Oakland Hotels, Chicago

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Check prices for these dates

Tonight
28 Apr - 29 Apr
Tomorrow
29 Apr - 30 Apr
This weekend
2 May - 4 May
Next weekend
9 May - 11 May

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4259 Cheap Hotels in Oakland - Specials, Reviews, & Last Minute Deals

Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very good, (2520)
"Nice stay, close to CTA and walkable to great dining and shops."
The price is AU$179
includes taxes & fees
26 May - 27 May
Best Western Grant Park Hotel
Le Méridien Essex Chicago
City view

Le Méridien Essex Chicago

4.0 star property
8.6 out of 10, Excellent, (1006)
"This is a great location and stay . "
The price is AU$279
includes taxes & fees
26 May - 27 May
Le Méridien Essex Chicago
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (1808)
"Always a great stay!"
The price is AU$367
includes taxes & fees
9 May - 10 May
Hilton Chicago
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.0 out of 10, Good, (2117)
"Place was clean....staff was friendly "
The price is AU$147
includes taxes & fees
30 Apr - 1 May
Travelodge by Wyndham Downtown Chicago
Congress Plaza Hotel
Aerial view

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (8731)
"Great stay"
The price is AU$263
includes taxes & fees
1 May - 2 May
Congress Plaza Hotel
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
Breakfast, lunch, dinner served; Regional cuisine

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

4.0 star property
9.6 out of 10, Exceptional, (1011)
"Amazing hotel"
The price is AU$248
includes taxes & fees
26 May - 27 May
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
The Buckingham Hotel
Lounge

The Buckingham Hotel

3.5 star property
9.0 out of 10, Wonderful, (1000)
"Clean, great amenities, location is great."
The price is AU$347
includes taxes & fees
1 May - 2 May
The Buckingham Hotel
Holiday Inn & Suites Chicago - Downtown by IHG
Pool

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
8.2 out of 10, Very good, (1011)
"We had a great time on this hotel!!"
The price is AU$233
includes taxes & fees
26 May - 27 May
Holiday Inn & Suites Chicago - Downtown by IHG
Central Loop Hotel
Exterior

Central Loop Hotel

4.0 star property
8.6 out of 10, Excellent, (1742)
"i really enjoyed my stay !"
The price is AU$232
includes taxes & fees
26 May - 27 May
Central Loop Hotel
Club Quarters Hotel, Central Loop, Chicago
Suite, 1 Queen Bed, Kitchenette

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.6 out of 10, Excellent, (3393)
"Staff was very friendly "
The price is AU$232
includes taxes & fees
26 May - 27 May
Club Quarters Hotel, Central Loop, Chicago
Chicago Athletic Association, a Hyatt Hotel
Exterior

Chicago Athletic Association, a Hyatt Hotel

4.5 star property
9.0 out of 10, Wonderful, (1000)
"Would definitely stay again. "
The price is AU$495
includes taxes & fees
30 Apr - 1 May
Chicago Athletic Association, a Hyatt Hotel
Silversmith Hotel Chicago Downtown
Lobby

Silversmith Hotel Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (1792)
"Great place to stay."
The price is AU$244
includes taxes & fees
26 May - 27 May
Silversmith Hotel Chicago Downtown
Hyatt Centric The Loop Chicago
Rooftop terrace

Hyatt Centric The Loop Chicago

4.0 star property
8.8 out of 10, Excellent, (1892)
"Amazing stay "
The price is AU$296
includes taxes & fees
2 May - 3 May
Hyatt Centric The Loop Chicago
Kimpton Gray Hotel by IHG
Exterior

Kimpton Gray Hotel by IHG

4.5 star property
9.4 out of 10, Exceptional, (1003)
"Lovely decor and front desk service! "
The price is AU$353
includes taxes & fees
11 May - 12 May
Kimpton Gray Hotel by IHG
Staypineapple, An Iconic Hotel, The Loop
Interior detail

Staypineapple, An Iconic Hotel, The Loop

4.0 star property
9.4 out of 10, Exceptional, (1010)
"Great stay, front desk very nice"
The price is AU$308
includes taxes & fees
11 May - 12 May
Staypineapple, An Iconic Hotel, The Loop
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, (2359)
"Clean comfortable rooms in an excellent location to explore downtown at a great price point."
The price is AU$217
includes taxes & fees
27 May - 28 May
La Quinta Inn & Suites by Wyndham Chicago Downtown
Arlo Chicago
Room, 1 King Bed (Millennium)

Arlo Chicago

4.0 star property
9.2 out of 10, Wonderful, (1735)
"Good room, comfortable bed, excellent location."
The price is AU$295
includes taxes & fees
11 May - 12 May
Arlo Chicago
Fairmont Chicago at Millennium Park
Front of property - evening/night

Fairmont Chicago at Millennium Park

4.5 star property
8.6 out of 10, Excellent, (1692)
"Great location for us to get to all the places we wanted to eat at at all the places we wanted to see"
The price is AU$375
includes taxes & fees
1 May - 2 May
Fairmont Chicago at Millennium Park
Cambria Hotel Chicago Loop - Theatre District
Miscellaneous

Cambria Hotel Chicago Loop - Theatre District

4.0 star property
8.8 out of 10, Excellent, (1336)
"I always enjoy staying here while in town. "
The price is AU$256
includes taxes & fees
26 May - 27 May
Cambria Hotel Chicago Loop - Theatre District
Hyatt Place Chicago/Downtown - The Loop
Exterior

Hyatt Place Chicago/Downtown - The Loop

3.0 star property
8.6 out of 10, Excellent, (1001)
"Great location "
The price is AU$277
includes taxes & fees
4 May - 5 May
Hyatt Place Chicago/Downtown - The 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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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.