Top 10 Oakland Hotels of 2026

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

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Our top choices for Oakland hotels

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

1. Hilton Chicago

The Loop, 5.7 km from Oakland

Konner

RM931 total

includes taxes & fees

9 Sept - 10 Sept

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

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

Streeterville, 7.5 km from Oakland

Ashraf

RM1,021 total

includes taxes & fees

8 Sept - 9 Sept

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

3. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 5.4 km from Oakland

AMBER

RM832 total

includes taxes & fees

7 Sept - 8 Sept

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

4. Best Western Grant Park Hotel

The Loop, 5.4 km from Oakland

Diego

RM688 total

includes taxes & fees

7 Sept - 8 Sept

An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

5. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 5.4 km from Oakland

Dhannetta

RM773 total

includes taxes & fees

10 Sept - 11 Sept

6. Hilton Vacation Club Hotel Blake Chicago

The Loop, 6.1 km from Oakland

Melanie

RM873 total

includes taxes & fees

7 Sept - 8 Sept

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

7. Congress Plaza Hotel

The Loop, 6 km from Oakland

George

RM551 total

includes taxes & fees

7 Sept - 8 Sept

An outdoor seating area with wicker chairs, a glass-top table, and a sofa with cushions.

8. Hyatt Centric The Loop Chicago

Theatre District, 6.8 km from Oakland

Tamika

RM1,021 total

includes taxes & fees

7 Sept - 8 Sept

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

9. Hyatt Regency Chicago

The Loop, 7.3 km from Oakland

Jerry

RM1,107 total

includes taxes & fees

7 Sept - 8 Sept

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

10. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 7.8 km from Oakland

Tonya

RM731 total

includes taxes & fees

9 Sept - 10 Sept

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

11. Hotel Riu Plaza Chicago

Streeterville, 7.9 km from Oakland

Donna

RM815 total

includes taxes & fees

7 Sept - 8 Sept

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

12. Hyatt Place Chicago/Downtown - The Loop

The Loop, 7.1 km from Oakland

LISA

RM957 total

includes taxes & fees

7 Sept - 8 Sept

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

13. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Streeterville, 7.6 km from Oakland

JUDY

RM895 total

includes taxes & fees

7 Sept - 8 Sept

A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

14. Le Méridien Essex Chicago

The Loop, 5.6 km from Oakland

amanda

RM789 total

includes taxes & fees

7 Sept - 8 Sept

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

15. Hilton Garden Inn Chicago Central Loop

The Loop, 6.6 km from Oakland

Theresa

RM900 total

includes taxes & fees

7 Sept - 8 Sept

A grand lobby with ornate ceiling artwork, chandeliers, and a central staircase.

16. Palmer House a Hilton Hotel

Theatre District, 6.7 km from Oakland

RM998 total

includes taxes & fees

9 Sept - 10 Sept

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

17. citizenM Chicago Downtown

Theatre District, 7.3 km from Oakland

lakadria

RM818 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.

18. Aloft by Marriott Chicago Mag Mile

Streeterville, 7.9 km from Oakland

Odessia

RM739 total

includes taxes & fees

7 Sept - 8 Sept

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

19. Crowne Plaza Chicago West Loop by IHG

7.3 km from Oakland

Jaclyn

RM928 total

includes taxes & fees

7 Sept - 8 Sept

A modern building with large glass windows and a covered walkway.

20. Holiday Inn & Suites Chicago - Downtown by IHG

West Loop, 6.4 km from Oakland

Julenny

RM823 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.

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

10/10 Excellent

"Na"

L7 Chicago by LOTTE

10/10 Excellent

"We came down for the Jill Scott concert and stayed here add the hotel was literally 2 blocked from the venue Chicago Theater. We were on the 4th floor and the view was spectacular. The room had 2 queen beds and was very spacious, but what took my breath away was the bed area in the window. I slept here because I wanted to see the view. Valet parking was $65 a night which is cheaper than a lot of places in Chicago. I paid for breakfast at the hotel with the reservation, which was an Asian/American mix restaurant. There were conventional breakfast choices are well as Asian choices, I'm more of a conventional breakfast person. The price for breakfast was $50 extra per person. There were many people in there for breakfast so the place is pretty popular, but next time I'll just go to a restaurant nearby. We didn't stay for dinner so I'm not sure of the choices with that. I will most definitely stay here again, and will recommend to others. I think this hotel is my favorite in Chicago so far."

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.

Hotels in Oakland, Chicago

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Our top choices for Oakland hotels

1. Hilton Chicago

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

3. Homewood Suites by Hilton Chicago Downtown South Loop

4. Best Western Grant Park Hotel

5. Hilton Garden Inn Chicago Downtown South Loop

6. Hilton Vacation Club Hotel Blake Chicago

7. Congress Plaza Hotel

8. Hyatt Centric The Loop Chicago

9. Hyatt Regency Chicago

10. DoubleTree by Hilton Chicago - Magnificent Mile

11. Hotel Riu Plaza Chicago

12. Hyatt Place Chicago/Downtown - The Loop

13. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

14. Le Méridien Essex Chicago

15. Hilton Garden Inn Chicago Central Loop

16. Palmer House a Hilton Hotel

17. citizenM Chicago Downtown

18. Aloft by Marriott Chicago Mag Mile

19. Crowne Plaza Chicago West Loop by IHG

20. Holiday Inn & Suites Chicago - Downtown by IHG

Where to stay in Oakland

Downtown Chicago

The Loop

Magnificent Mile

River North

Lincoln Park

Top Oakland Hotel Reviews

Hilton Chicago

Frequently asked questions

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