Find hotels in Oakland, Chicago from AED 527

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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, (2,493 reviews)
"Excellent staff, beautiful views."
United States
Daniel
The price is AED 674
AED 928 total
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio Collection by Hilton

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 6.7 km from Oakland
9.2 out of 10, Wonderful, (2,257 reviews)
"“I stayed at the Silversmith Hotel Chicago Downtown from April 4 to April 9, 2026. The hotel is in a great downtown location, close to everything. However, I was surprised by a daily historic preservation fee that was added to my bill. Future guests, please make sure you know about this fee ahead of time, as it isn’t included in the room rate. While my stay was overall pleasant, I would have appreciated knowing this in advance so I could plan better.”"
United States
Sashanna
The price is AED 349
AED 527 total
includes taxes & fees
2 Jun - 3 Jun
Silversmith Hotel Chicago Downtown

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,779 reviews)
"Always a great stay! Love this hotel. Great area with great restaurants and fun things to do close by. "
United States
Matt
The price is AED 584
AED 802 total
includes taxes & fees
25 May - 26 May
Hilton Chicago

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (4,080 reviews)
"The breakfast was delicious. A great stay in downtown Chicago."
United States
Kenneth
The price is AED 584
AED 799 total
includes taxes & fees
27 May - 28 May
Hotel Riu Plaza Chicago

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,308 reviews)
"Best service in Chicago!"
United States
Bianca
The price is AED 728
AED 995 total
includes taxes & fees
27 May - 28 May
Swissotel - Chicago

The Wade

The Wade
4.5 star property
Streeterville, 7.9 km from Oakland
8.4 out of 10, Very Good, (1,828 reviews)
"Wonderful place to stay in Chicago. Perfect location right by Navy Pier, amazing view from the window, clean rooms, comfortable beds, friendly staff, great food options."
United States
Tetyana
The price is AED 621
AED 738 total
includes taxes & fees
25 May - 26 May
The Wade

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very Good, (10,182 reviews)
"Bed was super comfy and location was great. "
United States
Kelly
The price is AED 460
AED 547 total
includes taxes & fees
8 May - 9 May
Congress Plaza Hotel

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,512 reviews)
"Increíble hotel súper friendly staff! "
United States
Alejandra
The price is AED 749
AED 1,022 total
includes taxes & fees
25 May - 26 May
Hyatt Regency 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, (1,985 reviews)
"Easy check in and clean rooms, comfortable beds and easy access to everything downtown."
United States
Megan
The price is AED 464
AED 551 total
includes taxes & fees
26 May - 27 May
Hilton Garden Inn Chicago Downtown South Loop

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,176 reviews)
"Convenient location and great river view. Room was small, but expected in Chicago. "
United States
Johanna
The price is AED 496
AED 590 total
includes taxes & fees
26 May - 27 May
River Hotel

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 7.4 km from Oakland
9.4 out of 10, Exceptional, (3,703 reviews)
"Comfortable beds and pillows, very friendly staff, location close to everything."
United States
michelle aimee
The price is AED 669
AED 903 total
includes taxes & fees
26 May - 27 May
LondonHouse Chicago, Curio Collection by Hilton

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 7.4 km from Oakland
8.6 out of 10, Excellent, (1,626 reviews)
"Great stay again. Great views. "
United States
JohNyra
The price is AED 790
AED 1,070 total
includes taxes & fees
25 May - 26 May
Sheraton Grand Chicago Riverwalk

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, (2,430 reviews)
"Clean rooms, great staff, great amenities. Next to the loop and the red line. In the heart of downtown Chicago, very historic and beautiful. "
United States
Washington
The price is AED 543
AED 755 total
includes taxes & fees
25 May - 26 May
Palmer House a Hilton Hotel

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 7.1 km from Oakland
9.4 out of 10, Exceptional, (2,112 reviews)
"Great location! Loved staying here"
United States
Nicole
The price is AED 493
AED 697 total
includes taxes & fees
25 May - 26 May
Arlo Chicago

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, (4,017 reviews)
"Great hotel, clean an super friendly staff.. would recommend"
United Kingdom
Joel
The price is AED 506
AED 601 total
includes taxes & fees
25 May - 26 May
L7 Chicago by LOTTE

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, (1,061 reviews)
"Wonderful restaurant, amazing food."
United States
Robert
The price is AED 489
AED 690 total
includes taxes & fees
25 May - 26 May
Staypineapple, An Iconic Hotel, The Loop

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 8.1 km from Oakland
9.0 out of 10, Wonderful, (3,513 reviews)
"Great hotel and proximity to everything in downtown. Friendly staff who greet you every time. "
United States
Marisa
The price is AED 529
AED 629 total
includes taxes & fees
10 May - 11 May
Eurostars Magnificent Mile

