Cheap flights from Boston to Chicago

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Easily compare round-trip flights from Boston to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Boston to Chicago by changing tabs
Quickest
Cheapest
Spirit Airlines
Spirit Airlines
10 Dec
BOS
5:26 pm
Boston Logan Intl airport
9h 29m
1 Stop
1:55 am
+1
ORD
Chicago O'Hare Intl airport
Spirit Airlines
14 Dec
ORD
2:40 pm
Chicago O'Hare Intl airport
9h 49m
1 Stop
1:29 am
+1
BOS
Boston Logan Intl airport
120 USD
Delta
Delta
05 Dec
BOS
1:00 am
Boston Logan Intl airport
3h 09m
3:09 am
ORD
Chicago O'Hare Intl airport
Delta
07 Dec
ORD
8:00 am
Chicago O'Hare Intl airport
2h 19m
11:19 am
BOS
Boston Logan Intl airport
125 USD
Frontier
Frontier
04 Feb
BOS
6:52 am
Boston Logan Intl airport
9h 11m
1 Stop
3:03 pm
ORD
Chicago O'Hare Intl airport
Frontier
07 Feb
ORD
2:57 am
Chicago O'Hare Intl airport
2h 12m
6:09 am
BOS
Boston Logan Intl airport
142 USD
American Airlines
American Airlines
29 Feb
BOS
4:00 am
Boston Logan Intl airport
2h 41m
5:41 am
ORD
Chicago O'Hare Intl airport
American Airlines
01 Mar
ORD
1:45 am
Chicago O'Hare Intl airport
2h 12m
4:57 am
BOS
Boston Logan Intl airport
157 USD
Major Airline
Major Airline
16 Mar
BOS
2:00 am
Boston Logan Intl airport
2h 41m
3:41 am
ORD
Chicago O'Hare Intl airport
Major Airline
21 Mar
ORD
5:19 pm
Chicago O'Hare Intl airport
2h 19m
8:38 pm
BOS
Boston Logan Intl airport
158 USD
Major Airline
Major Airline
27 Mar
BOS
2:00 am
Boston Logan Intl airport
2h 41m
3:41 am
ORD
Chicago O'Hare Intl airport
Major Airline
30 Mar
ORD
5:19 pm
Chicago O'Hare Intl airport
2h 19m
8:38 pm
BOS
Boston Logan Intl airport
158 USD

How to get the cheapest flight ticket from Boston to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago?
September
The cheapest time of year to fly to Chicago from Boston is September. Most expensive is July
What is the cheapest day to fly to Chicago?
Saturday
The cheapest day of the week is typically Saturday. The most expensive is typically Sunday
When is the cheapest time to fly to Chicago?
at noon
Boston to Chicago flights are approximately 30% more expensive in the afternoon than at noon
What is the cheapest airline that flies to Chicago?
Frontier
Frontier, Sun Country Air, and Spirit Airlines are the most popular carriers operating from Boston to Chicago
What is the cheapest route?
Boston Logan Intl - Chicago O'Hare Intl
Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Boston - Chicago flight prices
When is the cheapest time to book a flight to Chicago?
56 days before
The cheapest time to buy a flight from Boston to Chicago is approximately 56 days to departure
60
Days before departure
0

Flight information for Boston to Chicago (CHI - BOS)

Find info about flight duration, direct flights, and airports for your flight from Boston to Chicago
Fastest flight time 2h 44m The fastest flight from Boston to Chicago takes 2h 44m.
Direct flights Every day Direct flights go from Boston to Chicago every day.
Airports in Chicago 3 airports There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

Alternative routes for Boston to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Islip to Chicago
Fastest flight time
4h 12m
Cheapest price
128 USD
Providence to Chicago
Fastest flight time
2h 37m
Cheapest price
150 USD
Boston to Indianapolis
Fastest flight time
2h 40m
Cheapest price
157 USD
Islip to Indianapolis
Fastest flight time
4h 10m
Cheapest price
178 USD
Providence to Indianapolis
Fastest flight time
4h 15m
Cheapest price
242 USD
View more

Flights from Boston to:

*Flight prices to Chicago are based on prices for economy tickets found by momondo users during searches within the last 72 hours. These prices may no longer be available.