Search Hotels in Oakland, Chicago
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Our top choices for Oakland hotels
1. 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, (2,469 reviews)
"Good stay"
Pramukha
The price is ฿8,327
฿9,900 total
includes taxes & fees
2 Oct - 3 Oct
2. 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, (2,700 reviews)
"Amazing place to stay"
Shanequa
The price is ฿9,932
฿12,957 total
includes taxes & fees
27 Sept - 28 Sept
3. Hyatt Place Chicago/Downtown - The Loop
Hyatt Place Chicago/Downtown - The LoopThe Loop, 7.1 km from Oakland
8.8 out of 10, Excellent, (1,621 reviews)
"Great place to stay!"
LISA
The price is ฿7,704
฿9,159 total
includes taxes & fees
27 Sept - 28 Sept
4. 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, (3,011 reviews)
"The location was great; we were able to walk to a lot of places."
Melissa
The price is ฿7,619
฿10,036 total
includes taxes & fees
1 Oct - 2 Oct
5. Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,451 reviews)
"Really great stay and experience"
Whitney
The price is ฿11,462
฿14,816 total
includes taxes & fees
27 Sept - 28 Sept
6. InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHGMagnificent Mile, 7.7 km from Oakland
9.2 out of 10, Wonderful, (3,318 reviews)
"Excellent stay"
Darryl Halbert
The price is ฿9,330
฿12,258 total
includes taxes & fees
27 Sept - 28 Sept
7. Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG7.3 km from Oakland
9.0 out of 10, Wonderful, (2,662 reviews)
"Great stay, close to great food and ambiance in West Loop."
Victoria
The price is ฿6,287
฿7,476 total
includes taxes & fees
27 Sept - 28 Sept
8. L7 Chicago by LOTTE
L7 Chicago by LOTTETheatre District, 7.2 km from Oakland
9.6 out of 10, Exceptional, (4,849 reviews)
"Always a great stay, walking distances to great restaurants and staff is always friendly and accommodating."
Andrea
The price is ฿9,566
฿11,373 total
includes taxes & fees
27 Sept - 28 Sept
9. Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake ChicagoThe Loop, 6.1 km from Oakland
9.6 out of 10, Exceptional, (1,255 reviews)
"good location. airport shuttle service would have been nice."
Ann
The price is ฿8,285
฿9,850 total
includes taxes & fees
14 Oct - 15 Oct
10. Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesStreeterville, 8.6 km from Oakland
9.0 out of 10, Wonderful, (4,946 reviews)
"Very nice hotel, friendly staff, good location"
Brian
The price is ฿7,051
฿8,382 total
includes taxes & fees
27 Sept - 28 Sept
11. Residence Inn Chicago Downtown/Loop
Residence Inn Chicago Downtown/LoopTheatre District, 6.9 km from Oakland
9.4 out of 10, Exceptional, (1,004 reviews)
"We enjoyed our stay."
Karla
The price is ฿9,563
฿11,369 total
includes taxes & fees
2 Oct - 3 Oct
12. Congress Plaza Hotel
Congress Plaza HotelThe Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,180 reviews)
"Easy check in, rooms were clean, convenient location."
John
The price is ฿6,148
฿7,309 total
includes taxes & fees
27 Sept - 28 Sept
13. Hyatt Place Chicago/River North
Hyatt Place Chicago/River NorthRiver North, 7.8 km from Oakland
9.2 out of 10, Wonderful, (1,916 reviews)
"Great breakfast, kind staff, clean room"
Iminique
The price is ฿8,663
฿10,300 total
includes taxes & fees
27 Sept - 28 Sept
14. 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, (2,926 reviews)
"Our stay was great."
Mythli
The price is ฿7,597
฿9,626 total
includes taxes & fees
27 Sept - 28 Sept
15. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area7.5 km from Oakland
9.2 out of 10, Wonderful, (1,007 reviews)
"Nice place"
Brock
The price is ฿9,499
฿11,293 total
includes taxes & fees
2 Oct - 3 Oct
16. Best Western Grant Park Hotel
Best Western Grant Park HotelThe Loop, 5.4 km from Oakland
8.2 out of 10, Very good, (2,746 reviews)
"Nice hotel"
Sara
The price is ฿6,868
฿8,165 total
includes taxes & fees
27 Sept - 28 Sept
17. 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!"
Madelyn
The price is ฿7,789
฿9,260 total
includes taxes & fees
27 Sept - 28 Sept
18. 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, (6,011 reviews)
"Excellent stay , perfect location, worth it"
Shweta
The price is ฿7,804
฿9,278 total
includes taxes & fees
27 Sept - 28 Sept
19. Hyatt House Chicago/West Loop-Fulton Market
Hyatt House Chicago/West Loop-Fulton Market7.9 km from Oakland
9.0 out of 10, Wonderful, (1,313 reviews)
"A great hotel in a bustling area. We had a great stay."
Joel
The price is ฿9,296
฿11,052 total
includes taxes & fees
27 Sept - 28 Sept
20. Palmer House a Hilton Hotel
Palmer House a Hilton HotelTheatre District, 6.7 km from Oakland
8.6 out of 10, Excellent, (2,663 reviews)
"My stay was very pleasant and the bed was very comfortable loved the location aswell"
Gabriella
The price is ฿9,743
฿12,574 total
includes taxes & fees
2 Oct - 3 Oct
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.
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.
