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

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Check prices for these dates

Next weekend
5 Jun - 7 Jun
In two weeks
12 Jun - 14 Jun

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Our top choices for Oakland hotels

Terrace/patio

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, (2,512 reviews)
"Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!"
United States
Deborah
The price is €263
includes taxes & fees
30 Jun - 1 Jul
Sable at Navy Pier Chicago, Curio Collection by Hilton
Cocktail bar

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 7.9 km from Oakland
8.0 out of 10, Very good, (3,034 reviews)
"Great location nice room"
United States
Nolan
The price is €164
includes taxes & fees
29 Jun - 30 Jun
Freehand Chicago
Lobby

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, (1,520 reviews)
"A nice stay and lovely location. "
United States
Robin
The price is €159
includes taxes & fees
22 Jun - 23 Jun
The Chicago Hotel Collection Ambassador Gold Coast
Lobby

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 5.9 km from Oakland
7.4 out of 10, Good, (2,611 reviews)
"Staff was friendly and helpful.. location was great"
United States
Amber
The price is €137
includes taxes & fees
29 Jun - 30 Jun
Travelodge by Wyndham Downtown Chicago
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,125 reviews)
"Excellent stay"
United States
Jennifer
The price is €133
includes taxes & fees
29 Jun - 30 Jun
Congress Plaza Hotel
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 8.2 km from Oakland
7.8 out of 10, Good, (1,489 reviews)
"Great stay"
United States
Ontario
The price is €155
includes taxes & fees
28 Jun - 29 Jun
The Chicago Hotel Collection - Magnificent Mile
Exterior

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,838 reviews)
"great hotel and excellent to stay"
United States
Ruben
The price is €300
includes taxes & fees
12 Jun - 13 Jun
Hilton Chicago
Lobby

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, (2,245 reviews)
"Close to many attractions and shopping and nice unique hotel"
United States
Brittany
The price is €189
includes taxes & fees
28 Jun - 29 Jun
Silversmith Hotel Chicago Downtown
Restaurant

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, (2,705 reviews)
"Fantastic AC, clean rooms, friendly staff and an excellent location to walk to a ton of things"
United States
Derrick
The price is €193
includes taxes & fees
29 Jun - 30 Jun
Best Western Grant Park Hotel
Exterior

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 8.1 km from Oakland
8.6 out of 10, Excellent, (3,033 reviews)
"Clean room, friendly staff, nearby lots of stores and restaurants. "
United States
Nadiah
The price is €178
includes taxes & fees
28 Jun - 29 Jun
Warwick Allerton - Chicago
2 restaurants; breakfast, lunch and dinner served

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 7.4 km from Oakland
9.4 out of 10, Exceptional, (3,721 reviews)
"Can't beat the location; it's next to Michigan Avenue and across from the Riverwalk; we'd stay there again."
United States
Matson
The price is €254
includes taxes & fees
21 Jun - 22 Jun
LondonHouse Chicago, Curio Collection by Hilton
Interior detail

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, (1,077 reviews)
"Such a lovely hotel with a beautiful, excellent staff, and lots of character!"
United States
Debby
The price is €254
includes taxes & fees
29 Jun - 30 Jun
Staypineapple, An Iconic Hotel, The Loop
Exterior

Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott
4.0 star property
River North, 7.5 km from Oakland
9.0 out of 10, Wonderful, (1,003 reviews)
"The staff and up keep of the maintenance of the hotel was spectacular"
United States
Oziel Silva
The price is €188
includes taxes & fees
28 Jun - 29 Jun
Hotel Chicago Downtown, Autograph Collection by Marriott
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (4,292 reviews)
"Great location & breakfast was amazing."
United States
sierra
The price is €217
includes taxes & fees
30 Jun - 1 Jul
Hotel Riu Plaza Chicago
Exterior

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
The Loop, 6.1 km from Oakland
9.6 out of 10, Exceptional, (1,253 reviews)
"Overall comfortable stay and easy access by walk to downtown and all other places in the city."
United States
raghu
The price is €195
includes taxes & fees
28 Jun - 29 Jun
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Lobby sitting area

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, (1,946 reviews)
"The staff was super helpful and the rooms were super clean"
United States
Miguel
The price is €190
includes taxes & fees
14 Jun - 15 Jun
Hotel Saint Clair- Magnificent Mile
Exterior

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 8.6 km from Oakland
9.0 out of 10, Wonderful, (4,352 reviews)
"Great property, perfect area to walk around in, excellent cafe."
United States
Kayla
The price is €177
includes taxes & fees
28 Jun - 29 Jun
Hilton Chicago/Magnificent Mile Suites
Shopping centre

Millennium Hotel Knickerbocker Chicago

Millennium Hotel Knickerbocker Chicago
4.0 star property
Streeterville, 8.6 km from Oakland
8.6 out of 10, Excellent, (1,971 reviews)
"Loved everything including location and food options. Great hotel. "
United States
Eileen
The price is €159
includes taxes & fees
28 Jun - 29 Jun
Millennium Hotel Knickerbocker Chicago
Breakfast and dinner served

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Streeterville, 8.1 km from Oakland
9.2 out of 10, Wonderful, (1,788 reviews)
"Great place at a great location."
United States
Alejandro
The price is €207
includes taxes & fees
7 Jun - 8 Jun
Omni Chicago Hotel
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 8.1 km from Oakland
9.0 out of 10, Wonderful, (3,594 reviews)
"Great location, large rooms, we loved our stay and would definitely recommend "
Australia
Belinda
The price is €228
includes taxes & fees
30 Jun - 1 Jul
Eurostars 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.

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

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

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.

Panoramic view of Lincoln Park and the Chicago skyline.

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

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Great"
Holly 1-night trip
Posted less than an hour ago
The Chicago Hotel Collection - Magnificent Mile

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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