Users have found that booking a flight from Massachusetts to Chicago at least 24 days early can save you up to 33% on average compared to booking a flight this week. If booking 24 days before your flight isn’t an option for you, users have found flights from Massachusetts to Chicago for as little as $279 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $327 for flights departing within the next 3 days.
Due to multiple factors, expect to potentially pay more when booking in June. For low rates, January can be a great choice for travel to Chicago. Flights to Chicago from Massachusetts in January are about $273 on average during January, but can be found for as low as $106.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Massachusetts to Chicago as you normally would.
Fly from
Fly to
Budget
$53 - $167
Route
Depart
Return
Price
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/4
1 stop10h 17m
Chicago O'Hare Intl
Wed 6/5
Nonstop2h 29m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/4
1 stop12h 03m
Chicago O'Hare Intl
Wed 6/5
Nonstop2h 29m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Sat 6/8
Nonstop2h 54m
Chicago O'Hare Intl
Wed 6/12
Nonstop2h 29m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Wed 6/5
1 stop12h 38m
Chicago O'Hare Intl
Wed 6/12
Nonstop2h 29m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Thu 6/6
Nonstop2h 54m
Chicago O'Hare Intl
Tue 6/11
Nonstop2h 28m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/29
1 stop11h 25m
Chicago O'Hare Intl
Sat 6/1
1 stop6h 08m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/18
2 stops14h 29m
Chicago O'Hare Intl
Tue 5/21
1 stop19h 54m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Sat 6/1
Nonstop3h 13m
Chicago O'Hare Intl
Wed 6/5
Nonstop2h 26m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 5/28
Nonstop2h 54m
Chicago O'Hare Intl
Fri 5/31
Nonstop2h 26m
No data available for this route at this time. Please check back soon.
Food
Overall
Crew
Entertainment
Boarding
Comfort
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
Food
Overall
Crew
Entertainment
Boarding
Comfort
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
Food
Overall
Crew
Entertainment
Boarding
Comfort
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
Food
Overall
Crew
Entertainment
Boarding
Comfort
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
Food
Overall
Crew
Entertainment
Boarding
Comfort
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
Food
Overall
Crew
Entertainment
Boarding
Comfort
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
26%of flight departures | Early morningMidnight to 6 am |
---|---|
38%of flight departures | Morning6 am to noon |
31%of flight departures | AfternoonNoon to 6 pm |
5%of flight departures | Evening6 pm to midnight |
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