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, (2,492 reviews)
"Great place to stay "
United States
Mark
The price is CA $257
CA $352 total
includes taxes & fees
May 26 - May 27
Sable at Navy Pier Chicago, Curio Collection by Hilton

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 6.7 km from Oakland
9.2 out of 10, Wonderful, (2,256 reviews)
"Close to many attractions and shopping and nice unique hotel"
United States
Brittany
The price is CA $125
CA $190 total
includes taxes & fees
Jun 2 - Jun 3
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, (2,778 reviews)
"Clean room and great location "
United States
Diana
The price is CA $216
CA $297 total
includes taxes & fees
May 25 - May 26
Hilton 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, (4,070 reviews)
"It was great property, amazing location and the breakfast was fantastic. "
United States
Nichole
The price is CA $183
CA $256 total
includes taxes & fees
May 27 - May 28
Hotel Riu Plaza Chicago

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,306 reviews)
"Very good, would stay here again!"
United States
Lorena
The price is CA $270
CA $369 total
includes taxes & fees
May 27 - May 28
Swissotel - Chicago

The Wade

The Wade
4.5 star property
Streeterville, 7.9 km from Oakland
8.4 out of 10, Very good, (1,825 reviews)
"We enjoy our stay."
United States
Nuria
The price is CA $230
CA $273 total
includes taxes & fees
May 25 - May 26
The Wade

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,173 reviews)
"Great stay"
United States
Matthew
The price is CA $171
CA $203 total
includes taxes & fees
May 8 - May 9
Congress Plaza Hotel

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,511 reviews)
"Clean room , nice staff, nice view"
United States
John Hok-Lam
The price is CA $278
CA $379 total
includes taxes & fees
May 25 - May 26
Hyatt Regency Chicago

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, (1,983 reviews)
"Had a great stay-5 stars of 5"
United States
donald
The price is CA $178
CA $212 total
includes taxes & fees
May 26 - May 27
Hilton Garden Inn Chicago Downtown South Loop

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,172 reviews)
"Excellent location, very clean room and friendly staff"
United States
Alejandra
The price is CA $184
CA $219 total
includes taxes & fees
May 26 - May 27
River 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, (3,700 reviews)
"Very clean room, kind and courteous staff. Would definitely stay again! "
United States
Claire
The price is CA $246
CA $333 total
includes taxes & fees
May 26 - May 27
LondonHouse Chicago, Curio Collection by Hilton

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 7.4 km from Oakland
8.6 out of 10, Excellent, (1,626 reviews)
"It was very clean, beautiful place"
United States
Grisel
The price is CA $293
CA $397 total
includes taxes & fees
May 25 - May 26
Sheraton Grand Chicago Riverwalk

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, (2,429 reviews)
"We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff. "
United States
Cynthia
The price is CA $201
CA $280 total
includes taxes & fees
May 25 - May 26
Palmer House a Hilton Hotel

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 7.1 km from Oakland
9.4 out of 10, Exceptional, (2,110 reviews)
"Great breakfast and staff. "
United States
Kelly
The price is CA $183
CA $258 total
includes taxes & fees
May 25 - May 26
Arlo Chicago

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, (4,016 reviews)
"Clean hotel great restaurant "
United States
ELIZABETH
The price is CA $188
CA $223 total
includes taxes & fees
May 27 - May 28
L7 Chicago by LOTTE

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, (1,060 reviews)
"Wonderful restaurant, amazing food."
United States
Robert
The price is CA $181
CA $256 total
includes taxes & fees
May 25 - May 26
Staypineapple, An Iconic Hotel, The Loop

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 8.1 km from Oakland
9.0 out of 10, Wonderful, (3,508 reviews)
"The hotel was phenomenally clean, the staff was nice !"
United States
Rochelle
The price is CA $196
CA $233 total
includes taxes & fees
May 10 - May 11
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, (2,149 reviews)
"A great option to stay in the city! Nice hotel and friendly staff."
United States
Nicole
The price is CA $234
CA $327 total
includes taxes & fees
May 8 - May 9
Fairmont Chicago at Millennium Park

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, (3,428 reviews)
"Excellent location, staff was friendly and the room was spacious and clean. "
United States
Wendy
The price is CA $195
CA $275 total
includes taxes & fees
May 25 - May 26
The Royal Sonesta Chicago Downtown

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, (3,043 reviews)
"Great stay all around "
United States
Logan
The price is CA $271
CA $370 total
includes taxes & fees
May 26 - May 27
InterContinental Chicago Magnificent Mile by IHG
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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