Oakland Hotels, Chicago

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
22 May - 24 May
Next weekend
29 May - 31 May

Filter by

Guest rating
Guest rating
Star rating

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, (2,505 reviews)
"I loved it here and will definitely stay again."
United States
Gina
The price is NZ$475
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio 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, (1,485 reviews)
"A nice stay and lovely location. "
United States
Robin
The price is NZ$313
includes taxes & fees
2 June - 3 June
The Chicago Hotel Collection Ambassador Gold Coast
Restaurant

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
8.6 km from Oakland
9.4 out of 10, Exceptional, (2,474 reviews)
"Great location and super nice hotel"
United States
Karolina
The price is NZ$415
includes taxes & fees
26 May - 27 May
Sofitel Chicago Magnificent Mile
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, (2,004 reviews)
"Great location and clean room"
United States
Hyacinthe
The price is NZ$312
includes taxes & fees
27 May - 28 May
Hilton Garden Inn Chicago Downtown South Loop
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, (2,786 reviews)
"Very clean room, nice breakfast and really nice hotel restaurant"
United States
Hugo
The price is NZ$311
includes taxes & fees
25 May - 26 May
La Quinta Inn & Suites by Wyndham Chicago Downtown
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, (4,211 reviews)
"Great location & breakfast was amazing."
United States
sierra
The price is NZ$372
includes taxes & fees
27 May - 28 May
Hotel Riu Plaza Chicago
Lobby

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, (1,002 reviews)
"All around great stay. "
United States
Nicholas
The price is NZ$261
includes taxes & fees
25 May - 26 May
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
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, (1,241 reviews)
"Really nice stay. "
United States
Rachael Lindsay
The price is NZ$322
includes taxes & fees
25 May - 26 May
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,336 reviews)
"Wonderful location right on the river. Fitness area wonderful, staff helpful. Would stay again!"
United States
Saleem
The price is NZ$399
includes taxes & fees
25 May - 26 May
Swissotel - 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, (2,246 reviews)
"Close to many attractions and shopping and nice unique hotel"
United States
Brittany
The price is NZ$293
includes taxes & fees
25 May - 26 May
Silversmith Hotel Chicago Downtown
Lobby

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Streeterville, 8.6 km from Oakland
8.6 out of 10, Excellent, (2,457 reviews)
"Perfect location, very comfortable rooms, friendly staff."
United States
Annabelle
The price is NZ$309
includes taxes & fees
25 May - 26 May
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Outdoor pool, pool cabanas (surcharge), pool umbrellas

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, (2,480 reviews)
"This is a beautiful hotel and the location was perfect."
United States
Felisha
The price is NZ$344
includes taxes & fees
25 May - 26 May
DoubleTree by Hilton Chicago - Magnificent Mile
Exterior

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,808 reviews)
"Great staff and location. "
United States
Robert
The price is NZ$452
includes taxes & fees
25 May - 26 May
Hilton Chicago
2 bars/lounges

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 7.4 km from Oakland
8.6 out of 10, Excellent, (1,626 reviews)
"It was very clean, beautiful place"
United States
Grisel
The price is NZ$544
includes taxes & fees
25 May - 26 May
Sheraton Grand Chicago Riverwalk
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, (1,069 reviews)
"Clean rooms, comfy bed."
United States
Brenda
The price is NZ$337
includes taxes & fees
25 May - 26 May
Staypineapple, An Iconic Hotel, The Loop
Exterior

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 7.6 km from Oakland
8.2 out of 10, Very good, (2,845 reviews)
"Best hotel breakfast around...for free! Excellent buffet, and cook to order omelets are restaurant quality"
United States
Michael
The price is NZ$378
includes taxes & fees
27 May - 28 May
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Suite, 1 Bedroom, Corner | Private kitchen

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, (2,337 reviews)
"great place to stay and good location"
United States
Wayne Aubrey
The price is NZ$369
includes taxes & fees
27 May - 28 May
Homewood Suites by Hilton Chicago Downtown South Loop
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,130 reviews)
"Nice clean hotel downtown."
United States
Richard
The price is NZ$270
includes taxes & fees
25 May - 26 May
Congress Plaza Hotel
Lobby

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,239 reviews)
"Nice place to stay"
United States
Jimmie
The price is NZ$303
includes taxes & fees
26 May - 27 May
Aloft by Marriott Chicago Mag Mile
Exterior

Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop
3.0 star property
The Loop, 7.1 km from Oakland
8.8 out of 10, Excellent, (1,306 reviews)
"Excellent clean room & very nice staff"
United States
Anthony
The price is NZ$362
includes taxes & fees
25 May - 26 May
Hyatt Place Chicago/Downtown - The Loop
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.
View all properties

Our guide on 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

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

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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"I do a lot of traveling was very impressed by the staff money well spend"
James 2-night trip
Posted less than an hour ago
Hotel Riu Plaza Chicago

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.

Explore a world of travel with Expedia