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.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
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.
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.
Oakland Hotel Deals
Congress Plaza Hotel
"The only redeeming quality of this hotel is the location. For the price it is NOT worth it. The bed is a rock that doesn't even have a fitted sheet on it and did not come with adequate blankets. The AC works well, but with the thin blankets it was almost unbearable. And oh man, the bathroom! Severely ..."
Reviewed on Jun 8, 2026
The Chicago Hotel Collection - Magnificent Mile
"Elevator is very slow, showers are tiny"
Reviewed on Jun 8, 2026
The Chicago Hotel Collection Ambassador Gold Coast
"We just stayed one night but the hotel served its purpose. We would stay here again. We also liked the lobby of the hotel and bar"
Reviewed on Jun 8, 2026
Hyatt Regency O'Hare Chicago
"Very clean & will stay in this hotel again"
Reviewed on Jun 8, 2026
Freehand Chicago
"The room was okay, not very spacious, didn't have any soap in the shower, otherwise was okay."
Reviewed on Jun 8, 2026
River Hotel
"Friendly staff, clean room, let us check in early"
Reviewed on Jun 8, 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 Art Institute of Chicago 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 Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.
