When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 33 days in advance, which can save you up to 34% on flights from Illinois to Boston compared to booking the week you need them. Waiting 33 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 $228. For sooner than that we have options available in the next 3 days from $316.
Flights from Illinois to Boston lean towards being more expensive in June. Prices are generally better when you fly from Illinois to Boston in February, with the cheapest ticket starting at $76.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Boston as you normally would.
Fly from
Fly to
Budget
$74 - $179
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
Lambert-St LouisBoston Logan Intl
STL - BOS
STLBOS
Lambert-St Louis
Sat 5/11
1 stop14h 31m
Boston Logan Intl
Sat 5/18
1 stop7h 36m
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
Fri 5/10
Nonstop2h 30m
Boston Logan Intl
Tue 5/14
Nonstop2h 56m
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
Fri 5/17
Nonstop2h 21m
Boston Logan Intl
Sat 5/18
Nonstop2h 53m
Chicago O'Hare IntlBoston Logan Intl
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/10
Nonstop2h 36m
Boston Logan Intl
Mon 5/13
Nonstop2h 47m
No data available for this route at this time. Please check back soon.
Food
Boarding
Crew
Entertainment
Comfort
Overall
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.
Food
Boarding
Crew
Entertainment
Comfort
Overall
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.
Food
Boarding
Crew
Entertainment
Comfort
Overall
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.
Food
Boarding
Crew
Entertainment
Comfort
Overall
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.
Food
Boarding
Crew
Entertainment
Comfort
Overall
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.
Food
Boarding
Crew
Entertainment
Comfort
Overall
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 |
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