Find hotels in Oakland, Chicago from SAR 279

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Discover 4,596 Oakland hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Eurostars Magnificent Mile

4.0 star property
River North, 8.1 km from Oakland
8.8 out of 10, Excellent, (3129)
"Location was great "
United States
Hamik
The price is SAR 399
SAR 469 total
includes taxes & fees
16 Dec - 17 Dec
Eurostars Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
Streeterville, 7.8 km from Oakland
8.8 out of 10, Excellent, (2157)
"Great stay "
United States
Melinda
The price is SAR 366
SAR 430 total
includes taxes & fees
7 Dec - 8 Dec
DoubleTree by Hilton Chicago - Magnificent Mile

River Hotel

4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (4845)
"Front desk is amazing, rooms are clean and great location"
United States
Glen
The price is SAR 333
SAR 391 total
includes taxes & fees
27 Nov - 28 Nov
River Hotel

Aloft Chicago Mag Mile

3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (2937)
"Great location!!"
United States
sarah e
The price is SAR 338
SAR 396 total
includes taxes & fees
7 Dec - 8 Dec
Aloft Chicago Mag Mile

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, (2246)
"Room was spotless…staff was great!"
United States
Tamika
The price is SAR 332
SAR 518 total
includes taxes & fees
16 Dec - 17 Dec
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (4199)
"Great location. "
United States
Rodger
The price is SAR 300
SAR 352 total
includes taxes & fees
7 Dec - 8 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile

citizenM Chicago Downtown

4.0 star property
Theatre District, 7.3 km from Oakland
9.4 out of 10, Exceptional, (4082)
"Clean rooms, friendly staff, great breakfast, amazing location. "
Canada
Gokce
The price is SAR 401
SAR 471 total
includes taxes & fees
24 Dec - 25 Dec
citizenM Chicago Downtown

Hilton Chicago

4.0 star property
The Loop, 5.7 km from Oakland
8.4 out of 10, Very Good, (2320)
"Clean Rooms & very nice staff"
United States
Teresa
The price is SAR 397
SAR 576 total
includes taxes & fees
20 Dec - 21 Dec
Hilton Chicago

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Streeterville, 8.6 km from Oakland
9.0 out of 10, Wonderful, (3375)
"Great stay!"
United States
Rose
The price is SAR 312
SAR 367 total
includes taxes & fees
7 Dec - 8 Dec
Hilton Chicago/Magnificent Mile Suites

FOUND Hotel Chicago River North

2.0 star property
River North, 8.1 km from Oakland
8.4 out of 10, Very Good, (339)
"love this place definitely coming back !"
United States
Dayanara
The price is SAR 237
SAR 279 total
includes taxes & fees
7 Dec - 8 Dec
FOUND Hotel Chicago River North

Crowne Plaza Chicago West Loop by IHG

3.5 star property
7.3 km from Oakland
9.0 out of 10, Wonderful, (1707)
"The location was great!!"
United States
Yvette
The price is SAR 447
SAR 525 total
includes taxes & fees
20 Dec - 21 Dec
Crowne Plaza Chicago West Loop by IHG

Freehand Chicago

4.0 star property
River North, 7.9 km from Oakland
8.0 out of 10, Very Good, (2605)
"Rooms are clean, staff are nice and friendly "
United States
Karen
The price is SAR 261
SAR 372 total
includes taxes & fees
8 Dec - 9 Dec
Freehand Chicago

Congress Plaza Hotel

3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very Good, (9655)
"Great stay comfortable bed and great location!"
United States
Kimberly Noel
The price is SAR 427
SAR 501 total
includes taxes & fees
27 Nov - 28 Nov
Congress Plaza Hotel

Hotel Riu Plaza Chicago

4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (2858)
"Great service, great breakfast and a nice room "
United States
DeAnna
The price is SAR 341
SAR 506 total
includes taxes & fees
8 Dec - 9 Dec
Hotel Riu Plaza Chicago

Best Western River North Hotel

2.5 star property
River North, 8 km from Oakland
7.8 out of 10, Good, (1018)
"Staff was very friendly "
United States
david
The price is SAR 327
SAR 384 total
includes taxes & fees
9 Dec - 10 Dec
Best Western River North Hotel

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 SAR 342
SAR 447 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn & Suites Chicago - Downtown by IHG

Silversmith Hotel Chicago Downtown

4.0 star property
Theatre District, 6.7 km from Oakland
9.2 out of 10, Wonderful, (2087)
"Lovely hotel in a great spot!"
United States
Natasha
Silversmith Hotel 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, (2631)
"Enjoyed my stay here. "
United States
Vai
The price is SAR 385
SAR 518 total
includes taxes & fees
22 Dec - 23 Dec
La Quinta Inn & Suites by Wyndham Chicago Downtown

Palmer House a Hilton Hotel

4.0 star property
Theatre District, 6.7 km from Oakland
8.4 out of 10, Very Good, (2098)
"Great place to stay."
United States
Aaron
The price is SAR 384
SAR 545 total
includes taxes & fees
23 Dec - 24 Dec
Palmer House a Hilton Hotel

Hilton Garden Inn Chicago Downtown South Loop

3.0 star property
The Loop, 5.4 km from Oakland
8.8 out of 10, Excellent, (1731)
"Clean room, great hot tub."
United States
SHARON
The price is SAR 297
SAR 349 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.

