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Our top choices for Oakland hotels

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, (2,409 reviews)
"Great stay! I will stay here again on my next trip back this summer!"
United States
Letisha
The price is NT$4,721
NT$6,629 total
includes taxes & fees
Mar 30 - Mar 31
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,706 reviews)
"Amazing place to stay!"
United States
Nia
The price is NT$4,162
NT$5,822 total
includes taxes & fees
Apr 1 - Apr 2
Hilton Chicago

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,034 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is NT$3,147
NT$3,695 total
includes taxes & fees
Apr 5 - Apr 6
River Hotel

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very Good, (10,001 reviews)
"Clean room, nice hotel, nice staff"
United States
Melanie
The price is NT$3,706
NT$4,350 total
includes taxes & fees
Apr 1 - Apr 2
Congress Plaza Hotel

The Wade

The Wade
4.5 star property
Streeterville, 7.9 km from Oakland
8.4 out of 10, Very Good, (1,756 reviews)
"Loved this hotel, i will be back"
United States
Shari
The price is NT$4,852
NT$5,695 total
includes taxes & fees
Mar 29 - Mar 30
The Wade

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 7.1 km from Oakland
8.6 out of 10, Excellent, (2,093 reviews)
"lovely hotel "
United States
alyvia
The price is NT$5,399
NT$7,462 total
includes taxes & fees
Mar 24 - Mar 25
Fairmont Chicago at Millennium Park

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 7.9 km from Oakland
8.0 out of 10, Very Good, (2,816 reviews)
"Great location, clean and decent sized room, staff was helpful and amenities are very convenient!"
United States
MaryJane
The price is NT$2,462
NT$3,452 total
includes taxes & fees
Mar 31 - Apr 1
Freehand Chicago

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 6.9 km from Oakland
9.4 out of 10, Exceptional, (1,025 reviews)
"Lots of places to eat and shop nearby"
United States
Analicia
The price is NT$4,245
NT$5,918 total
includes taxes & fees
Apr 6 - Apr 7
Staypineapple, An Iconic Hotel, The Loop

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, (3,410 reviews)
"Wonderful hotel, friendly and accommodating staff! "
United States
Chevon
The price is NT$3,147
NT$3,695 total
includes taxes & fees
Apr 5 - Apr 6
Club Quarters Hotel, Central Loop, Chicago

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,154 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is NT$3,447
NT$4,047 total
includes taxes & fees
Mar 29 - Mar 30
Aloft Chicago Mag Mile

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,236 reviews)
"Excellent stay."
United States
Fenton
The price is NT$4,111
NT$5,950 total
includes taxes & fees
Mar 29 - Mar 30
Swissotel - Chicago

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 6.7 km from Oakland
8.6 out of 10, Excellent, (2,334 reviews)
"We had a great stay and the staff are very friendly and accommodating. "
United States
Krista
The price is NT$4,292
NT$5,837 total
includes taxes & fees
Apr 5 - Apr 6
Palmer House a Hilton Hotel

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, (2,128 reviews)
"Great stay!"
United States
Hannah
The price is NT$3,147
NT$3,695 total
includes taxes & fees
Apr 5 - Apr 6
Club Quarters Hotel Wacker at Michigan, 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, (1,930 reviews)
"Hotel was really nice"
United States
LaCarr
The price is NT$3,507
NT$4,117 total
includes taxes & fees
Apr 5 - Apr 6
Hilton Garden Inn Chicago Downtown South Loop

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 7.9 km from Oakland
8.8 out of 10, Excellent, (1,183 reviews)
"Clean friendly staff love the decor "
United States
Kiasha
Ivy Boutique Hotel

Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 5.4 km from Oakland
8.2 out of 10, Very Good, (2,687 reviews)
"Perfect location!!"
United States
Kelly
The price is NT$3,591
NT$4,216 total
includes taxes & fees
Apr 1 - Apr 2
Best Western Grant Park Hotel

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 7.2 km from Oakland
9.6 out of 10, Exceptional, (3,807 reviews)
"Will stay here again! "
United States
Bryn
The price is NT$5,429
NT$6,374 total
includes taxes & fees
Mar 31 - Apr 1
L7 Chicago by LOTTE

Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 5.6 km from Oakland
8.8 out of 10, Excellent, (1,003 reviews)
"Every aspect of our stay was wonderful!"
United States
Hillary
The price is NT$3,002
NT$4,086 total
includes taxes & fees
Apr 5 - Apr 6
Le Méridien Essex Chicago

