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Hotels in Oakland

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Our top choices for Oakland hotels

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, (2,499 reviews)
"Beautiful place to stay."
United States
Charles Otto
The price is S$383
includes taxes & fees
2 Jul - 3 Jul
Palmer House a Hilton Hotel

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,443 reviews)
"Staff was great."
United States
Marianne
The price is S$418
includes taxes & fees
1 Jul - 2 Jul
Hyatt Regency Chicago

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, (1,650 reviews)
"Very good location, breakfast is fantastic, dinner and bar are great."
United States
Zhiwen
The price is S$177
includes taxes & fees
1 Jul - 2 Jul
The Chicago Hotel Collection Ambassador Gold Coast

The Blackstone, Autograph Collection

The Blackstone, Autograph Collection
4.0 star property
The Loop, 5.8 km from Oakland
9.0 out of 10, Wonderful, (1,001 reviews)
"Great location, clean hotel, and very accommodating staff."
United States
Neydee
The price is S$337
includes taxes & fees
30 Jun - 1 Jul
The Blackstone, Autograph Collection

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,268 reviews)
"Excellent place to stay, as we found it central & walkable to most parks & attractions. The place was spotless & the staff were fantastic."
Canada
Jody
The price is S$251
includes taxes & fees
6 Jul - 7 Jul
River Hotel

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 7.9 km from Oakland
7.8 out of 10, Good, (3,131 reviews)
"It was good place to stay for the Go Fest Event"
United States
Ken
The price is S$237
includes taxes & fees
30 Jun - 1 Jul
Freehand Chicago

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 7.1 km from Oakland
9.4 out of 10, Exceptional, (2,135 reviews)
"Excellent hotel! Will definitely stay again."
United States
Justin
The price is S$303
includes taxes & fees
1 Jul - 2 Jul
Arlo 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, (1,117 reviews)
"Good location, friendly staff"
United Kingdom
Philip
The price is S$283
includes taxes & fees
6 Jul - 7 Jul
Staypineapple, An Iconic Hotel, The Loop

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,139 reviews)
"Great stay!"
United States
Daniel
The price is S$210
includes taxes & fees
30 Jun - 1 Jul
Congress Plaza Hotel

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, (2,265 reviews)
"Wonderful stay"
United States
Taylor
The price is S$228
includes taxes & fees
5 Jul - 6 Jul
Silversmith Hotel Chicago Downtown

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel
4.5 star property
Theatre District, 7.2 km from Oakland
9.0 out of 10, Wonderful, (1,017 reviews)
"Great hotel to stay."
United States
Josias
The price is S$343
includes taxes & fees
6 Jul - 7 Jul
theWit Chicago, a Hilton Hotel

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,423 reviews)
"Nice Hotel, rooms are clean , the best for us was the location, i would recommend"
United States
Sergio
The price is S$304
includes taxes & fees
5 Jul - 6 Jul
Swissotel - Chicago

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 8.1 km from Oakland
9.0 out of 10, Wonderful, (3,681 reviews)
"Had an amazing stay here!"
United States
Audrey
The price is S$246
includes taxes & fees
2 Jul - 3 Jul
Eurostars Magnificent Mile

Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown
4.0 star property
River North, 7.9 km from Oakland
8.8 out of 10, Excellent, (1,568 reviews)
"Great stay"
United States
Matt
The price is S$245
includes taxes & fees
2 Jul - 3 Jul
Hotel 55 Chicago Downtown

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
River North, 8.3 km from Oakland
8.8 out of 10, Excellent, (2,286 reviews)
"Would definitely stay there again"
United States
Benjy
The price is S$240
includes taxes & fees
6 Jul - 7 Jul
The Godfrey Hotel Chicago

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Streeterville, 8.1 km from Oakland
9.2 out of 10, Wonderful, (1,828 reviews)
"All around great property and a wonderful location"
United States
Bruce
The price is S$278
includes taxes & fees
5 Jul - 6 Jul
Omni Chicago Hotel

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, (650 reviews)
"Excellent stay in good location"
United States
Nicholas
The price is S$204
includes taxes & fees
29 Jun - 30 Jun
FOUND Hotel Chicago River North

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 7.4 km from Oakland
8.6 out of 10, Excellent, (1,689 reviews)
"Location was great"
United States
Pamela
The price is S$383
includes taxes & fees
5 Jul - 6 Jul
Sheraton Grand Chicago Riverwalk

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 6.6 km from Oakland
8.6 out of 10, Excellent, (2,193 reviews)
"Great hotel with awesome location"
United States
Daniel
The price is S$203
includes taxes & fees
1 Jul - 2 Jul
Central Loop Hotel

Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
River North, 8 km from Oakland
9.4 out of 10, Exceptional, (1,001 reviews)
"Great place!"
United States
Kelly
The price is S$222
includes taxes & fees
1 Jul - 2 Jul
Moxy Chicago Downtown
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 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.

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