Find hotels in Oakland, Chicago from ₩172,271

Most hotels are fully refundable. Because flexibility matters.

Save an average of 15% on thousands of hotels with Expedia Rewards.

Search over 2.9 million properties and 550 airlines worldwide

Filter by

Popular filters
Popular filters
Price per night
Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveler experience
Traveler experience

Discover 4,102 Oakland hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Terrace/patio
citizenM Chicago Downtown
4.0 star property
9.2 out of 10, Wonderful, (1339)
"Nice and clean place, location is centre of the city. Only downfall is the rooms are extremely small. Two guests maximum per room, the bed is against three walls at one end of the room. The provided fridge fits about 6 cans in it and that’s it. The only sink provided is very small. Shower is a good size though. The gym facility while not amazing, is the best I’ve stayed in for a boutique hotel setting. Has enough to get you by for your stay. There’s a smith machine, cable system , benches and...
The price is ₩172,369
per night
May 27 - May 28
citizenM Chicago Downtown
Lobby
LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
9.2 out of 10, Wonderful, (3517)
"Excellent quality. Comfortable bed, nice view from 12th floor over river. Friendly staff. "
The price is ₩277,911
per night
May 27 - May 28
LondonHouse Chicago, Curio Collection by Hilton
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.2 out of 10, Wonderful, (1899)
"Nice hotel close to shopping and restaurants. Hotel restaurant breakfast buffet food was cold. Valet parking too expensive. Staff was nice and accommodating. Our floor was noisy with people partying on Friday night."
The price is ₩289,539
per night
May 27 - May 28
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Rooftop terrace
Virgin Hotels Chicago
4.5 star property
9.2 out of 10, Wonderful, (1015)
"Just disappointed the rooftop was packed and had so many people on the elevator….would have liked to enjoy the rooftop just hotel guests.."
The price is ₩326,954
per night
May 27 - May 28
Virgin Hotels Chicago
Terrace/patio
Trump International Hotel & Tower Chicago
5.0 star property
9.2 out of 10, Wonderful, (1190)
"Beautiful experience Top shelf everything This was my 4th stay here while visiting Chicago "
The price is ₩507,874
per night
May 26 - May 27
Trump International Hotel & Tower Chicago
Exterior
Hyatt Regency Chicago
4.0 star property
9.0 out of 10, Wonderful, (3496)
"Its a great location to either walk or catch a ride to your favorite activities. I have stayed there many times for that reason. I am usually traveling with a group of 4 so i wish tne rooms were bigger with sofa-bed option. But convenience usually wins out when i decide which hotel to pick in downtown Chicago."
The price is ₩297,706
per night
May 27 - May 28
Hyatt Regency Chicago
Exterior
The Royal Sonesta Chicago Downtown
4.0 star property
9.0 out of 10, Wonderful, (1933)
"Everything was in walking distance "
The price is ₩284,614
per night
May 28 - May 29
The Royal Sonesta Chicago Downtown
Cocktail bar
ACME Hotel Company
3.5 star property
9.0 out of 10, Wonderful, (1397)
"LOCATION!! Best location in the city, near everything and felt safe also. Everyone very friendly and helpful. Rooms pretty comfortable, clean and chic. "
The price is ₩172,271
per night
May 27 - May 28
ACME Hotel Company
View from property
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2875)
"Good service "
The price is ₩258,622
per night
May 29 - May 30
River Hotel
Exterior
InterContinental Chicago Magnificent Mile, an IHG Hotel
4.5 star property
8.8 out of 10, Excellent, (1584)
"Good for a family trip in Chicago"
The price is ₩265,394
per night
May 27 - May 28
InterContinental Chicago Magnificent Mile, an IHG Hotel
City view from property
voco Chicago Downtown, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (1189)
"Front desk service was very accommodating and sweet, the service there was exceptional. The rooms were clean and the staff were all great. Definitely will stay here again in the future! "
The price is ₩246,228
per night
May 27 - May 28
voco Chicago Downtown, an IHG Hotel
Daily cooked-to-order breakfast for a fee
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2206)
"The sheet covering the window is kind of dirty. It would also be better if there were actual blinds covering the windows so I can let sunlight in without exposing the entire window. It would also be helpful to have an airport shuttle to ORD and MDW."
The price is ₩258,554
per night
May 27 - May 28
Aloft Chicago Mag Mile
Lake
DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
8.6 out of 10, Excellent, (2200)
"Good service and cleaning , the hotel is close to all principal areas of the city. "
The price is ₩212,315
per night
May 27 - May 28
DoubleTree by Hilton Chicago - Magnificent Mile
Exterior
Club Quarters Hotel, Central Loop, Chicago
4.0 star property
8.6 out of 10, Excellent, (3058)
"Love this property and location! "
The price is ₩196,306
per night
May 27 - May 28
Club Quarters Hotel, Central Loop, Chicago
Front of property - evening/night
Fairmont Chicago at Millennium Park
4.5 star property
8.6 out of 10, Excellent, (1486)
"Requested a fridge and microwave, as they do not come in each room. Wasn't there when we checked in, but came shortly and worked well. Nice hotel, but no pool and they only offer parking as a valet service for $80+ per day. Ended up parking at Aon Center for $17/day, which was VERY close. "
The price is ₩272,234
per night
May 27 - May 28
Fairmont Chicago at Millennium Park
Front of property - evening/night
Swissotel - Chicago
4.5 star property
8.6 out of 10, Excellent, (1982)
"Likes: Soaring cityscape, river and big lake views; food/service quality; staff experience and longevity (jumping jobs a rarity); 43rd floor fitness facility. Dislike: 0"
The price is ₩284,888
per night
May 23 - May 24
Swissotel - Chicago
Terrace/patio
Home2 Suites by Hilton Chicago River North
3.0 star property
8.4 out of 10, Very Good, (1488)
"Nice location, nice staff."
The price is ₩219,771
per night
May 27 - May 28
Home2 Suites by Hilton Chicago River North
Balcony
Eurostars Magnificent Mile
4.0 star property
8.4 out of 10, Very Good, (1927)
"Second time staying here, and just as great as the first. Definitely a spot to return to! "
The price is ₩246,242
per night
May 27 - May 28
Eurostars Magnificent Mile
Exterior
21c Museum Hotel Chicago
4.0 star property
8.4 out of 10, Very Good, (1838)
"Good"
The price is ₩219,771
per night
May 27 - May 28
21c Museum Hotel Chicago
Presidential Room, 2 Bedrooms, Non Smoking | Hypo-allergenic bedding, in-room safe, desk, iron/ironing board
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
8.2 out of 10, Very Good, (2438)
"This is a good midrange hotel in a great location. There were a few items in the bathroom in disrepair (broken corner of mirror and rust in bathtub) but overall fine. "
The price is ₩245,011
per night
May 28 - May 29
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Don't see what you're looking for?
See all available properties in Oakland
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.

Other neighborhoods around Oakland

Hotels in top Chicago neighborhoods Learn more about Oakland
Downtown Chicago showing a city

Downtown Chicago

4 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Oakland hotels information

Number of reviews
39,013
Accommodation
4,102 hotels
Lowest Price
₩172,271
Highest Price
₩507,874

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.

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 great outdoors at Lake Michigan, Lakefront Trail, 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.

Recent reviews of Oakland hotels

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

5/5 Excellent
"Great experience!!! "
A verified traveler stayed at Hilton Garden Inn Chicago Downtown/Magnificent Mile
Posted 2 hours ago
Hilton Garden Inn Chicago Downtown/Magnificent Mile