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.

The Best Hotels in Oakland, Chicago - 2026 Updated Prices

A cityscape with modern skyscrapers, a river, and a bridge.

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Our top choices for Oakland hotels

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

1. Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 7.5 km from Oakland

Ashraf

₹23,323 total

includes taxes & fees

8 Sept - 9 Sept

A hotel with a modern design, featuring a prominent curved glass facade and multiple floors.

2. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Streeterville, 7.6 km from Oakland

Valerie

₹23,342 total

includes taxes & fees

10 Sept - 11 Sept

A modern hotel with a glass facade, multiple floors, and a visible entrance.

3. Hyatt Place Chicago/Downtown - The Loop

The Loop, 7.1 km from Oakland

LISA

₹22,357 total

includes taxes & fees

7 Sept - 8 Sept

A large, historic building with a central courtyard surrounded by trees.

4. Hilton Chicago

The Loop, 5.7 km from Oakland

Lori

₹25,130 total

includes taxes & fees

7 Sept - 8 Sept

A modern kitchen with a large window, a dining area, and a view of the sea.

5. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 5.4 km from Oakland

AMBER

₹19,959 total

includes taxes & fees

8 Sept - 9 Sept

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

6. Hotel Riu Plaza Chicago

Streeterville, 7.9 km from Oakland

Donna

₹19,057 total

includes taxes & fees

7 Sept - 8 Sept

A modern interior with a bar area, seating, and decorative wooden panels.

7. Best Western Grant Park Hotel

The Loop, 5.4 km from Oakland

Diego

₹17,089 total

includes taxes & fees

8 Sept - 9 Sept

A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.

8. L7 Chicago by LOTTE

Theatre District, 7.2 km from Oakland

Jeff

₹29,029 total

includes taxes & fees

27 Sept - 28 Sept

A hotel lobby with a bar area, seating, and a large mirror.

9. Hilton Garden Inn Chicago Central Loop

The Loop, 6.6 km from Oakland

Theresa

₹22,358 total

includes taxes & fees

7 Sept - 8 Sept

A multi-story hotel with a prominent sign reading "Crowne Plaza."

10. Crowne Plaza Chicago West Loop by IHG

7.3 km from Oakland

Phillip

₹21,234 total

includes taxes & fees

7 Sept - 8 Sept

11. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Streeterville, 8.6 km from Oakland

Kelly

₹17,616 total

includes taxes & fees

7 Sept - 8 Sept

A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

12. Embassy Suites by Hilton Chicago Downtown River North

River North, 8 km from Oakland

Kristeen

₹20,110 total

includes taxes & fees

7 Sept - 8 Sept

A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

13. Hyatt Place Chicago/River North

River North, 7.8 km from Oakland

Shoma

₹22,469 total

includes taxes & fees

7 Sept - 8 Sept

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

14. Hilton Chicago/Magnificent Mile Suites

Streeterville, 8.6 km from Oakland

Jeremy

₹17,847 total

includes taxes & fees

8 Sept - 9 Sept

A spacious bar area with high ceilings and large windows, offering views of a cityscape.

15. Hyatt Regency Chicago

The Loop, 7.3 km from Oakland

Steve

₹30,783 total

includes taxes & fees

7 Sept - 8 Sept

A modern lobby with a grey sofa, checkered ottomans, and a coffee table. There are black chairs, a blue sofa, and a TV on a stand.

16. Aloft by Marriott Chicago Mag Mile

Streeterville, 7.9 km from Oakland

Odessia

₹17,279 total

includes taxes & fees

7 Sept - 8 Sept

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

17. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 7.8 km from Oakland

Tonya

₹18,903 total

includes taxes & fees

8 Sept - 9 Sept

A multi-story hotel with a prominent 'La Quinta' sign, featuring a modern architectural design with large windows and a flat facade.

18. La Quinta Inn & Suites by Wyndham Chicago Downtown

The Loop, 7 km from Oakland

Shilpa

₹20,109 total

includes taxes & fees

7 Sept - 8 Sept

The Intercontinental hotel facade with a large American flag and a floral display.

19. InterContinental Chicago Magnificent Mile by IHG

Magnificent Mile, 7.7 km from Oakland

Anfal

₹26,394 total

includes taxes & fees

8 Sept - 9 Sept

A modern building with a colorful facade and a red circular seating area.

20. citizenM Chicago Downtown

Theatre District, 7.3 km from Oakland

lakadria

₹19,548 total

includes taxes & fees

7 Sept - 8 Sept

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Where to stay in Oakland

Find the best Oakland areas 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 river with yellow boats, a bridge, and tall buildings.

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

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

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

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

Hilton Chicago O'Hare Airport

10/10 Excellent

"All great"

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Such a beautiful hotel. I loved that it has some history in it. Staff were very kind, friendly and helpful. The rooms were also very clean. Would definitely recommend and will definitely be coming back. If they could add some more elevators that would be awesome."

Hampton Inn Chicago Downtown/Magnificent Mile

8/10 Good

"Me and wife stay 3 nights is Hampton Inn from Aug 31 to Sept3 2026.It is 40 stories hotel. The hotel location is excellent, beautiful in Chicago, very close to Michgan Ave Magnificent Mile, the most beautiful area, high rise buildings and shopping stores. Close to Lake, close to chicago River side, close to Millennium park. Breakfast was ok, not high level, just so, so, Baggage in and out room service was not available when we reached we took our own bags to room. No swimming pool was available. Close to hospital block, .For food Asian food Indian restaurant available on walking distance. I recommend this hotel to tourists coming for Chicago buildings, and other attractions. Mahboob Mian Canada."

Search Hotels in Oakland, Chicago

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Our top choices for Oakland hotels

1. Sable at Navy Pier Chicago, Curio Collection by Hilton

2. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

3. Hyatt Place Chicago/Downtown - The Loop

4. Hilton Chicago

5. Homewood Suites by Hilton Chicago Downtown South Loop

6. Hotel Riu Plaza Chicago

7. Best Western Grant Park Hotel

8. L7 Chicago by LOTTE

9. Hilton Garden Inn Chicago Central Loop

10. Crowne Plaza Chicago West Loop by IHG

11. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

12. Embassy Suites by Hilton Chicago Downtown River North

13. Hyatt Place Chicago/River North

14. Hilton Chicago/Magnificent Mile Suites

15. Hyatt Regency Chicago

16. Aloft by Marriott Chicago Mag Mile

17. DoubleTree by Hilton Chicago - Magnificent Mile

18. La Quinta Inn & Suites by Wyndham Chicago Downtown

19. InterContinental Chicago Magnificent Mile by IHG

20. citizenM Chicago Downtown

Where to stay in Oakland

Downtown Chicago

The Loop

Magnificent Mile

River North

Lincoln Park

Top Oakland Hotel Reviews

Hilton Chicago O'Hare Airport

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