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25 Sep - 26 Sep
Tomorrow
26 Sep - 27 Sep
This weekend
26 Sep - 28 Sep
Next weekend
3 Oct - 5 Oct

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Discover 4,469 Oakland hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

LondonHouse Chicago, Curio Collection by Hilton
Lobby

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property
9.4 out of 10, Exceptional, (3324)
"Loved this hotel- best location and very nice staff. "
The price is SAR 877
SAR 1,029 total
includes taxes & fees
19 Oct - 20 Oct
LondonHouse Chicago, Curio Collection by Hilton
Silversmith Hotel Chicago Downtown
Lobby

Silversmith Hotel Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (1989)
"Excellent hotel, staff, location. "
Silversmith Hotel Chicago Downtown
Thompson Chicago, by Hyatt
Restaurant

Thompson Chicago, by Hyatt

4.5 star property
9.2 out of 10, Wonderful, (1245)
"Expensive, but comfortable and in a great location "
The price is SAR 758
SAR 1,000 total
includes taxes & fees
26 Oct - 27 Oct
Thompson Chicago, by Hyatt
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Exterior

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

4.0 star property
9.6 out of 10, Exceptional, (1035)
"Great stay"
The price is SAR 821
SAR 964 total
includes taxes & fees
5 Oct - 6 Oct
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2479)
"Nice hotel with amazing breakfasts and location."
The price is SAR 709
SAR 937 total
includes taxes & fees
1 Oct - 2 Oct
Hotel Riu Plaza Chicago
Staypineapple, An Iconic Hotel, The Loop
Interior detail

Staypineapple, An Iconic Hotel, The Loop

4.0 star property
9.4 out of 10, Exceptional, (1015)
"Great hotel!!"
The price is SAR 746
SAR 986 total
includes taxes & fees
28 Sep - 29 Sep
Staypineapple, An Iconic Hotel, The Loop
The Royal Sonesta Chicago River North
Terrace/patio

The Royal Sonesta Chicago River North

4.5 star property
9.2 out of 10, Wonderful, (2152)
"Great location and great staff."
The price is SAR 807
SAR 1,067 total
includes taxes & fees
2 Oct - 3 Oct
The Royal Sonesta Chicago River North
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (3864)
"Great stay"
The price is SAR 682
SAR 801 total
includes taxes & fees
28 Sep - 29 Sep
citizenM Chicago Downtown
Claridge House
Cocktail bar

Claridge House

4.0 star property
9.0 out of 10, Wonderful, (1384)
"We had a great stay"
The price is SAR 1,313
SAR 1,652 total
includes taxes & fees
27 Sep - 28 Sep
Claridge House
Kimpton Gray Hotel by IHG
Dinner served, Argentinean cuisine

Kimpton Gray Hotel by IHG

4.5 star property
9.2 out of 10, Wonderful, (1012)
"Amazing stay"
The price is SAR 934
SAR 1,206 total
includes taxes & fees
3 Oct - 4 Oct
Kimpton Gray Hotel by IHG
L7 Chicago by LOTTE
Exterior

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (3000)
"Love this hotel!"
The price is SAR 1,087
SAR 1,276 total
includes taxes & fees
28 Sep - 29 Sep
L7 Chicago by LOTTE
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2163)
"I enjoyed my stay cant wait to go back. "
The price is SAR 777
SAR 1,021 total
includes taxes & fees
2 Oct - 3 Oct
Sable at Navy Pier Chicago, Curio Collection by Hilton
Pendry Chicago
View from property

Pendry Chicago

4.5 star property
9.4 out of 10, Exceptional, (1091)
"Nice rooms and excellent service!"
The price is SAR 1,031
SAR 1,365 total
includes taxes & fees
23 Oct - 24 Oct
Pendry Chicago
Sofitel Chicago Magnificent Mile
Exterior

Sofitel Chicago Magnificent Mile

4.5 star property
9.4 out of 10, Exceptional, (2144)
"Nice Stay."
The price is SAR 1,009
SAR 1,295 total
includes taxes & fees
1 Oct - 2 Oct
Sofitel Chicago Magnificent Mile
Virgin Hotels Chicago
Rooftop terrace

Virgin Hotels Chicago

4.5 star property
9.2 out of 10, Wonderful, (1375)
"Staff was overly friendly and the location was great!"
The price is SAR 908
SAR 1,194 total
includes taxes & fees
2 Oct - 3 Oct
Virgin Hotels Chicago
Ivy Boutique Hotel
Front of property

Ivy Boutique Hotel

4.5 star property
8.8 out of 10, Excellent, (1016)
"I had a wonderful stay I will definitely be back again."
The price is SAR 698
SAR 820 total
includes taxes & fees
2 Oct - 3 Oct
Ivy Boutique Hotel
Omni Chicago Hotel
Breakfast and dinner served

Omni Chicago Hotel

4.5 star property
9.2 out of 10, Wonderful, (1577)
"Great stay!"
The price is SAR 1,043
SAR 1,334 total
includes taxes & fees
2 Oct - 3 Oct
Omni Chicago Hotel
Swissotel - Chicago
Exterior

Swissotel - Chicago

4.5 star property
9.0 out of 10, Wonderful, (2805)
"The hotel was in a great location. "
The price is SAR 757
SAR 999 total
includes taxes & fees
13 Oct - 14 Oct
Swissotel - Chicago
Loews Chicago Hotel
Exterior

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1560)
"Great location, clean rooms , friendly staff amazing modern design , great to stay with family."
The price is SAR 994
SAR 1,286 total
includes taxes & fees
26 Oct - 27 Oct
Loews Chicago Hotel
The Royal Sonesta Chicago Downtown
Exterior

The Royal Sonesta Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (2965)
"Wonderful property with wonderful staff will definitely stay here again. "
The price is SAR 826
SAR 1,089 total
includes taxes & fees
2 Oct - 3 Oct
The Royal Sonesta 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.
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Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most.
Downtown Chicago showing a city

Downtown Chicago

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Magnificent Mile - River North

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

The Loop - Downtown which includes a river or creek

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

River North showing railway items, street scenes and a city

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

Chicago which includes modern architecture and a city

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Top Oakland Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Kory at the reception was very friendly and helpful! Thank you "
Daiane 4-night trip
Posted 3 hours ago
The Chicago Hotel Collection - Magnificent Mile

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What's it like in Oakland?

Oakland is a neighborhood that travelers 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 neighborhood.

How many hotels are there in the Oakland area?

When you want to find places to stay in Chicago, start by booking one of Expedia's 6 hotels and other accommodations in Oakland.

If I need to cancel my hotel reservation in Oakland, will I receive a refund?

Yes, most hotel bookings are fully refundable if you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you have a non-refundable reservation, you might still have the option to cancel and receive a refund within a 24-hour period of booking. Plug in your dates, click on "Search", then filter by "fully refundable" to review the best deals in Oakland.

Where can I learn more about changing or cancelling my trip to Oakland?

To find more details about picking new dates or cancelling your trip to Oakland, go to https://www.expedia.com/service/.

What can I see and do in this Chicago neighborhood?

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 neighborhood. 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.