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

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

1. Hilton Vacation Club Hotel Blake Chicago

The Loop, 6.1 km from Oakland

Mario

₹20,476 total

includes taxes & fees

29 Oct - 30 Oct

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

2. Hotel Riu Plaza Chicago

Streeterville, 7.9 km from Oakland

Scott E

₹20,379 total

includes taxes & fees

11 Nov - 12 Nov

A room with two chairs and a small table, a large window with a city view at night.

3. Eurostars Magnificent Mile

River North, 8.1 km from Oakland

Kelby

₹18,057 total

includes taxes & fees

11 Nov - 12 Nov

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

4. Hyatt Place Chicago/River North

River North, 7.8 km from Oakland

Nilofar

₹19,412 total

includes taxes & fees

12 Nov - 13 Nov

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

5. Hyatt Regency Chicago

The Loop, 7.3 km from Oakland

Addison

₹32,052 total

includes taxes & fees

31 Oct - 1 Nov

A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

6. Hilton Chicago

The Loop, 5.7 km from Oakland

Anna

₹21,876 total

includes taxes & fees

13 Nov - 14 Nov

An outdoor seating area with modern furniture and potted plants.

7. Radisson Blu Aqua Hotel Chicago

7.1 km from Oakland

Shannon

₹29,650 total

includes taxes & fees

15 Nov - 16 Nov

A modern restaurant interior with a green wall, hanging lights, and a long dining area.

8. Hotel 505 River North

River North, 7.8 km from Oakland

Jordan

₹22,380 total

includes taxes & fees

25 Oct - 26 Oct

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

9. L7 Chicago by LOTTE

Theatre District, 7.2 km from Oakland

Amanda

₹19,603 total

includes taxes & fees

1 Nov - 2 Nov

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.

10. Aloft by Marriott Chicago Mag Mile

Streeterville, 7.9 km from Oakland

Jonathan M

₹16,946 total

includes taxes & fees

1 Nov - 2 Nov

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

11. InterContinental Chicago Magnificent Mile by IHG

Magnificent Mile, 7.7 km from Oakland

Said Lopez

₹27,248 total

includes taxes & fees

31 Oct - 1 Nov

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

Eliana

₹17,171 total

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with a marble island, fruit bowls, and a city view.

13. Fairmont Chicago at Millennium Park

The Loop, 7.1 km from Oakland

Ruby

₹37,132 total

includes taxes & fees

25 Oct - 26 Oct

A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

14. Silversmith Hotel Chicago Downtown

Theatre District, 6.7 km from Oakland

Guy

₹19,215 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large window offering a city view, a bed, a desk, and a chair.

15. Courtyard by Marriott Chicago Magnificent Mile

Streeterville, 7.9 km from Oakland

Richard

₹15,445 total

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.

16. Palmer House a Hilton Hotel

Theatre District, 6.7 km from Oakland

Christy

₹24,310 total

includes taxes & fees

31 Oct - 1 Nov

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

17. Best Western Grant Park Hotel

The Loop, 5.4 km from Oakland

Colin

₹12,088 total

includes taxes & fees

10 Nov - 11 Nov

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

18. Congress Plaza Hotel

The Loop, 6 km from Oakland

Ashya

₹12,055 total

includes taxes & fees

10 Nov - 11 Nov

A dining area with a table set for four, large windows offering a cityscape view at dusk.

19. The Royal Sonesta Chicago Downtown

The Loop, 7.3 km from Oakland

Ebony

₹22,111 total

includes taxes & fees

1 Nov - 2 Nov

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

20. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 7.8 km from Oakland

Poua

₹15,157 total

includes taxes & fees

1 Nov - 2 Nov

View all properties

Compare popular hotels in Oakland

Property	Property class	Guest rating
Hilton Vacation Club Hotel Blake Chicago	4.0 star property	9.6 Exceptional 1,222 reviews	View
Hotel Riu Plaza Chicago	4.0 star property	9.4 Exceptional 5,568 reviews	View
L7 Chicago by LOTTE	4.5 star property	9.6 Exceptional 5,076 reviews	View
Hyatt Regency Chicago	4.0 star property	9.4 Exceptional 3,521 reviews	View
Hyatt Place Chicago/River North	3.5 star property	9.2 Wonderful 1,923 reviews	View

Where to stay in Oakland

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

A cityscape with tall skyscrapers and a historic tower.

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 busy urban street at dusk with tall buildings, a historic tower, and pedestrians.

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 large, historic building with a central tower and multiple windows, located near a body of water.

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 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 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

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"very good"

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Our top choices for Oakland hotels

1. Hilton Vacation Club Hotel Blake Chicago

2. Hotel Riu Plaza Chicago

3. Eurostars Magnificent Mile

4. Hyatt Place Chicago/River North

5. Hyatt Regency Chicago

6. Hilton Chicago

7. Radisson Blu Aqua Hotel Chicago

8. Hotel 505 River North

9. L7 Chicago by LOTTE

10. Aloft by Marriott Chicago Mag Mile

11. InterContinental Chicago Magnificent Mile by IHG

12. Embassy Suites by Hilton Chicago Downtown River North

13. Fairmont Chicago at Millennium Park

14. Silversmith Hotel Chicago Downtown

15. Courtyard by Marriott Chicago Magnificent Mile

16. Palmer House a Hilton Hotel

17. Best Western Grant Park Hotel

18. Congress Plaza Hotel

19. The Royal Sonesta Chicago Downtown

20. DoubleTree by Hilton Chicago - Magnificent Mile

Compare popular hotels in Oakland

Where to stay in Oakland

Downtown Chicago

Magnificent Mile

River North

The Loop

Lincoln Park

Top Oakland Hotel Reviews

Club Quarters Hotel, Central Loop, Chicago

Frequently asked questions

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