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

FOUND Hotels, Chicago, Series by Marriott

River North, 8.1 km from Oakland

Lia

₩305,560 total

includes taxes & fees

Jul 26 - Jul 27

Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 7.5 km from Oakland

Jimmy

₩488,247 total

includes taxes & fees

Aug 9 - Aug 10

Freehand Chicago

River North, 7.9 km from Oakland

Charles

₩285,049 total

includes taxes & fees

Aug 9 - Aug 10

The Wade

Streeterville, 7.9 km from Oakland

Hector

₩440,049 total

includes taxes & fees

Aug 6 - Aug 7

The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 9.4 km from Oakland

Anna

₩276,388 total

includes taxes & fees

Jul 27 - Jul 28

Travelodge by Wyndham Downtown Chicago

The Loop, 5.9 km from Oakland

Danny

₩281,236 total

includes taxes & fees

Aug 10 - Aug 11

Palmer House a Hilton Hotel

Theatre District, 6.7 km from Oakland

Charles Otto

₩519,000 total

includes taxes & fees

Aug 9 - Aug 10

Omni Chicago Hotel

Streeterville, 8.1 km from Oakland

Megan

₩422,389 total

includes taxes & fees

Aug 9 - Aug 10

Superior Apartment, 2 Bedrooms, Kitchen | Living area | LED TV, Netflix, Hulu, streaming services

LIVN - West Loop Chicago

6.8 km from Oakland

Jarrett

₩347,537 total

includes taxes & fees

Jul 12 - Jul 13

Congress Plaza Hotel

The Loop, 6 km from Oakland

Daniel

₩339,409 total

includes taxes & fees

Aug 10 - Aug 11

Warwick Allerton - Chicago

Streeterville, 8.1 km from Oakland

Peter Anthony

₩303,247 total

includes taxes & fees

Aug 9 - Aug 10

2 restaurants; breakfast, lunch, and dinner served

LondonHouse Chicago, Curio Collection by Hilton

The Loop, 7.4 km from Oakland

Sucharitha

₩459,596 total

includes taxes & fees

Aug 9 - Aug 10

Hyatt Centric The Loop Chicago

Theatre District, 6.8 km from Oakland

Freddy

₩394,019 total

includes taxes & fees

Jul 12 - Jul 13

Presidential Suite, 1 Bedroom, Non Smoking | Premium bedding, in-room safe, desk, blackout drapes

Hotel 55 Chicago Downtown

River North, 7.9 km from Oakland

Matt

₩391,764 total

includes taxes & fees

Jul 26 - Jul 27

Hotel Saint Clair- Magnificent Mile

Streeterville, 7.9 km from Oakland

Rocio

₩270,873 total

includes taxes & fees

Jul 12 - Jul 13

Best Western Grant Park Hotel

The Loop, 5.4 km from Oakland

Tammy

₩257,162 total

includes taxes & fees

Aug 9 - Aug 10

Swissotel - Chicago

7.2 km from Oakland

Scott

₩423,312 total

includes taxes & fees

Jul 26 - Jul 27

The Allegro Royal Sonesta Hotel Chicago Loop

Theatre District, 7.2 km from Oakland

Katie

₩384,150 total

includes taxes & fees

Aug 9 - Aug 10

River Hotel

The Loop, 7.4 km from Oakland

Ashley

₩303,335 total

includes taxes & fees

Aug 9 - Aug 10

The Buckingham Hotel

The Loop, 6.3 km from Oakland

Christopher

₩311,769 total

includes taxes & fees

Jul 19 - Jul 20

View all properties

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland

A busy city street with tall buildings, a bus, and cars.

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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A historic castle-like building with intricate stonework and a paved walkway.

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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A river with yellow boats, a bridge, and tall buildings.

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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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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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A river with a city skyline in the background, surrounded by green trees and grass.

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

"Awesome stay!"

The Royal Sonesta Chicago Downtown

10/10 Excellent

"This hotel is located in the heart of downtown Chicago. The river walk is directly across the street. If you don’t mind a 15 minute walk, you can also walk to Navy Pier. This hotel is also steps away from Hello Kitty Cafe, Michigan Ave, and plenty of restaurants and stores. If you’re u want to go to grab a cup of coffee at the World’s largest Starbucks, stay here because it’s a short walk to pretty much everything. The train station is about a 10 minute walk and Spot Hero is the best option if you have a car. The hotel is spotless and employees are nice. I would definitely recommend this hotel to friends and family."

River Hotel

10/10 Excellent

"Super-friendly helpful staff! This hotel is in a great location by the river walk and the newly-opened Hello Kitty Cafe. The rates were lower than others, and it was great it didn't cost extra for my pet. The room was very clean, and the temperature was good, but I do wish it could've gotten cooler. They offer valet parking, but the garage for self-parking is a short walk away. It's best to use public transportation as much as you can in this area. Overall, a great price compared to other hotels, a fantastic location, and amazing staff. Thank you for a great stay!"

Freehand Chicago

8/10 Good

"We enjoyed out short stay at the Freehand in Chicago. We were originally placed in a room on the 17th floor. However, the air conditioning wasn't working so they quickly moved us to another quad room on the 4th floor. The space worked great for my family of 4 adults. We also enjoyed talking with Selma at the bar while watching World Cup games."

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

FOUND Hotels, Chicago, Series by Marriott

Sable at Navy Pier Chicago, Curio Collection by Hilton

Freehand Chicago

The Wade

The Chicago Hotel Collection Ambassador Gold Coast

Travelodge by Wyndham Downtown Chicago

Palmer House a Hilton Hotel

Omni Chicago Hotel

LIVN - West Loop Chicago

Congress Plaza Hotel

Warwick Allerton - Chicago

LondonHouse Chicago, Curio Collection by Hilton

Hyatt Centric The Loop Chicago

Hotel 55 Chicago Downtown

Hotel Saint Clair- Magnificent Mile

Best Western Grant Park Hotel

Swissotel - Chicago

The Allegro Royal Sonesta Hotel Chicago Loop

River Hotel

The Buckingham Hotel

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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