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Check availability on Oakland Boutique Hotels

Our top choices for Oakland boutique hotels

Bar (on property)
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Downtown Chicago
8.2 out of 10, Very good, (3802)
"Comfortable Room, great location and Excellent Staff. "
United States
Charles
The price is ₹6,945
₹8,153 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Whitehall Hotel, BW Premier Collection
Reception hall
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3163)
"Amazing stay very clean and beautiful views "
United States
Deigo
The price is ₹8,739
₹10,258 total
includes taxes & fees
11 Jan - 12 Jan 2026
Eurostars Magnificent Mile
American cuisine
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1011)
"Great hotel location and friendly staff! "
United States
Kathleen
The price is ₹8,835
₹13,030 total
includes taxes & fees
7 Jan - 8 Jan 2026
Staypineapple, An Iconic Hotel, The Loop
Nightclub
Central Loop Hotel

Central Loop Hotel

Central Loop Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1942)
"Easy check in and room was good for the time I was there"
United States
WILLIAM
The price is ₹6,719
₹7,887 total
includes taxes & fees
29 Dec - 30 Dec
Central Loop Hotel
55-inch LCD TV with cable channels, TV, pay films
L7 Chicago by LOTTE

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3378)
"Enjoyed my stay"
United States
Karen
The price is ₹12,788
₹15,012 total
includes taxes & fees
1 Jan - 2 Jan 2026
L7 Chicago by LOTTE
Exterior
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1120)
"Amazing hotel "
United States
Alondra
The price is ₹8,638
₹10,140 total
includes taxes & fees
6 Jan - 7 Jan 2026
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Breakfast, lunch, dinner served; American cuisine
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2322)
"The room was beautiful ❤️❤️ I enjoyed the hot tub and the views !! "
United States
Mary
The price is ₹10,071
₹14,726 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Royal Sonesta Chicago River North
Lobby
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (2444)
"Decent hotel in a great location with extremely helpful staff. "
United States
Aaron
The price is ₹6,288
₹10,150 total
includes taxes & fees
18 Dec - 19 Dec
Hotel Felix River North/Magnificent Mile
Exterior
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1423)
"Staff was wonderful."
United States
Jamie
Sports Illustrated Resorts Chicago
Bar (on property)
Ivy Boutique Hotel

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1041)
"Staff was amazing! "
United States
Ahren
Ivy Boutique Hotel
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.
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Top Oakland Hotel Reviews

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

10/10 Excellent
"Everything was great!"
Henry 1-night trip
Posted 14 hours ago
Palmer House a Hilton Hotel

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Frequently asked questions

What's there to see and do in Oakland?
Once you've decided where you'd like to stay in family-friendly Oakland, plan what to do for fun on your holiday. While you're out and about in Oakland, popular attractions like Michigan Avenue, Wrigley Field and Soldier Field are worth a visit. You might also want to see places like Navy Pier, United Center and Harold Washington Cultural Center during your trip.