Oakland, IL
Chicago
Visit Oakland
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.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
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.
Six Flags Great America
Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.
Things to do
Wendella's 90-min Chicago River Architecture Tour
Chicago: Navy Pier Centennial Wheel Ticket
Oakland Hotel Deals
Congress Plaza Hotel
"Room is fine, clean and updated. Hotel is pretty lame. While Lobby is cool, the rest has hallways with peeling wallpaper and holes in the wall. Weird maze of passages to the rooms. Windows in my room frozen shut, even though they exit to fire escape. Super bright lamps right outside and curtains ..."
Reviewed on Jun 24, 2026
Hilton Chicago/Magnificent Mile Suites
"Good location, bar and brunch were great. View from the pool and fitness centers was u real. Room was clean but sink faucet was loose and leaking and the bathroom door locks didn’t work well or would stick. Other than that it was nice."
Reviewed on Jun 24, 2026
The Chicago Hotel Collection - Magnificent Mile
"The hotel and the room were lovely and comfortable. The staff was friendly and seemed helpful, but they were ineffective and overcharged me. I was charged for several nights of valet parking that I had cancelled. I have been trying every avenue (email, phone, text) to try to get the charges reimbursed ..."
Reviewed on Jun 24, 2026
Hyatt Regency O'Hare Chicago
"The only thing missing was a pool."
Reviewed on Jun 24, 2026
The Chicago Hotel Collection Ambassador Gold Coast
"The Ambassador Gold Coast was our first hotel stay as we embarked on an AmTrak Rail Pass trek across the country and back, and they set the bar very high! The staff was very helpful, the room was large with a big window, very clean, great bed, and nice bathroom. The buffet breakfast (included) was ..."
Reviewed on Jun 24, 2026
River Hotel
"From the minute we checked in and met Jock at the front desk, we knew it was the right hotel! He was BEYOND the best staff member we’ve ever had the pleasure of meeting. He understood our needs and was extremely helpful in all areas of our stay! The hotel was very centrally located and a short walk ..."
Reviewed on Jun 24, 2026
Where to stay in Oakland
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.
Magnificent Mile
Michigan Avenue and Chicago Water Tower are just a few worthwhile attractions to visit in Magnificent Mile. Travelers also love the fascinating museums, panoramic lake views, and popular shops.
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.
River North
Known for its fantastic nightlife, stunning river views, and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Oz Park, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.
Oakland, IL
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- Visit Downtown Chicago
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- Supreme Life Building
- Visit Bronzeville
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- Visit Armour Square
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- Obama's House
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- Kam Synagogue
- Visit Dearborn Homes
- Lakefront Trail
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