - 209 USD
Temperature
33 - 84 °F
Rainfall
1 - 4 inches
Most popular in April High demand for flights, 7% potential price rise
Cheapest in September Best time to find cheap flights, 2% potential price drop
Average price $185 Price for this month
Cheapest price $129 From Boston to Chicago

Cheap flights from Boston to Chicago in June 2019

The best prices found for BOS to CHI flights for June
4 Jun - 12 Jun
$140pp
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
5 Jun - 12 Jun
$140pp
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
8 Jun - 12 Jun
$140pp
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

Boston to Chicago 2019 flight deals

Cheap flights to Chicago from Boston found for this year
25 Sep - 28 Sep
$139pp
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
7 Sep - 11 Sep
$141pp
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
20 Sep - 24 Sep
$141pp
BOS
Boston Logan Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BOS
Boston Logan Intl

Non-stop flights to Chicago from Boston

Save time with Boston to Chicago direct flight deals
4 Jun - 12 Jun
$140pp
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
5 Jun - 12 Jun
$140pp
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
8 Jun - 12 Jun
$140pp
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

Last minute flights from Boston to Chicago

Late deals on round-trip flights to Chicago from Boston, departing today and this week
30 May - 8 Jun
$150pp
BOS
Boston Logan Intl
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BOS
Boston Logan Intl
31 May - 4 Jun
$154pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
29 May - 5 Jun
$160pp
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

Destination information for Chicago

Things to know before you go. Useful info for your trip from Boston to Chicago
Flight duration
2h 34m

Airports servicing Boston

Boston (BOS)

Airports servicing Chicago

Chicago Midway (MDW)
Chicago-O'Hare Intl (ORD)
Rockford (RFD)
Average temperature for May in Chicago
21.6 °C
Avg rainfall for May in Chicago
108.9 mm
During this time it is forecast that there will be 0.58 inch more rainfall in Chicago than in Boston .
During the next 10 days, the weather in Chicago is expected to be 2.9°F warmer than Boston (68.0°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 25 airlines offering direct flights from Boston to Chicago , including Japan Airlines, Icelandair, Delta.
So far this month, there have been 2374 searches for flights from Boston to Chicago.

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
How many passenger seats are available on a flight on this route?
Popular American Airlines Inc. operates 214 flight per week
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