
Oakland Vacations from $233
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Your Oakland Vacation
With a tailor-made vacation package to Oakland, you'll spend less time planning and more time simply enjoying this appealing neighborhood. 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 vacation is easy with Expedia.
The Latest Oakland Vacation Packages

Holiday Inn Chicago - Schaumburg by IHG
Reviewed on Jan 11, 2026

Hotel Riu Plaza Chicago
Reviewed on Feb 1, 2026

Hotel Felix River North/Magnificent Mile
Reviewed on Jan 20, 2026

Level Chicago – Old Town
Reviewed on Jan 18, 2026

Pendry Chicago
Reviewed on Jan 31, 2026
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.
Oakland Hotel Deals

Congress Plaza Hotel
Awesome location
Reviewed on Jan 30, 2026

Embassy Suites by Hilton Chicago Downtown River North
Friendly desk staff, clean room. Fridge didn't have temp adjuster and contents froze, bottles broke.
Reviewed on Jan 28, 2026

DoubleTree by Hilton Chicago - Magnificent Mile
Loved it! Everything was near
Reviewed on Jan 31, 2026
Discover the most popular places to visit in Oakland

Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do

Chicago: Navy Pier Centennial Wheel Ticket
























