Oakland, IL
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.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Things to do
Skydeck - Willis Tower Admission
Wendella's 90-min Chicago River Architecture Tour
Chicago: Navy Pier Centennial Wheel Ticket
LEGOLAND® Discovery Center Chicago
Oakland Hotel Deals
Hotel Felix River North/Magnificent Mile
Clean room
Reviewed on Apr 30, 2026
River Hotel
Beautiful, clean room with an incredible downtown Chicago view. Totally worth it
Reviewed on Apr 29, 2026
Club Quarters Hotel, Central Loop, Chicago
Great check in and check out experience
Reviewed on Apr 29, 2026
Hilton Chicago/Magnificent Mile Suites
Clean
Reviewed on Apr 30, 2026
Hotel Riu Plaza Chicago
King bed room with sofa was clean and very roomy with lots of storage. I especially appreciated the outlets above the nightstands on both sides of the bed for charging devices. The staff was the ultimate in friendliness and helpfulness. Loved the rooftop bar! This is a great location just 1/2 block ...
Reviewed on Apr 30, 2026
Hilton Chicago O'Hare Airport
After two international flights this was a welcome overnight and we loved the view of the airport and downtown from our room. The restaurant was decent for a quick bite, and when our coffee machine didn’t work, they kindly gave us a voucher to buy one at their cafe. Comfortable overall stay with ...
Reviewed on Apr 29, 2026
Other neighborhoods 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
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 Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
