Hotels in Oakland, Chicago

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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, (2,406 reviews)
"Great spot and view, would stay again!"
United States
Kimberly
The price is RM586
RM822 total
includes taxes & fees
30 Mar - 31 Mar
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,704 reviews)
"Amazing place to stay!"
United States
Nia
The price is RM513
RM718 total
includes taxes & fees
1 Apr - 2 Apr
Hilton Chicago

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,032 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is RM388
RM456 total
includes taxes & fees
5 Apr - 6 Apr
River Hotel

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (9,997 reviews)
"Clean room, nice hotel, nice staff"
United States
Melanie
The price is RM457
RM537 total
includes taxes & fees
1 Apr - 2 Apr
Congress Plaza Hotel

The Wade

The Wade
4.5 star property
Streeterville, 7.9 km from Oakland
8.4 out of 10, Very good, (1,754 reviews)
"Loved this hotel, i will be back"
United States
Shari
The price is RM598
RM703 total
includes taxes & fees
29 Mar - 30 Mar
The Wade

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 RM666
RM920 total
includes taxes & fees
24 Mar - 25 Mar
Fairmont Chicago at Millennium Park

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 7.9 km from Oakland
8.0 out of 10, Very good, (2,814 reviews)
"Great location, clean and decent sized room, staff was helpful and amenities are very convenient!"
United States
MaryJane
The price is RM280
RM398 total
includes taxes & fees
25 Mar - 26 Mar
Freehand Chicago

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, (1,023 reviews)
"Lots of places to eat and shop nearby"
United States
Analicia
The price is RM528
RM735 total
includes taxes & fees
5 Apr - 6 Apr
Staypineapple, An Iconic Hotel, The Loop

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 6.6 km from Oakland
8.8 out of 10, Excellent, (3,409 reviews)
"Wonderful hotel, friendly and accommodating staff! "
United States
Chevon
The price is RM388
RM456 total
includes taxes & fees
5 Apr - 6 Apr
Club Quarters Hotel, Central Loop, Chicago

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,151 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is RM425
RM499 total
includes taxes & fees
29 Mar - 30 Mar
Aloft Chicago Mag Mile

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,233 reviews)
"Excellent stay."
United States
Fenton
The price is RM507
RM734 total
includes taxes & fees
29 Mar - 30 Mar
Swissotel - Chicago

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 6.7 km from Oakland
8.6 out of 10, Excellent, (2,334 reviews)
"We had a great stay and the staff are very friendly and accommodating. "
United States
Krista
The price is RM529
RM720 total
includes taxes & fees
5 Apr - 6 Apr
Palmer House a Hilton Hotel

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (2,128 reviews)
"Great stay!"
United States
Hannah
The price is RM388
RM456 total
includes taxes & fees
5 Apr - 6 Apr
Club Quarters Hotel Wacker at Michigan, Chicago

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, (1,925 reviews)
"Hotel was really nice"
United States
LaCarr
The price is RM449
RM527 total
includes taxes & fees
5 Apr - 6 Apr
Hilton Garden Inn Chicago Downtown South Loop

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 7.9 km from Oakland
8.8 out of 10, Excellent, (1,178 reviews)
"Clean friendly staff love the decor "
United States
Kiasha
Ivy Boutique Hotel

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, (2,687 reviews)
"Perfect location!!"
United States
Kelly
The price is RM443
RM520 total
includes taxes & fees
1 Apr - 2 Apr
Best Western Grant Park Hotel

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 7.2 km from Oakland
9.6 out of 10, Exceptional, (3,802 reviews)
"Will stay here again! "
United States
Bryn
The price is RM670
RM786 total
includes taxes & fees
31 Mar - 1 Apr
L7 Chicago by LOTTE

Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 5.6 km from Oakland
8.8 out of 10, Excellent, (1,002 reviews)
"Every aspect of our stay was wonderful!"
United States
Hillary
The price is RM408
RM548 total
includes taxes & fees
24 Mar - 25 Mar
Le Méridien Essex Chicago

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 6.6 km from Oakland
8.6 out of 10, Excellent, (2,037 reviews)
"Staff was friendly and location was central to walk to many of the big sights "
United States
Jensen
The price is RM398
RM468 total
includes taxes & fees
24 Mar - 25 Mar
Central Loop Hotel

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
River North, 8.1 km from Oakland
8.6 out of 10, Excellent, (509 reviews)
"Lots of stuff close by , cool vibe inside and very nice staff"
United States
Abel
The price is RM315
RM370 total
includes taxes & fees
24 Mar - 25 Mar
FOUND Hotel Chicago River North
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

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

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.

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

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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