Hotels in Oakland, Chicago

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28 Nov - 29 Nov
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29 Nov - 30 Nov
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28 Nov - 30 Nov
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5 Dec - 7 Dec

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Top 10 Hotels in Oakland, Chicago

Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
River North, 8.1 km from Oakland
8.8 out of 10, Excellent, (3135)
"Location was great "
United States
Hamik
The price is RM422
RM496 total
includes taxes & fees
29 Dec - 30 Dec
Eurostars Magnificent Mile
Terrace/patio
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
Streeterville, 7.8 km from Oakland
8.8 out of 10, Excellent, (2165)
"Great stay "
United States
Melinda
The price is RM403
RM473 total
includes taxes & fees
7 Dec - 8 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
Reception
River Hotel

River Hotel

4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (4850)
"Front desk is amazing, rooms are clean and great location"
United States
Glen
The price is RM378
RM444 total
includes taxes & fees
7 Dec - 8 Dec
River Hotel
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (2943)
"Great location!!"
United States
sarah e
The price is RM372
RM436 total
includes taxes & fees
7 Dec - 8 Dec
Aloft Chicago Mag Mile
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
Streeterville, 7.5 km from Oakland
9.4 out of 10, Exceptional, (2250)
"Room was spotless…staff was great!"
United States
Tamika
The price is RM360
RM563 total
includes taxes & fees
23 Dec - 24 Dec
Sable at Navy Pier Chicago, Curio Collection by Hilton
Exterior
Hilton Chicago

Hilton Chicago

4.0 star property
The Loop, 5.7 km from Oakland
8.4 out of 10, Very good, (2323)
"Clean Rooms & very nice staff"
United States
Teresa
The price is RM437
RM634 total
includes taxes & fees
20 Dec - 21 Dec
Hilton Chicago
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Streeterville, 8.6 km from Oakland
9.0 out of 10, Wonderful, (3399)
"Great stay!"
United States
Rose
The price is RM344
RM404 total
includes taxes & fees
7 Dec - 8 Dec
Hilton Chicago/Magnificent Mile Suites
Bar (on property)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
River North, 7.8 km from Oakland
8.4 out of 10, Very good, (4207)
"Great location. "
United States
Rodger
The price is RM324
RM380 total
includes taxes & fees
9 Dec - 10 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Lobby
citizenM Chicago Downtown

citizenM Chicago Downtown

4.0 star property
Theatre District, 7.3 km from Oakland
9.4 out of 10, Exceptional, (4091)
"Clean rooms, friendly staff, great breakfast, amazing location. "
Canada
Gokce
The price is RM442
RM519 total
includes taxes & fees
24 Dec - 25 Dec
citizenM Chicago Downtown
American cuisine
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 star property
7.3 km from Oakland
9.0 out of 10, Wonderful, (1717)
"The location was great!!"
United States
Yvette
The price is RM525
RM616 total
includes taxes & fees
30 Nov - 1 Dec
Crowne Plaza Chicago West Loop by IHG
Exterior
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, (343)
"love this place definitely coming back !"
United States
Dayanara
The price is RM290
RM341 total
includes taxes & fees
7 Dec - 8 Dec
FOUND Hotel Chicago River North
Cocktail bar
Freehand Chicago

Freehand Chicago

4.0 star property
River North, 7.9 km from Oakland
8.0 out of 10, Very good, (2611)
"Rooms are clean, staff are nice and friendly "
United States
Karen
The price is RM331
RM461 total
includes taxes & fees
7 Dec - 8 Dec
Freehand Chicago
Banquet hall
Congress Plaza Hotel

Congress Plaza Hotel

3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (9665)
"Great stay comfortable bed and great location!"
United States
Kimberly Noel
Congress Plaza Hotel
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (2881)
"Great service, great breakfast and a nice room "
United States
DeAnna
The price is RM375
RM556 total
includes taxes & fees
8 Dec - 9 Dec
Hotel Riu Plaza Chicago
Rooftop terrace
Best Western River North Hotel

Best Western River North Hotel

2.5 star property
River North, 8 km from Oakland
7.8 out of 10, Good, (1020)
"Staff was very friendly "
United States
david
The price is RM360
RM423 total
includes taxes & fees
7 Dec - 8 Dec
Best Western River North Hotel
Lobby
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, (2093)
"Lovely hotel in a great spot!"
United States
Natasha
Silversmith Hotel Chicago Downtown
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
West Loop, 6.4 km from Oakland
8.4 out of 10, Very good, (1013)
"Really great location and warm and friendly staff"
United Kingdom
David
The price is RM377
RM492 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn & Suites Chicago - Downtown by IHG
Exterior
La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
The Loop, 7 km from Oakland
8.6 out of 10, Excellent, (2638)
"Enjoyed my stay here. "
United States
Vai
The price is RM424
RM570 total
includes taxes & fees
22 Dec - 23 Dec
La Quinta Inn & Suites by Wyndham Chicago Downtown
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Theatre District, 6.7 km from Oakland
8.4 out of 10, Very good, (2104)
"Great place to stay."
United States
Aaron
The price is RM451
RM632 total
includes taxes & fees
28 Dec - 29 Dec
Palmer House a Hilton Hotel
Pool
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3.0 star property
The Loop, 5.4 km from Oakland
8.8 out of 10, Excellent, (1733)
"Clean room, great hot tub."
United States
SHARON
The price is RM327
RM384 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Chicago Downtown South Loop
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 for the activities you enjoy most.
Downtown Chicago which includes 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 featuring 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.

Lincoln Park showing modern architecture and a 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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Nice rooms, great price"
Jeremy 5-night trip
Posted 1 day ago
Congress Plaza Hotel

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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.