Oakland Hotels, Chicago

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Check prices for these dates

Tonight
18 Feb - 19 Feb
Tomorrow
19 Feb - 20 Feb
This weekend
20 Feb - 22 Feb
Next weekend
27 Feb - 1 Mar

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Our top choices for Oakland hotels

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, (2,677 reviews)
"Clean room and the staff are great. "
United States
Doug
The price is NZ$138
includes taxes & fees
1 Mar - 2 Mar
Best Western Grant Park Hotel
Interior

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 7.9 km from Oakland
8.0 out of 10, Very good, (2,765 reviews)
"I enjoyed my stay"
United States
Emily
The price is NZ$134
includes taxes & fees
22 Feb - 23 Feb
Freehand 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, (9,908 reviews)
"Great location, beautiful historic hotel with clean, updated rooms. "
United States
Jennifer
The price is NZ$370
includes taxes & fees
13 Mar - 14 Mar
Congress Plaza Hotel
Property amenity

The Wade

The Wade
4.5 star property
Streeterville, 7.9 km from Oakland
8.4 out of 10, Very good, (1,682 reviews)
"Thoroughly enjoyed my stay at The Wade"
United States
Danielle
The price is NZ$173
includes taxes & fees
22 Feb - 23 Feb
The Wade
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, (1,862 reviews)
"Absolutely enjoyed my time here"
United States
Quayshaun
The price is NZ$165
includes taxes & fees
26 Feb - 27 Feb
Hilton Garden Inn Chicago Downtown South Loop
Bar (on property)

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 8.6 km from Oakland
8.4 out of 10, Very good, (3,963 reviews)
"Great location, the room was nice and the breakfast was good. Overall great value for this property"
United States
Jorge
The price is NZ$143
includes taxes & fees
22 Feb - 23 Feb
The Whitehall Hotel, BW Premier Collection
Shared kitchen

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, (461 reviews)
"Amazing staff and very clean, modern rooms!"
United States
genevieve
The price is NZ$119
includes taxes & fees
4 Mar - 5 Mar
FOUND Hotel Chicago River North
Lobby

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,085 reviews)
"Great location and friendly staff. "
United States
Pablo
The price is NZ$192
includes taxes & fees
22 Feb - 23 Feb
Aloft Chicago Mag Mile
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, (2,316 reviews)
"Great staff, room spotless, great price."
United States
Robert
The price is NZ$189
includes taxes & fees
26 Feb - 27 Feb
DoubleTree by Hilton Chicago - Magnificent 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, (2,378 reviews)
"Great stay"
United States
Blake
The price is NZ$313
includes taxes & fees
22 Feb - 23 Feb
Sable at Navy Pier Chicago, Curio Collection by Hilton
Lobby

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,012 reviews)
"Great stay, good location, accommodating staff."
United States
Ian
The price is NZ$180
includes taxes & fees
22 Feb - 23 Feb
River Hotel
Exterior

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 8.1 km from Oakland
8.6 out of 10, Excellent, (3,039 reviews)
"Great place"
United States
Omar
The price is NZ$209
includes taxes & fees
22 Feb - 23 Feb
Warwick Allerton - Chicago
Bar (on property)

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (1,125 reviews)
"I always stay here when in town. "
United States
Jeffrey
Ivy Boutique 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, (3,370 reviews)
"Amazing place, breakfast is great , location is great - honestly great hotel! "
United States
Brisa
The price is NZ$239
includes taxes & fees
4 Mar - 5 Mar
Hotel Riu Plaza Chicago
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, (2,516 reviews)
"Always a good stay"
Canada
Domenic
The price is NZ$147
includes taxes & fees
22 Feb - 23 Feb
Travelodge by Wyndham Downtown Chicago
Exterior

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Gold Coast, 9.3 km from Oakland
9.0 out of 10, Wonderful, (1,524 reviews)
"Great location, friendly staff and nice room"
United States
Srinivasa
The price is NZ$172
includes taxes & fees
22 Feb - 23 Feb
Claridge House Chicago, Tapestry Collection by Hilton
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, (1,282 reviews)
"Great hotel with great location. Would definitely stay here again. "
United States
Sheila
The price is NZ$205
includes taxes & fees
19 Feb - 20 Feb
The Chicago Hotel Collection Ambassador Gold Coast
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,202 reviews)
"Place is always top notch..stay here anytime we stay in Chicago."
United States
Jon
The price is NZ$294
includes taxes & fees
22 Feb - 23 Feb
Swissotel - Chicago
Exterior

Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile
2.5 star property
Streeterville, 8.1 km from Oakland
8.0 out of 10, Very good, (1,406 reviews)
"Great hotel,, like so much"
United States
Ilham
The price is NZ$173
includes taxes & fees
22 Feb - 23 Feb
Hampton Inn Chicago Downtown/Magnificent Mile
Cocktail bar

ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
River North, 7.9 km from Oakland
9.0 out of 10, Wonderful, (1,962 reviews)
"Very convenient place to stay friendly and helpful staff."
United States
Rick
The price is NZ$158
includes taxes & fees
25 Feb - 26 Feb
ACME Hotel Chicago, Outset Collection by Hilton
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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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.

Water Tower Place

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 showing railway items, street scenes and a city

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.

Underground passage in the Chicago O'Hare airport

O'Hare

Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago.

Top Oakland Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"The room and hotel is a bit run down as most places over a century old"
John Benjamin 2-night trip
Posted 17 hours 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 6 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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