Hotels in Oakland

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
Aug 15 - Aug 16
Tomorrow
Aug 16 - Aug 17
Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30

Where to stay in Oakland?

1. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
Streeterville, 7.5 km from Oakland
United States
Aaron
$176
$244 total
includes taxes & fees
Sep 7 - Sep 8
Sable at Navy Pier Chicago, Curio Collection by Hilton

2. Congress Plaza Hotel

Congress Plaza Hotel
The Loop, 6 km from Oakland
United States
Jason
$135
$161 total
includes taxes & fees
Sep 7 - Sep 8
Congress Plaza Hotel

3. Hilton Chicago

Hilton Chicago
The Loop, 5.7 km from Oakland
United States
Eva
$169
$230 total
includes taxes & fees
Sep 7 - Sep 8
Hilton Chicago

4. Best Western Grant Park Hotel

Best Western Grant Park Hotel
The Loop, 5.4 km from Oakland
United States
Jamison
$143
$170 total
includes taxes & fees
Aug 30 - Aug 31
Best Western Grant Park Hotel

5. Le Méridien Essex Chicago

Le Méridien Essex Chicago
The Loop, 5.6 km from Oakland
United States
Michael
$143
$188 total
includes taxes & fees
Sep 7 - Sep 8
Le Méridien Essex Chicago

6. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
The Loop, 5.9 km from Oakland
United States
Natalie
$110
$130 total
includes taxes & fees
Aug 31 - Sep 1
Travelodge by Wyndham Downtown Chicago

7. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
The Loop, 5.4 km from Oakland
United States
Wayne Aubrey
$156
$186 total
includes taxes & fees
Sep 7 - Sep 8
Homewood Suites by Hilton Chicago Downtown South Loop

8. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
The Loop, 5.4 km from Oakland
United States
Laurel
$161
$189 total
includes taxes & fees
Aug 30 - Aug 31
Hilton Garden Inn Chicago Downtown South Loop

9. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Streeterville, 7.6 km from Oakland
United States
David
$156
$215 total
includes taxes & fees
Sep 1 - Sep 2
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

10. La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
The Loop, 7 km from Oakland
United States
SamuelDavid
$143
$188 total
includes taxes & fees
Sep 8 - Sep 9
La Quinta Inn & Suites by Wyndham Chicago Downtown

11. Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG
West Loop, 6.4 km from Oakland
United States
Dameon
$157
$199 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn & Suites Chicago - Downtown by IHG

12. Arlo Chicago

Arlo Chicago
Theatre District, 7.1 km from Oakland
United States
Linda
$137
$195 total
includes taxes & fees
Sep 7 - Sep 8
Arlo Chicago

13. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
Theatre District, 6.7 km from Oakland
United States
Jessica
$173
$236 total
includes taxes & fees
Sep 7 - Sep 8
Palmer House a Hilton Hotel

14. Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
Streeterville, 7.9 km from Oakland
United States
Mark
$154
$183 total
includes taxes & fees
Sep 7 - Sep 8
Aloft by Marriott Chicago Mag Mile

15. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
Gold Coast, 9.3 km from Oakland
United States
Elizabeth
$114
$165 total
includes taxes & fees
Sep 7 - Sep 8
Claridge House Chicago, Tapestry Collection by Hilton

16. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Gold Coast, 9.4 km from Oakland
United States
Steven
$143
$170 total
includes taxes & fees
Aug 30 - Aug 31
The Chicago Hotel Collection Ambassador Gold Coast

17. Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
Theatre District, 7.1 km from Oakland
United States
Lisa
$147
$175 total
includes taxes & fees
Sep 7 - Sep 8
Cambria Hotel Chicago Loop - Theatre District

18. Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop
The Loop, 6.6 km from Oakland
United States
Stephanie
$169
$201 total
includes taxes & fees
Sep 7 - Sep 8
Hilton Garden Inn Chicago Central Loop

19. Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown
River North, 7.9 km from Oakland
United States
Kristie
$154
$213 total
includes taxes & fees
Sep 2 - Sep 3
Hotel 55 Chicago Downtown

20. Central Loop Hotel

Central Loop Hotel
Theatre District, 6.6 km from Oakland
United States
Pauline
$147
$174 total
includes taxes & fees
Aug 20 - Aug 21
Central Loop Hotel
View all properties
Our prices for hotels in Chicago are cheapest in January
Price trends for hotels in Chicago
Pricing is based on two traveler single night rates
View properties in August
Typical weather for Chicago
August
High 26°C / low 20°C. Sunny most days.
View properties in August
26°
20°
23°
17°
16°
10°
-2°
-1°
-6°
-6°
11°
17°
11°
23°
17°
26°
20°
Monthly weather averages (˚C)

Top landmarks in Oakland

41st Street Beach

When the beach is calling your name, you might want to head down to 41st Street Beach, located 4.3 mi (7 km) from central Chicago. Enjoy the sunset by the shore at Rainbow Beach, 49th Street Beach, and 63rd Street Beach.
See properties

Check out reviews of Oakland hotels guests love

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"Staff members were helpful and friendly. Cleaned room."
Indiana 1-night trip
Posted 2 hours ago
Hyatt Regency O'Hare Chicago
Hilton Chicago

Hilton Chicago

10/10 Excellent
"Great location, amazing staff"
Brenda 2-night trip
Posted 2 hours ago
Hilton Chicago
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Parking sucks! No pool. But staff was satisfactory. Except for 1 guy who was over the top. Loved location. Overall great place convenient location. We would stay there again."
Sheila 4-night trip
Posted 5 hours ago
Crowne Plaza Chicago West Loop by IHG
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

10/10 Excellent
"Room was clean! Great location"
Ashley 1-night trip
Posted 6 hours ago
Holiday Inn Chicago Dwtn - The Mart by IHG
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"The staff at the property was very accommodating."
Mudit 1-night trip
Posted 9 hours ago
Fairmont Chicago at Millennium Park
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

8/10 Good
"Clean room。nearly airport."
Ming 2-night trip
Posted 12 hours ago
Hilton Chicago O'Hare Airport
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

8/10 Good
"Comfortable, cozy. We just didn't know that we couldn't use the pool or the oven"
Brayan D 4-night trip
Posted 15 hours ago
Kasa Magnificent Mile Chicago
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Beautiful hotel with an amazing pool! Spa services are fantastic!"
Elizabeth 1-night trip
Posted 19 hours ago
InterContinental Chicago Magnificent Mile by IHG
Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"Very clean room. Good location. Close to metro. Welcoming staff. "
Maryann 4-night trip
Posted 21 hours ago
Eurostars Magnificent Mile
Find out more about Oakland

Keep exploring