Where to stay in Oakland

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

Downtown Chicago

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Top Oakland Hotel Reviews

Find out more about Oakland

Top reasons to visit Oakland

  • Diverse Activities: Oakland offers a range of activities for families and business travelers, from arena entertainment to photo tours.
  • Urban Parks: Explore beautiful urban parks and historic houses, perfect for outdoor fun and relaxation.
  • Cultural Experiences: Engage in local cuisine and cultural experiences, ensuring a memorable visit.
  • Vibrant Atmosphere: Enjoy the lively charm of Oakland, filled with friendly locals and a welcoming community.
  • Variety of Accommodations: Choose from hotels and cozy bed & breakfasts that cater to all traveler needs.

Find great hotels near Oakland

Oakland offers a diverse selection of accommodations, including hotels and charming bed & breakfasts, perfect for every traveler. Whether you prioritize business-friendly amenities, pet-friendly policies, or an LGBTQIA-welcoming environment, you'll find options that cater to your needs. With air-conditioned rooms and positive hotel reviews highlighting the best places to stay, your Oakland experience is sure to be comfortable and enjoyable.

  • Congress Plaza Hotel: Nestled in the heart of Chicago's vibrant shopping district, Congress Plaza Hotel is a 3.5-star gem that caters to both business travelers and shopping enthusiasts. With its rich history and classic architecture, the hotel exudes a timeless charm. Guests can enjoy spacious accommodations equipped with modern amenities, along with on-site dining options that reflect the local culinary scene. The hotel also features a business center and meeting facilities, making it an ideal choice for those mixing work with leisure.
  • Hyatt Regency Chicago: This 4-star hotel epitomizes urban sophistication and is perfect for travelers seeking a blend of business, shopping, and nature-themed experiences. Located close to Oakland, Hyatt Regency Chicago boasts breathtaking views of the Chicago River and the city skyline. Guests can enjoy a range of amenities including a fitness center, on-site dining, and expansive meeting spaces. The hotel's proximity to parks and the scenic waterfront makes it a fantastic choice for those wanting to unwind amidst nature while still being in the city's hustle and bustle.
  • Best Western Grant Park Hotel: Ideal for families and shopping aficionados, Best Western Grant Park Hotel is a welcoming retreat just 4.8km from Oakland. This property is designed with family-friendly amenities, including cribs and safety features for children, ensuring a comfortable stay for guests of all ages. The hotel's location in the shopping district allows easy access to local attractions and entertainment. Additionally, the hotel provides a complimentary breakfast and a cozy atmosphere that invites families to relax and enjoy their time together.

Where to stay near Oakland

Experience the vibrant charm of Oakland, Chicago, where family-friendly activities and urban exploration await. Discover the nearby allure of San Francisco, offering scenic views and outdoor spaces perfect for relaxation. Enjoy the lively atmosphere filled with friendly locals, ideal for family vacations or business trips. Whether you're strolling through parks or indulging in local cuisine, Oakland promises an unforgettable travel experience that beautifully blends urban vibes with serene landscapes.

  • Chicago: As a vibrant metropolis, Chicago offers a rich tapestry of experiences for visitors. Located in the heart of the city, Oakland provides easy access to a myriad of attractions. Travelers flock to Chicago for family-friendly activities, outdoor adventures, and its dynamic city atmosphere. Explore iconic shopping areas, catch a show at a renowned theater, or enjoy a game at a local sports facility. The city's landmarks, like the picturesque urban parks and bustling tourist precincts, create an unforgettable backdrop for your vacation.
  • Downtown Chicago: Just 8.0km from Oakland, Downtown Chicago is a bustling neighborhood that encapsulates the city's energy. It attracts visitors year-round, with peak travel times occurring from July to September. Here, you can indulge in family activities, outdoor fun, and immerse yourself in the urban experience. With numerous shopping venues, vibrant theaters, and major arena entertainment facilities, Downtown Chicago is a hub of excitement. Don’t miss the opportunity to visit its local landmarks, including the scenic urban parks and lively sports facilities.
  • Kenwood: Located a mere 1.4km from Oakland, Kenwood is a charming neighborhood that captivates visitors with its historic appeal. Popular year-round, this area sees increased traveler interest from July to September. Kenwood is perfect for families and those seeking outdoor adventures while being enveloped in a city atmosphere. Engage in educational experiences, enjoy shopping, or explore its renowned arena entertainment venues. Local highlights include historic college campuses and event conference venues, making Kenwood a delightful stop during your Chicago adventure.

Things to do near Oakland

Oakland, Chicago, is perfect for family and business vacations, offering a variety of activities. Visitors can enjoy the arena entertainment facility, explore local restaurants, and take part in photo tours. The city also features great outdoor seating options and event venues, making it a vibrant destination for shopping and education. Whether you're looking to relax or engage, Oakland has something for everyone.

