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.
Oakland Hotel Deals
Congress Plaza Hotel
"Big clean room, with a big clean shower/tub combo. Right next to grant park so it was super close to all of the cool things. Night time was a little iffy, but in the day time this area was super convenient"
Reviewed on 2026/6/22
Hilton Chicago/Magnificent Mile Suites
"Nice property right near everything"
Reviewed on 2026/6/22
The Chicago Hotel Collection - Magnificent Mile
"Location"
Reviewed on 2026/6/22
Hyatt Regency O'Hare Chicago
"Just okay"
Reviewed on 2026/6/22
The Chicago Hotel Collection Ambassador Gold Coast
"There are so many things to like about the Ambassador Hotel, starting with its incredible Gold Coast location, it’s amazing history as a landmark hotel in Chicago, it’s traditional, elegant interiors nicely updated. Last but not least a big shout out to the front desk as well as restaurant/cocktail ..."
Reviewed on 2026/6/22
Hilton Chicago O'Hare Airport
"Perfect place to stay when you have an early morning flight the next day."
Reviewed on 2026/6/22
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
Explore a world of travel with Expedia
- Resorts in Cermak-Chinatown Station
- Gay friendly Hotels in Downtown Chicago
- Beach Hotels in Oakland
- South Loop Hotels
- Hotels with Free Parking in Near South Side
- Hotels near Harold Washington Library Center
- Englewood Hotels
- Family Hotels in Chicago
- Hotels near Millennium Station
- Business Hotels in Downtown Chicago
- Hyde Park Hotels
- Green Hotels in The Loop
- Omni Hotels in Chicago
- 3 Star Hotels in Hyde Park
- Steigenberger Hotels in Chicago
- Hotels near Chicago McCormick Place Station
- Hotels near Cottage Grove Station
- Hotels near Adler Planetarium and Astronomy Museum
- Four Seasons Hotels in Grand Boulevard
- Hotels with Early Check-in in Chicago
- Cheap Hotels in The Loop
- Cheap Hotels in Hyde Park
- Hotels near Chicago 35th Street-Lou Jones-Bronzeville Station
- Hotels near Mary Bartelme Park
- Green Hotels in Chicago
- Lakeshore East Hotels
- Casino Hotels in Armour Square
- Boutique Hotels in Chicago
- Hotels with an Indoor Pool in South Loop
- Beach Hotels in Kenwood
- Cabin Rentals in Chicago
- Casino Hotels in Chicago
- Hotels near Burnham Park
- Romantic Hotels in Chicago
- Hotels near Wintrust Arena
- Romantic Hotels in Hyde Park
- Hotels near McCormick Tribune Center
- Boutique Hotels in Downtown Chicago
- Hotels with a Pool in Downtown Chicago
- Pet-Friendly Hotels in South Loop
- Hotels near McCormick Place
- 5 Star Hotels in Hyde Park
- Preferred Hotels in Chicago
- Chinatown Hotels
- Hotel Wedding Venues Hotels in South Loop
- Gay friendly Hotels in South Loop
- Boutique Hotels in South Loop
- Resorts & Hotels with Spas in Hyde Park
- Nuclear Energy Sculpture
- Visit Bronzeville
- Visit United Center
- Chicago Theatre
- Visit Fuller Park
- Visit The Loop
- Visit East Village
- University of Chicago
- Civic Opera House
- American Police Center & Museum
- Visit Avalon Park
- Visit South Loop
- Visit Near South Side
- Ida B Wells House
- Bond Chapel
- Visit Grace Abbott Homes
- Visit West Loop
- Muddy Waters’ House
- Visit Kenwood
- Chicago Vacations
- Hyde Park Hair Salon
- Visit Wicker Park
- Visit Chicago Museum Campus
- 49th Street Beach
- Visit Jackson Park Highlands
- Visit Old Town Chicago
- Visit East Garfield Park
- Visit Dearborn Homes
- Visit Douglas
- Visit South Shore
- Visit Chicago
- Visit Downtown Chicago
- Visit West Town
- Visit Chicago Lawn
- Visit Hyde Park
- Visit Goose Island
- Visit Roseland
- Visit Near East Side
- Visit Grand Boulevard
- Grant Park
- Visit Greektown
- Visit North Lawndale
- Car rentals near Chicago
- Hertz Rental Cars in Hyde Park
- Sixt Rental Cars in Chicago Museum Campus
- Ok Mobility Rental Cars in Chicago
- Dollar Rent A Car Rental Cars in Grand Boulevard
- Midsize Car Rentals in Chicago
- Car rentals near Hyde Park Hair Salon
- Apex Car Rentals Rental Cars in Chicago
- Car rentals near Printers Row
- Car rentals near Armour Square
