
Oakland Vacations
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Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland

Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Oakland Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩199,443 per night from May 26 to May 27
₩199,443
₩237,116 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,167 reviews)
"I had an amazing view of Lake Michigan and the area but unfortunately Michigan Ave is very noisy at all times of the day and night. In addition, there were no black out shades and due to the rooms facing East, the sunrise was bright and early. I had to buy a sleeping mask just to sleep to 7am. The ..."
Reviewed on May 19, 2026

Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩224,609 per night from May 25 to May 26
₩224,609
₩310,021 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,190 reviews)
"New amenities, awesome breakfast, great location. Pleasently surprised, especially by the quality of the breakfast."
Reviewed on May 19, 2026

The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩181,317 per night from May 25 to May 26
₩181,317
₩215,567 total
May 25 - May 26
includes taxes & fees
7.8/10 Good! (1,437 reviews)
"Booked 1 bedroom for 1 night based on the pictures and the reviews. Staff was basically one person. He was leaving at 4 pm when I arrived. He showed me to my room which was nothing like the pictures. The room I booked on the app looked clean simple with a modern vibe. The room I walked into looked ..."
Reviewed on May 19, 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.
Frequently asked questions
Discover the most popular places to visit in Oakland

Navy Pier
4.5/5(4,925 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Millennium Park
4.5/5(7,309 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Grant Park
4.5/5(3,360 reviews)
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



