
Oakland Holidays from AU$808
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Your Oakland Holiday
With a tailor-made holiday package to Oakland, you'll spend less time planning and more time simply enjoying this appealing neighbourhood. From its nature to its walking, there's plenty to discover here. Kick start your trip to Oakland by heading to nearby attractions such as University of Chicago, Chicago Museum of Science and Industry and Guaranteed Rate Field. No matter your travel goals or budget, booking your ideal Oakland holiday is easy with Expedia.
Top Holiday Package Deals in Oakland

The Drake
Reviewed on 14 Oct 2025

Park Hyatt Chicago
Reviewed on 14 Oct 2025

Trump International Hotel & Tower Chicago
Reviewed on 15 Oct 2025


Pendry Chicago
Reviewed on 11 Oct 2025
Our guide on where to stay in Oakland

Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Our pick of the best Oakland Hotel Deals

Congress Plaza Hotel
Reviewed on 13 Oct 2025

Freehand Chicago
Reviewed on 15 Oct 2025

Hilton Chicago/Magnificent Mile Suites
Reviewed on 13 Oct 2025
Frequently asked questions
Discover the most popular places to visit in Oakland

Navy Pier
A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Millennium Park
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Grant Park
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
Activities

Skydeck - Willis Tower Admission
