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.

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

1. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 5.4 km from Oakland

Nicole

RM510 total

includes taxes & fees

23 Nov - 24 Nov

A multi-story building with a prominent entrance featuring a large archway and a sign.

2. Hilton Chicago

The Loop, 5.7 km from Oakland

Christian

RM642 total

includes taxes & fees

27 Nov - 28 Nov

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

3. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 5.4 km from Oakland

Aran

RM469 total

includes taxes & fees

23 Nov - 24 Nov

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

4. Hilton Vacation Club Hotel Blake Chicago

The Loop, 6.1 km from Oakland

Kanokkan

RM773 total

includes taxes & fees

22 Nov - 23 Nov

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

5. Best Western Grant Park Hotel

The Loop, 5.4 km from Oakland

Michelle

RM473 total

includes taxes & fees

23 Nov - 24 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.

6. L7 Chicago by LOTTE

Theatre District, 7.2 km from Oakland

Matthew

RM699 total

includes taxes & fees

22 Nov - 23 Nov

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

7. Hyatt Place Chicago/Downtown - The Loop

The Loop, 7.1 km from Oakland

Cordula

RM571 total

includes taxes & fees

23 Nov - 24 Nov

A dining table set for six with a cityscape view through large windows.

8. Swissotel - Chicago

7.2 km from Oakland

Oleg

RM705 total

includes taxes & fees

26 Nov - 27 Nov

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

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

Streeterville, 7.5 km from Oakland

Bonnie

RM774 total

includes taxes & fees

23 Nov - 24 Nov

A hotel entrance with a glass door, a sign above the door, and two potted plants on either side.

10. Hampton Inn Majestic Chicago Theatre District

Theatre District, 6.7 km from Oakland

Michael

RM552 total

includes taxes & fees

23 Nov - 24 Nov

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

11. Courtyard by Marriott Chicago Magnificent Mile

Streeterville, 7.9 km from Oakland

Richard

RM553 total

includes taxes & fees

24 Nov - 25 Nov

A grand lobby with a staircase, ornate chandeliers, and a clock on the wall.

12. Palmer House a Hilton Hotel

Theatre District, 6.7 km from Oakland

Christy

RM763 total

includes taxes & fees

24 Nov - 25 Nov

13. Hilton Garden Inn Chicago Central Loop

The Loop, 6.6 km from Oakland

Jasmine

RM652 total

includes taxes & fees

22 Nov - 23 Nov

14. Hyatt Centric The Loop Chicago

Theatre District, 6.8 km from Oakland

David

RM920 total

includes taxes & fees

22 Nov - 23 Nov

A multi-story building with a prominent curved glass facade, surrounded by other high-rise buildings.

15. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Streeterville, 7.6 km from Oakland

Serge

RM700 total

includes taxes & fees

24 Nov - 25 Nov

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

16. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 7.8 km from Oakland

Jodi

RM488 total

includes taxes & fees

23 Nov - 24 Nov

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

17. Hyatt Place Chicago/River North

River North, 7.8 km from Oakland

Pamela

RM675 total

includes taxes & fees

22 Nov - 23 Nov

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

18. Le Méridien Essex Chicago

The Loop, 5.6 km from Oakland

Taso

RM615 total

includes taxes & fees

24 Nov - 25 Nov

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

19. LondonHouse Chicago, Curio Collection by Hilton

The Loop, 7.4 km from Oakland

Lorena

RM814 total

includes taxes & fees

23 Nov - 24 Nov

A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

20. Hyatt House Chicago/West Loop-Fulton Market

7.9 km from Oakland

Carole

RM569 total

includes taxes & fees

22 Nov - 23 Nov

View all properties

Compare popular hotels in Oakland

Property	Property class	Guest rating
L7 Chicago by LOTTE	4.5 star property	9.6 Exceptional 5,163 reviews	View
Hilton Vacation Club Hotel Blake Chicago	4.0 star property	9.6 Exceptional 1,218 reviews	View
LondonHouse Chicago, Curio Collection by Hilton	4.5 star property	9.4 Exceptional 3,901 reviews	View
Hotel Riu Plaza Chicago	4.0 star property	9.4 Exceptional 5,639 reviews	View
Hyatt Place Chicago/River North	3.5 star property	9.2 Wonderful 1,918 reviews	View

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

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 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

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"The hotel was very clean and in the heart of shopping areas and restaurants. The room was clean and tidy upon arrival. The only issue was the elevator taking a while as it is a capacity of 5 people and others were utilizing it to check out at the same time, so just be mindful of that. Otherwise, great stay!"

Arlo Chicago

10/10 Excellent

"Absolute enjoyed our stay here. The moment we walked in, we were greeted by the staff and every single one of them was wonderful and helpful. It was actually our first comment when we got to our room. The room itself was a bit smaller than I expected but it worked out for our trip. Def. A nice central location for food, stores and walking distance to Navy Pier, Bean and museums. Wouldn’t mind coming back here for a good deal and price. Also, loved the gym and how they provided mini deodorants and cooling towels."

Sports Illustrated Resorts Chicago

8/10 Good

"Overall my stay was pretty good. The only two issues were my mini fridge wasn’t working and I lost my leftovers that sat in there for the two days I stayed. Secondly, I had a staff member tell me about a special tour and promotion, only to tell me somehow I was not eligible. Then he had me bring my son down to see if he could be eligible. He was only 18,not 21. So he was not. That was not very pleasant considering it was basically pulled back for some reason . I visit 3-4 times a year. I either stay at the Westin River north or the Royal Sonesta River North. The lost food was no biggie but being given a whole rundown about how the hotel was trying to build a new customer base and then being told I wasn’t eligible was crappy. I can’t lie. Everything else was pretty good. The happy hours were cool. Staff outside of that was generally ok."

Hotels in Oakland, Chicago

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Check prices for these dates

Filter by

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Guest rating

Our top choices for Oakland hotels

1. Homewood Suites by Hilton Chicago Downtown South Loop

2. Hilton Chicago

3. Hilton Garden Inn Chicago Downtown South Loop

4. Hilton Vacation Club Hotel Blake Chicago

5. Best Western Grant Park Hotel

6. L7 Chicago by LOTTE

7. Hyatt Place Chicago/Downtown - The Loop

8. Swissotel - Chicago

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

10. Hampton Inn Majestic Chicago Theatre District

11. Courtyard by Marriott Chicago Magnificent Mile

12. Palmer House a Hilton Hotel

13. Hilton Garden Inn Chicago Central Loop

14. Hyatt Centric The Loop Chicago

15. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

16. DoubleTree by Hilton Chicago - Magnificent Mile

17. Hyatt Place Chicago/River North

18. Le Méridien Essex Chicago

19. LondonHouse Chicago, Curio Collection by Hilton

20. Hyatt House Chicago/West Loop-Fulton Market

Compare popular hotels in Oakland

Where to stay in Oakland

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Oakland Hotel Reviews

Hotel Saint Clair- Magnificent Mile

Frequently asked questions

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