Search Hotels in Oakland, Chicago

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Our top choices for Oakland hotels

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, (2,461 reviews)
"Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. "
United States
Christopher
The price is ₹22,921
₹30,102 total
includes taxes & fees
30 Apr - 1 May
Sable at Navy Pier Chicago, Curio Collection by Hilton

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,115 reviews)
"Really good location "
United States
Amanda
The price is ₹12,100
₹14,205 total
includes taxes & fees
26 Apr - 27 Apr
River Hotel

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
River North, 8.1 km from Oakland
8.4 out of 10, Very good, (564 reviews)
"Lots of stuff close by , cool vibe inside and very nice staff"
United States
Abel
The price is ₹7,495
₹8,798 total
includes taxes & fees
26 Apr - 27 Apr
FOUND Hotel Chicago River North

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 7.9 km from Oakland
8.0 out of 10, Very good, (2,901 reviews)
"Great location, clean and decent sized room, staff was helpful and amenities are very convenient!"
United States
MaryJane
The price is ₹8,132
₹11,199 total
includes taxes & fees
28 Apr - 29 Apr
Freehand Chicago

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 7.1 km from Oakland
9.4 out of 10, Exceptional, (2,087 reviews)
"Great location! Loved staying here"
United States
Nicole
The price is ₹13,423
₹18,558 total
includes taxes & fees
26 Apr - 27 Apr
Arlo Chicago

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, (2,407 reviews)
"Beautiful property, great resturant on site, an the pool and spa was amazing."
United States
Tim
The price is ₹16,460
₹21,916 total
includes taxes & fees
10 May - 11 May
Palmer House a Hilton Hotel

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (3,934 reviews)
"Had an amazing time at RIU hotel , the rooms were extremely clean , the breakfast was huge with many different options and very delicious . Definitely recommend for anyone traveling to Chicago. "
United States
Arelis
The price is ₹13,099
₹18,218 total
includes taxes & fees
10 May - 11 May
Hotel Riu Plaza Chicago

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,167 reviews)
"Perfect location and views!"
United States
Angel
The price is ₹10,760
₹12,631 total
includes taxes & fees
26 Apr - 27 Apr
Congress Plaza Hotel

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,194 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is ₹10,412
₹12,223 total
includes taxes & fees
27 Apr - 28 Apr
Aloft Chicago Mag Mile

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Streeterville, 7.9 km from Oakland
8.4 out of 10, Very good, (1,881 reviews)
"Great location and a very high class hotel."
United States
Cornelius
The price is ₹8,714
₹10,404 total
includes taxes & fees
26 Apr - 27 Apr
Hotel Saint Clair- Magnificent Mile

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 7.2 km from Oakland
9.6 out of 10, Exceptional, (3,954 reviews)
"Great hotel, clean an super friendly staff.. would recommend"
United Kingdom
Joel
The price is ₹13,562
₹15,921 total
includes taxes & fees
26 Apr - 27 Apr
L7 Chicago by LOTTE

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, (1,954 reviews)
"Easy check in and clean rooms, comfortable beds and easy access to everything downtown."
United States
Megan
The price is ₹12,858
₹15,095 total
includes taxes & fees
26 Apr - 27 Apr
Hilton Garden Inn Chicago Downtown South Loop

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, (2,237 reviews)
"Clean and quiet, very attentive staff and a great location. Would absolutely return for another stay!"
United States
Robyn
The price is ₹11,149
₹15,943 total
includes taxes & fees
26 Apr - 27 Apr
Silversmith Hotel Chicago Downtown

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
8.2 out of 10, Very good, (1,379 reviews)
"This hotel is superb value and I will definitely return"
United Kingdom
Andrew
The price is ₹12,283
₹14,420 total
includes taxes & fees
26 Apr - 27 Apr
The Chicago Hotel Collection Ambassador Gold Coast

Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 5.6 km from Oakland
8.8 out of 10, Excellent, (1,000 reviews)
"Centrally located to all I needed. "
United States
Gerald
The price is ₹11,725
₹15,417 total
includes taxes & fees
26 Apr - 27 Apr
Le Méridien Essex Chicago

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,745 reviews)
"We always book this hotel when staying in Chicago. The overall atmosphere, staff and room cleanliness is what brings us back."
United States
OSCAR
The price is ₹16,075
₹21,866 total
includes taxes & fees
10 May - 11 May
Hilton Chicago

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 6.9 km from Oakland
9.4 out of 10, Exceptional, (1,045 reviews)
"Lots of places to eat and shop nearby"
United States
Analicia
The price is ₹12,579
₹17,703 total
includes taxes & fees
10 May - 11 May
Staypineapple, An Iconic Hotel, The Loop

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 6.6 km from Oakland
8.6 out of 10, Excellent, (2,089 reviews)
"Great hotel in a great location."
United States
Ben
The price is ₹11,162
₹13,104 total
includes taxes & fees
26 Apr - 27 Apr
Central Loop Hotel

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
7.7 km from Oakland
9.0 out of 10, Wonderful, (1,000 reviews)
"Super cute hotel. Great bar and food "
United States
Patricia
The price is ₹15,955
₹21,724 total
includes taxes & fees
10 May - 11 May
The Hoxton Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (2,208 reviews)
"Perfect location great room for the price "
United States
Lisa
The price is ₹10,881
₹12,774 total
includes taxes & fees
26 Apr - 27 Apr
Club Quarters Hotel Wacker at Michigan, Chicago
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.

Where to stay in Oakland

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

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.

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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.

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

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 5 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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