Default HTG hotel image

Hotels in Oakland, Chicago

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Star rating

Our top choices for Oakland hotels

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Streeterville, 8.1 km from Oakland
9.2 out of 10, Wonderful, (1,814 reviews)
"All around great property and a wonderful location"
United States
Bruce
The price is CA $214
CA $301 total
includes taxes & fees
Jul 5 - Jul 6
Omni Chicago Hotel

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, (1,249 reviews)
"The best place I’ve stayed in Chicago"
United States
Robyn
The price is CA $237
CA $281 total
includes taxes & fees
Jul 5 - Jul 6
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (4,466 reviews)
"Clean room, great breakfast and close to everything we needed"
United States
Kyle
The price is CA $224
CA $306 total
includes taxes & fees
Jul 6 - Jul 7
Hotel Riu Plaza Chicago

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,293 reviews)
"Great stay!"
United States
Daniel
The price is CA $191
CA $227 total
includes taxes & fees
Jun 29 - Jun 30
Congress Plaza Hotel

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,862 reviews)
"Great stay"
United States
Jose saul
The price is CA $274
CA $367 total
includes taxes & fees
Jul 1 - Jul 2
Hilton Chicago

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, (2,253 reviews)
"Wonderful stay"
United States
Taylor
The price is CA $197
CA $277 total
includes taxes & fees
Jul 5 - Jul 6
Silversmith Hotel Chicago Downtown

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,233 reviews)
"Excellent place to stay, as we found it central & walkable to most parks & attractions. The place was spotless & the staff were fantastic."
Canada
Jody
The price is CA $195
CA $232 total
includes taxes & fees
Jul 1 - Jul 2
River Hotel

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 8.1 km from Oakland
9.0 out of 10, Wonderful, (3,649 reviews)
"Had an amazing stay here!"
United States
Audrey
The price is CA $213
CA $253 total
includes taxes & fees
Jul 1 - Jul 2
Eurostars Magnificent Mile

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 7.1 km from Oakland
9.4 out of 10, Exceptional, (2,121 reviews)
"Excellent hotel! Will definitely stay again."
United States
Justin
The price is CA $312
CA $414 total
includes taxes & fees
Jul 1 - Jul 2
Arlo Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 8.1 km from Oakland
8.6 out of 10, Excellent, (3,007 reviews)
"Great location, historic charm, friendly and helpful staff."
United States
Peter Anthony
The price is CA $176
CA $251 total
includes taxes & fees
Jul 1 - Jul 2
Warwick Allerton - 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, (3,451 reviews)
"Incredible location, comfortable rooms, great bar and a restaurant attached! Loved staying here!"
United States
Feng
The price is CA $257
CA $351 total
includes taxes & fees
Jul 1 - Jul 2
The Royal Sonesta Chicago Downtown

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, (2,595 reviews)
"Great location and helpful staff."
United States
Ming
The price is CA $177
CA $211 total
includes taxes & fees
Jul 5 - Jul 6
Travelodge by Wyndham Downtown Chicago

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 7.6 km from Oakland
8.2 out of 10, Very good, (2,903 reviews)
"Excelent stay in Chicago with a great breakfast that is include. Awesome location and staff was very helpful."
United States
Joseph
The price is CA $282
CA $376 total
includes taxes & fees
Jul 1 - Jul 2
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

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, (2,509 reviews)
"This is a beautiful hotel and the location was perfect."
United States
Felisha
The price is CA $263
CA $312 total
includes taxes & fees
Jul 1 - Jul 2
DoubleTree by Hilton Chicago - Magnificent Mile

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 8.6 km from Oakland
9.0 out of 10, Wonderful, (4,435 reviews)
"Great stay!"
United States
Avradita
The price is CA $195
CA $232 total
includes taxes & fees
Jul 1 - Jul 2
Hilton Chicago/Magnificent Mile Suites

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, (1,014 reviews)
"Great location and excellent service"
United States
JAVIER
The price is CA $222
CA $289 total
includes taxes & fees
Jul 7 - Jul 8
Le Méridien Essex Chicago

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, (3,282 reviews)
"Very great hotel"
United States
Allesandra
The price is CA $238
CA $283 total
includes taxes & fees
Jul 5 - Jul 6
Aloft by Marriott Chicago Mag Mile

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 8.2 km from Oakland
7.8 out of 10, Good, (1,584 reviews)
"Enjoyed our stay"
United States
keary
The price is CA $223
CA $266 total
includes taxes & fees
Jul 1 - Jul 2
The Chicago Hotel Collection - Magnificent Mile

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, (1,603 reviews)
"Very good location, breakfast is fantastic, dinner and bar are great."
United States
Zhiwen
The price is CA $219
CA $260 total
includes taxes & fees
Jul 1 - Jul 2
The Chicago Hotel Collection Ambassador Gold Coast

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Streeterville, 8.6 km from Oakland
8.6 out of 10, Excellent, (2,499 reviews)
"Good breakfast, great view from room"
United States
Randy
The price is CA $231
CA $274 total
includes taxes & fees
Jul 2 - Jul 3
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
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.

Explore a world of travel with Expedia