Search Hotels in Oakland, 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, (2,518 reviews)
"Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!"
Deborah
The price is ฿7,432
฿9,957 total
includes taxes & fees
2 Jul - 3 Jul
Palmer House a Hilton Hotel
Palmer House a Hilton HotelTheatre District, 6.7 km from Oakland
8.6 out of 10, Excellent, (2,469 reviews)
"Beautiful place to stay."
Charles Otto
The price is ฿5,970
฿8,064 total
includes taxes & fees
2 Jul - 3 Jul
River Hotel
River HotelThe Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,216 reviews)
"Great location"
Nashadia
The price is ฿4,117
฿4,894 total
includes taxes & fees
1 Jul - 2 Jul
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown ChicagoThe Loop, 5.9 km from Oakland
7.4 out of 10, Good, (2,613 reviews)
"Staff was friendly and helpful.. location was great"
Amber
The price is ฿4,144
฿4,928 total
includes taxes & fees
1 Jul - 2 Jul
Congress Plaza Hotel
Congress Plaza HotelThe Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,140 reviews)
"Excellent stay"
Jennifer
The price is ฿4,534
฿5,391 total
includes taxes & fees
29 Jun - 30 Jun
Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The LoopTheatre District, 6.9 km from Oakland
9.4 out of 10, Exceptional, (1,081 reviews)
"Such a lovely hotel with a beautiful, excellent staff, and lots of character!"
Debby
The price is ฿4,518
฿6,335 total
includes taxes & fees
1 Jul - 2 Jul
Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (4,306 reviews)
"Great location & breakfast was amazing."
sierra
The price is ฿6,144
฿8,230 total
includes taxes & fees
30 Jun - 1 Jul
Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,491 reviews)
"Staff was great."
Marianne
The price is ฿6,338
฿8,695 total
includes taxes & fees
2 Jul - 3 Jul
Sheraton Grand Chicago Riverwalk
Sheraton Grand Chicago RiverwalkStreeterville, 7.4 km from Oakland
8.6 out of 10, Excellent, (1,650 reviews)
"I LOVED my stay , i WILL be back."
Latonia
The price is ฿6,475
฿8,857 total
includes taxes & fees
2 Jul - 3 Jul
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium ParkThe Loop, 7.1 km from Oakland
8.8 out of 10, Excellent, (2,174 reviews)
"Great place"
JOSE
The price is ฿6,793
฿9,236 total
includes taxes & fees
1 Jul - 2 Jul
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, (1,253 reviews)
"Overall comfortable stay and easy access by walk to downtown and all other places in the city."
raghu
The price is ฿5,695
฿6,770 total
includes taxes & fees
2 Jul - 3 Jul
Hilton Chicago
Hilton ChicagoThe Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,848 reviews)
"great hotel and excellent to stay"
Ruben
The price is ฿6,370
฿8,527 total
includes taxes & fees
2 Jul - 3 Jul
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, (2,017 reviews)
"Great hotel, clean efficient and not too far from Downtown would stay again!"
Justin
The price is ฿4,945
฿5,880 total
includes taxes & fees
1 Jul - 2 Jul
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, (1,527 reviews)
"Clean room, helpful staff and breakfast was amazing."
Scott
The price is ฿5,081
฿6,040 total
includes taxes & fees
22 Jun - 23 Jun
Arlo Chicago
Arlo ChicagoTheatre District, 7.1 km from Oakland
9.4 out of 10, Exceptional, (2,116 reviews)
"Love our stay! Will def stay again!!"
Stephany
The price is ฿5,898
฿7,995 total
includes taxes & fees
2 Jul - 3 Jul
Eurostars Magnificent Mile
Eurostars Magnificent MileRiver North, 8.1 km from Oakland
9.0 out of 10, Wonderful, (3,601 reviews)
"Great location, large rooms, we loved our stay and would definitely recommend "
Belinda
The price is ฿6,501
฿7,729 total
includes taxes & fees
1 Jul - 2 Jul
Swissotel - Chicago
Swissotel - Chicago7.2 km from Oakland
9.0 out of 10, Wonderful, (3,362 reviews)
"Great location!"
Maria
The price is ฿7,869
฿10,501 total
includes taxes & fees
2 Jul - 3 Jul
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonThe Loop, 7.4 km from Oakland
9.4 out of 10, Exceptional, (3,725 reviews)
"Can't beat the location; it's next to Michigan Avenue and across from the Riverwalk; we'd stay there again."
Matson
The price is ฿7,211
฿9,528 total
includes taxes & fees
21 Jun - 22 Jun
The Royal Sonesta Chicago Downtown
The Royal Sonesta Chicago DowntownThe Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,446 reviews)
"Great location, nice property, helpful staff, and spacious, comfortable rooms."
Sunil
The price is ฿5,656
฿7,764 total
includes taxes & fees
2 Jul - 3 Jul
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, (2,300 reviews)
"Wonderful location and very friendly and helpful staff."
George R. Bamberger
The price is ฿4,388
฿5,217 total
includes taxes & fees
1 Jul - 2 Jul
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 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
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
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.
