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.
Navy Pier
A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.
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
Chicago: Navy Pier Centennial Wheel Ticket
Top hotels in Oakland
Congress Plaza Hotel
renovate room barhroom
Reviewed on 22 Mar 2026
Hotel Riu Plaza Chicago
We loved the breakfast and how convenient the hotel is from the Magnificent Mile and the river walk.
Reviewed on 23 Mar 2026
Embassy Suites by Hilton Chicago Downtown River North
The staff was super helpful and friendly. The room was clean and the bed was super comfortable! Perfect place to walk to lots of things.
Reviewed on 22 Mar 2026
Hilton Chicago/Magnificent Mile Suites
This Hilton is outdated. There is rust and pealing paint throughout the rooms; especially in the bathrooms. The linen and towels were stained. This is too much for the price and choice of $62 (off-site) and $82 (on property) parking prices.
Reviewed on 23 Mar 2026
Hilton Chicago O'Hare Airport
Clean room and friendly staff
Reviewed on 21 Mar 2026
Eurostars Magnificent Mile
Everything was perfect. We own a cleaning company so when traveling or staycationing we check the beds for bedbugs, lice and any other critters. Everything was pristine. I also let the phone staff know we were staying for my wife’s birthday and requested a higher room and they did say they couldn’t ...
Reviewed on 23 Mar 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.
