Hotels in Oakland, Chicago from CA $135

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Our top choices for Oakland hotels

1. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (3,526 reviews)
"Enjoyed my stay will book again!"
United States
Jordan
The price is CA $151
CA $220 total
includes taxes & fees
Nov 27 - Nov 28
Hilton Chicago

2. 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, (2,765 reviews)
"Best stay, wonderful property."
Canada
Bonnie
The price is CA $183
CA $266 total
includes taxes & fees
Nov 23 - Nov 24
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (2,195 reviews)
"Great place to stay at"
United States
Aran
The price is CA $136
CA $159 total
includes taxes & fees
Nov 23 - Nov 24
Hilton Garden Inn Chicago Downtown South Loop

4. 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, (2,530 reviews)
"Wonderful room and great breakfast buffet!"
United States
Nicole
The price is CA $148
CA $173 total
includes taxes & fees
Nov 23 - Nov 24
Homewood Suites by Hilton Chicago Downtown South Loop

5. 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, (2,737 reviews)
"Room was dated but clean, staff was friendly, location was perfect for my needs"
United States
Michelle
The price is CA $119
CA $142 total
includes taxes & fees
Dec 7 - Dec 8
Best Western Grant Park Hotel

6. 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, (1,000 reviews)
"Fantastic location and facility. Comfortable bed and nice shower! Perfect hotel for the Bears Game!"
United States
Taso
The price is CA $157
CA $211 total
includes taxes & fees
Dec 7 - Dec 8
Le Méridien Essex Chicago

7. 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, (1,270 reviews)
"good breakfast, friendly staff"
United States
Donna
The price is CA $142
CA $185 total
includes taxes & fees
Nov 23 - Nov 24
Holiday Inn & Suites Chicago - Downtown by IHG

8. Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District
3.0 star property
Theatre District, 6.7 km from Oakland
9.2 out of 10, Wonderful, (1,002 reviews)
"we liked our stay here"
United States
Michael
The price is CA $160
CA $190 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn Majestic Chicago Theatre District

9. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop, 6.1 km from Oakland
9.6 out of 10, Exceptional, (1,217 reviews)
"Great location from both airports. Lovely hotel clean and convenient"
United Kingdom
Kanokkan
The price is CA $195
CA $231 total
includes taxes & fees
Dec 6 - Dec 7
Hilton Vacation Club Hotel Blake Chicago

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, (2,577 reviews)
"Great location and beautiful hotel!"
United States
Jodi
The price is CA $135
CA $161 total
includes taxes & fees
Dec 7 - Dec 8
DoubleTree by Hilton Chicago - Magnificent Mile

11. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
7.9 km from Oakland
9.0 out of 10, Wonderful, (1,308 reviews)
"Loved the continental breakfast and how close different bars and restaurants were at :)"
United States
Carole
The price is CA $209
CA $248 total
includes taxes & fees
Nov 22 - Nov 23
Hyatt House Chicago/West Loop-Fulton Market

12. Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
3.5 star property
7.3 km from Oakland
9.0 out of 10, Wonderful, (2,789 reviews)
"Nice hotel and location was perfect."
United States
Chriselda
The price is CA $161
CA $191 total
includes taxes & fees
Nov 22 - Nov 23
Crowne Plaza Chicago West Loop by IHG

13. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,567 reviews)
"Good location and nice hotel"
United States
Oleg
The price is CA $182
CA $265 total
includes taxes & fees
Nov 26 - Nov 27
Swissotel - Chicago

14. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,105 reviews)
"It was a wonderful stay!"
United States
Ashya
The price is CA $162
CA $193 total
includes taxes & fees
Nov 23 - Nov 24
Congress Plaza Hotel

15. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 5.9 km from Oakland
7.8 out of 10, Good, (2,953 reviews)
"It has a great location, near everything and the rooms was clean and comfortable."
United States
Gabriela
The price is CA $164
CA $196 total
includes taxes & fees
Dec 3 - Dec 4
Travelodge by Wyndham Downtown Chicago

16. Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop
3.0 star property
The Loop, 7.1 km from Oakland
8.8 out of 10, Excellent, (1,692 reviews)
"Great location and the front desk staff was exceptional - Addy, Julian and the whole crew on Thursday and Friday morning!"
United States
maribeth
The price is CA $165
CA $197 total
includes taxes & fees
Nov 23 - Nov 24
Hyatt Place Chicago/Downtown - The Loop

17. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 6.7 km from Oakland
8.6 out of 10, Excellent, (2,728 reviews)
"Beautiful hotel with wonderful staff!"
United States
Christy
The price is CA $185
CA $261 total
includes taxes & fees
Nov 24 - Nov 25
Palmer House a Hilton Hotel

18. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 7.4 km from Oakland
9.4 out of 10, Exceptional, (3,889 reviews)
"Excellent location"
Switzerland
Kevin
The price is CA $201
CA $281 total
includes taxes & fees
Nov 23 - Nov 24
LondonHouse Chicago, Curio Collection by Hilton

19. Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Streeterville, 7.9 km from Oakland
9.0 out of 10, Wonderful, (2,080 reviews)
"Great location Staff was terrific"
United States
Richard
The price is CA $154
CA $183 total
includes taxes & fees
Dec 6 - Dec 7
Courtyard by Marriott Chicago Magnificent Mile

20. Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,313 reviews)
"Great location . Would definitely come back there"
United States
Kevin
The price is CA $153
CA $182 total
includes taxes & fees
Nov 22 - Nov 23
Aloft by Marriott Chicago Mag Mile
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
A modern hotel with a glass facade, a waterfront location, and a large Ferris wheel in the background.
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.4
Exceptional
2,765 reviews
View
A grand hotel lobby with a central staircase, ornate columns, and a decorative ceiling.
Hilton Chicago
4.0 star property
8.6
Excellent
3,526 reviews
View
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
8.8
Excellent
2,195 reviews
View
A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.
Le Méridien Essex Chicago
4.0 star property
9.0
Wonderful
1,000 reviews
View
A modern kitchen with a large window, a dining area, and a view of the sea.
Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
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.

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

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 from CA $135 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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