Oakland, IL
Chicago
Visit Oakland
Stay near popular Oakland attractions
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$158
per adult
80% of travellers recommend
LEGOLAND® Discovery Center Chicago
$26
per adult
92% of travellers recommend
Museum of Illusions Chicago Admission Ticket
$43
per adult
City Cruises Chicago: Signature Lunch Cruise on Lake Michigan
$74
per adult
Oakland Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
$108 nightly
The price is $129 total per night from Nov 11 to Nov 12
$129 total
Nov 11 - Nov 12
Total with taxes and 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 ...
River Hotel
75 East Wacker Drive Chicago IL
$152 nightly
The price is $181 total per night from Nov 1 to Nov 2
$181 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
$121 nightly
The price is $143 total per night from Nov 11 to Nov 12
$143 total
Nov 11 - Nov 12
Total with taxes and 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! (2,538 reviews)
"Just mid for real over priced for what it is"
Reviewed on Oct 20, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $169 total per night from Nov 9 to Nov 10
$169 total
Nov 9 - Nov 10
Total with taxes and fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very Good! (2,430 reviews)
"Cl"
Reviewed on Oct 19, 2026
The Wade
644 N Lake Shore Dr Chicago IL
$142 nightly
The price is $169 total per night from Nov 1 to Nov 2
$169 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
Hilton Chicago
720 S Michigan Ave Chicago IL
$194 nightly
The price is $230 total per night from Nov 13 to Nov 14
$230 total
Nov 13 - Nov 14
Total with taxes and fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
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. Learn more about Oakland
Learn more about 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 Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
Photo by © City of Chicago
Open Photo by © City of Chicago
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 Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.
Oakland, IL
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