Oakland
Chicago
Visit Oakland
Stay near popular Oakland attractions
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Chicago By Night River and Lake Cruise
CA $70
per adult
92% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $57
per adult
94% of travellers recommend
Oakland Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
The price is CA $199 per night from Aug 30 to Aug 31
CA $199
CA $237 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very good! (10,210 reviews)
"Best experience"
Reviewed on Aug 5, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
The price is CA $206 per night from Aug 30 to Aug 31
CA $206
CA $245 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very good! (1,925 reviews)
"I stayed at The Chicago Hotel Collection Ambassador Gold Coast while in Chicago for a work event at Wrigley Field, and it was a great choice for my visit. The hotel’s location in the Gold Coast neighborhood was ideal — close enough to easily get around the city while still offering a quieter, more ..."
Reviewed on Aug 5, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
The price is CA $299 per night from Aug 30 to Aug 31
CA $299
CA $351 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
The price is CA $238 per night from Aug 30 to Aug 31
CA $238
CA $271 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
The price is CA $247 per night from Aug 30 to Aug 31
CA $247
CA $338 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
9/10 Wonderful! (2,729 reviews)
"The property was old and defiantly not 4 star hotel. At best its a 3 Star hotel. Location was great"
Reviewed on Aug 5, 2026
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
The price is CA $308 per night from Aug 30 to Aug 31
CA $308
CA $407 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,242 reviews)
"Very clean"
Reviewed on Aug 5, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most.
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.
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.
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.
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.
Photo by Mattyboy876
Open Photo by Mattyboy876
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).
