- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
Our top choices for Oakland hotels

1. Hilton Chicago
Hilton ChicagoThe Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (3,526 reviews)
The price is CA $151
CA $220 total
includes taxes & fees
Nov 27 - Nov 28

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, (2,765 reviews)
The price is CA $183
CA $266 total
includes taxes & fees
Nov 23 - Nov 24

3. 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, (2,195 reviews)
The price is CA $136
CA $159 total
includes taxes & fees
Nov 23 - Nov 24

4. 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, (2,530 reviews)
The price is CA $148
CA $173 total
includes taxes & fees
Nov 23 - Nov 24

5. Best Western Grant Park Hotel
Best Western Grant Park HotelThe Loop, 5.4 km from Oakland
8.2 out of 10, Very good, (2,737 reviews)
The price is CA $119
CA $142 total
includes taxes & fees
Dec 7 - Dec 8

6. 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 $157
CA $211 total
includes taxes & fees
Dec 7 - Dec 8

7. 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, (1,270 reviews)
The price is CA $142
CA $185 total
includes taxes & fees
Nov 23 - Nov 24

8. 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 $160
CA $190 total
includes taxes & fees
Nov 23 - Nov 24

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, (1,217 reviews)
The price is CA $195
CA $231 total
includes taxes & fees
Dec 6 - Dec 7

10. DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent MileStreeterville, 7.8 km from Oakland
8.8 out of 10, Excellent, (2,577 reviews)
The price is CA $135
CA $161 total
includes taxes & fees
Dec 7 - Dec 8

11. Hyatt House Chicago/West Loop-Fulton Market
Hyatt House Chicago/West Loop-Fulton Market7.9 km from Oakland
9.0 out of 10, Wonderful, (1,308 reviews)
The price is CA $209
CA $248 total
includes taxes & fees
Nov 22 - Nov 23

12. Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG7.3 km from Oakland
9.0 out of 10, Wonderful, (2,789 reviews)
The price is CA $161
CA $191 total
includes taxes & fees
Nov 22 - Nov 23

13. Swissotel - Chicago
Swissotel - Chicago7.2 km from Oakland
9.0 out of 10, Wonderful, (3,568 reviews)
The price is CA $182
CA $265 total
includes taxes & fees
Nov 26 - Nov 27

14. Congress Plaza Hotel
Congress Plaza HotelThe Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,106 reviews)
The price is CA $162
CA $193 total
includes taxes & fees
Nov 23 - Nov 24

15. Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown ChicagoThe Loop, 5.9 km from Oakland
7.8 out of 10, Good, (2,953 reviews)
The price is CA $164
CA $196 total
includes taxes & fees
Dec 3 - Dec 4

16. Hyatt Place Chicago/Downtown - The Loop
Hyatt Place Chicago/Downtown - The LoopThe Loop, 7.1 km from Oakland
8.8 out of 10, Excellent, (1,693 reviews)
The price is CA $165
CA $197 total
includes taxes & fees
Nov 23 - Nov 24

17. Palmer House a Hilton Hotel
Palmer House a Hilton HotelTheatre District, 6.7 km from Oakland
8.6 out of 10, Excellent, (2,728 reviews)
The price is CA $185
CA $261 total
includes taxes & fees
Nov 24 - Nov 25

18. LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonThe Loop, 7.4 km from Oakland
9.4 out of 10, Exceptional, (3,889 reviews)
The price is CA $201
CA $281 total
includes taxes & fees
Nov 23 - Nov 24

19. Courtyard by Marriott Chicago Magnificent Mile
Courtyard by Marriott Chicago Magnificent MileStreeterville, 7.9 km from Oakland
9.0 out of 10, Wonderful, (2,081 reviews)
The price is CA $154
CA $183 total
includes taxes & fees
Dec 6 - Dec 7

20. Aloft by Marriott Chicago Mag Mile
Aloft by Marriott Chicago Mag MileStreeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,313 reviews)
The price is CA $153
CA $182 total
includes taxes & fees
Nov 22 - Nov 23
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 2,765 reviews | View | ||||||
![]() Hilton Chicago | 8.6 Excellent 3,526 reviews | View | ||||||
![]() Hilton Garden Inn Chicago Downtown South Loop | 8.8 Excellent 2,195 reviews | View | ||||||
![]() Le Méridien Essex Chicago | 9.0 Wonderful 1,000 reviews | View | ||||||
![]() Homewood Suites by Hilton Chicago Downtown South Loop | 8.8 Excellent 2,530 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

Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake ChicagoDowntown Chicago

























































































