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 6.6 km from Oakland
8.6 out of 10, Excellent, (2,037 reviews)
"Great hotel in a great location."
United States
Ben
The price is NT$3,229
NT$3,790 total
includes taxes & fees
Mar 24 - Mar 25
Central Loop Hotel

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, (509 reviews)
"Lots of stuff close by , cool vibe inside and very nice staff"
United States
Abel
The price is NT$2,413
NT$2,833 total
includes taxes & fees
Mar 24 - Mar 25
FOUND Hotel Chicago River North
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

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

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 Culinary Scene: Oakland boasts an array of restaurants offering flavors from around the world, perfect for food enthusiasts.
  • Vibrant Outdoor Spaces: Enjoy beautiful parks and stunning views of San Francisco across the bay, ideal for relaxation and recreation.
  • Rich Cultural Attractions: Explore historic homes, renowned colleges, and vibrant urban parks that showcase the city's unique heritage.
  • Family-Friendly Activities: Oakland is packed with attractions suitable for families, ensuring fun for all ages.
  • Welcoming Accommodations: From cozy B&Bs to modern hotels, Oakland offers diverse lodging options that cater to all travelers.

Find great hotels near Oakland

Discover a diverse selection of accommodations in Oakland, where you can enjoy everything from cozy bed & breakfasts to modern hotels tailored for business travelers. Many establishments offer pet-friendly options and warmly welcome LGBTQIA guests, ensuring a memorable stay. With essential amenities like air conditioning and top-notch service, you're sure to find the perfect home away from home. Explore hotel reviews to guide your choice for an unforgettable experience in this vibrant city.

  • Congress Plaza Hotel: Situated a mere 6.4km from Oakland, the Congress Plaza Hotel is a classic 3.5-star hotel that embodies the charm of Chicago's historic architecture. Ideal for travelers focused on shopping and business, this property is nestled in a vibrant shopping district, offering easy access to local boutiques and dining options. Guests can enjoy comfortable accommodations with essential amenities, including a fitness center and a business center, making it a perfect choice for both leisure and work-related stays. The hotel's rich history adds an element of elegance to your visit.
  • Hyatt Regency Chicago: Located 8.0km from Oakland, the Hyatt Regency Chicago is a luxurious 4-star hotel that captures the essence of urban sophistication. This property is perfect for those looking for a city-themed vacation, blending business and leisure seamlessly. Positioned in the heart of the city center, guests can explore nearby shopping spots and attractions with ease. The hotel features spacious rooms, a state-of-the-art fitness center, an array of dining options, and stunning views of the skyline, ensuring a memorable stay for both families and business travelers alike.
  • Best Western Grant Park Hotel: Just 4.8km from Oakland, the Best Western Grant Park Hotel is a family-friendly accommodation that offers a welcoming atmosphere. This hotel provides thoughtful amenities designed for children, including window guards, a first aid kit, and complimentary cribs, making it an excellent choice for families traveling with young ones. Located in the shopping district, guests can easily venture out for shopping and dining. With comfortable rooms and a commitment to family-friendly service, this hotel ensures that your stay is both enjoyable and convenient.

Where to stay near Oakland

Oakland offers a vibrant mix of family-friendly attractions and urban experiences perfect for any traveler. Explore its beautiful outdoor spaces, enjoy the friendly atmosphere, and take in the stunning views of San Francisco across the bay. With great locations and a welcoming community, Oakland is an ideal base for discovering nearby neighborhoods, indulging in local cuisine, and enjoying a variety of recreational activities. Your vacation here will be full of unforgettable moments.

  • Chicago: As a bustling metropolis, Chicago offers a vibrant urban experience with a rich tapestry of culture and history. Located in the heart of the Midwest, it features a mix of iconic architecture and scenic outdoor spaces. Visitors can indulge in a variety of family-friendly activities, explore shopping districts, and enjoy world-class theater performances. Key attractions include sports stadiums, urban parks, and popular tourist precincts, making it a perfect destination for travelers seeking an exciting city-themed getaway.
  • Downtown Chicago: Just 8.0km from Oakland, Downtown Chicago is a dynamic neighborhood that serves as the city's commercial and cultural hub. This area boasts an array of shopping options, renowned theaters, and entertainment venues, ensuring there’s always something to do. It’s a great spot for families and outdoor enthusiasts alike, with easy access to urban parks and stunning waterfront views along Lake Michigan. The vibrant atmosphere and diverse attractions make Downtown Chicago a must-visit during your stay.
  • North Kenwood: Located a mere 966m from Oakland, North Kenwood is a charming neighborhood that blends residential tranquility with cultural vibrancy. Known for its strong sense of community, this area offers educational attractions, recreational spaces, and cultural centers that cater to families and individuals looking for engaging experiences. With urban parks and tourist precincts nearby, North Kenwood provides a welcoming atmosphere where visitors can immerse themselves in local culture and enjoy a leisurely outdoor experience.

