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Our top choices for Oakland hotels

1. Hilton Chicago
Hilton ChicagoThe Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (3,534 reviews)
The price is CA $191
CA $269 total
includes taxes & fees
Nov 26 - Nov 27

2. 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)
The price is CA $121
CA $144 total
includes taxes & fees
Dec 7 - Dec 8

3. 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, (2,775 reviews)
The price is CA $185
CA $269 total
includes taxes & fees
Nov 23 - Nov 24

4. Le Méridien Essex Chicago
Le Méridien Essex ChicagoThe Loop, 5.6 km from Oakland
9.0 out of 10, Wonderful, (1,000 reviews)
The price is CA $158
CA $213 total
includes taxes & fees
Dec 7 - Dec 8

5. 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)
The price is CA $137
CA $160 total
includes taxes & fees
Dec 9 - Dec 10

6. Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake ChicagoThe Loop, 6.1 km from Oakland
9.6 out of 10, Exceptional, (1,221 reviews)
The price is CA $157
CA $187 total
includes taxes & fees
Dec 9 - Dec 10

7. 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, (2,535 reviews)
The price is CA $149
CA $175 total
includes taxes & fees
Nov 23 - Nov 24

8. DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent MileStreeterville, 7.8 km from Oakland
8.8 out of 10, Excellent, (2,582 reviews)
The price is CA $137
CA $163 total
includes taxes & fees
Dec 7 - Dec 8

9. Swissotel - Chicago
Swissotel - Chicago7.2 km from Oakland
9.0 out of 10, Wonderful, (3,580 reviews)
The price is CA $183
CA $267 total
includes taxes & fees
Nov 26 - Nov 27

10. ACME Hotel Chicago, Outset Collection by Hilton
ACME Hotel Chicago, Outset Collection by HiltonRiver North, 7.9 km from Oakland
9.0 out of 10, Wonderful, (1,958 reviews)
The price is CA $120
CA $142 total
includes taxes & fees
Dec 7 - Dec 8

11. Palmer House a Hilton Hotel
Palmer House a Hilton HotelTheatre District, 6.7 km from Oakland
8.6 out of 10, Excellent, (2,731 reviews)
The price is CA $183
CA $259 total
includes taxes & fees
Nov 24 - Nov 25

12. Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHGWest Loop, 6.4 km from Oakland
8.6 out of 10, Excellent, (1,272 reviews)
The price is CA $143
CA $187 total
includes taxes & fees
Nov 23 - Nov 24

13. Courtyard by Marriott Chicago Magnificent Mile
Courtyard by Marriott Chicago Magnificent MileStreeterville, 7.9 km from Oakland
9.0 out of 10, Wonderful, (2,087 reviews)
The price is CA $156
CA $185 total
includes taxes & fees
Dec 6 - Dec 7

14. Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Embassy Suites by Hilton Chicago Downtown Magnificent MileStreeterville, 7.6 km from Oakland
8.4 out of 10, Very good, (3,021 reviews)
The price is CA $168
CA $241 total
includes taxes & fees
Nov 24 - Nov 25

15. Hampton Inn Majestic Chicago Theatre District
Hampton Inn Majestic Chicago Theatre DistrictTheatre District, 6.7 km from Oakland
9.2 out of 10, Wonderful, (1,002 reviews)
The price is CA $161
CA $191 total
includes taxes & fees
Nov 23 - Nov 24

16. Congress Plaza Hotel
Congress Plaza HotelThe Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,139 reviews)
The price is CA $164
CA $195 total
includes taxes & fees
Nov 22 - Nov 23

17. 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)
The price is CA $211
CA $250 total
includes taxes & fees
Nov 22 - Nov 23

18. Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG7.3 km from Oakland
9.0 out of 10, Wonderful, (2,808 reviews)
The price is CA $162
CA $193 total
includes taxes & fees
Nov 22 - Nov 23

19. Hilton Garden Inn Chicago Central Loop
Hilton Garden Inn Chicago Central LoopThe Loop, 6.6 km from Oakland
9.2 out of 10, Wonderful, (1,442 reviews)
The price is CA $179
CA $213 total
includes taxes & fees
Nov 22 - Nov 23

20. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio HotelTheatre District, 6.7 km from Oakland
8.6 out of 10, Excellent, (1,010 reviews)
The price is CA $168
CA $200 total
includes taxes & fees
Dec 3 - Dec 4
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 | Star rating | Guest rating | Breakfast included | Pool | Spa | Pet-friendly | WiFi included | |
|---|---|---|---|---|---|---|---|---|
![]() Sable at Navy Pier Chicago, Curio Collection by Hilton | 9.4 Exceptional 2,775 reviews | View | ||||||
![]() Hilton Chicago | 8.6 Excellent 3,534 reviews | View | ||||||
![]() Le Méridien Essex Chicago | 9.0 Wonderful 1,000 reviews | View | ||||||
![]() Hilton Garden Inn Chicago Downtown South Loop | 8.8 Excellent 2,198 reviews | View | ||||||
![]() Homewood Suites by Hilton Chicago Downtown South Loop | 8.8 Excellent 2,535 reviews | View |
Where to stay in Oakland
Find the best Oakland areas and neighborhoods 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
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Top Oakland Hotel Reviews

Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by HiltonDowntown Chicago













































































































