Oakland
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 find the perfect gifts to bring home 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.
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
Wendella's 90-min Chicago River Architecture Tour
Chicago Crime and Mob Bus Tour
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Top hotels in Oakland
Congress Plaza Hotel
Great place
Reviewed on 22 Feb 2026
Hotel Riu Plaza Chicago
So clean, amazing breakfast - high quality rooms
Reviewed on 22 Feb 2026
Embassy Suites by Hilton Chicago Downtown River North
Room was clean and beds were comfortable and breakfast was great but response time on guest services lacked
Reviewed on 22 Feb 2026
Hilton Chicago
Bathrooms and furniture was not clean at all. Splatter of dark brown-red substance on lampshade. Bathroom shower grout had similar brown-red stains and hair stuck in tub. Otherwise good. Room was spacious.
Reviewed on 20 Feb 2026
Hilton Chicago O'Hare Airport
Staff personable. Room was old & it showed.
Reviewed on 21 Feb 2026
Hilton Chicago/Magnificent Mile Suites
The room smelled very musty. Granted, it's an old building, but more effort should be put into adding fragrance. Also found hairs and rubbish on the bathroom floor. Hilton should do better.
Reviewed on 22 Feb 2026
Other neighbourhoods around Oakland
Near South Side
Travellers choose Near South Side for its ample dining options. Hop aboard the metro at Cermak-McCormick Place Station or Roosevelt Station and check out top sights like Soldier Field.
South Loop
Soldier Field and Lake Michigan are a few top attractions in South Loop. Hop around the city on the metro at Roosevelt Station or Cermak-McCormick Place Station and check out the area's fascinating museums, panoramic lake views and popular shops.
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 of the city at Washington Station or Monroe Station (Blue Line).
The Loop
Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.
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.
Near West Side
Live music, theatres 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 Polk Station (Pink Line) or Racine Station to get around town.