Things to do near Oakland

Oakland offers a variety of activities perfect for family and business vacations. Visitors can enjoy arena entertainment, explore diverse restaurants, and shop at local centers. Additionally, the city features event venues and opportunities for photo tours, along with outdoor seating options to enhance your experience. Whether you're looking to unwind or engage in city-themed adventures, Oakland has something for everyone.

Shopping

For shopping in Oakland, visit the Chicago Place Mall, just 8.0km away, offering a blend of city and family vibes. Another option is the Shops at North Bridge, also 8.0km away, featuring entertainment and business ambiance. Don't miss the Maxwell Street Market, located 6.4km away, for a vibrant public market experience.

Recreation

At Northerly Island Natural Area, enjoy serene walks and tranquil views, perfect for relaxation. Wrigley Field offers an energetic atmosphere for sports enthusiasts, while the House of Blues Chicago provides vibrant live music and entertainment, creating an unforgettable experience in Oakland.

Adventure

Embark on a scenic adventure along the Salt Creek Trail, a beautiful hiking path located 19.3km from Oakland, where you'll enjoy stunning views and nature's tranquility. For family fun, visit Rainbow Falls Waterpark, 38.6km away, offering thrilling water slides and entertainment for all ages.

Nightlife

The nightlife in Oakland offers a vibrant mix of experiences. Catch a show at the Chicago Theatre, just 8.0km away, for a dose of culture and romance. For family-friendly fun, enjoy a movie at Film Row Cinema, 4.8km away, or explore the thrills of Amazing Chicago's Funhouse Maze, also 8.0km 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 between December and February when hotel prices are lower. Mondays are the cheapest days to stay, while Saturdays are the most expensive. Use Expedia to compare room rates, cancellation options, and book packages that include flights and activities for added savings. For budget-friendly transport, explore local public transit options and look for free activities in the area to make the most of your visit without overspending.

  • 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 refine your choices based on your budget, desired location, and preferred hotel type. For the best prices and deals, be sure to sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by booking an Expedia package that combines your hotel in Oakland with your flights and activities.

Find the best attractions near Oakland

Oakland offers a delightful vacation experience for families and business travelers alike, with a rich array of attractions. Visitors can explore urban parks, historic houses, and renowned colleges and universities, all of which provide a glimpse into the city's vibrant culture and history. Whether you're seeking family-friendly activities or a taste of local heritage, Oakland has something to cater to every traveler's interests.

  • McCormick Place: A premier event and conference center located 3.2km from Oakland, McCormick Place buzzes with business energy and innovation. It's the perfect spot to attend expos, conventions, and trade shows, showcasing the latest in various industries.
  • Grant Park: Situated 6.4km away, Grant Park is Chicago's front yard, offering a beautiful urban escape. Enjoy outdoor activities, family picnics, and stunning city views, along with cultural events and festivals throughout the year.
  • University of Chicago: Located just 3.2km from Oakland, this historic institution is renowned for its stunning Gothic architecture and rich cultural atmosphere. Explore its museums and gardens, making it a great spot for history and art enthusiasts.

Best time to go to Oakland

The best time to visit Oakland can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Oakland falls in July, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature around Oakland falls in January, 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

When visiting Oakland, Chicago, you have convenient access to several major airports. Chicago O'Hare International Airport (ORD) is situated 30.6km away, with notable hotels like the 4.5-star Loews Chicago O'Hare Hotel and the 4-star Hyatt Regency O'Hare, both just 3.2km from the airport. Another option is Chicago Midway International Airport (MDW), located 12.9km away, with luxurious stays such as The Langham, Chicago and Nobu Hotel Chicago, both offering easy access to the airport. For a quieter experience, Chicago Executive Airport (PWK) is 40.2km away, with accommodations like the 4.5-star Deer Path Inn within a 16.1km radius.

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 6 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.

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