What's it like in Oakland?

Oakland is a neighborhood that travelers like for its beaches, restaurants, and shopping. Looking for sights you might find in a travel guide about Oakland? Consider a visit to Lake Michigan while you're in the neighborhood.

How many hotels are there in the Oakland area?

When you want to find places to stay in Chicago, start by booking one of Expedia's 7 hotels and other accommodations in Oakland.

If I need to cancel my hotel reservation in Oakland, will I receive a refund?

Yes, most hotel bookings are fully refundable if you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you have a non-refundable reservation, you might still have the option to cancel and receive a refund within a 24-hour period of booking. Plug in your dates, click on "Search", then filter by "fully refundable" to review the best deals in Oakland.

Where can I learn more about changing or cancelling my trip to Oakland?

To find more details about picking new dates or cancelling your trip to Oakland, go to https://www.expedia.com/service/ .

What can I see and do in this Chicago neighborhood?

Spend some time exploring the natural setting of Oakland with a visit to Lake Michigan and Burnham Park. A visit to 41st Street Beach is also worth the trip while you're discovering the neighborhood. A few places to visit in the area around Oakland include Soldier Field, Nat King Cole Residence, and Muddy Waters’ House. While you're out sightseeing, Ida B. Wells-Barnett Residence and Ida B Wells House are a couple of additional sights to visit in Chicago.

Top Oakland Hotels

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Our top choices for Oakland hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 7.5 km from Oakland

Deborah

￥48,789 total

includes taxes & fees

Jun 30 - Jul 1

Freehand Chicago

River North, 7.9 km from Oakland

Nolan

￥30,489 total

includes taxes & fees

Jun 29 - Jun 30

The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 9.4 km from Oakland

Robin

￥29,597 total

includes taxes & fees

Jun 22 - Jun 23

Travelodge by Wyndham Downtown Chicago

The Loop, 5.9 km from Oakland

Amber

￥25,393 total

includes taxes & fees

Jun 28 - Jun 29

Congress Plaza Hotel

The Loop, 6 km from Oakland

Jennifer

￥24,653 total

includes taxes & fees

Jun 29 - Jun 30

The Chicago Hotel Collection - Magnificent Mile

Streeterville, 8.2 km from Oakland

Ontario

￥28,783 total

includes taxes & fees

Jun 28 - Jun 29

Hilton Chicago

The Loop, 5.7 km from Oakland

Ruben

￥59,399 total

includes taxes & fees

Jun 7 - Jun 8

Silversmith Hotel Chicago Downtown

Theatre District, 6.7 km from Oakland

Brittany

￥35,139 total

includes taxes & fees

Jun 28 - Jun 29

Best Western Grant Park Hotel

The Loop, 5.4 km from Oakland

Derrick

￥35,622 total

includes taxes & fees

Jun 3 - Jun 4

Warwick Allerton - Chicago

Streeterville, 8.1 km from Oakland

Nadiah

￥34,973 total

includes taxes & fees

Jun 29 - Jun 30

2 restaurants; breakfast, lunch, and dinner served

LondonHouse Chicago, Curio Collection by Hilton

The Loop, 7.4 km from Oakland

Matson

￥47,166 total

includes taxes & fees

Jun 21 - Jun 22

Staypineapple, An Iconic Hotel, The Loop

Theatre District, 6.9 km from Oakland

Debby

￥47,159 total

includes taxes & fees

Jun 29 - Jun 30

Hotel Chicago Downtown, Autograph Collection by Marriott

River North, 7.5 km from Oakland

Oziel Silva

￥34,843 total

includes taxes & fees

Jun 28 - Jun 29

Hotel Riu Plaza Chicago

Streeterville, 7.9 km from Oakland

sierra

￥40,329 total

includes taxes & fees

Jun 30 - Jul 1

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

The Loop, 6.1 km from Oakland

raghu

￥36,206 total

includes taxes & fees

Jun 28 - Jun 29

Hotel Saint Clair- Magnificent Mile

Streeterville, 7.9 km from Oakland

Miguel

￥35,335 total

includes taxes & fees

Jun 14 - Jun 15

Hilton Chicago/Magnificent Mile Suites

Streeterville, 8.6 km from Oakland

Nereida

￥32,926 total

includes taxes & fees

Jun 28 - Jun 29

Millennium Hotel Knickerbocker Chicago

Streeterville, 8.6 km from Oakland

Eileen

￥31,053 total

includes taxes & fees

Jun 28 - Jun 29

Omni Chicago Hotel

Streeterville, 8.1 km from Oakland

Alejandro

￥38,441 total

includes taxes & fees

Jun 7 - Jun 8

Eurostars Magnificent Mile

River North, 8.1 km from Oakland

Belinda

￥42,415 total

includes taxes & fees

Jun 29 - Jun 30

View all properties

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.

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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.

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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.

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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.

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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.

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Top Oakland Hotel Reviews

Hotel Riu Plaza Chicago

10/10 Excellent

"Hotel room was very neat and clean. The continental breakfast on the second floor was fantastic and had a vast variety of breakfast food to choose from. For the amount of food and people for this room, the staff did an excellent job keeping this cleaned and very well maintained. Upon checking in and checking out, the staff was very warm and friendly. The customer service was top-notch. Would recommend to anyone staying in Chicago to stay here!"

Hyatt Regency O'Hare Chicago

2/10 Terrible

"Everything was very good except for the cleanliness. The hotel is beautiful and luxurious, but the bedsheets or mattress had a very strong unpleasant odor whenever I lay down. It smelled very unhygienic and made me feel very uncomfortable. Even though they moved me to another room, I still had the same concern, and it left me feeling really uneasy."

Freehand Chicago

2/10 Terrible

"So this was the only hotel that was in our budget for the weekend we were in town. Going in, we knew it a bunk bed hostel style, however the pics make it look nicer than how it was. The room was so small for my family of four, no space to open our suitcases and hardly any light in the room. It was very dirty and the pillows smelled like dirty feet. The whole room had a bad aroma and very dusty everywhere. The staff was not the kindest either. Only stay here if coming alone or you’re a backpack traveller. Will not be coming back to Chicago Freehand."

River Hotel

4/10 Poor

"This is not a four-star hotel, as advertised. It's the old Club Quarters with a new name, which means a drab room for a reasonable price, with unhelpful front desks as an added feature. The desk clerk sent me on a wild goose chase looking for a drug store that had been closed at that location for months (at least) and then refused to send me my driver's license, which I left in my room after I checked out. I told them I'd pay whatever it cost to send it to me. But no, I had to arrange for Fedex to pick it up myself. YOu get what you pay for, which isn't much."

Find hotels in Oakland, Chicago

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Our top choices for Oakland hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

Freehand Chicago

The Chicago Hotel Collection Ambassador Gold Coast

Travelodge by Wyndham Downtown Chicago

Congress Plaza Hotel

The Chicago Hotel Collection - Magnificent Mile

Hilton Chicago

Silversmith Hotel Chicago Downtown

Best Western Grant Park Hotel

Warwick Allerton - Chicago

LondonHouse Chicago, Curio Collection by Hilton

Staypineapple, An Iconic Hotel, The Loop

Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Riu Plaza Chicago

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Hotel Saint Clair- Magnificent Mile

Hilton Chicago/Magnificent Mile Suites

Millennium Hotel Knickerbocker Chicago

Omni Chicago Hotel

Eurostars Magnificent Mile

Where to stay in Oakland

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Oakland Hotel Reviews

Hotel Riu Plaza Chicago

Frequently asked questions

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