
Oakland Vacations from $205
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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


Level Chicago Fulton Market
Reviewed on Sep 21, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
Reviewed on Sep 25, 2025

Trump International Hotel & Tower Chicago
Reviewed on Sep 24, 2025

DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove
Reviewed on Sep 23, 2025
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
Reviewed on Sep 25, 2025

Freehand Chicago
Reviewed on Sep 24, 2025

Hilton Chicago/Magnificent Mile Suites
Reviewed on Sep 24, 2025
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

Wendella's 90-min Chicago River Architecture Tour
