Chicago Hotel Guide. Hotels in Oakland, Chicago, United States of America

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Our top choices for Oakland hotels

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 7.9 km from Oakland
8.0 out of 10, Very good, (2,872 reviews)
"Great location, clean and decent sized room, staff was helpful and amenities are very convenient!"
United States
MaryJane
The price is €94
includes taxes & fees
28 Apr - 29 Apr
Freehand Chicago

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,092 reviews)
"Great location and nice hotel! "
United States
James
The price is €118
includes taxes & fees
28 Apr - 29 Apr
River Hotel

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 9.4 km from Oakland
8.2 out of 10, Very good, (1,366 reviews)
"The staff is so amazing, and accommodating, Cristin and David are amazing when helping! The area is so fun and so close to so many shopping centers and great places to eat. In a very convenient spot for traveling in !! "
United States
Sonovia
The price is €113
includes taxes & fees
28 Apr - 29 Apr
The Chicago Hotel Collection Ambassador Gold Coast

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,182 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is €128
includes taxes & fees
19 Apr - 20 Apr
Aloft Chicago Mag Mile

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
River North, 8.1 km from Oakland
8.6 out of 10, Excellent, (547 reviews)
"Love this place. Kind of like a college dorm with community kitchen. Will stay there again. "
United States
William
The price is €84
includes taxes & fees
27 Apr - 28 Apr
FOUND Hotel Chicago River North

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 7.4 km from Oakland
9.4 out of 10, Exceptional, (3,643 reviews)
"Great location"
United States
Margaret
The price is €241
includes taxes & fees
7 May - 8 May
LondonHouse Chicago, Curio Collection by Hilton

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,147 reviews)
"Clean room, nice hotel, nice staff"
United States
Melanie
The price is €115
includes taxes & fees
26 Apr - 27 Apr
Congress Plaza Hotel

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (3,837 reviews)
"The property was absolutely stunning and the staff was great."
United States
Pamela
The price is €148
includes taxes & fees
19 Apr - 20 Apr
Hotel Riu Plaza Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 8.1 km from Oakland
8.6 out of 10, Excellent, (3,047 reviews)
"Excellent service, clean, comfortable, and a great location. "
United States
Lisa
The price is €144
includes taxes & fees
30 Apr - 1 May
Warwick Allerton - Chicago

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Streeterville, 7.9 km from Oakland
9.0 out of 10, Wonderful, (1,017 reviews)
"Rooms were very clean and the staff were all very professional."
United States
Mitchell
The price is €116
includes taxes & fees
27 Apr - 28 Apr
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,502 reviews)
"Increíble hotel súper friendly staff! "
United States
Alejandra
The price is €276
includes taxes & fees
9 May - 10 May
Hyatt Regency Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (2,189 reviews)
"Great room, lovely staff and fantastic location "
United Kingdom
Jessica
The price is €110
includes taxes & fees
16 Apr - 17 Apr
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 6.6 km from Oakland
8.8 out of 10, Excellent, (3,460 reviews)
"Wonderful hotel, friendly and accommodating staff! "
United States
Chevon
The price is €108
includes taxes & fees
29 Apr - 30 Apr
Club Quarters Hotel, Central Loop, Chicago

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, (1,954 reviews)
"The staff here were extremely friendly and made the stay more enjoyable "
United States
Trinity
The price is €118
includes taxes & fees
27 Apr - 28 Apr
Hilton Garden Inn Chicago Downtown South Loop

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Gold Coast, 9.3 km from Oakland
9.0 out of 10, Wonderful, (1,519 reviews)
"Very nice hotel, great location. Will stay again!"
United States
Monica
The price is €114
includes taxes & fees
27 Apr - 28 Apr
Claridge House Chicago, Tapestry Collection by Hilton

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, (2,464 reviews)
"Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. "
United States
Christopher
The price is €258
includes taxes & fees
27 Apr - 28 Apr
Sable at Navy Pier Chicago, Curio Collection by Hilton

Millennium Hotel Knickerbocker Chicago

Millennium Hotel Knickerbocker Chicago
4.0 star property
Streeterville, 8.6 km from Oakland
8.6 out of 10, Excellent, (1,962 reviews)
"Great location, clean hotel"
United States
Andre
The price is €127
includes taxes & fees
19 Apr - 20 Apr
Millennium Hotel Knickerbocker Chicago

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, (2,422 reviews)
"Perfect location, beautiful clean rooms and friendly staff "
United Kingdom
Maureen
The price is €146
includes taxes & fees
26 Apr - 27 Apr
DoubleTree by Hilton Chicago - Magnificent Mile

ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
River North, 7.9 km from Oakland
9.0 out of 10, Wonderful, (1,998 reviews)
"Excellent location for shops,restaurants and casino."
United States
Deborah
The price is €113
includes taxes & fees
26 Apr - 27 Apr
ACME Hotel Chicago, Outset Collection by Hilton

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,266 reviews)
"Great connecting room and always an amazing stay I always come for the atmosphere and great staff!"
United States
Kavita
The price is €247
includes taxes & fees
8 May - 9 May
Swissotel - Chicago
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.

Where to stay in Oakland

Find the best Oakland areas for the activities you enjoy most.

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

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

O'Hare

Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago.

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.

Top Oakland Hotel Reviews

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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