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.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
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.
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.
Six Flags Great America
Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.
Things to do
Wendella's 90-min Chicago River Architecture Tour
Field Museum of Natural History Admission Tickets
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Top hotels in Oakland
Congress Plaza Hotel
The closest parking was $62 for 24hrs and the bed was extremely firm making the sleep terrible but other than that, the stay was great
Reviewed on 12 Apr 2026
Hilton Chicago/Magnificent Mile Suites
All treated us so well. Especially appreciated valet’s assistance in getting us to self-park
Reviewed on 12 Apr 2026
Embassy Suites by Hilton Chicago Downtown River North
Ok
Reviewed on 12 Apr 2026
Hotel Riu Plaza Chicago
The hotel has the best location, the staff is very friendly, and it is very clean and quiet
Reviewed on 12 Apr 2026
Hilton Chicago O'Hare Airport
Excellent location. Great bathroom. Comfortable bed.
Reviewed on 12 Apr 2026
The Wade
It felt that after the acquisition, this property has really fell off the wagon. The staff was nonexistent, when I was trying to check out there was nobody at the front desk. Upon checking in experience was also disorganized. One night I tried to call room service, then tried to call the front desk, ...
Reviewed on 12 Apr 2026
Other neighbourhoods 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
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.
