Oakland Vacation Packages

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Our top choices for Oakland hotels

Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
Downtown Chicago
8.2 out of 10, Very good, (2,676 reviews)
"Clean room and the staff are great. "
United States
Doug
The price is CA $92
CA $108 total
includes taxes & fees
Mar 4 - Mar 5
Best Western Grant Park Hotel

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2,765 reviews)
"I enjoyed my stay"
United States
Emily
The price is CA $78
CA $116 total
includes taxes & fees
Feb 22 - Feb 23
Freehand Chicago

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (9,908 reviews)
"Great location, beautiful historic hotel with clean, updated rooms. "
United States
Jennifer
The price is CA $122
CA $143 total
includes taxes & fees
Feb 19 - Feb 20
Congress Plaza Hotel

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,682 reviews)
"Thoroughly enjoyed my stay at The Wade"
United States
Danielle
The price is CA $135
CA $158 total
includes taxes & fees
Mar 5 - Mar 6
The Wade

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,862 reviews)
"Absolutely enjoyed my time here"
United States
Quayshaun
The price is CA $116
CA $137 total
includes taxes & fees
Feb 26 - Feb 27
Hilton Garden Inn Chicago Downtown South Loop

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Downtown Chicago
8.4 out of 10, Very good, (3,963 reviews)
"Great location, the room was nice and the breakfast was good. Overall great value for this property"
United States
Jorge
The price is CA $100
CA $118 total
includes taxes & fees
Feb 22 - Feb 23
The Whitehall Hotel, BW Premier Collection

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
Downtown Chicago
8.4 out of 10, Very good, (461 reviews)
"Amazing staff and very clean, modern rooms!"
United States
genevieve
The price is CA $80
CA $94 total
includes taxes & fees
Mar 1 - Mar 2
FOUND Hotel Chicago River North

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,085 reviews)
"Great location and friendly staff. "
United States
Pablo
The price is CA $135
CA $158 total
includes taxes & fees
Mar 5 - Mar 6
Aloft Chicago Mag Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,315 reviews)
"Great staff, room spotless, great price."
United States
Robert
The price is CA $133
CA $156 total
includes taxes & fees
Feb 26 - Feb 27
DoubleTree by Hilton Chicago - Magnificent Mile

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,378 reviews)
"Great stay"
United States
Blake
The price is CA $180
CA $258 total
includes taxes & fees
Feb 24 - Feb 25
Sable at Navy Pier Chicago, Curio Collection by Hilton

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,012 reviews)
"Great stay, good location, accommodating staff."
United States
Ian
The price is CA $118
CA $138 total
includes taxes & fees
Feb 22 - Feb 23
River Hotel

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,039 reviews)
"Great place"
United States
Omar
The price is CA $93
CA $149 total
includes taxes & fees
Mar 1 - Mar 2
Warwick Allerton - Chicago

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,125 reviews)
"I always stay here when in town. "
United States
Jeffrey
The price is CA $100
CA $118 total
includes taxes & fees
Feb 24 - Feb 25
Ivy Boutique Hotel

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,370 reviews)
"Amazing place, breakfast is great , location is great - honestly great hotel! "
United States
Brisa
The price is CA $135
CA $197 total
includes taxes & fees
Mar 4 - Mar 5
Hotel Riu Plaza Chicago

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
Downtown Chicago
7.4 out of 10, Good, (2,516 reviews)
"Always a good stay"
Canada
Domenic
The price is CA $104
CA $122 total
includes taxes & fees
Feb 22 - Feb 23
Travelodge by Wyndham Downtown Chicago

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,524 reviews)
"Great location, friendly staff and nice room"
United States
Srinivasa
The price is CA $87
CA $142 total
includes taxes & fees
Feb 22 - Feb 23
Claridge House Chicago, Tapestry Collection by Hilton

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (1,282 reviews)
"Great hotel with great location. Would definitely stay here again. "
United States
Sheila
The price is CA $144
CA $169 total
includes taxes & fees
Feb 19 - Feb 20
The Chicago Hotel Collection Ambassador Gold Coast

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,202 reviews)
"Place is always top notch..stay here anytime we stay in Chicago."
United States
Jon
The price is CA $166
CA $243 total
includes taxes & fees
Feb 22 - Feb 23
Swissotel - Chicago

Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile
2.5 star property
Downtown Chicago
8.0 out of 10, Very good, (1,406 reviews)
"Great hotel,, like so much"
United States
Ilham
The price is CA $122
CA $143 total
includes taxes & fees
Feb 22 - Feb 23
Hampton Inn Chicago Downtown/Magnificent Mile

ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,962 reviews)
"Very convenient place to stay friendly and helpful staff."
United States
Rick
The price is CA $111
CA $130 total
includes taxes & fees
Feb 25 - Feb 26
ACME Hotel Chicago, Outset Collection by Hilton
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.
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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.

O'Hare

Home to O'Hare International Airport, this transportation hub offers easy access to downtown via the Blue Line. The area also hosts various corporate headquarters and international consulates.

Stay near popular Oakland attractions

Top Oakland Hotel Reviews

Recent Reviews in Oakland

More cheap stays in Oakland

Hotels in Oakland with star rating

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 from CA $58 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.