Users have found that booking a flight from Massachusetts to Chicago at least 52 days early can save you up to 38% on average compared to booking a flight this week. If booking 52 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 $328 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 $271 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 - $156
Route
Depart
Return
Price
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/11
Nonstop2h 54m
Chicago O'Hare Intl
Wed 6/12
1 stop7h 19m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Mon 6/10
Nonstop2h 54m
Chicago O'Hare Intl
Thu 6/13
Nonstop2h 28m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/11
Nonstop2h 54m
Chicago O'Hare Intl
Wed 6/12
Nonstop2h 29m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/11
Nonstop2h 54m
Chicago O'Hare Intl
Wed 6/12
1 stop7h 19m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Fri 9/20
Nonstop2h 33m
Chicago O'Hare Intl
Sat 9/21
Nonstop2h 18m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Fri 6/7
1 stop16h 52m
Chicago O'Hare Intl
Tue 6/11
Nonstop2h 28m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 8/14
1 stop7h 37m
Chicago Midway
Tue 8/20
1 stop10h 26m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 8/13
Nonstop2h 59m
Chicago O'Hare Intl
Sat 8/17
Nonstop2h 28m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/18
Nonstop2h 54m
Chicago O'Hare Intl
Wed 6/26
1 stop4h 40m
No data available for this route at this time. Please check back soon.
Overall
Comfort
Food
Boarding
Entertainment
Crew
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Overall
Comfort
Food
Boarding
Entertainment
Crew
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Overall
Comfort
Food
Boarding
Entertainment
Crew
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Overall
Comfort
Food
Boarding
Entertainment
Crew
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Overall
Comfort
Food
Boarding
Entertainment
Crew
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Overall
Comfort
Food
Boarding
Entertainment
Crew
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
15%of flight departures | Early morningMidnight to 6 am |
---|---|
37%of flight departures | Morning6 am to noon |
40%of flight departures | AfternoonNoon to 6 pm |
8%of flight departures | Evening6 pm to midnight |
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