Oakland Hotels, Chicago

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4 Oct - 5 Oct
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5 Oct - 6 Oct
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10 Oct - 12 Oct
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4472 Cheap Hotels in Oakland - Specials, Reviews, & Last Minute Deals

Eurostars Magnificent Mile
Reception

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3057)
"Perfect location, walkable to many restaurants and shops"
The price is NZ$221
includes taxes & fees
3 Nov - 4 Nov
Eurostars Magnificent Mile
River Hotel
Reception

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4707)
"Staff friendly and helpful..and accommodations just right..great location! "
The price is NZ$320
includes taxes & fees
5 Oct - 6 Oct
River Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2076)
"Great hotel"
The price is NZ$321
includes taxes & fees
2 Nov - 3 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Aloft Chicago Mag Mile
Cocktail bar

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2844)
"Had a great stay!"
The price is NZ$290
includes taxes & fees
2 Nov - 3 Nov
Aloft Chicago Mag Mile
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, (2166)
"Great hotel "
The price is NZ$435
includes taxes & fees
2 Nov - 3 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very good, (4023)
"We definitely will stay there again place was very nice "
The price is NZ$361
includes taxes & fees
19 Oct - 20 Oct
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2410)
"Great walkable location to all the sights! "
The price is NZ$253
includes taxes & fees
27 Oct - 28 Oct
Freehand Chicago
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (9286)
"Beautiful hotel!"
Congress Plaza Hotel
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3900)
"Great place to stay. "
The price is NZ$349
includes taxes & fees
4 Nov - 5 Nov
citizenM Chicago Downtown
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (3015)
"Enjoyed our stay"
The price is NZ$291
includes taxes & fees
3 Nov - 4 Nov
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (2239)
"Very nice hotel "
The price is NZ$421
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1017)
"Great stay"
The price is NZ$255
includes taxes & fees
2 Nov - 3 Nov
Best Western River North Hotel
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.0 out of 10, Very good, (263)
"Loved this place if you want something affordable and nice! "
The price is NZ$196
includes taxes & fees
4 Nov - 5 Nov
FOUND Hotel Chicago River North
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2531)
"Location is great and the breakfast buffet is amazing"
The price is NZ$371
includes taxes & fees
3 Nov - 4 Nov
Hotel Riu Plaza Chicago
La Quinta Inn & Suites by Wyndham Chicago Downtown
Exterior

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
8.6 out of 10, Excellent, (2562)
"Good place to stay"
The price is NZ$350
includes taxes & fees
2 Nov - 3 Nov
La Quinta Inn & Suites by Wyndham Chicago Downtown
Crowne Plaza Chicago West Loop by IHG
American cuisine

Crowne Plaza Chicago West Loop by IHG

3.5 star property
9.0 out of 10, Wonderful, (1571)
"Hotel was very comfortable and I felt very safe during my entire stay. "
The price is NZ$304
includes taxes & fees
2 Nov - 3 Nov
Crowne Plaza Chicago West Loop by IHG
Hyatt Centric The Loop Chicago
Rooftop terrace

Hyatt Centric The Loop Chicago

4.0 star property
9.0 out of 10, Wonderful, (2158)
"The hotel was quiet and clean and restaurant was right next door in addition to inside the hotel"
The price is NZ$450
includes taxes & fees
23 Oct - 24 Oct
Hyatt Centric The Loop Chicago
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2381)
"Comfortable bed, bright room, good shower, very accessible location."
The price is NZ$228
includes taxes & fees
4 Nov - 5 Nov
Travelodge by Wyndham Downtown Chicago
Silversmith Hotel Chicago Downtown
Lobby

Silversmith Hotel Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (1995)
"Excellent hotel, staff, location. "
Silversmith Hotel Chicago Downtown
Palmer House a Hilton Hotel
Ballroom

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very good, (1996)
"Great property with great staff and amenities. "
The price is NZ$397
includes taxes & fees
30 Oct - 31 Oct
Palmer House a Hilton Hotel
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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Our guide on where to stay in Oakland

Find the best Oakland areas for the activities you enjoy most.
Downtown Chicago featuring a city

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 - River North

Magnificent Mile

An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.

The Loop - Downtown which includes a river or creek

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.

Chicago showing a city and modern architecture

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

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"Very comfortable stay, excellent location. "
Andrea 3-night trip
Posted 1 day ago
Hilton Garden Inn Chicago Downtown/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 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.