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, (2,505 reviews)
"I loved it here and will definitely stay again."
Gina
The price is NZ$475
includes taxes & fees
26 May - 27 May
The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold CoastGold Coast, 9.4 km from Oakland
8.2 out of 10, Very good, (1,486 reviews)
"A nice stay and lovely location. "
Robin
The price is NZ$313
includes taxes & fees
2 June - 3 June
Sofitel Chicago Magnificent Mile
Sofitel Chicago Magnificent Mile8.6 km from Oakland
9.4 out of 10, Exceptional, (2,474 reviews)
"Great location and super nice hotel"
Karolina
The price is NZ$415
includes taxes & fees
26 May - 27 May
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, (2,004 reviews)
"Clean quiet hotel"
Daniel
The price is NZ$312
includes taxes & fees
27 May - 28 May
La Quinta Inn & Suites by Wyndham Chicago Downtown
La Quinta Inn & Suites by Wyndham Chicago DowntownThe Loop, 7 km from Oakland
8.6 out of 10, Excellent, (2,786 reviews)
"Very clean room, nice breakfast and really nice hotel restaurant"
Hugo
The price is NZ$311
includes taxes & fees
25 May - 26 May
Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (4,212 reviews)
"Great location & breakfast was amazing."
sierra
The price is NZ$372
includes taxes & fees
27 May - 28 May
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Fairfield Inn & Suites Chicago Downtown / Magnificent MileStreeterville, 7.9 km from Oakland
9.0 out of 10, Wonderful, (1,002 reviews)
"All around great stay. "
Nicholas
The price is NZ$261
includes taxes & fees
25 May - 26 May
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Bluegreen Vacations Hotel Blake, an Ascend Collection HotelThe Loop, 6.1 km from Oakland
9.6 out of 10, Exceptional, (1,241 reviews)
"Really nice stay. "
Rachael Lindsay
The price is NZ$322
includes taxes & fees
25 May - 26 May
Swissotel - Chicago
Swissotel - Chicago7.2 km from Oakland
9.0 out of 10, Wonderful, (3,336 reviews)
"Great location and very convenient to river walk and vicinity."
Sridhar
The price is NZ$399
includes taxes & fees
25 May - 26 May
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago DowntownTheatre District, 6.7 km from Oakland
9.2 out of 10, Wonderful, (2,246 reviews)
"Close to many attractions and shopping and nice unique hotel"
Brittany
The price is NZ$293
includes taxes & fees
25 May - 26 May
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Sonesta ES Suites Chicago Downtown Magnificent Mile - MedicalStreeterville, 8.6 km from Oakland
8.6 out of 10, Excellent, (2,458 reviews)
"Perfect location, very comfortable rooms, friendly staff."
Annabelle
The price is NZ$309
includes taxes & fees
25 May - 26 May
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent MileStreeterville, 7.8 km from Oakland
8.8 out of 10, Excellent, (2,480 reviews)
"This is a beautiful hotel and the location was perfect."
Felisha
The price is NZ$344
includes taxes & fees
25 May - 26 May
Hilton Chicago
Hilton ChicagoThe Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,809 reviews)
"Great staff and location. "
Robert
The price is NZ$452
includes taxes & fees
25 May - 26 May
Sheraton Grand Chicago Riverwalk
Sheraton Grand Chicago RiverwalkStreeterville, 7.4 km from Oakland
8.6 out of 10, Excellent, (1,626 reviews)
"It was very clean, beautiful place"
Grisel
The price is NZ$544
includes taxes & fees
25 May - 26 May
Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The LoopTheatre District, 6.9 km from Oakland
9.4 out of 10, Exceptional, (1,069 reviews)
"Clean rooms, comfy bed."
Brenda
The price is NZ$337
includes taxes & fees
25 May - 26 May
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Embassy Suites by Hilton Chicago Downtown Magnificent MileStreeterville, 7.6 km from Oakland
8.2 out of 10, Very good, (2,845 reviews)
"Breakfast was excellent."
Janine
The price is NZ$378
includes taxes & fees
27 May - 28 May
Homewood Suites by Hilton Chicago Downtown South Loop
Homewood Suites by Hilton Chicago Downtown South LoopThe Loop, 5.4 km from Oakland
8.8 out of 10, Excellent, (2,337 reviews)
"great place to stay and good location"
Wayne Aubrey
The price is NZ$369
includes taxes & fees
27 May - 28 May
Congress Plaza Hotel
Congress Plaza HotelThe Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,131 reviews)
"Excellent stay"
Jennifer
The price is NZ$271
includes taxes & fees
25 May - 26 May
Aloft by Marriott Chicago Mag Mile
Aloft by Marriott Chicago Mag MileStreeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,239 reviews)
"Nice place to stay"
Jimmie
The price is NZ$303
includes taxes & fees
26 May - 27 May
Hyatt Place Chicago/Downtown - The Loop
Hyatt Place Chicago/Downtown - The LoopThe Loop, 7.1 km from Oakland
8.8 out of 10, Excellent, (1,306 reviews)
"Excellent clean room & very nice staff"
Anthony
The price is NZ$364
includes taxes & fees
25 May - 26 May
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.
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
An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
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.
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