Find a great deal and save up to 34% by booking at least 33 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Illinois to Massachusetts within the next two weeks, with the cheapest ticket starting at $228.
Our data shows that February tends to be the cheapest month to fly to Massachusetts from Illinois. Users have commonly found prices around $250 for the month, but tickets can be as low as $76. Due to multiple factors, prepare for potentially higher prices in June.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Massachusetts as you normally would.
Fly from
Fly to
Budget
$74 - $188
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 6/5
Nonstop2h 18m
Boston Logan Intl
Wed 6/12
Nonstop2h 33m
Chicago O'Hare IntlBoston Logan Intl
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 6/5
1 stop13h 20m
Boston Logan Intl
Tue 6/11
Nonstop2h 33m
Chicago MidwayBoston Logan Intl
MDW - BOS
MDWBOS
Chicago Midway
Sat 5/11
1 stop10h 51m
Boston Logan Intl
Wed 5/15
1 stop11h 44m
Chicago O'Hare IntlBoston Logan Intl
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/18
1 stop14h 47m
Boston Logan Intl
Tue 5/21
1 stop10h 08m
Chicago O'Hare IntlBoston Logan Intl
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 5/9
Nonstop2h 27m
Boston Logan Intl
Wed 5/15
Nonstop2h 55m
Chicago O'Hare IntlBoston Logan Intl
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/25
Nonstop2h 26m
Boston Logan Intl
Tue 5/28
Nonstop2h 55m
Chicago O'Hare IntlBoston Logan Intl
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 5/15
1 stop4h 44m
Boston Logan Intl
Wed 5/29
Nonstop2h 56m
Chicago O'Hare IntlBoston Logan Intl
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 5/9
Nonstop2h 21m
Boston Logan Intl
Sat 5/11
1 stop6h 05m
No data available for this route at this time. Please check back soon.
Overall
Food
Crew
Entertainment
Boarding
Comfort
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.
Overall
Food
Crew
Entertainment
Boarding
Comfort
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.
Overall
Food
Crew
Entertainment
Boarding
Comfort
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.
Overall
Food
Crew
Entertainment
Boarding
Comfort
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.
Overall
Food
Crew
Entertainment
Boarding
Comfort
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.
Overall
Food
Crew
Entertainment
Boarding
Comfort
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.
5%of flight departures | Early morningMidnight to 6 am |
---|---|
33%of flight departures | Morning6 am to noon |
53%of flight departures | AfternoonNoon to 6 pm |
9%of flight departures | Evening6 pm to midnight |
Cheapflights makes it easy to find Illinois to Massachusetts flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
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