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, (2,498 reviews)
"Great place to stay "
United States
Mark
The price is CA $270
CA $368 total
includes taxes & fees
May 25 - May 26
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (2,433 reviews)
"We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff. "
United States
Cynthia
The price is CA $238
CA $324 total
includes taxes & fees
May 25 - May 26
Palmer House a Hilton Hotel

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,313 reviews)
"Breakfasr good, view great"
United States
Jan
The price is CA $271
CA $370 total
includes taxes & fees
May 27 - May 28
Swissotel - Chicago

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, (1,425 reviews)
"Clean rooms, staff was prompt, bar was awesome!"
United States
Sterling
The price is CA $210
CA $250 total
includes taxes & fees
May 25 - May 26
The Chicago Hotel Collection Ambassador Gold Coast

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, (2,155 reviews)
"A great option to stay in the city! Nice hotel and friendly staff."
United States
Nicole
The price is CA $275
CA $375 total
includes taxes & fees
May 26 - May 27
Fairmont Chicago at Millennium Park

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 6.7 km from Oakland
9.2 out of 10, Wonderful, (2,259 reviews)
"Close to many attractions and shopping and nice unique hotel"
United States
Brittany
The price is CA $163
CA $236 total
includes taxes & fees
May 27 - May 28
Silversmith Hotel Chicago Downtown

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, (1,993 reviews)
"Had a great stay-5 stars of 5"
United States
donald
The price is CA $198
CA $235 total
includes taxes & fees
May 26 - May 27
Hilton Garden Inn Chicago Downtown South Loop

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 7.1 km from Oakland
9.4 out of 10, Exceptional, (2,115 reviews)
"Great place"
United States
Dawn
The price is CA $183
CA $259 total
includes taxes & fees
May 10 - May 11
Arlo Chicago

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 8.1 km from Oakland
9.0 out of 10, Wonderful, (3,520 reviews)
"The hotel was phenomenally clean, the staff was nice !"
United States
Rochelle
The price is CA $197
CA $234 total
includes taxes & fees
May 11 - May 12
Eurostars Magnificent Mile

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,191 reviews)
"Great stay"
United States
Matthew
The price is CA $183
CA $217 total
includes taxes & fees
May 11 - May 12
Congress Plaza Hotel

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, (3,710 reviews)
"Amazing hotel and staff!"
United States
erin
The price is CA $239
CA $324 total
includes taxes & fees
May 26 - May 27
LondonHouse Chicago, Curio Collection by Hilton

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,784 reviews)
"Clean room and great location "
United States
Diana
The price is CA $217
CA $299 total
includes taxes & fees
May 25 - May 26
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, (1,062 reviews)
"Wonderful restaurant, amazing food."
United States
Robert
The price is CA $182
CA $257 total
includes taxes & fees
May 25 - May 26
Staypineapple, An Iconic Hotel, The Loop

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,232 reviews)
"The design of the property and location is great!"
United States
Fedna
The price is CA $211
CA $250 total
includes taxes & fees
May 21 - May 22
Aloft Chicago Mag Mile

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (4,096 reviews)
"Great hotel in an amazing location!"
United States
Samer
The price is CA $204
CA $281 total
includes taxes & fees
May 25 - May 26
Hotel Riu Plaza Chicago

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Theatre District, 7.2 km from Oakland
9.2 out of 10, Wonderful, (1,397 reviews)
"Nice location nestled I'm the middle of it all. Great stay the staff was communicative."
United States
Erik
The price is CA $228
CA $309 total
includes taxes & fees
May 25 - May 26
Sports Illustrated Resorts Chicago

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Magnificent Mile, 7.7 km from Oakland
9.2 out of 10, Wonderful, (3,050 reviews)
"Great stay all around "
United States
Logan
The price is CA $272
CA $371 total
includes taxes & fees
May 26 - May 27
InterContinental Chicago Magnificent Mile by IHG

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 7.4 km from Oakland
8.6 out of 10, Excellent, (1,627 reviews)
"It was very clean, beautiful place"
United States
Grisel
The price is CA $307
CA $413 total
includes taxes & fees
May 26 - May 27
Sheraton Grand Chicago Riverwalk

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 7.2 km from Oakland
9.6 out of 10, Exceptional, (4,028 reviews)
"Clean hotel great restaurant "
United States
ELIZABETH
The price is CA $273
CA $324 total
includes taxes & fees
May 20 - May 21
L7 Chicago by LOTTE

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 7.9 km from Oakland
8.0 out of 10, Very good, (2,964 reviews)
"Great central location, lots to do nearby."
United States
Michael
The price is CA $125
CA $173 total
includes taxes & fees
May 25 - May 26
Freehand 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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