Hotels in Oakland

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Dates

May 2026

June 2026

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Where to stay in Oakland

Find the best Oakland areas 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

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

Fairmont Chicago at Millennium Park

10/10 Excellent

"Great place"

Embassy Suites by Hilton Chicago Downtown River North

8/10 Good

"Our room was clean. The breakfast as hot and consistent with great attendants and cooks. The evening snacks and drinks were very much appreciated and enjoyed. 1 dresser drawer would not open. The shower leaked onto the floor. 2 of the exercise machines were very broken. The bathroom mirror is difficult to use for makeup application for short persons. I appreciated the location for shopping and eating out. We are very happy with the amount of exercise walking to get to Navy Pier, river boat tours, and easy access to ride shares for the museums and fountains."

Hilton Chicago/Magnificent Mile Suites

8/10 Good

"Valet and bellmen were great as always. Polite and helpful. The staff brought up an extra valet for my kids on the pullout couch. Great setup for family with kids! And the restaurant on the corner has the best coffee. We stay here every time we visit, can’t beat location, price and separate space from the kids!"

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"The location was perfect for us adjacent to Northwestern Hospital. The staff were extremely helpful and friendly, particularly the manager of the rooftop bar/restaurant. Lovely Spring sunset on the roof overlooking the downtown. Definitely will stay again"

Crowne Plaza Chicago West Loop by IHG

6/10 Okay

"We had bagels and orange juice. It was ok. I was not aware I had to pay for parking, it should have been included since I am staying at their establishment. I had to remember to get a ticket out of the machine and have it validated every time I went in and out, unnecessary hassle. It's a nice place however it's next to the freeway so and rush hour it's noisy, I doubt their windows are sound proof. The beds are hard, should be not too hard not too soft. One big issue, we got a message saying they were working on the hot water and browish water would be coming out to just let it drain. Well, that's unsettling when you're trying to brush your teeth and take a shower. Kind of disappointing. "

Central Loop Hotel

10/10 Excellent

"The pub below was nice to have and the rooms were clean. They were able to hold our bags for us when we got there and when we left with no extra charge. Our room was ready when we got there thanks to the online checking in. Check out was easy and there was almost always someone at the front desk. The only thing I didn’t like was no exhaust in the bathroom so it made the room hot, but we just turned the temp down."

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good

"The hotel is beautiful and has very helpful staff. Room is not as nice as shown in pictures- feels a little musty and dark. The view is also not amazing at least from the lower levels. However, it is a great place for a short visit and in a beautiful location."

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 6 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.

Hotels in Oakland

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Our top choices for Oakland hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

Hilton Chicago

The Wade

Fairmont Chicago at Millennium Park

Congress Plaza Hotel

Swissotel - Chicago

Hyatt Regency Chicago

Aloft Chicago Mag Mile

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Hotel Riu Plaza Chicago

LondonHouse Chicago, Curio Collection by Hilton

Palmer House a Hilton Hotel

The Chicago Hotel Collection Ambassador Gold Coast

Sports Illustrated Resorts Chicago

Warwick Allerton - Chicago

Sheraton Grand Chicago Riverwalk

Silversmith Hotel Chicago Downtown

Arlo Chicago

River Hotel

Hyatt Centric The Loop Chicago

Where to stay in Oakland

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Oakland Hotel Reviews

Fairmont Chicago at Millennium Park

Frequently asked questions

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