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 7.1 km from Oakland
8.8 out of 10, Excellent, (2,150 reviews)
"A great option to stay in the city! Nice hotel and friendly staff."
United States
Nicole
The price is AED 694
AED 956 total
includes taxes & fees
8 May - 9 May
Fairmont Chicago at Millennium Park

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,432 reviews)
" Hotels really clean restaurant really good"
United States
Raul
The price is AED 584
AED 812 total
includes taxes & fees
25 May - 26 May
The Royal Sonesta Chicago Downtown

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Magnificent Mile, 7.7 km from Oakland
9.2 out of 10, Wonderful, (3,045 reviews)
"The hotel was beautifully maintained and the pool was wonderful. "
United States
Joan
The price is AED 731
AED 998 total
includes taxes & fees
26 May - 27 May
InterContinental Chicago Magnificent Mile by IHG
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 Navy Pier and Michigan Avenue 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 Dining Options: Oakland is known for its wide range of restaurants offering various cuisines, perfect for food enthusiasts.
  • Vibrant Outdoor Spaces: Enjoy beautiful parks and outdoor seating areas, ideal for relaxation and family activities.
  • Rich Cultural Experiences: Explore historic sites and colleges that reflect the city's unique heritage.
  • Entertainment Venues: Visit popular arenas for live events and entertainment, catering to all interests.
  • Welcoming Atmosphere: Experience the friendly local community that adds to Oakland’s charm.

Find great hotels near Oakland

Discover a variety of hotel accommodations in Oakland, Chicago, designed to suit every traveler's needs. Whether you're looking for a cozy bed & breakfast or a modern hotel equipped with essential business amenities, Oakland has you covered. Enjoy pet-friendly options and LGBTQIA welcoming experiences, all while ensuring comfort with air conditioning and top-notch services. Check out reviews to find the best hotel that fits your vacation style.

  • Congress Plaza Hotel: A historic 3.5-star hotel with a rich heritage, Congress Plaza Hotel is the perfect choice for travelers seeking a blend of business and leisure. Located in the vibrant shopping district, this hotel offers easy access to a variety of retail options and local attractions. Guests will appreciate the comfortable accommodations, complemented by business facilities and meeting rooms ideal for corporate travelers. The hotel’s classic design, combined with modern amenities, provides a unique atmosphere that reflects Chicago's history while ensuring a pleasant stay.
  • Hyatt Regency Chicago: An eco-friendly 4-star hotel, Hyatt Regency Chicago stands out for its commitment to sustainability while providing a luxurious experience. Situated in the bustling shopping district, this property caters to both business and leisure travelers. The hotel features spacious rooms with contemporary decor, an on-site restaurant serving locally inspired cuisine, and extensive meeting spaces. Guests will enjoy its eco-certified status, making it a perfect choice for environmentally-conscious visitors looking to explore the city without compromising comfort.
  • Best Western Grant Park Hotel: Ideal for family vacations, Best Western Grant Park Hotel combines convenience with comfort. Located just 4.8km from Oakland, this hotel is situated in a lively shopping district, making it easy for families to explore the area. The property offers family-friendly amenities, including free cribs and safety features for children. Guests can enjoy spacious accommodations, a complimentary breakfast, and easy access to nearby attractions, ensuring a stress-free and enjoyable stay for families traveling together.

Where to stay near Oakland

Oakland, Chicago, is a vibrant neighborhood perfect for family-friendly and business-themed vacations. Visitors can explore its great outdoor spaces and enjoy the welcoming atmosphere of friendly locals. Just a short distance away, the iconic city of San Francisco offers even more urban excitement. Whether you’re seeking scenic views or a bustling urban vibe, Oakland and its surrounding areas provide an unforgettable experience for every traveler.

  • Chicago: As a sprawling metropolis, Chicago offers visitors a vibrant urban experience where Oakland is nestled within its diverse landscape. The city attracts travelers year-round, with peak visitation from June to August. Chicago is ideal for families and those seeking outdoor adventures. You can explore its robust shopping districts, catch a game at a local sports stadium, or enjoy a performance at one of its renowned theaters. The city's urban parks provide a refreshing escape with green spaces perfect for relaxation or recreational activities.
  • Downtown Chicago: Located a mere 8.0km from Oakland, Downtown Chicago is the bustling heart of the city. Like its neighboring areas, it experiences consistent traveler interest throughout the year, peaking in summer. Here, families can enjoy a wealth of attractions, including vibrant shopping areas and cutting-edge entertainment venues. The proximity to sports facilities and urban parks makes it an excellent spot for both cultural and outdoor experiences, allowing visitors to soak up the energetic atmosphere while exploring the city's iconic skyline.
  • Kenwood: Just 1.4km from Oakland, Kenwood is a charming neighborhood that draws visitors for its cultural offerings and family-friendly environment. With a steady flow of tourists year-round, especially in summer, Kenwood is known for its educational institutions and lively shopping areas. The historic college and conference venues add to the neighborhood's appeal, making it a great place for those interested in learning and cultural events. Visitors can enjoy local cafes and shops while engaging with the rich history that surrounds this vibrant community.

