Cheap flights from Chicago to Boston

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Easily compare round-trip flights from Chicago to Boston

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 Chicago to Boston by changing tabs
Quickest
Cheapest
Spirit Airlines
Spirit Airlines
09 Nov
ORD
8:20 am
Chicago O'Hare Intl airport
2h 28m
11:48 am
BOS
Boston Logan Intl airport
Spirit Airlines
12 Nov
BOS
8:25 am
Boston Logan Intl airport
2h 55m
10:20 am
ORD
Chicago O'Hare Intl airport
80 USD
Spirit Airlines
Spirit Airlines
09 Nov
ORD
8:20 am
Chicago O'Hare Intl airport
2h 28m
11:48 am
BOS
Boston Logan Intl airport
Spirit Airlines
12 Nov
BOS
8:25 am
Boston Logan Intl airport
2h 55m
10:20 am
ORD
Chicago O'Hare Intl airport
80 USD
Spirit Airlines
Spirit Airlines
02 Nov
ORD
9:20 am
Chicago O'Hare Intl airport
2h 28m
12:48 pm
BOS
Boston Logan Intl airport
Spirit Airlines
05 Nov
BOS
8:25 am
Boston Logan Intl airport
2h 55m
10:20 am
ORD
Chicago O'Hare Intl airport
85 USD
Major Airline
Major Airline
27 Oct
ORD
12:01 am
Chicago O'Hare Intl airport
2h 15m
3:16 am
BOS
Boston Logan Intl airport
Major Airline
28 Oct
BOS
6:50 pm
Boston Logan Intl airport
2h 44m
8:34 pm
ORD
Chicago O'Hare Intl airport
97 USD
Major Airline
Major Airline
27 Oct
ORD
12:01 am
Chicago O'Hare Intl airport
2h 15m
3:16 am
BOS
Boston Logan Intl airport
Major Airline
28 Oct
BOS
6:50 pm
Boston Logan Intl airport
2h 44m
8:34 pm
ORD
Chicago O'Hare Intl airport
97 USD
American Airlines
American Airlines
14 Dec
ORD
11:20 am
Chicago O'Hare Intl airport
2h 17m
2:37 pm
BOS
Boston Logan Intl airport
American Airlines
16 Dec
BOS
2:59 pm
Boston Logan Intl airport
2h 46m
4:45 pm
ORD
Chicago O'Hare Intl airport
125 USD

How to get the cheapest flight ticket from Chicago to Boston

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 Boston?
September
The cheapest time of year to fly to Boston from Chicago is September. Most expensive is July
What is the cheapest day to fly to Boston?
Wednesday
The cheapest day of the week is typically Wednesday. The most expensive is typically Sunday
When is the cheapest time to fly to Boston?
at noon
Chicago to Boston flights are approximately 29% more expensive in the afternoon than at noon
What is the cheapest airline that flies to Boston?
Spirit Airlines
Spirit Airlines, Delta, and Envoy Air are the most popular carriers operating from Chicago to Boston
What is the cheapest route?
Chicago O'Hare Intl - Boston Logan Intl
Fly from Chicago O'Hare Intl to Boston Logan Intl for the best Chicago - Boston flight prices
When is the cheapest time to book a flight to Boston?
60 days before
The cheapest time to buy a flight from Chicago to Boston is approximately 60 days to departure
60
Days before departure
0

Flight information for Chicago to Boston (BOS - CHI)

Find info about flight duration, direct flights, and airports for your flight from Chicago to Boston
Fastest flight time 2h 5m The fastest flight from Chicago to Boston takes 2h 5m.
Direct flights Every day Direct flights go from Chicago to Boston every day.
Airports in Boston 1 airport There is 1 airport near Boston: Boston Logan Intl (BOS)

Alternative routes for Chicago to Boston

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Indianapolis to Boston
Fastest flight time
2h 13m
Cheapest price
175 USD
Chicago to Islip
Fastest flight time
3h 55m
Cheapest price
194 USD
Indianapolis to Islip
Fastest flight time
4h 48m
Cheapest price
204 USD
Chicago to Providence
Fastest flight time
2h 20m
Cheapest price
213 USD
View more

Flights from Chicago to: