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

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Check prices for these dates

This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

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Our top choices for Oakland hotels

Lobby

1. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,261 reviews)
"The hotel offers an amazing, perfect location, and historic hotel experience."
United States
George
The price is €118
includes taxes & fees
7 Sept - 8 Sept
Congress Plaza Hotel
Bar (on property)

2. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (3,131 reviews)
"Very nice place would stay again"
United States
Konner
The price is €199
includes taxes & fees
10 Sept - 11 Sept
Hilton Chicago
Pool

3. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 5.4 km from Oakland
8.8 out of 10, Excellent, (2,146 reviews)
"Great stay"
United States
Dhannetta
The price is €166
includes taxes & fees
7 Sept - 8 Sept
Hilton Garden Inn Chicago Downtown South Loop
Restaurant

4. Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 5.4 km from Oakland
8.2 out of 10, Very good, (2,730 reviews)
"Very good hotel"
United States
Diego
The price is €147
includes taxes & fees
7 Sept - 8 Sept
Best Western Grant Park Hotel
Terrace/patio

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

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 7.5 km from Oakland
9.4 out of 10, Exceptional, (2,685 reviews)
"Nice place to stay"
United States
Ashraf
The price is €220
includes taxes & fees
8 Sept - 9 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
Suite, 1 Bedroom, Corner | Private kitchen

6. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
The Loop, 5.4 km from Oakland
8.8 out of 10, Excellent, (2,445 reviews)
"Clean, friendly staff, quick valet, and a decent breakfast"
United States
AMBER
The price is €182
includes taxes & fees
8 Sept - 9 Sept
Homewood Suites by Hilton Chicago Downtown South Loop
Nightclub

7. Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 6.6 km from Oakland
8.6 out of 10, Excellent, (2,275 reviews)
"Great location."
United States
Yiyang
The price is €125
includes taxes & fees
7 Sept - 8 Sept
Central Loop Hotel
Lobby

8. Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 5.6 km from Oakland
9.0 out of 10, Wonderful, (1,008 reviews)
"This hotel was perfect. Room was a great size, clean, very friendly staff. Perfect for our work trip!"
United States
amanda
The price is €168
includes taxes & fees
7 Sept - 8 Sept
Le Méridien Essex Chicago
Superior Apartment, 2 Bedrooms, Kitchen | Living area

9. LIVN - West Loop Chicago

LIVN - West Loop Chicago
4.0 star property
6.8 km from Oakland
9.4 out of 10, Exceptional, (246 reviews)
"Great stay!"
United States
Tomas
The price is €122
includes taxes & fees
7 Sept - 8 Sept
LIVN - West Loop Chicago
Lobby

10. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 5.9 km from Oakland
7.6 out of 10, Good, (2,817 reviews)
"Great place"
United States
Matthew
The price is €135
includes taxes & fees
8 Sept - 9 Sept
Travelodge by Wyndham Downtown Chicago
Lobby

11. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 9.4 km from Oakland
8.0 out of 10, Very good, (2,143 reviews)
"Loved this hotel, great location and wonderful accommodations, just perfect"
United States
Laura
The price is €125
includes taxes & fees
8 Sept - 9 Sept
The Chicago Hotel Collection Ambassador Gold Coast
Front of property

12. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop, 6.1 km from Oakland
9.6 out of 10, Exceptional, (1,270 reviews)
"The staff were really nice and friendly. Our room was nice and clean. I would stay here again!"
United States
Melanie
The price is €186
includes taxes & fees
7 Sept - 8 Sept
Hilton Vacation Club Hotel Blake Chicago
Lobby

13. River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,392 reviews)
"Really good location and very helpful staff."
United States
Timothy
The price is €162
includes taxes & fees
7 Sept - 8 Sept
River Hotel
Outdoor pool, pool cabanas (surcharge), pool umbrellas

14. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 7.8 km from Oakland
8.8 out of 10, Excellent, (2,570 reviews)
"Great hotel will book again"
United States
Tonya
The price is €156
includes taxes & fees
9 Sept - 10 Sept
DoubleTree by Hilton Chicago - Magnificent Mile
Lobby

15. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Streeterville, 7.9 km from Oakland
9.0 out of 10, Wonderful, (1,006 reviews)
"Clean rooms and good breakfast"
United States
Sarwat
The price is €135
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Reception

16. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 6.7 km from Oakland
8.6 out of 10, Excellent, (2,622 reviews)
"We loved our stay here!"
United States
G.
The price is €217
includes taxes & fees
9 Sept - 10 Sept
Palmer House a Hilton Hotel
Nightclub

17. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 6.6 km from Oakland
8.8 out of 10, Excellent, (3,646 reviews)
"Great location very central"
United Kingdom
Simon
The price is €136
includes taxes & fees
7 Sept - 8 Sept
Club Quarters Hotel, Central Loop, Chicago
Lobby

18. Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 6.7 km from Oakland
9.2 out of 10, Wonderful, (2,369 reviews)
"Great location."
United States
Xiao
The price is €182
includes taxes & fees
9 Sept - 10 Sept
Silversmith Hotel Chicago Downtown
Rooftop terrace

19. Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Theatre District, 6.8 km from Oakland
9.0 out of 10, Wonderful, (2,731 reviews)
"Great place to stay!"
United States
Tamika
The price is €218
includes taxes & fees
7 Sept - 8 Sept
Hyatt Centric The Loop Chicago
Premium bedding, in-room safe, desk, blackout curtains

20. Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Streeterville, 7.9 km from Oakland
9.0 out of 10, Wonderful, (2,045 reviews)
"Great stay"
United States
Jyothi Swaroop
The price is €147
includes taxes & fees
7 Sept - 8 Sept
Courtyard by Marriott Chicago Magnificent Mile
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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.

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.

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

Magnificent Mile

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

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.

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.

Top Oakland Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"It’s a classic Chicago hotel. It’s was clean and comfortable. Also a great location for walking to downtown parks and food!"
Angela 1-night trip
Posted 1 hour ago
Congress Plaza Hotel

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.

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