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Hotels in Oakland, Chicago

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Our top choices for Oakland hotels

1. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 7.5 km from Oakland
9.4 out of 10, Exceptional, (2,643 reviews)
"Great stay."
United States
Dawn
The price is CA $279
CA $380 total
includes taxes & fees
Aug 31 - Sep 1
Sable at Navy Pier Chicago, Curio Collection by Hilton

2. Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 5.4 km from Oakland
8.2 out of 10, Very good, (2,757 reviews)
"Good stay!"
United States
Adit
The price is CA $201
CA $238 total
includes taxes & fees
Aug 31 - Sep 1
Best Western Grant Park Hotel

3. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 5.4 km from Oakland
8.8 out of 10, Excellent, (2,118 reviews)
"helpful staff, great location, comfortable rooms and great views"
United States
Jordan Leigh
The price is CA $225
CA $264 total
includes taxes & fees
Sep 1 - Sep 2
Hilton Garden Inn Chicago Downtown South Loop

4. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 5.9 km from Oakland
7.6 out of 10, Good, (2,731 reviews)
"Great location, clean rooms, would stay here again!"
United States
Adam
The price is CA $159
CA $189 total
includes taxes & fees
Aug 30 - Aug 31
Travelodge by Wyndham Downtown Chicago

5. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
The Loop, 5.4 km from Oakland
8.8 out of 10, Excellent, (2,406 reviews)
"Great stay"
United Kingdom
jayne
The price is CA $225
CA $264 total
includes taxes & fees
Aug 31 - Sep 1
Homewood Suites by Hilton Chicago Downtown South Loop

6. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,212 reviews)
"Perfect location loved our stay!"
United States
Christina
The price is CA $201
CA $239 total
includes taxes & fees
Aug 30 - Aug 31
Congress Plaza Hotel

7. Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 5.6 km from Oakland
9.0 out of 10, Wonderful, (1,009 reviews)
"Very welcoming and helpful staff!"
United States
Daniel
The price is CA $200
CA $263 total
includes taxes & fees
Aug 31 - Sep 1
Le Méridien Essex Chicago

8. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,986 reviews)
"Great location, friendly staff, various amenities for the family."
Canada
kun
The price is CA $273
CA $365 total
includes taxes & fees
Aug 31 - Sep 1
Hilton Chicago

9. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
The Loop, 6.1 km from Oakland
9.6 out of 10, Exceptional, (1,296 reviews)
"Very helpful front desk staff and friendly cleaners. Very pleasant stay"
United States
Aleace
The price is CA $235
CA $280 total
includes taxes & fees
Aug 30 - Aug 31
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

10. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 7.8 km from Oakland
8.8 out of 10, Excellent, (2,555 reviews)
"Loved the pool and the close proximity downtown!"
United States
Macy
The price is CA $226
CA $269 total
includes taxes & fees
Aug 30 - Aug 31
DoubleTree by Hilton Chicago - Magnificent Mile

11. The Wade

The Wade
4.5 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (1,977 reviews)
"Great stay and friendly staff!"
Canada
Richard
The price is CA $237
CA $282 total
includes taxes & fees
Aug 23 - Aug 24
The Wade

12. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 9.4 km from Oakland
8.0 out of 10, Very good, (1,928 reviews)
"Great stay"
United States
Judy
The price is CA $206
CA $245 total
includes taxes & fees
Aug 30 - Aug 31
The Chicago Hotel Collection Ambassador Gold Coast

13. Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG
3.0 star property
West Loop, 6.4 km from Oakland
8.6 out of 10, Excellent, (1,133 reviews)
"good hotel"
United States
Chimere
The price is CA $259
CA $325 total
includes taxes & fees
Aug 30 - Aug 31
Holiday Inn & Suites Chicago - Downtown by IHG

14. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 6.6 km from Oakland
8.8 out of 10, Excellent, (3,610 reviews)
"Great location, clean room, and friendly staff"
United States
Kelli
The price is CA $196
CA $233 total
includes taxes & fees
Aug 9 - Aug 10
Club Quarters Hotel, Central Loop, Chicago

15. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
3.0 star property
7.5 km from Oakland
9.2 out of 10, Wonderful, (1,012 reviews)
"Great location"
United States
Carmen
The price is CA $189
CA $225 total
includes taxes & fees
Aug 23 - Aug 24
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

16. Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
4.0 star property
Theatre District, 7.1 km from Oakland
8.8 out of 10, Excellent, (1,675 reviews)
"Great location, easy to access, clean rooms very nice."
United States
Andrew
The price is CA $206
CA $245 total
includes taxes & fees
Aug 31 - Sep 1
Cambria Hotel Chicago Loop - Theatre District

17. Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 6.7 km from Oakland
9.4 out of 10, Exceptional, (2,314 reviews)
"Fantastic hotel!"
Canada
Gillian
The price is CA $225
CA $310 total
includes taxes & fees
Aug 30 - Aug 31
Silversmith Hotel Chicago Downtown

18. Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop
3.0 star property
The Loop, 6.6 km from Oakland
9.2 out of 10, Wonderful, (1,402 reviews)
"Very nice would stay again"
United States
Dawn
The price is CA $297
CA $353 total
includes taxes & fees
Aug 23 - Aug 24
Hilton Garden Inn Chicago Central Loop

19. La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
The Loop, 7 km from Oakland
8.6 out of 10, Excellent, (2,863 reviews)
"This property is so nice to stay at, will continue to stay here in the future."
United States
Paige
The price is CA $238
CA $308 total
includes taxes & fees
Aug 9 - Aug 10
La Quinta Inn & Suites by Wyndham Chicago Downtown

20. Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Theatre District, 6.8 km from Oakland
9.0 out of 10, Wonderful, (2,684 reviews)
"Great location"
United States
Dee
The price is CA $262
CA $346 total
includes taxes & fees
Aug 23 - Aug 24
Hyatt Centric The Loop Chicago
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 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.

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.

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.

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.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).

Top Oakland Hotel Reviews

Frequently asked questions

What are the best hotels in Oakland that travellers recommend?
Two of the best hotels in Oakland that receive consistently high recommendations from travellers are the Sophy Hyde Park and the Hyatt Place Chicago-South/University Medical Center.

Sophy Hyde Park is a 4-star hotel with an outstanding 9.6 rating. Guests frequently compliment the friendly and great staff, the comfortable and clean rooms, and the convenient location. The hotel provides bathrobes and premium bedding, ensuring a comfortable stay.

Another highly recommended option is the 3-star Hyatt Place Chicago-South/University Medical Center, which has an 8.8 rating. Customers often highlight the friendly and helpful staff, the great location, and the fresh and good breakfast. The hotel offers spacious and clean rooms, an indoor pool, and connecting rooms, making it suitable for families.
What are the best family hotels in Oakland?
For family-friendly hotels in Oakland, consider the Hyatt Place Chicago-South/University Medical Center or the Sophy Hyde Park.

The 3-star Hyatt Place Chicago-South/University Medical Center, with an 8.8 rating, is an excellent choice for families. Guests frequently mention the friendly and helpful staff, the spacious and clean rooms, and the fresh and good breakfast. It offers amenities like connecting rooms, sofa beds, a child-friendly window design, kids' meals, and free cribs. It is also conveniently located near attractions such as Jackson Park and the 57th Street Beach.

Another highly recommended option is the 4-star Sophy Hyde Park, which boasts an impressive 9.6 rating. This hotel is praised by guests for its friendly staff, comfortable and clean rooms, and convenient location. Family amenities include free cribs, a child-friendly window design, connecting rooms, and free toiletries. It is also close to recreational areas like Jackson Park and Washington Park.
What are the top pet-friendly hotels in Oakland?
For top pet-friendly hotels in Oakland, Illinois, consider the Sophy Hyde Park and the Hyatt Place Chicago-South/University Medical Center.

The 4-star Sophy Hyde Park, with an excellent 9.6 rating, is a fantastic choice for travellers with dogs. Guests consistently praise the friendly and great staff, comfortable and clean rooms, and convenient location. It is also close to several green spaces, including Jackson Park (2.5 km), Paul H. Douglas Nature Sanctuary (1.5 km), and Washington Park (1.7 km), great for walks with your pet.

Another highly-rated option is the 3-star Hyatt Place Chicago-South/University Medical Center, holding an 8.8 rating. This hotel also permits pets and offers spacious and clean rooms. Travellers often highlight the friendly and helpful staff, the great location, and the fresh and good breakfast. It is similarly close to outdoor areas like Paul H. Douglas Nature Sanctuary (1.4 km) and Garden of the Phoenix (1.6 km).
What are the best budget hotels in Oakland?
For a highly-rated budget hotel in Oakland, consider the Hyatt Place Chicago-South/University Medical Center.

This 3-star hotel has an impressive 8.8 rating and offers excellent value. Guests frequently praise the friendly and helpful staff, the good location, and the fresh and tasty breakfast. The rooms are described as spacious and clean, and parking is noted as easy and excellent. Key amenities include free WiFi, free cribs, and a complimentary area shuttle. It is conveniently located near several points of interest, such as the Hyde Park Art Centre, which is just 0.4 km away, and the Barack Obama Residence, 0.9 km away.
What are the most romantic hotels in Oakland for couples?
For a romantic couples' stay in Oakland, the Sophy Hyde Park is an excellent choice.

This 4-star hotel, with an impressive 9.6 rating, offers a delightful experience for couples. Guests frequently praise its comfortable and clean rooms, as well as the friendly and great staff. The hotel provides couples dining options, complimentary toiletries, and free WiFi, ensuring a pleasant and convenient stay. Its location is considered great and convenient, with several points of interest nearby, such as the Hyde Park Art Centre, just 0.6 km away, and the historic Robie House, 1.1 km from the hotel. The Sophy Hyde Park also features a great bar and comfortable beds, contributing to a relaxing and enjoyable escape.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Oakland hotel for you.
How much is the nightly rate at a Oakland hotel?
Hotel prices in Oakland often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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