Oakland, IL
Chicago
Visit Oakland
Stay near popular Oakland attractions
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
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
Oakland Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
$115 nightly
The price is $136 total per night from Sep 7 to Sep 8
$136 total
Sep 7 - Sep 8
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 ...
8/10 Very Good! (10,269 reviews)
"Nice"
Reviewed on Sep 4, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
$143 nightly
The price is $170 total per night from Sep 7 to Sep 8
$170 total
Sep 7 - Sep 8
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! (2,152 reviews)
"I enjoyed this room truly! the place was perfectly located! loved the stay and will for sureee book again"
Reviewed on Sep 4, 2026
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (888 reviews)
"We thoroughly enjoyed our stay at Kasa- check in instructions were clear and hassle free. The unit was spacious and clean, with a terrific view. Highly recommended!"
Reviewed on Sep 4, 2026
River Hotel
75 East Wacker Drive Chicago IL
$159 nightly
The price is $190 total per night from Sep 8 to Sep 9
$190 total
Sep 8 - Sep 9
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 ...
8.8/10 Excellent! (5,397 reviews)
"Check-in was fast, the staff was nice. The room and lobby were very clean. We had a microwave mini fridge that actually worked.? We got the 24th floor and waiting for the elevator was annoying. Don't forget to tap your card before selecting floor button on the elevator. The location was great, just ..."
Reviewed on Sep 4, 2026
Hampton Inn Chicago Downtown/Magnificent Mile
160 E Huron Street Chicago IL
$139 nightly
The price is $166 total per night from Sep 7 to Sep 8
$166 total
Sep 7 - Sep 8
Total with taxes and fees
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the ...
8/10 Very Good! (1,566 reviews)
"Parking : called ahead to ask about parking our trailer we pulled and was told a garage to use then it was an issue once we got there."
Reviewed on Sep 3, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
$227 nightly
The price is $266 total per night from Sep 7 to Sep 8
$266 total
Sep 7 - Sep 8
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 ...
8.6/10 Excellent! (3,140 reviews)
"Enjoyable stay and a delicious breakfast."
Reviewed on Sep 4, 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. 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.
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.
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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- Visit Grand Boulevard
- Visit Wicker Park
- Visit Magnificent Mile
- Visit Streeterville
- Visit South Side
- Visit South Loop
- Visit Indian Village
- Where to stay in Chicago
- Visit River North
- Visit Cicero
- Visit Oak Park
- Visit Lincoln Square
- Visit Chicago
- Visit Fuller Park
- Visit Bronzeville
- Visit The Loop
- Visit Douglas
- Visit United Center
- Visit Rush Street
- Visit Gold Coast
- Visit Armour Square
- Visit Chinatown
- Visit West Loop
- Visit Canaryville
- Visit Wrigleyville
- Visit Downtown Chicago
- Visit Hyde Park
- Visit Chicago Museum Campus
- Visit Kenwood
- Chicago Vacations
- Visit Near South Side
- Visit Printers Row
