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
12 Jun
BOS
8:10 am
Boston Logan Intl airport
2h 52m
10:02 am
ORD
Chicago O'Hare Intl airport
Spirit Airlines
15 Jun
ORD
9:06 am
Chicago O'Hare Intl airport
2h 35m
12:41 pm
BOS
Boston Logan Intl airport
137 USD
Spirit Airlines
Spirit Airlines
29 May
BOS
8:10 am
Boston Logan Intl airport
2h 52m
10:02 am
ORD
Chicago O'Hare Intl airport
Spirit Airlines
05 Jun
ORD
9:10 am
Chicago O'Hare Intl airport
2h 36m
12:46 pm
BOS
Boston Logan Intl airport
140 USD
Spirit Airlines
Spirit Airlines
04 Jun
BOS
8:10 am
Boston Logan Intl airport
2h 52m
10:02 am
ORD
Chicago O'Hare Intl airport
Spirit Airlines
05 Jun
ORD
9:10 am
Chicago O'Hare Intl airport
2h 36m
12:46 pm
BOS
Boston Logan Intl airport
140 USD
Southwest
Southwest
06 Jun
BOS
1:45 am
Boston Logan Intl airport
2h 45m
3:30 am
MDW
Chicago Midway airport
Southwest
18 Jun
MDW
5:30 pm
Chicago Midway airport
2h 10m
8:40 pm
BOS
Boston Logan Intl airport
176 USD
United Airlines
United Airlines
11 Sep
BOS
1:25 am
Boston Logan Intl airport
2h 40m
3:05 am
ORD
Chicago O'Hare Intl airport
United Airlines
15 Sep
ORD
1:00 am
Chicago O'Hare Intl airport
2h 16m
4:16 am
BOS
Boston Logan Intl airport
143 USD
United Airlines
United Airlines
11 Jun
BOS
1:25 am
Boston Logan Intl airport
2h 40m
3:05 am
ORD
Chicago O'Hare Intl airport
United Airlines
18 Jun
ORD
4:18 pm
Chicago O'Hare Intl airport
2h 25m
7:43 pm
BOS
Boston Logan Intl airport
143 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
CHEAPEST MONTH TO FLY
September
The cheapest time of year to fly to Chicago from Boston is September. Most expensive is April
CHEAPEST DAY TO FLY
Tuesday
The cheapest day of the week is typically Tuesday. The most expensive is typically Friday
CHEAPEST TIME TO FLY
in the Morning
Boston to Chicago flights are approximately 25% more expensive in the Afternoon than in the Morning
CHEAPEST AIRLINE
Sun Country Air
Sun Country Air, Spirit Airlines, and Delta are the most popular carriers operating from Boston to Chicago
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
CHEAPEST TIME TO BOOK
27 days before
The cheapest time to buy a flight from Boston to Chicago is approximately 27 days to departure
60
Days before departure
0

Flight information for Boston to Chicago (BOS - CHI)

Find info about flight duration, direct flights, and airports for your flight from Boston to Chicago
Fastest flight time
2h 37m
The fastest flight from Boston to Chicago takes 2h 37m.
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

Flights from Boston to:

Flights to Chicago from:

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