Travelers have found it’s best to book a flight 33 days in advance to save up to 34% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 33 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago O'Hare Intl Airport to Massachusetts 1-2 weeks in advance for as low as $228, or $316 for flights within the next 24 hours.
The best pricing can be found in the month of February. Prices to Massachusetts from Chicago O'Hare Intl Airport average $250. You can even find prices in February for less than $250, as users have found deals to Massachusetts from as low as $76. The month of June appears to be one of the more expensive times to travel to Massachusetts from Chicago O'Hare Intl Airport. Flying in the targeted month can save you up to 34%.
When flying from Chicago O'Hare Intl Airport to Massachusetts, 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
$74 - $189
Route
Depart
Return
Price
Chicago O'Hare IntlBoston Logan Intl
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 6/5
Nonstop2h 18m
Boston Logan Intl
Tue 6/11
Nonstop2h 33m
Chicago O'Hare IntlBoston Logan Intl
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 8/21
Nonstop2h 18m
Boston Logan Intl
Tue 8/27
Nonstop2h 33m
Chicago O'Hare IntlBoston Logan Intl
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 6/12
Nonstop2h 29m
Boston Logan Intl
Tue 6/18
Nonstop2h 54m
Chicago O'Hare IntlBoston Logan Intl
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/11
1 stop22h 43m
Boston Logan Intl
Wed 5/15
1 stop14h 36m
Chicago O'Hare IntlBoston Logan Intl
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 5/7
1 stop7h 35m
Boston Logan Intl
Thu 5/16
1 stop15h 42m
Chicago O'Hare IntlBoston Logan Intl
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 8/19
Nonstop2h 25m
Boston Logan Intl
Tue 8/27
Nonstop2h 54m
Chicago O'Hare IntlBoston Logan Intl
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/10
Nonstop2h 36m
Boston Logan Intl
Tue 5/14
Nonstop2h 54m
Chicago O'Hare IntlBoston Logan Intl
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 5/22
1 stop5h 37m
Boston Logan Intl
Sun 5/26
Nonstop2h 58m
Chicago O'Hare IntlBoston Logan Intl
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/24
Nonstop2h 35m
Boston Logan Intl
Sun 5/26
Nonstop2h 50m
No data available for this route at this time. Please check back soon.
Entertainment
Comfort
Overall
Boarding
Food
Crew
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Entertainment
Comfort
Overall
Boarding
Food
Crew
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Entertainment
Comfort
Overall
Boarding
Food
Crew
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Entertainment
Comfort
Overall
Boarding
Food
Crew
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Entertainment
Comfort
Overall
Boarding
Food
Crew
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Entertainment
Comfort
Overall
Boarding
Food
Crew
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
4%of flight departures | Early morningMidnight to 6 am |
---|---|
33%of flight departures | Morning6 am to noon |
55%of flight departures | AfternoonNoon to 6 pm |
8%of flight departures | Evening6 pm to midnight |
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