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

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Our top choices for Oakland hotels

1. Hyatt Place Chicago/Downtown - The Loop

The Loop, 7.1 km from Oakland

Treniscia

6.343.075 ₫ total

includes taxes & fees

16 Aug - 17 Aug

Suite, 1 Bedroom, Corner | Private kitchen | Coffee/tea maker, full-sized fridge, microwave, stovetop

2. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 5.4 km from Oakland

jayne

5.710.332 ₫ total

includes taxes & fees

30 Aug - 31 Aug

3. La Quinta Inn & Suites by Wyndham Chicago Downtown

The Loop, 7 km from Oakland

Paige

6.019.578 ₫ total

includes taxes & fees

30 Aug - 31 Aug

4. Hotel Riu Plaza Chicago

Streeterville, 7.9 km from Oakland

Cicely

7.279.812 ₫ total

includes taxes & fees

30 Aug - 31 Aug

5. River Hotel

The Loop, 7.4 km from Oakland

Yousef

5.658.457 ₫ total

includes taxes & fees

31 Aug - 1 Sept

6. Silversmith Hotel Chicago Downtown

Theatre District, 6.7 km from Oakland

Gillian

5.801.089 ₫ total

includes taxes & fees

30 Aug - 31 Aug

7. Crowne Plaza Chicago West Loop by IHG

7.3 km from Oakland

Evelyn

6.427.817 ₫ total

includes taxes & fees

20 Aug - 21 Aug

55-inch LCD TV with cable channels, TV, pay films

8. L7 Chicago by LOTTE

Theatre District, 7.2 km from Oakland

Julie Ann

8.073.827 ₫ total

includes taxes & fees

17 Aug - 18 Aug

Outdoor pool, pool cabanas (surcharge), pool umbrellas

9. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 7.8 km from Oakland

Macy

5.019.777 ₫ total

includes taxes & fees

30 Aug - 31 Aug

10. Hyatt Centric The Loop Chicago

Theatre District, 6.8 km from Oakland

Dee

6.469.272 ₫ total

includes taxes & fees

23 Aug - 24 Aug

11. Hyatt Place Chicago/River North

River North, 7.8 km from Oakland

Michelle

5.311.936 ₫ total

includes taxes & fees

16 Aug - 17 Aug

12. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

The Loop, 6.1 km from Oakland

Aleace

5.227.226 ₫ total

includes taxes & fees

30 Aug - 31 Aug

13. citizenM Chicago Downtown

Theatre District, 7.3 km from Oakland

lakadria

5.596.134 ₫ total

includes taxes & fees

31 Aug - 1 Sept

14. Hyatt Regency Chicago

The Loop, 7.3 km from Oakland

Emily

7.936.731 ₫ total

includes taxes & fees

30 Aug - 31 Aug

15. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 5.4 km from Oakland

Heather

5.019.778 ₫ total

includes taxes & fees

1 Sept - 2 Sept

16. The Allegro Royal Sonesta Hotel Chicago Loop

Theatre District, 7.2 km from Oakland

Mucio

7.996.513 ₫ total

includes taxes & fees

9 Aug - 10 Aug

17. Swissotel - Chicago

7.2 km from Oakland

Isaac

9.029.005 ₫ total

includes taxes & fees

9 Aug - 10 Aug

18. Hilton Chicago

The Loop, 5.7 km from Oakland

kun

7.927.177 ₫ total

includes taxes & fees

30 Aug - 31 Aug

19. Travelodge by Wyndham Downtown Chicago

The Loop, 5.9 km from Oakland

Adam

3.524.624 ₫ total

includes taxes & fees

30 Aug - 31 Aug

20. Le Méridien Essex Chicago

The Loop, 5.6 km from Oakland

Daniel

4.937.145 ₫ total

includes taxes & fees

30 Aug - 31 Aug

View all properties

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

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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A river with yellow boats, a bridge, and tall buildings.

The Loop

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.

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

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

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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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The Chicago Theatre with illuminated marquee and a wet street reflecting lights.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

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Top Oakland Hotel Reviews

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"good"

The Royal Sonesta Chicago Downtown

10/10 Excellent

"The room was clean and the perfect location to watch the river get dyed. Because we were there for St Patricks Day, the elevators were a huge problem to get down from our room so ended up taking the stairs. This is not the hotels fault by any means. There is a small restaurant and bar. We only got drinks from there. The decor was great and we were so comfy in our bed. I would definitely stay here again!!"

Fairmont Chicago at Millennium Park

10/10 Excellent

"Great location- most attractions were an easy walk from the hotel. The hotel staff were all very nice and provided exceptional customer service. The room was well-appointed, with comfy beds and a beautiful bathroom. We paid extra for Fairmont Gold (concierge level) and found it to be a great value. The food at the buffet breakfast was delicious and they had nice snacks at other times of the day. The staff in the Concierge Lounge was top notch!"

Search Hotels in Oakland, Chicago

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Star rating

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Our top choices for Oakland hotels

1. Hyatt Place Chicago/Downtown - The Loop

2. Homewood Suites by Hilton Chicago Downtown South Loop

3. La Quinta Inn & Suites by Wyndham Chicago Downtown

4. Hotel Riu Plaza Chicago

5. River Hotel

6. Silversmith Hotel Chicago Downtown

7. Crowne Plaza Chicago West Loop by IHG

8. L7 Chicago by LOTTE

9. DoubleTree by Hilton Chicago - Magnificent Mile

10. Hyatt Centric The Loop Chicago

11. Hyatt Place Chicago/River North

12. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

13. citizenM Chicago Downtown

14. Hyatt Regency Chicago

15. Hilton Garden Inn Chicago Downtown South Loop

16. The Allegro Royal Sonesta Hotel Chicago Loop

17. Swissotel - Chicago

18. Hilton Chicago

19. Travelodge by Wyndham Downtown Chicago

20. Le Méridien Essex Chicago

Where to stay in Oakland

Downtown Chicago

The Loop

Magnificent Mile

River North

Theatre District

Top Oakland Hotel Reviews

The Allegro Royal Sonesta Hotel Chicago Loop

Frequently asked questions

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