The Best Hotels in Oakland, Chicago - 2026 Updated Prices

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Where to stay in Oakland

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

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

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

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The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

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Top Oakland Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

6/10 Okay

"There isn't a coffee machine in the room one is supposed to be in the lobby but although the machines there were 4 there wasn't any tea or coffee pods."

Eurostars Magnificent Mile

10/10 Excellent

"I purchased four rooms and I was there for four to five days with different family members. I have to say the best part about this hotel is the staff; they're very helpful and nice, absolutely every one of them. The shower is really amazing. It was probably the strongest rainfall shower I'd ever visited in any hotel in over 20 years. Nice refrigerator, coffee maker, great desk area, lots of places to put your luggage. The air conditioner: as long as you don't leave it on auto and put it on low, it was perfect to cool the room. You put it on auto then it does auto shut off. TV system was great. I was able to hook up my own super box and the internet was 50 Mbps or faster. The hotel location is perfect. Ubers were able to pick us up right out in front and we're within walking distance for everything that we wanted. The beds and the linen were perfect, no problems there. The only thing I would say is if you're used to a blackout room, make sure you bring an eye mask because most of the hotels in Chicago have a blind system so you'll get cracks of light. There were some door slam issues. You know how some hotel doors will slam but really I didn't have any problems sleeping. Some of my other guests said that it can get loud but everybody was able to sleep well enough."

Congress Plaza Hotel

6/10 Okay

"The hotel was clean for the most part. Corridors smells like soap because I truly believe the housekeeping works hard to keep them that way. Unfortunately the hotel was just old and needs much needed upgrade. The bathroom was looking noticeably old too and the water in the bath area needs to be at certain angle to release enough pressure and hot water. Still doable and workable with but maybe not for $600 a night... Our room ended being family suite which we didn't realize upon booking much and the front desk didnt debrief it until we reclarify it after. The first receptionist almost said the main room was not part of our room until another lady came to correct her (thankfully). I do wish that the picture of the property on expedia is more reflective to the current hotel situation though. Because it looks similar but the actual looks way older than it actually is...."

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Great stay! I wasn’t sure what to expect since I didn’t know much about the hotel beforehand, but I was pleasantly surprised. The staff was friendly and welcoming, especially the team at the bar, who provided excellent service throughout our stay. The rooms were spacious and comfortable, with plenty of room to relax. The hotel has a lot of character, and you can tell it’s a historic building, which adds to its charm. At the same time, the décor is tasteful and well maintained. The surrounding area is very walkable, making it easy to explore nearby attractions, restaurants, and shops. Overall, it was a wonderful experience, and I would definitely stay here again."

Frequently asked questions

What's it like in Oakland?

Oakland is a neighbourhood that travellers 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 neighbourhood.

How many hotels can I expect to find in Oakland?

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

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

Yes, you'll find most hotel room reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of check in. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of booking. Add your dates and click on "Search", then filter by "fully refundable" to view the top deals on offer in Oakland.

What can I see and do in this Chicago neighbourhood?

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 neighbourhood. 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.

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Our top choices for Oakland hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

Hyatt Regency Chicago

Hilton Chicago

Omni Chicago Hotel

Congress Plaza Hotel

Sheraton Grand Chicago Riverwalk

The Blackstone, Autograph Collection

Swissotel - Chicago

Silversmith Hotel Chicago Downtown

Hotel Riu Plaza Chicago

LondonHouse Chicago, Curio Collection by Hilton

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Hilton Chicago/Magnificent Mile Suites

Staypineapple, An Iconic Hotel, The Loop

Arlo Chicago

Radisson Blu Aqua Hotel Chicago

River Hotel

Eurostars Magnificent Mile

The Royal Sonesta Chicago Downtown

Sports Illustrated Resorts Chicago

Where to stay in Oakland

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Oakland Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

Frequently asked questions

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