Oakland Hotels, Chicago
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Our top choices for Oakland hotels
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by HiltonStreeterville, 7.5 km from Oakland
9.4 out of 10, Exceptional, (2,412 reviews)
"Great spot and view, would stay again!"
Kimberly
The price is AU$287
includes taxes & fees
24 Mar - 25 Mar
Hilton Chicago
Hilton ChicagoThe Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,689 reviews)
"Amazing place to stay!"
Nia
The price is AU$257
includes taxes & fees
5 Apr - 6 Apr
River Hotel
River HotelThe Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,021 reviews)
"very beautiful hotel and great location "
Ciandra
The price is AU$163
includes taxes & fees
31 Mar - 1 Apr
Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (3,563 reviews)
"Great location ans staff was amazing!!"
Bianca
The price is AU$258
includes taxes & fees
6 Apr - 7 Apr
FOUND Hotel Chicago River North
FOUND Hotel Chicago River NorthRiver North, 8.1 km from Oakland
8.6 out of 10, Excellent, (503 reviews)
"Lots of stuff close by , cool vibe inside and very nice staff"
Abel
The price is AU$138
includes taxes & fees
23 Mar - 24 Mar
Swissotel - Chicago
Swissotel - Chicago7.2 km from Oakland
9.0 out of 10, Wonderful, (3,220 reviews)
"Helpful staff, great location with views, restaurant and bar on-site"
Natalie
The price is AU$262
includes taxes & fees
29 Mar - 30 Mar
Congress Plaza Hotel
Congress Plaza HotelThe Loop, 6 km from Oakland
8.0 out of 10, Very good, (9,973 reviews)
"Great location, beautiful historic hotel with clean, updated rooms. "
Jennifer
The price is AU$208
includes taxes & fees
20 Mar - 21 Mar
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent MileStreeterville, 7.8 km from Oakland
8.8 out of 10, Excellent, (2,360 reviews)
"Loved this hotel!"
Ellen
The price is AU$188
includes taxes & fees
25 Mar - 26 Mar
L7 Chicago by LOTTE
L7 Chicago by LOTTETheatre District, 7.2 km from Oakland
9.6 out of 10, Exceptional, (3,786 reviews)
"Amazing hotel-- Loved staying here."
Maureen
The price is AU$281
includes taxes & fees
31 Mar - 1 Apr
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago DowntownTheatre District, 6.7 km from Oakland
9.2 out of 10, Wonderful, (2,232 reviews)
"Bed was comfortable, fresh fruit at breakfast. "
Bradford
The price is AU$231
includes taxes & fees
5 Apr - 6 Apr
Arlo Chicago
Arlo ChicagoTheatre District, 7.1 km from Oakland
9.4 out of 10, Exceptional, (2,024 reviews)
"Great location and very clean hotel with nice staff. "
Carrie
The price is AU$263
includes taxes & fees
26 Mar - 27 Mar
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesStreeterville, 8.6 km from Oakland
9.0 out of 10, Wonderful, (3,934 reviews)
"Great hotel great location. "
Michael
The price is AU$202
includes taxes & fees
31 Mar - 1 Apr
Club Quarters Hotel Wacker at Michigan, Chicago
Club Quarters Hotel Wacker at Michigan, ChicagoThe Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (2,127 reviews)
"Prefect location to walk to everything we wanted & the staff was great!"
Michael
The price is AU$161
includes taxes & fees
5 Apr - 6 Apr
Best Western Grant Park Hotel
Best Western Grant Park HotelThe Loop, 5.4 km from Oakland
8.2 out of 10, Very good, (2,676 reviews)
"Perfect location!!"
Kelly
The price is AU$186
includes taxes & fees
12 Apr - 13 Apr
Freehand Chicago
Freehand ChicagoRiver North, 7.9 km from Oakland
8.0 out of 10, Very good, (2,809 reviews)
"Great location, clean and decent sized room, staff was helpful and amenities are very convenient!"
MaryJane
The price is AU$126
includes taxes & fees
25 Mar - 26 Mar
Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The LoopTheatre District, 6.9 km from Oakland
9.4 out of 10, Exceptional, (1,019 reviews)
"Lots of places to eat and shop nearby"
Analicia
The price is AU$246
includes taxes & fees
26 Mar - 27 Mar
Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South LoopThe Loop, 5.4 km from Oakland
8.8 out of 10, Excellent, (1,914 reviews)
"Clean room and view was incredible "
Chloe
The price is AU$195
includes taxes & fees
13 Apr - 14 Apr
Aloft Chicago Mag Mile
Aloft Chicago Mag MileStreeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,137 reviews)
"Nice location and good hotel"
Taneshia
The price is AU$191
includes taxes & fees
22 Mar - 23 Mar
The Hoxton Chicago
The Hoxton Chicago7.7 km from Oakland
9.0 out of 10, Wonderful, (1,000 reviews)
"Super cute hotel. Great bar and food "
Patricia
The price is AU$292
includes taxes & fees
22 Mar - 23 Mar
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.
Our guide on where to stay in Oakland
Find the best Oakland areas for the activities you enjoy most. Learn more about Oakland
Learn more about Oakland
Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Magnificent Mile
A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.
The Loop
Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.
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
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
