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.
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.
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.
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
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.
Navy Pier
A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Chicago Crime and Mob Bus Tour
Top hotels in Oakland
Congress Plaza Hotel
Yes it was clean when we came in. However, the front desk didn't let us know that the cleaning staff come every other day, which would have been helpful to know. Also, our shower got clogged and was fixed immediately, which I appreciate. The bellman was not sure what to call him, he was kinda rude ...
Reviewed on 25 Mar, 2026
Hotel Riu Plaza Chicago
Service was terrific in every way! Warm and helpful staff. Fantastic breakfast included!
Reviewed on 25 Mar, 2026
Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago/Magnificent Mile Suites
Excellent location and staff, extra space of suite style room a plus, very good restaurant adjacent, Would stay again.
Reviewed on 25 Mar, 2026
Hilton Chicago O'Hare Airport
Aside from the location for an overnight between flights & a great staff this hotel leaves a lot to be desired. Worn out carpets and fixtures and a climate system that is in need of an update.
Reviewed on 25 Mar, 2026
Aloft Chicago Mag Mile
Everything was perfect
Reviewed on 25 Mar, 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.
