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
20 Aug
BOS
8:35 am
Boston Logan Intl airport
2h 51m
10:26 am
ORD
Chicago O'Hare Intl airport
Spirit Airlines
24 Aug
ORD
9:16 am
Chicago O'Hare Intl airport
2h 29m
12:45 pm
BOS
Boston Logan Intl airport
93 USD
Spirit Airlines
Spirit Airlines
27 Aug
BOS
8:35 am
Boston Logan Intl airport
2h 51m
10:26 am
ORD
Chicago O'Hare Intl airport
Spirit Airlines
28 Aug
ORD
9:16 am
Chicago O'Hare Intl airport
2h 29m
12:45 pm
BOS
Boston Logan Intl airport
93 USD
Spirit Airlines
Spirit Airlines
07 Sep
BOS
8:57 am
Boston Logan Intl airport
2h 53m
10:50 am
ORD
Chicago O'Hare Intl airport
Spirit Airlines
08 Sep
ORD
8:46 am
Chicago O'Hare Intl airport
2h 35m
12:21 pm
BOS
Boston Logan Intl airport
101 USD
United Airlines
United Airlines
19 Aug
BOS
1:20 am
Boston Logan Intl airport
2h 39m
2:59 am
ORD
Chicago O'Hare Intl airport
United Airlines
21 Aug
ORD
9:16 am
Chicago O'Hare Intl airport
2h 29m
12:45 pm
BOS
Boston Logan Intl airport
135 USD
United Airlines
United Airlines
24 Aug
BOS
1:25 am
Boston Logan Intl airport
2h 40m
3:05 am
ORD
Chicago O'Hare Intl airport
United Airlines
26 Aug
ORD
9:16 am
Chicago O'Hare Intl airport
2h 29m
12:45 pm
BOS
Boston Logan Intl airport
131 USD
United Airlines
United Airlines
25 Aug
BOS
1:25 am
Boston Logan Intl airport
2h 40m
3:05 am
ORD
Chicago O'Hare Intl airport
United Airlines
27 Aug
ORD
9:16 am
Chicago O'Hare Intl airport
2h 29m
12:45 pm
BOS
Boston Logan Intl airport
131 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 April
WHAT IS THE CHEAPEST DAY TO FLY TO CHICAGO?
Tuesday
The cheapest day of the week is typically Tuesday. The most expensive is typically Friday
WHEN IS THE CHEAPEST TIME TO FLY TO CHICAGO?
in the morning
Boston to Chicago flights are approximately 126% more expensive in the afternoon than in the morning
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?
51 days before
The cheapest time to buy a flight from Boston to Chicago is approximately 51 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 35m The fastest flight from Boston to Chicago takes 2h 35m.
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
Providence to Chicago
Fastest flight time
2h 40m
Cheapest price
177 USD
Islip to Chicago
Fastest flight time
4h 47m
Cheapest price
197 USD
Providence to Chicago
Fastest flight time
3h 45m
Cheapest price
230 USD

Flights from Boston to:

Flights to Chicago from:

  • Boston Logan Intl
  • Massachusetts
  • United States
  • North America
*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.