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.

Oakland hotels, Chicago, United States of America: Chicago Hotel Guide

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

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Our top choices for Oakland hotels

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

1. Best Western Grant Park Hotel

The Loop, 5.4 km from Oakland

Colin

includes taxes & fees

10 Nov - 11 Nov

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

2. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 5.4 km from Oakland

Aran

includes taxes & fees

11 Nov - 12 Nov

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

3. Congress Plaza Hotel

The Loop, 6 km from Oakland

Ashya

includes taxes & fees

10 Nov - 11 Nov

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

4. Hilton Chicago

The Loop, 5.7 km from Oakland

Anna

includes taxes & fees

13 Nov - 14 Nov

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

Cynthia

includes taxes & fees

11 Nov - 12 Nov

A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

6. Travelodge by Wyndham Downtown Chicago

The Loop, 5.9 km from Oakland

Sandra

includes taxes & fees

11 Nov - 12 Nov

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

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

Streeterville, 7.5 km from Oakland

Shanequa

includes taxes & fees

12 Nov - 13 Nov

A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.

8. Hilton Vacation Club Hotel Blake Chicago

The Loop, 6.1 km from Oakland

Mario

includes taxes & fees

3 Nov - 4 Nov

A Holiday Inn & Suites building with multiple parking spaces and a modern architectural design.

9. Holiday Inn & Suites Chicago - Downtown by IHG

West Loop, 6.4 km from Oakland

Donna

includes taxes & fees

11 Nov - 12 Nov

A spacious lobby with a central coffee table, sofas, and a large mirror.

10. The Chicago Hotel Collection Ambassador Gold Coast

9.4 km from Oakland

Christian

includes taxes & fees

11 Nov - 12 Nov

11. The Allegro Royal Sonesta Hotel Chicago Loop

Theatre District, 7.2 km from Oakland

David

includes taxes & fees

15 Nov - 16 Nov

A historic building with a glass entrance, large columns, and decorative planters with flowers.

12. Warwick Allerton - Chicago

Streeterville, 8.1 km from Oakland

Nelza

includes taxes & fees

10 Nov - 11 Nov

A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

13. The Wade

Streeterville, 7.9 km from Oakland

Sheilaann

includes taxes & fees

1 Nov - 2 Nov

A rooftop terrace with lounge chairs and tables, offering a city skyline view.

14. Best Western River North Hotel

River North, 8 km from Oakland

Jordan

includes taxes & fees

9 Nov - 10 Nov

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

15. Crowne Plaza Chicago West Loop by IHG

7.3 km from Oakland

Chriselda

includes taxes & fees

1 Nov - 2 Nov

A high-rise hotel with a prominent curved glass facade, multiple floors, and a visible "EMBASSY" sign.

16. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Streeterville, 7.6 km from Oakland

jaimie

includes taxes & fees

1 Nov - 2 Nov

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

17. Silversmith Hotel Chicago Downtown

Theatre District, 6.7 km from Oakland

Guy

includes taxes & fees

1 Nov - 2 Nov

A spacious lobby with a wooden floor, a central round table with decorative items, a reception desk, and framed artwork on the walls.

18. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

7.5 km from Oakland

Brock

includes taxes & fees

31 Oct - 1 Nov

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.

19. L7 Chicago by LOTTE

Theatre District, 7.2 km from Oakland

Jeffrey Thomas

includes taxes & fees

1 Nov - 2 Nov

A bar area with a long counter, bar stools, and a mirrored wall.

20. The Whitehall Hotel, BW Premier Collection

Streeterville, 8.6 km from Oakland

KURT

includes taxes & fees

2 Nov - 3 Nov

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Where to stay in Oakland

Find the best Oakland areas for the activities you enjoy most.

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

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

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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 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 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

"Everything was nice in the room. Staff was very accommodating. We had a package mailed to this hotel overnight due to my forgetfulness and Hilton did an amazing job at getting it to me on time. Thanks to everyone."

Chicago Hotel Guide. Hotels in Oakland, Chicago, United States of America

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Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Oakland hotels

1. Best Western Grant Park Hotel

2. Hilton Garden Inn Chicago Downtown South Loop

3. Congress Plaza Hotel

4. Hilton Chicago

5. Homewood Suites by Hilton Chicago Downtown South Loop

6. Travelodge by Wyndham Downtown Chicago

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

8. Hilton Vacation Club Hotel Blake Chicago

9. Holiday Inn & Suites Chicago - Downtown by IHG

10. The Chicago Hotel Collection Ambassador Gold Coast

11. The Allegro Royal Sonesta Hotel Chicago Loop

12. Warwick Allerton - Chicago

13. The Wade

14. Best Western River North Hotel

15. Crowne Plaza Chicago West Loop by IHG

16. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

17. Silversmith Hotel Chicago Downtown

18. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

19. L7 Chicago by LOTTE

20. The Whitehall Hotel, BW Premier Collection

Where to stay in Oakland

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Oakland Hotel Reviews

Hilton Chicago O'Hare Airport

Frequently asked questions

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