Search Hotels in Oakland, Chicago
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Our top choices for Oakland hotels
1. Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake ChicagoThe Loop, 6.1 km from Oakland
9.6 out of 10, Exceptional, (1,215 reviews)
"Great location !"
Josee
The price is ฿5,405
฿6,426 total
includes taxes & fees
25 Nov - 26 Nov
2. Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (5,617 reviews)
"All the stay was perfect, location is near to all the best places"
JESUS VERA
The price is ฿5,285
฿7,244 total
includes taxes & fees
23 Nov - 24 Nov
3. LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonThe Loop, 7.4 km from Oakland
9.4 out of 10, Exceptional, (3,876 reviews)
"It was a very nice stay! We enjoyed the hotel
The views were amazing"
James
The price is ฿4,847
฿6,766 total
includes taxes & fees
22 Nov - 23 Nov
4. Hyatt Place Chicago/River North
Hyatt Place Chicago/River NorthRiver North, 7.8 km from Oakland
9.2 out of 10, Wonderful, (1,914 reviews)
"Great location, clean hotel and overall a great place to stay."
Pamela
The price is ฿4,724
฿5,616 total
includes taxes & fees
22 Nov - 23 Nov
5. L7 Chicago by LOTTE
L7 Chicago by LOTTETheatre District, 7.2 km from Oakland
9.6 out of 10, Exceptional, (5,133 reviews)
"Amazing hotel will stay again"
Matthew
The price is ฿4,892
฿5,816 total
includes taxes & fees
22 Nov - 23 Nov
6. Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River NorthRiver North, 8 km from Oakland
8.6 out of 10, Excellent, (5,978 reviews)
"Great location! Walkable to several nice spots and easy to get to parking."
Stacy
The price is ฿4,273
฿5,080 total
includes taxes & fees
23 Nov - 24 Nov
7. Swissotel - Chicago
Swissotel - Chicago7.2 km from Oakland
9.0 out of 10, Wonderful, (3,569 reviews)
"Good location and nice hotel"
Oleg
The price is ฿3,932
฿5,864 total
includes taxes & fees
26 Nov - 27 Nov
8. Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,491 reviews)
"Wonderful will stay again"
Kristee
The price is ฿5,901
฿8,218 total
includes taxes & fees
23 Nov - 24 Nov
9. Hilton Chicago
Hilton ChicagoThe Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (3,497 reviews)
"Great location!! Clean hotel and kids loved the pool!"
Joanna
The price is ฿3,642
฿5,321 total
includes taxes & fees
27 Nov - 28 Nov
10. Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium ParkThe Loop, 7.1 km from Oakland
8.8 out of 10, Excellent, (2,313 reviews)
"Beautiful hotel and great location."
Ruby
The price is ฿6,714
฿9,187 total
includes taxes & fees
23 Nov - 24 Nov
11. Courtyard by Marriott Chicago Magnificent Mile
Courtyard by Marriott Chicago Magnificent MileStreeterville, 7.9 km from Oakland
9.0 out of 10, Wonderful, (2,101 reviews)
"Great location Staff was terrific"
Richard
The price is ฿3,867
฿4,597 total
includes taxes & fees
23 Nov - 24 Nov
12. 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, (2,198 reviews)
"Great place to stay at"
Aran
The price is ฿3,269
฿3,887 total
includes taxes & fees
23 Nov - 24 Nov
13. 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, (2,525 reviews)
"Wonderful room and great breakfast buffet!"
Nicole
The price is ฿3,556
฿4,228 total
includes taxes & fees
23 Nov - 24 Nov
14. 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, (2,753 reviews)
"Best stay, wonderful property."
Bonnie
The price is ฿4,417
฿6,414 total
includes taxes & fees
23 Nov - 24 Nov
15. Hotel 505 River North
Hotel 505 River NorthRiver North, 7.8 km from Oakland
9.2 out of 10, Wonderful, (2,989 reviews)
"Great stay!"
Miya
The price is ฿3,755
฿5,545 total
includes taxes & fees
22 Nov - 23 Nov
16. Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago7.1 km from Oakland
8.6 out of 10, Excellent, (2,155 reviews)
"Loved the hotel!"
Shannon
The price is ฿5,315
฿7,362 total
includes taxes & fees
23 Nov - 24 Nov
17. Aloft by Marriott Chicago Mag Mile
Aloft by Marriott Chicago Mag MileStreeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,328 reviews)
"Stayed during Lollapalooza and loved it."
Jena
The price is ฿3,781
฿4,496 total
includes taxes & fees
23 Nov - 24 Nov
18. DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent MileStreeterville, 7.8 km from Oakland
8.8 out of 10, Excellent, (2,580 reviews)
"Great location and beautiful hotel!"
Jodi
The price is ฿3,413
฿4,057 total
includes taxes & fees
23 Nov - 24 Nov
19. The Royal Sonesta Chicago Downtown
The Royal Sonesta Chicago DowntownThe Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,668 reviews)
"Location of hotel and room view of river was outstanding!"
Scott
The price is ฿4,518
฿6,451 total
includes taxes & fees
23 Nov - 24 Nov
20. Eurostars Magnificent Mile
Eurostars Magnificent MileRiver North, 8.1 km from Oakland
9.0 out of 10, Wonderful, (3,973 reviews)
"Nice rooms and great location"
Gabriela
The price is ฿4,859
฿5,776 total
includes taxes & fees
22 Nov - 23 Nov
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.
Compare popular hotels in Oakland
Property | Property class | Guest rating | Breakfast included | Pool | Spa | Pet-friendly | WiFi included | |
|---|---|---|---|---|---|---|---|---|
 Hilton Vacation Club Hotel Blake Chicago | 9.6 Exceptional 1,215 reviews | View | ||||||
 Hotel Riu Plaza Chicago | 9.4 Exceptional 5,617 reviews | View | ||||||
 LondonHouse Chicago, Curio Collection by Hilton | 9.4 Exceptional 3,876 reviews | View | ||||||
 L7 Chicago by LOTTE | 9.6 Exceptional 5,133 reviews | View | ||||||
 Hyatt Place Chicago/River North | 9.2 Wonderful 1,914 reviews | View |
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.
Photo by © City of Chicago
Open Photo by © City of Chicago
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.
