Menu
Menu
New York

Cheap flights from Chicago to Boston (CHI - BOS)

Know your dates, get live prices in seconds:

From
To
Depart
–
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
Add another flight clear all

We work with more than 300 partners to bring you better travel deals

The best prices from Chicago to Boston are usually found in September or October, booked 58 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

CHI
Chicago
BOS
Boston
 Add details to search for flights
Cheap flights from Chicago to Boston
+45.0%
+30.0%
+15.0%
Base
Price
141 - 199 USD
Temperature
40 - 84 °F
Rainfall
3 - 4 inches
Most popular in March High demand for flights, 6% potential price rise
Cheapest in September Best time to find cheap flights, 2% potential price drop
Average price $176 Price for this month
Cheapest price $141 From Chicago to Boston

Cheap flights from Chicago to Boston in June 2019

The best prices found for CHI to BOS flights for June
5 Jun - 11 Jun
$140pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
8 Jun - 11 Jun
$140pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
11 Jun - 18 Jun
$140pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Chicago to Boston 2019 flight deals

Cheap flights to Boston from Chicago found for this year
7 Sep - 10 Sep
$139pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
24 Sep - 28 Sep
$139pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
25 Sep - 29 Sep
$141pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Non-stop flights to Boston from Chicago

Save time with Chicago to Boston direct flight deals
5 Jun - 11 Jun
$140pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
8 Jun - 11 Jun
$140pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
11 Jun - 18 Jun
$140pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Boston

Late deals on round-trip flights to Boston from Chicago, departing today and this week
31 May - 4 Jun
$150pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
30 May - 4 Jun
$152pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Destination information for Boston

Things to know before you go. Useful info for your trip from Chicago to Boston
Flight duration
2h 39m

Airports servicing Chicago

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

Airports servicing Boston

Boston (BOS)
Average temperature for May in Boston
20.0 °C
Avg rainfall for May in Boston
94.1 mm
There will be 0.58 inch less rainfall in Boston than in Chicago over the next ten days.
Over the next ten days, Boston (68.0°F) is expected to be 2.9°F cooler than Chicago (70.9°F).
Recently Sun, Mon, Tue, Wed, Thu, Fri and Sat are the days when direct flights are available.
Which airlines fly from Chicago to Boston?
Direct flights from Chicago to Boston are currently served by 25 airlines, including Japan Airlines, Icelandair and Delta.
In the last month, 1673 people have been searching for flights from Chicago to Boston.

Related info for your journey

Useful info, stats and facts about Chicago to Boston flights.
Flight FAQs
From Chicago to Boston
What percent of flights are delayed?
A delay of 1 hr 0 mins is common
How many passenger seats are available on a flight on this route?
On average, all flights from Chicago offer a total of 2,388 seats to Boston per day
How many passenger seats are available on a flight on this route?
Popular American Airlines Inc. operates 206 flight per week
Related searches
Flights to Boston from Chicago
Flights to Chicago
Flights to Boston