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Hotels in Oakland, Chicago

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Our top choices for Oakland hotels

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, (2,545 reviews)
"Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!"
United States
Deborah
The price is CA $309
CA $416 total
includes taxes & fees
Jul 2 - Jul 3
Sable at Navy Pier Chicago, Curio Collection by Hilton

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Streeterville, 8.1 km from Oakland
9.2 out of 10, Wonderful, (1,807 reviews)
"All around great property and a wonderful location"
United States
Bruce
The price is CA $179
CA $259 total
includes taxes & fees
Jul 1 - Jul 2
Omni Chicago Hotel

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, (2,507 reviews)
"Beautiful place to stay."
United States
Charles Otto
The price is CA $257
CA $347 total
includes taxes & fees
Jul 2 - Jul 3
Palmer House a Hilton Hotel

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,510 reviews)
"Staff was great."
United States
Marianne
The price is CA $284
CA $388 total
includes taxes & fees
Jul 2 - Jul 3
Hyatt Regency Chicago

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,382 reviews)
"Nice Hotel, rooms are clean , the best for us was the location, i would recommend"
United States
Sergio
The price is CA $246
CA $342 total
includes taxes & fees
Jul 1 - Jul 2
Swissotel - Chicago

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (4,436 reviews)
"The breakfast, location, and staff were amazing."
United States
Corey
The price is CA $224
CA $306 total
includes taxes & fees
Jul 6 - Jul 7
Hotel Riu Plaza Chicago

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 7.4 km from Oakland
8.6 out of 10, Excellent, (1,667 reviews)
"Location was great"
United States
Pamela
The price is CA $279
CA $381 total
includes taxes & fees
Jul 2 - Jul 3
Sheraton Grand Chicago Riverwalk

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,265 reviews)
"Great stay thanks"
United States
Felipa
The price is CA $190
CA $226 total
includes taxes & fees
Jun 29 - Jun 30
Congress Plaza Hotel

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 8.1 km from Oakland
9.0 out of 10, Wonderful, (3,644 reviews)
"Had an amazing stay here!"
United States
Audrey
The price is CA $201
CA $239 total
includes taxes & fees
Jul 2 - Jul 3
Eurostars Magnificent Mile

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 7.1 km from Oakland
8.8 out of 10, Excellent, (2,196 reviews)
"Location is excellent!"
United States
Michele
The price is CA $301
CA $407 total
includes taxes & fees
Jul 7 - Jul 8
Fairmont Chicago at Millennium Park

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, (3,737 reviews)
"Great location, excellent room and amenities proactively attentive staff."
United States
Robert
The price is CA $295
CA $391 total
includes taxes & fees
Jul 1 - Jul 2
LondonHouse Chicago, Curio Collection by Hilton

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, (2,253 reviews)
"Awesome place"
United States
Mellany
The price is CA $171
CA $246 total
includes taxes & fees
Jul 5 - Jul 6
Silversmith Hotel Chicago Downtown

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,867 reviews)
"Great stay"
United States
Jose saul
The price is CA $274
CA $367 total
includes taxes & fees
Jul 1 - Jul 2
Hilton Chicago

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 6.9 km from Oakland
9.4 out of 10, Exceptional, (1,099 reviews)
"Good location, friendly staff"
United Kingdom
Philip
The price is CA $194
CA $272 total
includes taxes & fees
Jul 6 - Jul 7
Staypineapple, An Iconic Hotel, The Loop

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
7.1 km from Oakland
8.6 out of 10, Excellent, (1,965 reviews)
"Beautiful hotel, amazing staff, perfect location. Will definitely make this a regular hotel to stay at while in Chicago."
United States
April
The price is CA $282
CA $378 total
includes taxes & fees
Jul 1 - Jul 2
Radisson Blu Aqua Hotel Chicago

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,464 reviews)
"Very enjoying stay!"
United States
DI
The price is CA $243
CA $334 total
includes taxes & fees
Jul 5 - Jul 6
The Royal Sonesta Chicago Downtown

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 7.3 km from Oakland
9.4 out of 10, Exceptional, (4,331 reviews)
"Great place to stay! Would book again without a doubt!"
United States
Tyshun
The price is CA $225
CA $268 total
includes taxes & fees
Jul 1 - Jul 2
citizenM Chicago Downtown

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
8.2 out of 10, Very good, (1,602 reviews)
"Very good location, breakfast is fantastic, dinner and bar are great."
United States
Zhiwen
The price is CA $215
CA $256 total
includes taxes & fees
Jul 5 - Jul 6
The Chicago Hotel Collection Ambassador Gold Coast

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, (2,042 reviews)
"Great room and view. Clean, near by Grant park, great staff."
United States
Kimberly
The price is CA $205
CA $244 total
includes taxes & fees
Jul 1 - Jul 2
Hilton Garden Inn Chicago Downtown South Loop

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 8.1 km from Oakland
8.6 out of 10, Excellent, (3,062 reviews)
"Great location, historic charm, friendly and helpful staff."
United States
Peter Anthony
The price is CA $183
CA $258 total
includes taxes & fees
Jul 5 - Jul 6
Warwick Allerton - 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.

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 can I save on a Oakland hotel booking with Expedia?
With Expedia, you'll unlock our lowest prices by becoming a member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Oakland hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings.
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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