Oakland Hotels, Chicago

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Tonight
12 Oct - 13 Oct
Tomorrow
13 Oct - 14 Oct
Next weekend
17 Oct - 19 Oct
In two weeks
24 Oct - 26 Oct

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4457 Cheap Hotels in Oakland - Specials, Reviews, & Last Minute Deals

Eurostars Magnificent Mile
Reception

Eurostars Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (3074)
"The hotel has a restaurant on the first floor with patio seating and great views."
The price is AU$196
includes taxes & fees
11 Nov - 12 Nov
Eurostars Magnificent Mile
River Hotel
Reception

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4739)
"Staff friendly and helpful..and accommodations just right..great location! "
The price is AU$199
includes taxes & fees
9 Nov - 10 Nov
River Hotel
Aloft Chicago Mag Mile
Cocktail bar

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2860)
"Had a great stay!"
The price is AU$250
includes taxes & fees
9 Nov - 10 Nov
Aloft Chicago Mag Mile
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, (2087)
"Great hotel"
The price is AU$289
includes taxes & fees
2 Nov - 3 Nov
DoubleTree by Hilton Chicago - Magnificent 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, (2182)
"Great hotel "
The price is AU$341
includes taxes & fees
9 Nov - 10 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3940)
"Great place to stay. "
The price is AU$253
includes taxes & fees
10 Nov - 11 Nov
citizenM Chicago Downtown
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (9387)
"Beautiful hotel!"
The price is AU$305
includes taxes & fees
26 Oct - 27 Oct
Congress Plaza Hotel
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2457)
"Great place"
The price is AU$149
includes taxes & fees
12 Nov - 13 Nov
Freehand Chicago
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, (4071)
"We definitely will stay there again place was very nice "
The price is AU$291
includes taxes & fees
2 Nov - 3 Nov
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (3083)
"Our stay was great"
The price is AU$260
includes taxes & fees
9 Nov - 10 Nov
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (2256)
"We loved this hotel it was beautiful and convenient . "
The price is AU$379
includes taxes & fees
23 Oct - 24 Oct
Hilton Chicago
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very good, (273)
"Perfect location! Tons of restaurants and shopping nearby! "
The price is AU$141
includes taxes & fees
10 Nov - 11 Nov
FOUND Hotel Chicago River North
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1023)
"Great stay"
The price is AU$183
includes taxes & fees
9 Nov - 10 Nov
Best Western River North Hotel
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2586)
"Great place to stay "
The price is AU$310
includes taxes & fees
9 Nov - 10 Nov
Hotel Riu Plaza Chicago
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, (1592)
"Great Hotel"
The price is AU$236
includes taxes & fees
9 Nov - 10 Nov
Crowne Plaza Chicago West Loop by IHG
voco Chicago Downtown - Riverwalk by IHG
Bar (on property)

voco Chicago Downtown - Riverwalk by IHG

3.5 star property
8.8 out of 10, Excellent, (3203)
"Great stay "
The price is AU$289
includes taxes & fees
9 Nov - 10 Nov
voco Chicago Downtown - Riverwalk by IHG
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, (2576)
"Good place to stay"
The price is AU$287
includes taxes & fees
9 Nov - 10 Nov
La Quinta Inn & Suites by Wyndham Chicago Downtown
Hyatt Centric The Loop Chicago
Rooftop terrace

Hyatt Centric The Loop Chicago

4.0 star property
9.0 out of 10, Wonderful, (2176)
"It was an amazing stay!"
The price is AU$330
includes taxes & fees
9 Nov - 10 Nov
Hyatt Centric The Loop Chicago
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.4 out of 10, Good, (2406)
"Comfortable bed, bright room, good shower, very accessible location."
The price is AU$174
includes taxes & fees
12 Nov - 13 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, (2016)
"Great place to stay "
The price is AU$278
includes taxes & fees
12 Nov - 13 Nov
Silversmith Hotel 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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Our guide on where to stay in Oakland

Find the best Oakland areas for the activities you enjoy most. Learn more about Oakland
Learn more about Oakland
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

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

The Loop - Downtown which includes a river or creek

The Loop

Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.

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

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

10/10 Excellent
"Great hotel - great location. It's a bummer that the view from the restaurant/bar isn't as cool as it used to be, because of the new buildings in front of it, but it's still pretty - and the drinks and food are very good. Room was very nice and clean. "
Sarah 2-night trip
Posted 2 days ago
Holiday Inn Chicago Dwtn - The Mart by IHG

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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