View of downtown Chicago with Chicago River and boats

5 Stars Hotels in Oakland, Chicago from CA $236

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Check availability on Oakland 5 Star Hotels

Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

Our top choices for Oakland 5-star hotels

A person sitting by a window with a view of a cityscape, including a tall tower.

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,004 reviews)
"Liked the layout of our suite and that the hotel was right inside the shopping Mall & Bloomingdales."
United States
August
The price is CA $758
CA $901 total
includes taxes & fees
Sep 7 - Sep 8
Four Seasons Hotel Chicago
A cityscape with a river, a bridge, and a dining area with tables and chairs.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,993 reviews)
"It was a great place to stay"
United States
Jorge
The price is CA $704
CA $837 total
includes taxes & fees
Sep 7 - Sep 8
Trump International Hotel & Tower Chicago
A modern hotel lobby with a reception desk, seating area, and large windows offering city views.

3. The Langham, Chicago

The Langham, Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,003 reviews)
"This place is a true 5 star hotel no question!"
United States
Michael
The price is CA $869
CA $1,033 total
includes taxes & fees
Sep 7 - Sep 8
The Langham, Chicago
A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.

4. The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,000 reviews)
"First time staying at this Property and we absolutely loved it! Will definitely go back and recommend"
United States
Angela
The price is CA $850
CA $1,011 total
includes taxes & fees
Sep 7 - Sep 8
The Peninsula Chicago
A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,004 reviews)
"Beautiful property and excellent service from all staff."
United States
Jim
The price is CA $798
CA $949 total
includes taxes & fees
Sep 7 - Sep 8
Waldorf Astoria Chicago
A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.

6. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,001 reviews)
"Great hotel only complaint is on day of check in I sat in lobby and waited 6 hours."
United States
Eric
The price is CA $827
CA $984 total
includes taxes & fees
Sep 7 - Sep 8
The Ritz-Carlton, Chicago
A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.

7. Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (920 reviews)
"incredible staff and stay here. The team here crushed it and the rooms were fantastic"
Canada
Jordan
The price is CA $486
CA $613 total
includes taxes & fees
Aug 31 - Sep 1
Nobu Hotel Chicago
A couple dining at a table with a view of a cityscape and a sunset.

8. Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,004 reviews)
"Top notch hotel, we were only there for a night but it likely ruined staying at any other hotel now, it was a great experience."
United States
Catherine
The price is CA $770
CA $915 total
includes taxes & fees
Sep 7 - Sep 8
Park Hyatt Chicago
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.

9. The St. Regis Chicago

The St. Regis Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (130 reviews)
"We had a great stay and will come back again in the near future!"
United States
Princess
The price is CA $895
CA $1,065 total
includes taxes & fees
Sep 21 - Sep 22
The St. Regis Chicago
A rooftop lounge with a city skyline view, featuring a sofa set with patterned cushions and a table with drinks and snacks.

10. Art Villa

Art Villa
5.0 star property
West Town
10.0 out of 10, Exceptional, (2 reviews)
Art Villa
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Oakland.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
The price is CA $305 per night from Sep 11 to Sep 12
CA $305
CA $358 total
Sep 11 - Sep 12
includes taxes & fees
8.4/10 Very good! (2,459 reviews)
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Top Oakland Hotel Reviews

Find out more about Oakland

Five Star Hotels in Oakland

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Oakland so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Oakland and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Oakland

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

Make Your Escape to Oakland

The results are in, and Oakland 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Oakland! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Oakland today and settle down in the lap of luxury tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Oakland?
You'll find a variety of pricing options for 5-star hotels in Oakland on Expedia. How much you'll pay will depend on when you want to travel, trip length and other factors. Compare available accommodations for your chosen dates and use our pricing and other filters to discover the ideal upscale stay.

  • Search for the lowest price per night from CA $236

What makes a hotel 5 stars in Oakland?
From high-end dining venues and fitness centres to pools and the finest bedding, the 5-star experience in Oakland is all about comfort and indulgence. But it calls for more than just top-notch amenities to receive a 5-star rating. Hotels also have to deliver remarkable services like beauty treatments, on-site laundry and dry cleaning and concierge services.
Are there any 5-star all-inclusive resorts in Oakland?
Find a luxurious stay that includes your room, meals, activities and entertainment in Oakland with our filters. Search for hotels rated 5 stars and select the "All inclusive" filter. Be sure to check what's included in the price. That way, you can take full advantage of all the perks on offer when you get there.

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