When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 52 days in advance, which can save you up to 36% on flights from Hyannis to Chicago compared to booking the week you need them. Waiting 52 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 $328.
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
$323 - $762
Route
Depart
Return
Price
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
So 7/21
1 stop19h 47m
Chicago O'Hare Intl
Di 7/23
1 stop5h 23m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
So 7/21
1 stop19h 47m
Chicago O'Hare Intl
Di 7/23
2 stops14h 02m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
So 7/21
2 stops10h 41m
Chicago O'Hare Intl
Di 7/23
2 stops14h 02m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Mi 6/19
1 stop5h 49m
Chicago O'Hare Intl
Sa 6/22
1 stop4h 39m
Hyannis BarnstableChicago O'Hare Intl
HYA - ORD
HYAORD
Hyannis Barnstable
Do 5/16
1 stop8h 30m
Chicago O'Hare Intl
So 5/19
1 stop8h 00m
No data available for this route at this time. Please check back soon.
Crew
Entertainment
Comfort
Overall
Boarding
Food
Reviews
Haven’t been on a JetBlue flight in years that was on time.
Crew
Entertainment
Comfort
Overall
Boarding
Food
Reviews
Haven’t been on a JetBlue flight in years that was on time.
Crew
Entertainment
Comfort
Overall
Boarding
Food
Reviews
Haven’t been on a JetBlue flight in years that was on time.
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