Oakland, IL
Chicago
Popular places to visit
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.
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Things to do
Skydeck - Willis Tower Admission
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Blackhawks Ice Hockey Game at United Center
Chicago Museum of Contemporary Art: General Admission Ticket
Oakland Hotel Deals
Hilton Chicago
Staff members were friendly and helpful. Great location walking distance and transportation options.
Reviewed on Jan 9, 2026
Hilton Chicago/Magnificent Mile Suites
Room and hotel overall very clean. Noted some things that could be updated in bathroom(stopper in sink didnt go all the way down, peeling caulk and some missing grout). Minor updates. Our sink was clogged when we checked in and I called the front desk, housekeeping and the hotel hotline 4 different ...
Reviewed on Jan 7, 2026
Palmer House a Hilton Hotel
This stay was perfection from beginning to end. Totally wonderful experience in every way.
Reviewed on Jan 9, 2026
Club Quarters Hotel Wacker at Michigan, Chicago
Pedro and front office staff made our stay excellent. Return customer love the location, room quality and value overall. Room size and features make this our first choice in the city
Reviewed on Jan 7, 2026
Embassy Suites by Hilton Chicago Downtown River North
The hotel is well kept: clean, no bad smell, updated, and clean. The staff at the happy hour and breakfast were all professional, friendly and hard working. The room was clean and nice. The w
Reviewed on Jan 10, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
It was clean , staff was very nice, Beautiful building !
Reviewed on Jan 9, 2026
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).
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.
Downtown Chicago
Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
Oakland, IL
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