When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 55 days in advance, which can save you up to 24% on flights from Hyannis to Chicago compared to booking the week you need them. Waiting 55 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 $237. For sooner than that we have options available in the next 3 days from $310.
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 Hyannis in January are about $260 on average during January, but can be found for as low as $79.
When flying from Hyannis to Chicago, 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
$306 - $702
Route
Depart
Return
Price
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Tue 6/25
1 stop4h 23m
Chicago O'Hare Intl
Wed 6/26
1 stop4h 19m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Tue 6/25
2 stops10h 40m
Chicago O'Hare Intl
Wed 6/26
1 stop4h 19m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Wed 6/19
1 stop5h 49m
Chicago O'Hare Intl
Sat 6/22
1 stop4h 39m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Sat 7/6
1 stop7h 29m
Chicago O'Hare Intl
Sat 7/13
1 stop4h 42m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Wed 5/15
1 stop8h 30m
Chicago O'Hare Intl
Sat 5/18
1 stop4h 59m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Thu 5/23
1 stop8h 20m
Chicago O'Hare Intl
Fri 5/31
1 stop6h 03m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Mon 5/13
1 stop8h 30m
Chicago O'Hare Intl
Wed 5/15
1 stop4h 59m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Sat 8/24
1 stop8h 04m
Chicago O'Hare Intl
Sun 9/8
1 stop6h 03m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Wed 5/15
1 stop8h 30m
Chicago O'Hare Intl
Sun 5/19
1 stop6h 48m
No data available for this route at this time. Please check back soon.
Overall
Crew
Food
Comfort
Boarding
Entertainment
Reviews
Flight was okay aside from 1 extremely unhappy with her life flight attendant and another passenger behind me kicking my seat for 6 hrs.
Overall
Crew
Food
Comfort
Boarding
Entertainment
Reviews
Flight was okay aside from 1 extremely unhappy with her life flight attendant and another passenger behind me kicking my seat for 6 hrs.
Overall
Crew
Food
Comfort
Boarding
Entertainment
Reviews
Flight was okay aside from 1 extremely unhappy with her life flight attendant and another passenger behind me kicking my seat for 6 hrs.
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