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
22 Oct
BOS
9:25 am
Boston Logan Intl airport
2h 55m
11:20 am
ORD
Chicago O'Hare Intl airport
Spirit Airlines
23 Oct
ORD
9:20 am
Chicago O'Hare Intl airport
2h 28m
12:48 pm
BOS
Boston Logan Intl airport
73 USD
Spirit Airlines
Spirit Airlines
30 Oct
BOS
9:25 am
Boston Logan Intl airport
2h 55m
11:20 am
ORD
Chicago O'Hare Intl airport
Spirit Airlines
02 Nov
ORD
9:20 am
Chicago O'Hare Intl airport
2h 28m
12:48 pm
BOS
Boston Logan Intl airport
80 USD
Spirit Airlines
Spirit Airlines
25 Sep
BOS
8:57 am
Boston Logan Intl airport
2h 53m
10:50 am
ORD
Chicago O'Hare Intl airport
Spirit Airlines
28 Sep
ORD
8:46 am
Chicago O'Hare Intl airport
2h 35m
12:21 pm
BOS
Boston Logan Intl airport
82 USD
JetBlue
JetBlue
26 Oct
BOS
4:52 pm
Boston Logan Intl airport
2h 49m
6:41 pm
ORD
Chicago O'Hare Intl airport
JetBlue
29 Oct
ORD
12:01 am
Chicago O'Hare Intl airport
2h 15m
3:16 am
BOS
Boston Logan Intl airport
105 USD
JetBlue
JetBlue
30 Sep
BOS
4:52 pm
Boston Logan Intl airport
2h 49m
6:41 pm
ORD
Chicago O'Hare Intl airport
JetBlue
03 Oct
ORD
12:40 am
Chicago O'Hare Intl airport
2h 18m
3:58 am
BOS
Boston Logan Intl airport
105 USD
JetBlue
JetBlue
29 Sep
BOS
2:45 am
Boston Logan Intl airport
2h 55m
4:40 am
ORD
Chicago O'Hare Intl airport
JetBlue
30 Sep
ORD
12:40 am
Chicago O'Hare Intl airport
2h 18m
3:58 am
BOS
Boston Logan Intl airport
105 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?
Tuesday
The cheapest day of the week is typically Tuesday. The most expensive is typically Sunday
When is the cheapest time to fly to Chicago?
at noon
Boston to Chicago flights are approximately 25% more expensive in the afternoon than at noon
What is the cheapest airline that flies to Chicago?
Sun Country Air
Sun Country Air, Spirit Airlines, and Delta 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?
59 days before
The cheapest time to buy a flight from Boston to Chicago is approximately 59 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 40m The fastest flight from Boston to Chicago takes 2h 40m.
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
162 USD
Boston to Indianapolis
Fastest flight time
2h 38m
Cheapest price
182 USD
Providence to Chicago
Fastest flight time
2h 37m
Cheapest price
188 USD
Islip to Indianapolis
Fastest flight time
3h 47m
Cheapest price
226 USD
Providence to Indianapolis
Fastest flight time
4h 00m
Cheapest price
241 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.