$296 Cheap flight deals from Chicago (CHI) to Oak Bluffs (ACK)
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Airfares from $296 One Way, $569 Round Trip from Chicago to Oak Bluffs
Prices starting at $569 for return flights and $296 for one-way flights to Oak Bluffs were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Oak Bluffs economy flight packages
Margaritaville Resort Cape Cod
Dec 11 - Dec 14
Chicago (ORD) to Hyannis (HYA)
Reviewed on Oct 18, 2026
Vineyard Harbor Motel - Private Beach
Dec 11 - Dec 14
Chicago (ORD) to Vineyard Haven (MVY)
Vineyard Haven (MVY) to Chicago (ORD)
More About Flying To Oak Bluffs from Chicago
Route Information for Flights from Chicago to Oak Bluffs
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | ACK |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Oak Bluffs
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.