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 acclaimed theater scene 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.
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 acclaimed art scene.
McCormick Place
During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed theater scene and notable monuments in this vibrant area.
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 fascinating museums in this vibrant area.
Soldier Field
Catch an event at Soldier Field during your trip to Chicago. Stroll along the lakeside or visit the notable monuments in this vibrant area.
Oakland Hotel Deals
Hilton Chicago
Great staff, good location .
Reviewed on 14 January 2026
Hilton Chicago/Magnificent Mile Suites
10/10
Reviewed on 14 January 2026
Palmer House a Hilton Hotel
Clean, attractive classic looking room and bathroom.
Reviewed on 13 January 2026
Club Quarters Hotel Wacker at Michigan, Chicago
Staff was wonderful and the city is amazin
Reviewed on 14 January 2026
Embassy Suites by Hilton Chicago Downtown River North
The room was clean. The staff was friendly. The breakfast was not great, but not bad.
Reviewed on 14 January 2026
Hilton Chicago O'Hare Airport
Stayed prior to flight, clean, quiet room!
Reviewed on 13 January 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.
Oakland, IL
- Places of interest
- Oakland Hotels by Star Rating
- Hotels in top Chicago neighborhoods
- Oakland Hotels by Brand
- 41st Street Beach
- Wrigley Field
- Michigan Avenue
- Navy Pier
- McCormick Place
- Millennium Park
- Soldier Field
- Lake Michigan
- Chicago Riverwalk
- United Center
- Grant Park
- University of Chicago
- Northwestern University
- Willis Tower
- Art Institute of Chicago
- Donald E. Stephens Convention Center
- State Street
- Loyola University Chicago
- Chicago Theatre
- Field Museum of Natural History
- Griffin Museum of Science and Industry
- Cloud Gate
- Merchandise Mart
- University of Illinois Chicago
- Rosemont Theatre
- Water Tower Place
- Wintrust Arena
- Rate Field
- DePaul University-Lincoln Park
- Lincoln Park Zoo
- 875 North Michigan Avenue
