When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 24 days in advance, which can save you up to 33% on flights from Hyannis to Chicago compared to booking the week you need them. Waiting 24 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 $279. For sooner than that we have options available in the next 3 days from $327.
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 $273 on average during January, but can be found for as low as $106.
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
$388 - $747
Route
Depart
Return
Price
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Tue 6/25
2 stops10h 40m
Chicago O'Hare Intl
Wed 6/26
1 stop5h 18m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Tue 6/25
2 stops10h 40m
Chicago O'Hare Intl
Wed 6/26
2 stops14h 58m
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
Fri 6/7
1 stop5h 25m
Chicago O'Hare Intl
Wed 6/12
1 stop4h 39m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Fri 9/13
1 stop6h 25m
Chicago O'Hare Intl
Mon 9/16
1 stop4h 08m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Fri 10/18
1 stop6h 45m
Chicago O'Hare Intl
Mon 10/21
1 stop5h 20m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Sun 6/9
1 stop5h 49m
Chicago O'Hare Intl
Tue 6/11
1 stop4h 19m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Fri 5/24
1 stop8h 20m
Chicago O'Hare Intl
Mon 5/27
1 stop5h 20m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Fri 5/24
1 stop8h 20m
Chicago O'Hare Intl
Mon 5/27
1 stop4h 59m
No data available for this route at this time. Please check back soon.
Food
Comfort
Boarding
Crew
Overall
Entertainment
Reviews
Haven’t been on a JetBlue flight in years that was on time.
Food
Comfort
Boarding
Crew
Overall
Entertainment
Reviews
Haven’t been on a JetBlue flight in years that was on time.
Food
Comfort
Boarding
Crew
Overall
Entertainment
Reviews
Haven’t been on a JetBlue flight in years that was on time.
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