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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, (2,413 reviews)
"Great spot and view, would stay again!"
United States
Kimberly
The price is ฿4,866
฿6,816 total
includes taxes & fees
31 Mar - 1 Apr
Sable at Navy Pier Chicago, Curio Collection by Hilton

The Wade

The Wade
4.5 star property
Streeterville, 7.9 km from Oakland
8.4 out of 10, Very good, (1,758 reviews)
"Loved this hotel, i will be back"
United States
Shari
The price is ฿5,000
฿5,869 total
includes taxes & fees
29 Mar - 30 Mar
The Wade

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,238 reviews)
"Excellent stay."
United States
Fenton
The price is ฿4,707
฿6,684 total
includes taxes & fees
29 Mar - 30 Mar
Swissotel - Chicago

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, (2,374 reviews)
"Loved this hotel!"
United States
Ellen
The price is ฿3,693
฿4,335 total
includes taxes & fees
31 Mar - 1 Apr
DoubleTree by Hilton Chicago - Magnificent Mile

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, (2,814 reviews)
"Great location,an organized "
United States
Karmella
The price is ฿3,921
฿5,568 total
includes taxes & fees
6 Apr - 7 Apr
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
7.1 km from Oakland
8.6 out of 10, Excellent, (1,879 reviews)
"Overall a great stay."
United States
Joshua
The price is ฿4,868
฿6,570 total
includes taxes & fees
29 Mar - 30 Mar
Radisson Blu Aqua Hotel Chicago

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 7.1 km from Oakland
8.6 out of 10, Excellent, (2,093 reviews)
"lovely hotel "
United States
alyvia
The price is ฿5,480
฿7,574 total
includes taxes & fees
30 Mar - 31 Mar
Fairmont Chicago at Millennium Park

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,156 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is ฿3,256
฿3,823 total
includes taxes & fees
5 Apr - 6 Apr
Aloft Chicago Mag Mile

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 7.9 km from Oakland
8.8 out of 10, Excellent, (1,187 reviews)
"Clean friendly staff love the decor "
United States
Kiasha
Ivy Boutique Hotel

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, (2,403 reviews)
"Staff very friendly and we had a great time."
United States
Juan
The price is ฿4,121
฿4,838 total
includes taxes & fees
30 Mar - 31 Mar
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

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, (1,004 reviews)
"Great stay "
United States
Jennifer
The price is ฿3,355
฿3,938 total
includes taxes & fees
5 Apr - 6 Apr
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

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, (3,975 reviews)
"Friendly staff, clean and nice rooms!"
United States
Michael
The price is ฿3,959
฿4,647 total
includes taxes & fees
31 Mar - 1 Apr
Hilton Chicago/Magnificent Mile Suites

Millennium Hotel Knickerbocker Chicago

Millennium Hotel Knickerbocker Chicago
4.0 star property
Streeterville, 8.6 km from Oakland
8.6 out of 10, Excellent, (1,978 reviews)
"The Knickerbocker is by fire one of our favorite places to stay. Perfect location to everything. They have the cutest martini bar in the lobby with great people that work there, and I always meet a fun new friend."
United States
Lisa
The price is ฿3,013
฿4,298 total
includes taxes & fees
5 Apr - 6 Apr
Millennium Hotel Knickerbocker Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,464 reviews)
"Great stay! Wonderful location!"
United States
Renae
The price is ฿5,590
฿7,704 total
includes taxes & fees
1 Apr - 2 Apr
Hyatt Regency Chicago

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Streeterville, 8 km from Oakland
9.0 out of 10, Wonderful, (1,087 reviews)
"Clean room, very new, excellent stay"
United States
Anthony
The price is ฿4,374
฿6,085 total
includes taxes & fees
1 Apr - 2 Apr
Hyatt Centric Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Streeterville, 7.9 km from Oakland
9.0 out of 10, Wonderful, (1,800 reviews)
"Great Hotel"
United States
Dwayne
The price is ฿3,849
฿4,518 total
includes taxes & fees
12 Apr - 13 Apr
Courtyard by Marriott Chicago Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 8.2 km from Oakland
7.6 out of 10, Good, (1,250 reviews)
"Amazing stay "
United States
Napoleon
The Chicago Hotel Collection - Magnificent Mile

Homewood Suites by Hilton Chicago Downtown/Magnificent Mile

Homewood Suites by Hilton Chicago Downtown/Magnificent Mile
3.0 star property
Streeterville, 8.1 km from Oakland
8.2 out of 10, Very good, (1,000 reviews)
"Perfect place to stay in Chicago!!"
United States
Ignacio
The price is ฿4,379
฿5,140 total
includes taxes & fees
31 Mar - 1 Apr
Homewood Suites by Hilton Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile
2.5 star property
Streeterville, 8.1 km from Oakland
8.2 out of 10, Very good, (1,391 reviews)
"Clean room great location "
United States
Karen
The price is ฿3,693
฿4,335 total
includes taxes & fees
26 Mar - 27 Mar
Hampton Inn Chicago Downtown/Magnificent Mile

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (3,619 reviews)
"Great location ans staff was amazing!!"
United States
Bianca
The price is ฿4,340
฿6,022 total
includes taxes & fees
6 Apr - 7 Apr
Hotel Riu Plaza 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.

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.

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.

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.

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 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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