
Oakland Vacations from $230
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Find the right fit
Rest easy
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

The Allegro Royal Sonesta Hotel Chicago Loop
Reviewed on Sep 19, 2025

Hotel Riu Plaza Chicago
Reviewed on Sep 17, 2025

The Emily Hotel
Reviewed on Sep 18, 2025

Hilton Chicago O'Hare Airport
Reviewed on Sep 18, 2025

Level Chicago Fulton Market
Reviewed on Sep 19, 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 18, 2025

Warwick Allerton - Chicago
Reviewed on Sep 19, 2025

citizenM Chicago Downtown
Reviewed on Sep 17, 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