Shopping

Experience shopping in Oakland with the Chicago Place Mall, a dynamic shopping center just 8.0km away, offering a mix of family and business vibes. For more excitement, visit the Shops at North Bridge, also 8.0km away, featuring entertainment and city vibes, or explore the Maxwell Street Market, located 6.4km away, with its vibrant city atmosphere.

Recreation

Experience the excitement at Wrigley Field, a historic stadium perfect for sports enthusiasts. For a tranquil retreat, head to Northerly Island Natural Area, where you can unwind in nature. Enjoy live music at the House of Blues Chicago, offering a vibrant atmosphere for entertainment lovers.

Adventure

Experience the beauty of nature on the Salt Creek Trail, located 19.3km from Oakland, where you can enjoy scenic views and outdoor adventure. For family fun, visit Rainbow Falls Waterpark, 38.6km away, offering exciting water rides and entertainment for all ages.

Nightlife

Experience the vibrant nightlife in Oakland by visiting the Chicago Theatre for a romantic show, or catch a family-friendly film at Film Row Cinema. For a thrilling adventure, explore Amazing Chicago's Funhouse Maze, where excitement awaits just a short distance away.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Oakland

To save money on your trip to Oakland, consider visiting during the off-peak months of December to February, when prices are lower. Booking your stay for a Monday can also help you avoid the higher rates typically seen on Saturdays. Utilize Expedia to compare accommodations, filter for eco-friendly options, and sort prices from low to high. Additionally, consider bundling your hotel, flights, and activities for potential savings. Look for deals on room rates and cancellation options to ensure you get the best value for your trip.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Oakland are December to February, where the prices are slightly lower. This is in comparison to June and September to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Oakland is Monday. The most expensive day to stay around Oakland is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to customize your options based on your budget, desired location, and type of hotel you prefer. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels currently available. To find the best prices and offers, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can potentially save money by combining your hotel stay in Oakland with your flights and activities by booking an Expedia package.

Find the best attractions near Oakland

Oakland, Chicago, is perfect for family, business, and city-themed vacations, boasting attractions like urban parks, historic houses, and universities. Visitors can explore cultural experiences and family-friendly activities, ensuring a memorable stay in this vibrant area. Whether you seek history or outdoor fun, Oakland has something for everyone to enjoy.

  • McCormick Place: Located 3.2km from Oakland, McCormick Place is a premier convention center known for its impressive architecture and business atmosphere. It's a hub for conferences and trade shows, offering a unique opportunity to network and experience the latest in various industries.
  • Grant Park: Situated 6.4km away, Grant Park is a sprawling urban park that serves as the city's front yard. With lush green spaces, beautiful gardens, and family-friendly activities, it's perfect for leisurely strolls, picnics, and enjoying outdoor concerts during the summer.
  • University of Chicago: Just 3.2km from Oakland, this historic university boasts stunning Gothic architecture and a rich cultural heritage. Explore its museums, libraries, and the picturesque campus, which offers a glimpse into academic excellence and intellectual vibrancy.

Best time to go to Oakland

The best time to visit Oakland is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyAverageSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnyAverageAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnySlightly HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnyAverageAverage
August73.0°F (22.8°C)Light RainMostly SunnyAverageAverage
September67.1°F (19.5°C)Light RainMostly SunnySlightly HighSlightly High
October54.9°F (12.7°C)Light RainMostly SunnySlightly HighSlightly High
November42.3°F (5.7°C)Light RainMostly SunnySlightly LowAverage
December33.1°F (0.6°C)Light RainMostly CloudySlightly LowSlightly Low

The nearest major airports for your trip to Oakland

Traveling to Oakland, Chicago, is convenient with access to several major airports. Chicago O'Hare International Airport (ORD) is situated 30.6km from Oakland, with nearby hotels such as the 4.5-star Loews Chicago O'Hare Hotel, 3.2km away, and the 4-star Hilton Chicago O'Hare Airport, just 161m from the terminal. Midway International Airport (MDW), located 12.9km away, features luxurious options like the 5-star Nobu Hotel Chicago and The Langham, Chicago. For those considering Chicago Executive Airport (PWK), 40.2km from Oakland, the 4.5-star Deer Path Inn and the 4-star Embassy Suites by Hilton are excellent choices nearby.

Explore a world of travel with Expedia

Frequently asked questions

What's it like in Oakland?
Oakland is a neighborhood that travelers 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 neighborhood.
How many hotels are there in the Oakland area?
When you want to find places to stay in Chicago, start by booking one of Expedia's 7 hotels and other accommodations in Oakland.
If I need to cancel my hotel reservation in Oakland, will I receive a refund?
Yes, most hotel bookings are fully refundable if you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you have a non-refundable reservation, you might still have the option to cancel and receive a refund within a 24-hour period of booking. Plug in your dates, click on "Search", then filter by "fully refundable" to review the best deals in Oakland.
Where can I learn more about changing or cancelling my trip to Oakland?
To find more details about picking new dates or cancelling your trip to Oakland, go to https://www.expedia.com/service/.
What can I see and do in this Chicago neighborhood?
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 neighborhood. 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.