
Oakland Vacations from $173
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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

theWit Chicago, a Hilton Hotel
Reviewed on Nov 6, 2025



Hilton Grand Vacations Club Chicago Magnificent Mile
Reviewed on Oct 28, 2025

Level Chicago – Old Town
Reviewed on Oct 29, 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

Embassy Suites by Hilton Chicago Downtown River North
Our first time staying! Great location, lovee the free breakfast. Felt safe as well. We really enjoyed having the living room area too.
Reviewed on Nov 5, 2025

Congress Plaza Hotel
The Congress is a very welcome change from where we have been staying in Chicago for some time now. The staff was very nice and the room, but that’s tall ceilings and it also look to be freshly made over, was a very welcome change from where we used to stay. Highly recommend, excellent location right ...
Reviewed on Nov 7, 2025

Hilton Chicago/Magnificent Mile Suites
Met expectations, check in staff was friendly and efficient.
Reviewed on Nov 6, 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

Skydeck - Willis Tower Admission
