Things to do near Oakland

Oakland offers a vibrant mix of activities perfect for families, business travelers, and city explorers. Discover popular attractions including an arena entertainment facility, diverse dining options, and shopping centers. Engage with the local culture by exploring event venues, enjoying photo tours, and relaxing in outdoor seating areas. With something for everyone, Oakland is an ideal destination for your vacation.

Shopping

For a fantastic shopping experience in Oakland, visit Chicago Place Mall, just 8.0km away, offering a vibrant city and family atmosphere. Also, check out the Shops at North Bridge, 8.0km away, which combines entertainment and business vibes. Don’t miss Maxwell Street Market, located 6.4km away, for a unique public market experience.

Recreation

At Wrigley Field, immerse yourself in the vibrant sports atmosphere while enjoying a game. Northerly Island Natural Area offers serene landscapes perfect for relaxation and nature walks. Experience live music and entertainment at the House of Blues Chicago, enhancing your wellness journey through rhythm and connection.

Adventure

Explore the Salt Creek Trail, a scenic hiking trail located 19.3km from Oakland, where you can immerse yourself in nature and enjoy breathtaking views. For family fun, head to Rainbow Falls Waterpark, situated 38.6km away, offering thrilling water attractions and entertainment for all ages.

Nightlife

In Oakland, the Chicago Theatre offers a romantic and cultural experience just 8.0km away, perfect for live performances. Film Row Cinema, 4.8km away, combines family fun with cinematic thrills. For adventure seekers, Amazing Chicago's Funhouse Maze, also 8.0km away, promises excitement for all ages.

*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 prices are lower. Mondays are typically the cheapest days to stay, while Saturdays are the most expensive. Use Expedia's search tool to compare hotel rates, find eco-friendly options, and book package deals that combine flights and activities for additional savings. Additionally, take advantage of free activities and affordable public transport to explore the city without breaking the bank. Walking is also a great way to enjoy Oakland’s attractions while saving on transportation costs.

  • 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: Expedia's search tool enables you to choose your budget, desired location, and additional preferences. You can easily sort your results to display hotels from the lowest to the highest price, allowing you to find the most affordable options first. Additionally, you have the ability to refine your search by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are available for booking.
  • Consider bundling your trip: You can save money by combining your hotel stay in Oakland with your flights and activities through an Expedia package deal.

Find the best attractions near Oakland

Oakland offers a delightful mix of attractions perfect for family and city-themed vacations. Visitors can explore urban parks, historic houses, and historic college universities, making it an ideal destination for those seeking cultural experiences and family-friendly activities. Whether you’re interested in history or simply enjoying the vibrant city atmosphere, Oakland has something for everyone to enjoy during their stay.

  • McCormick Place: Located 3.2km from Oakland, McCormick Place is the largest convention center in North America. It boasts a dynamic business atmosphere, hosting various trade shows and events, making it a hub for networking and innovation.
  • Grant Park: Situated 6.4km from Oakland, Grant Park is a sprawling urban park perfect for families and outdoor enthusiasts. Enjoy picturesque landscapes, public art installations, and recreational activities amidst the vibrant city vibes.
  • University of Chicago: Just 3.2km from Oakland, the University of Chicago is renowned for its stunning Gothic architecture and rich academic history. Wander through its beautiful campus and soak in the cultural ambiance that has inspired many great minds.

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

Traveling to Oakland, Chicago, is convenient with access to three major airports. Chicago O'Hare International Airport (ORD) is 30.6km away, with nearby accommodations such as the 4.5-star Loews Chicago O'Hare Hotel and Hyatt Regency O'Hare, both just 3.2km from the airport. Midway International Airport (MDW) is 12.9km from Oakland, offering luxurious options like the 5-star Nobu Hotel Chicago, located 12.9km away. Lastly, Chicago Executive Airport (PWK) is 40.2km distant, featuring hotels like the 4.5-star Deer Path Inn, 16.1km away. All these hotels provide various transportation services for easy airport access.

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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 5 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.