Oakland, IL
Chicago
Popular places to visit
Wrigley Field
Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.
Michigan Avenue
You can enjoy some retail therapy 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
During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.
Navy Pier
With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its fascinating museums.
Millennium Park
After visiting Millennium Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
Oakland Hotel Deals
Congress Plaza Hotel
Nice quiet hotel walking distance to a lot of the tourist hot spots. Hotel was nice, could use some cleaning. Hotel is magnificent.
Reviewed on 23 March 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 March 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 March 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This Hilton is outdated.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 March 2026
Hilton Chicago O'Hare Airport
Clean room and friendly staff
Reviewed on 21 March 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 March 2026
Other neighborhoods around Oakland
Near South Side
Travelers choose Near South Side for its abundant dining options. Hop aboard the metro at Cermak-McCormick Place Station or Roosevelt Station and check out top sights like Soldier Field.
South Loop
Known for its fascinating museums, panoramic lake views, and popular shops, there's plenty to explore in South Loop. Top attractions like Soldier Field and Lake Michigan are major draws. Catch the metro at Roosevelt Station or Cermak-McCormick Place Station to see more of the city.
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 the city at Washington Station or Monroe Station (Blue Line).
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
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, theaters, 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.
