Oakland, IL
Chicago
Popular places to visit
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.
McCormick Place
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Things to do
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Sightseeing River and Lake Cruise
Wendella's 90-min Chicago River Architecture Tour
Chicago Architecture Center River Cruise aboard First Lady
Oakland Hotel Deals
Congress Plaza Hotel
absolutely loved the view from my room on the 14th floor
Reviewed on Oct 23, 2025
Holiday Inn Chicago Dwtn - The Mart by IHG
We didn’t know what to expect from a Holiday Inn in a tower and were pleasantly surprised. The building — hotel actually starts on the 15th floor — is like new and was very clean. The staff was universally friendly. The lobby floor has a grab-and-go food option available 24 hours and a nontraditional ...
Reviewed on Oct 20, 2025
Hilton Chicago/Magnificent Mile Suites
Great
Reviewed on Oct 23, 2025
Freehand Chicago
Everything was amazing, the only issue during my stay was that the heater didn’t work.
Reviewed on Oct 23, 2025
Palmer House a Hilton Hotel
Empty shampoo bottle for days. Hotel rooms are not as clean being an old building. The common areas are beautiful and the vibe is amazing. Easy check in and out. Great location.
Reviewed on Oct 22, 2025
citizenM Chicago Downtown
Had the best experience! Very modernized and fun!
Reviewed on Oct 23, 2025
Other neighborhoods around Oakland
Hyde Park
Hyde Park is noteworthy for its museums, and you can make a stop at top attractions like Lake Michigan and Robie House.
Near South Side
Travelers choose Near South Side for its abundant dining options. Hop aboard the metro at Cermak-McCormick Place Station or Roosevelt Station and check out top sights like Soldier Field.
South Loop
Known for its fascinating museums, panoramic lake views, and popular shops, there's plenty to explore in South Loop. Top attractions like Soldier Field and Lake Michigan are major draws. Catch the metro at Roosevelt Station or Cermak-McCormick Place Station to see more of the city.
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).
Near West Side
Live music, theaters, and shopping highlight some notable features of Near West Side. Make a stop by United Center or Credit Union 1 Arena while you're visiting, and jump aboard the metro at Racine Station or Polk Station (Pink Line) to get around town.
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.
Oakland, IL
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