Oakland
Chicago
Popular places to visit
Wrigley Field
Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.
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 waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.
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
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.
Things to do
Skydeck - Willis Tower Admission
Wendella's 90-min Chicago River Architecture Tour
LEGOLAND® Discovery Center Chicago
Top hotels in Oakland
Congress Plaza Hotel
The bar being open late is nice and the staff are very helpful.
Reviewed on 12 May, 2026
Hotel Riu Plaza Chicago
Breakfast was good.
Reviewed on 13 May, 2026
Hilton Chicago/Magnificent Mile Suites
Valet and bellmen were great as always. Polite and helpful. The staff brought up an extra valet for my kids on the pullout couch. Great setup for family with kids! And the restaurant on the corner has the best coffee. We stay here every time we visit, can’t beat location, price and separate space ...
Reviewed on 13 May, 2026
River Hotel
Friendly staff and excellent location. Loved our 2 bed suite with 2 bathrooms and a kitchen! Would absolutely stay again!
Reviewed on 11 May, 2026
Hotel Felix River North/Magnificent Mile
All was good
Reviewed on 12 May, 2026
Club Quarters Hotel, Central Loop, Chicago
Definitely In going to this hotel again soon Very nice hotel staff and clean and the location was great
Reviewed on 12 May, 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 Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
