Oakland Vacations from $313
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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
Hotel Riu Plaza Chicago
Reviewed on Aug 10, 2026
Hotel Saint Clair- Magnificent Mile
Reviewed on Aug 10, 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.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).
Oakland Hotel Deals
Congress Plaza Hotel
"Stay was fine. I’d love to leave five stars but I have been asking why I was charged an additional 104 usd to my credit card after we left via hotels.com chat and emailing the hotel directly but they have yet to respond. Hoping this gets me a reply and I can update my review"
Reviewed on Aug 10, 2026
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport
Stay near popular Oakland attractions
41st Street Beach
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
