Oakland, IL
Chicago
Visit Oakland
Stay near popular Oakland attractions
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
90% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
LEGOLAND® Discovery Center Chicago
$29
per adult
92% of travellers recommend
Oakland Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
$109 nightly
The price is $130 total per night from Sep 8 to Sep 9
$130 total
Sep 8 - Sep 9
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
$143 nightly
The price is $170 total per night from Aug 30 to Aug 31
$170 total
Aug 30 - Aug 31
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (1,961 reviews)
"I was double charged. Still trying to get resolved!!"
Reviewed on Aug 9, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
$214 nightly
The price is $251 total per night from Aug 30 to Aug 31
$251 total
Aug 30 - Aug 31
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,379 reviews)
"Go place to stay if your traveling and have a connection next day. Also very safe! A bit expensive especially the valet parking"
Reviewed on Aug 9, 2026
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
$202 nightly
The price is $240 total per night from Sep 7 to Sep 8
$240 total
Sep 7 - Sep 8
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
$169 nightly
The price is $193 total per night from Aug 30 to Aug 31
$193 total
Aug 30 - Aug 31
Total with taxes and fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Fully refundableReserve now, pay when you stay
$211 nightly
The price is $251 total per night from Sep 1 to Sep 2
$251 total
Sep 1 - Sep 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
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 and neighborhoods for the activities you enjoy most. Learn more about Oakland
Learn more about Oakland
Downtown Chicago
Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Lake Michigan are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
The Loop
Lake Michigan and Michigan Avenue are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops, and acclaimed art galleries.
Magnificent Mile
Michigan Avenue and Chicago Water Tower are just a few worthwhile attractions to visit in Magnificent Mile. Travelers also love the fascinating museums, panoramic lake views, and popular shops.
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.
Photo by Mattyboy876
Open Photo by Mattyboy876
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).
Oakland, IL
Explore a world of travel with Expedia
- Extended Stay Hotels in Chicago
- Motels in Chicago
- Hotels with Free Airport Shuttle in Chicago
- Hotels with Suites in Chicago
- Hotels near Wrigley Field
- Hotels near Chicago Union Station
- Cheap Hotels in Downtown Chicago
- Hotels near Soldier Field
- Hotels with Hot Tubs in Chicago
- Cheap Hotels in Chicago
- Romantic Hotels in Chicago
- Hotels near O'Hare Intl.
- Hotels near Grant Park
- Marriott Hotels & Resorts in Chicago
- Downtown Chicago Hotels
- Hotels near Navy Pier
- Luxury Hotels in Downtown Chicago
- Hotels with Free Parking in Chicago
- Hotels near United Center
- Cabin Rentals in Chicago
- Hotels near Midway Intl.
- All-Inclusive Resorts in Chicago
- Chicago Hotels
- Hotels with a View in Downtown Chicago
- Magnificent Mile Hotels
- Hotels near McCormick Place
- Flights from Pittsburgh (PIT) to Chicago (ORD)
- Flights from Minneapolis (MSP) to Chicago (ORD)
- Flights from Indianapolis (IND) to Chicago (ORD)
- Flights from San Diego (SAN) to Chicago (ORD)
- Flights from Atlanta (ATL) to Chicago (ORD)
- Flights from San Francisco (SFO) to Chicago (ORD)
- Flights from Austin (AUS) to Chicago (ORD)
- Flights from O'Hare Intl.
- Flights from Salt Lake City (SLC) to Chicago (ORD)
- Flights from Nashville (BNA) to Chicago (ORD)
- Flights from Detroit (DTW) to Chicago (ORD)
- Flights from Kansas City (MCI) to Chicago (ORD)
- Flights from Seattle (SEA) to Chicago (ORD)
- Flights from Miami (MIA) to Chicago (ORD)
- Flights from St. Louis (STL) to Chicago (ORD)
- Flights from Hartford (BDL) to Chicago (ORD)
- Flights from Philadelphia (PHL) to Chicago (ORD)
- Flights from Fort Lauderdale (FLL) to Chicago (ORD)
- Flights from Chicago
- Flights from Baltimore (BWI) to Chicago (ORD)
- Flights from Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
- Flights from Columbus (CMH) to Chicago (ORD)
- Flights from Dallas (DFW) to Chicago (ORD)
- Flights from Orlando (MCO) to Chicago (ORD)
- Flights from Las Vegas (LAS) to Chicago (ORD)
- Flights from Portland (PDX) to Chicago (ORD)
- Flights to O'Hare Intl.
- Flights from Los Angeles (LAX) to Chicago (ORD)
- Flights to Chicago
- Flights from Washington (DCA) to Chicago (ORD)
- Flights from New York (NYC) to Chicago (ORD)
- Flights from Midway Intl.
- Flights from Houston (HOU) to Chicago (ORD)
- Flights from Charlotte (CLT) to Chicago (ORD)
- Flights from Denver (DEN) to Chicago (ORD)
- Flights from Raleigh (RDU) to Chicago (ORD)
- Flights from New York (LGA) to Chicago (ORD)
- Visit Grand Boulevard
- Visit Wicker Park
- Visit Magnificent Mile
- Visit Streeterville
- Visit South Side
- Visit South Loop
- Visit Indian Village
- Where to stay in Chicago
- Visit River North
- Visit Cicero
- Visit Oak Park
- Visit Lincoln Square
- Visit Chicago
- Visit Fuller Park
- Visit Bronzeville
- Visit The Loop
- Visit Douglas
- Visit United Center
- Visit Rush Street
- Visit Gold Coast
- Visit Armour Square
- Visit Chinatown
- Visit West Loop
- Visit Canaryville
- Visit Wrigleyville
- Visit Downtown Chicago
- Visit Hyde Park
- Visit Chicago Museum Campus
- Visit Kenwood
- Chicago Vacations
- Visit Near South Side
- Visit Printers Row