Menu

Cheap flights from Boston to Chicago (BOS - CHI)

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

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

The best prices from Boston to Chicago are usually found in September or October, booked 54 days in advance, depart on a Saturday or Tuesday and return on a Wednesday

$250
$220
$190
$157
Price
$157 - $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 $173 Price for this month
Cheapest price $157 From Boston to Chicago

Cheap flights from Boston to Chicago in February 2020

The best prices found for BOS to ORD flights for February
7 Feb - 10 Feb
$95pp
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
18 Feb - 25 Feb
$114pp
BOS
Boston Logan Intl
Delta
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
BOS
Boston Logan Intl
28 Feb - 4 Mar
$121pp
BOS
Boston Logan Intl
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
BOS
Boston Logan Intl

Boston to Chicago 2020 flight deals

Cheap flights to Chicago from Boston found for this year
5 May - 6 May
$76pp
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
15 May - 20 May
$81pp
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
4 May - 6 May
$87pp
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
1 Feb - 3 Feb
$95pp
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
10 Apr - 12 Apr
$117pp
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
1 Feb - 3 Feb
$95pp
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
31 Jan - 2 Feb
$103pp
BOS
Boston Logan Intl
Major Airline
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Major Airline
 
1 STOP
BOS
Boston Logan Intl
30 Jan - 14 Apr
$111pp
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

Alternative routes for Boston to Chicago

Destination information for Chicago

Things to know before you go. Useful info for your trip from Boston to Chicago
Flight duration
2h 39m
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing Boston

Airports servicing Chicago

Chicago-O'Hare Intl (ORD)
Rockford (RFD)
Weekly flight availability
from Boston to Chicago
Sunday
20 daily flights
Monday
57 daily flights
Tuesday
56 daily flights
Wednesday
61 daily flights
Thursday
55 daily flights
Friday
54 daily flights
Saturday
16 daily flights

Related info for your journey

Useful info, stats and facts about Boston to Chicago flights.

Flight FAQs

From Boston to Chicago

What days are nonstop flights available from Boston to Chicago?

Days when nonstop flights are available for this flight are: Sunday, Monday, Tuesday, Wednesday, Thursday, Friday, Saturday.

How popular is this flight route?

This flight path from Boston Logan Intl to Chicago was viewed by 171 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

What percent of flights are delayed?

Flights from Boston to Chicago are usually delayed by 73min. so prepare accordingly.

How many passenger seats are available on a flight on this route?

On average, there are a total of 2,337 seats offered from Boston Logan Intl to Chicago per day.

What is the cheapest airline for this route?

The cheapest airline for this route is American Airlines Inc.. When flying this airline from Boston to Chicago on average you can expect to find 214 flights available for this route daily.

How long does the flight from Boston to Chicago take?

A nonstop flight takes up to 3 hours, covering a distance of 536 miles.

How many flights depart from Boston to Chicago on average per day?

On average, you can expect to see 150 flights from Boston Logan Intl to Chicago a day.
Early Morning (Midnight to 6am) - 8% of flight departures
Morning (6am - Noon) - 37% of flight departures
Afternoon (Noon - 6pm) - 32% of flight departures
Evening (6pm - Midnight) - 23% of flight departures

Is Boston weather warmer or cooler than Chicago?

We forecast the temperature to be around the 84 °F's in July, on average. The temperature in Chicago is generally the same as in Boston. Book flights in a timely manner in correlation to your departure date.