When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 24 days in advance, which can save you up to 33% on flights from Massachusetts to Chicago O'Hare Intl Airport compared to booking the week you need them. Waiting 24 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $279. For sooner than that we have options available in the next 3 days from $327.
January can be a great time to fly to Chicago O'Hare Intl Airport from Massachusetts with a flight ticket averaging about $273. Cheapflights users have found deals in the month of January for as cheap as $106. The most expensive prices can be found in the month of June.
When flying from Massachusetts to Chicago O'Hare Intl Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$140 - $216
Route
Depart
Return
Price
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 5/14
2 stops27h 45m
Chicago O'Hare Intl
Thu 5/23
1 stop13h 02m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Mon 6/10
2 stops24h 51m
Chicago O'Hare Intl
Thu 6/13
Nonstop2h 28m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Thu 5/30
1 stop7h 39m
Chicago O'Hare Intl
Fri 5/31
1 stop15h 46m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 5/28
1 stop26h 45m
Chicago O'Hare Intl
Fri 5/31
1 stop15h 46m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Wed 6/5
Nonstop2h 55m
Chicago O'Hare Intl
Wed 6/12
Nonstop2h 28m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Mon 5/13
1 stop15h 35m
Chicago O'Hare Intl
Thu 5/16
1 stop19h 54m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 5/28
Nonstop2h 54m
Chicago O'Hare Intl
Sat 6/1
Nonstop2h 26m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Thu 5/23
Nonstop2h 50m
Chicago O'Hare Intl
Sun 5/26
Nonstop2h 31m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Thu 5/23
1 stop5h 22m
Chicago O'Hare Intl
Wed 5/29
Nonstop2h 26m
No data available for this route at this time. Please check back soon.
Comfort
Crew
Entertainment
Overall
Boarding
Food
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
Comfort
Crew
Entertainment
Overall
Boarding
Food
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
Comfort
Crew
Entertainment
Overall
Boarding
Food
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
Comfort
Crew
Entertainment
Overall
Boarding
Food
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
Comfort
Crew
Entertainment
Overall
Boarding
Food
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
Comfort
Crew
Entertainment
Overall
Boarding
Food
Reviews
The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.
28%of flight departures | Early morningMidnight to 6 am |
---|---|
37%of flight departures | Morning6 am to noon |
32%of flight departures | AfternoonNoon to 6 pm |
3%of flight departures | Evening6 pm to midnight |
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