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.
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.
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 Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Things to do
Skydeck - Willis Tower Admission
Wendella's 90-min Chicago River Architecture Tour
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Oakland Hotel Deals
Congress Plaza Hotel
"The Congress is old but it never fails!!! Great location!!! I have stayed there many of times …"
Reviewed on May 28, 2026
Hotel Riu Plaza Chicago
"Amazing breakfasts"
Reviewed on May 29, 2026
The Chicago Hotel Collection - Magnificent Mile
"The hotel was amazing looked exactly like the photos. The staff was awesome 10/10 I would for sure stay here again!"
Reviewed on May 29, 2026
River Hotel
"prime location, very friendly staff!! above and beyond. clean rooms."
Reviewed on May 29, 2026
Hotel Felix River North/Magnificent Mile
"The hotel location and room was nice. I didn’t like that you had to pay $5 per bag for storage if you wanted to check out if the room early. I thought giving the room before noon would be better for them especially since I was coming back before that checkout time. So I just brought my stuff back ..."
Reviewed on May 29, 2026
Fairmont Chicago at Millennium Park
"I rented a suite. It was relatively very expensive so I expect more. There was orange seeds on the floor and a piece of orange peel and some M&M shell pieces on the floor when I arrived. The staff were just fair when I asked were certain things wise. It was almost like I expected me to know use terms ..."
Reviewed on May 28, 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.
Oakland, IL
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