Oakland Hotels, Chicago

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19 Nov - 20 Nov
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20 Nov - 21 Nov
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21 Nov - 23 Nov
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4614 Cheap Hotels in Oakland - Specials, Reviews, & Last Minute Deals

Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
River North, 8.1 km from Oakland
8.8 out of 10, Excellent, (3105)
"Excellent stay, close to everything and the staff was super nice "
United States
Kieata
The price is NZ$217
includes taxes & fees
18 Dec - 19 Dec
Eurostars Magnificent Mile
Reception
River Hotel

River Hotel

4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (4816)
"Front desk is amazing, rooms are clean and great location"
United States
Glen
The price is NZ$184
includes taxes & fees
20 Nov - 21 Nov
River Hotel
Terrace/patio
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, (2138)
"Great stay "
United States
Melinda
The price is NZ$202
includes taxes & fees
25 Nov - 26 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (2915)
"Great location!!"
United States
sarah e
The price is NZ$201
includes taxes & fees
24 Nov - 25 Nov
Aloft Chicago Mag Mile
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, (2237)
"Room was spotless…staff was great!"
United States
Tamika
The price is NZ$244
includes taxes & fees
16 Dec - 17 Dec
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio
citizenM Chicago Downtown

citizenM Chicago Downtown

4.0 star property
Theatre District, 7.3 km from Oakland
9.4 out of 10, Exceptional, (4048)
"Clean rooms, friendly staff, great breakfast, amazing location. "
Canada
Gokce
The price is NZ$243
includes taxes & fees
25 Nov - 26 Nov
citizenM Chicago Downtown
Meeting facility
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
River North, 7.8 km from Oakland
8.4 out of 10, Very good, (4179)
"Great location. "
United States
Rodger
The price is NZ$158
includes taxes & fees
7 Dec - 8 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior
Hilton Chicago

Hilton Chicago

4.0 star property
The Loop, 5.7 km from Oakland
8.4 out of 10, Very good, (2305)
"Clean Rooms & very nice staff"
United States
Teresa
The price is NZ$271
includes taxes & fees
25 Nov - 26 Nov
Hilton Chicago
Ballroom
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, (3325)
"Great stay!"
United States
Rose
The price is NZ$173
includes taxes & fees
7 Dec - 8 Dec
Hilton Chicago/Magnificent Mile Suites
Cocktail bar
Freehand Chicago

Freehand Chicago

4.0 star property
River North, 7.9 km from Oakland
8.0 out of 10, Very good, (2582)
"Rooms are clean, staff are nice and friendly "
United States
Karen
The price is NZ$171
includes taxes & fees
25 Nov - 26 Nov
Freehand Chicago
Exterior
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, (329)
"very clean and modern, staff was very friendly"
United States
Edrick
The price is NZ$140
includes taxes & fees
7 Dec - 8 Dec
FOUND Hotel Chicago River North
American cuisine
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 star property
7.3 km from Oakland
9.0 out of 10, Wonderful, (1686)
"very nice staff & very clean hotel "
United States
Amy
The price is NZ$187
includes taxes & fees
14 Dec - 15 Dec
Crowne Plaza Chicago West Loop by IHG
Banquet hall
Congress Plaza Hotel

Congress Plaza Hotel

3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (9603)
"Great stay comfortable bed and great location!"
United States
Kimberly Noel
Congress Plaza Hotel
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, (2816)
"Great service, great breakfast and a nice room "
United States
DeAnna
The price is NZ$264
includes taxes & fees
8 Dec - 9 Dec
Hotel Riu Plaza 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, (2074)
"Lovely hotel in a great spot!"
United States
Natasha
Silversmith Hotel Chicago Downtown
Exterior
La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
The Loop, 7 km from Oakland
8.6 out of 10, Excellent, (2617)
"Enjoyed my stay here. "
United States
Vai
The price is NZ$244
includes taxes & fees
23 Nov - 24 Nov
La Quinta Inn & Suites by Wyndham Chicago Downtown
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Theatre District, 6.7 km from Oakland
8.4 out of 10, Very good, (2073)
"Great place to stay."
United States
Aaron
The price is NZ$264
includes taxes & fees
25 Nov - 26 Nov
Palmer House a Hilton Hotel
Pool
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, (1712)
"Clean room, great hot tub."
United States
SHARON
The price is NZ$173
includes taxes & fees
25 Nov - 26 Nov
Hilton Garden Inn Chicago Downtown South Loop
Rooftop terrace
Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago

4.0 star property
Theatre District, 6.7 km from Oakland
9.0 out of 10, Wonderful, (2240)
"Clean room, friendly staff, convenient location. "
United States
Arthera
The price is NZ$309
includes taxes & fees
23 Nov - 24 Nov
Hyatt Centric The Loop Chicago
Bar (on property)
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

3.5 star property
River North, 7.7 km from Oakland
8.8 out of 10, Excellent, (3377)
"Great hotel!!"
United States
Deja
The price is NZ$241
includes taxes & fees
19 Dec - 20 Dec
voco Chicago Downtown - Riverwalk by IHG
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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Hotels in Oakland with a pool

Meeting facility
Sheraton Grand Chicago Riverwalk
Sheraton Grand Chicago Riverwalk
4.0 star property
  • Pool
8.4 out of 10, Very good, (1562)
The price is NZ$362
includes taxes & fees
15 Dec - 16 Dec
Sheraton Grand Chicago Riverwalk
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Top guest rated hotels in Oakland

Ballroom
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 star property
    9.0 out of 10, Wonderful, (3325)
    The price is NZ$173
    includes taxes & fees
    7 Dec - 8 Dec
    Hilton Chicago/Magnificent Mile Suites
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    Our guide on where to stay in Oakland

    Find the best Oakland areas for the activities you enjoy most.
    Downtown Chicago featuring a city

    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 - River North

    Magnificent Mile

    An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.

    The Loop - Downtown which includes a river or creek

    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.

    Chicago showing a city and modern architecture

    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 Whitehall Hotel, BW Premier Collection

    The Whitehall Hotel, BW Premier Collection

    10/10 Excellent
    "Clean room"
    Amber 3-night trip
    Posted 7 hours ago
    The Whitehall Hotel, BW Premier Collection

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    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.