Find hotels in Oakland, Chicago from $100

Top reasons to visit Oakland

• Outdoor Activities: Enjoy beautiful parks perfect for picnics and leisurely walks.
• Cultural Exploration: Visit historic homes and art museums for a rich cultural experience.
• Diverse Dining: Savor delicious meals at local restaurants showcasing diverse cuisines.
• Family-Friendly Fun: Oakland offers attractions that cater to families and outdoor enthusiasts.
• Varied Accommodations: Choose from modern hotels to charming bed & breakfasts for a comfortable stay.

Find great hotels near Oakland

Oakland offers a diverse selection of accommodations, from modern hotels to charming bed & breakfasts, catering to every type of traveler. Whether you seek a business-friendly environment, a pet-friendly stay, or an LGBTQIA welcoming experience, you'll find options that meet your needs. With essential amenities like air conditioning and a variety of hotel reviews to guide your choice, Oakland is sure to provide a memorable vacation experience.

• Congress Plaza Hotel: A historic gem located 4 miles from Oakland, Congress Plaza Hotel offers a unique blend of shopping and business amenities, making it an ideal choice for corporate travelers. This 3.5-star hotel features multiple meeting rooms, a fully accessible business center, and expansive conference spaces to cater to your professional needs. Nestled in the vibrant shopping district, guests can easily explore nearby boutiques and eateries after a productive day. The hotel’s classic architecture, combined with modern conveniences, ensures a comfortable stay for those seeking both leisure and business opportunities.
• Best Western Grant Park Hotel: Just 3 miles from Oakland, Best Western Grant Park Hotel is perfect for families looking for a fun-filled vacation. This family-friendly hotel offers a range of child-friendly amenities, including free cribs, window guards, and a first aid kit for peace of mind. Located in the bustling shopping district, families can enjoy easy access to local attractions and dining options. The warm atmosphere and attentive staff ensure that both parents and children feel right at home, making it an excellent choice for a memorable family getaway.
• Hyatt Regency Chicago: Experience upscale comfort at Hyatt Regency Chicago, situated 5 miles from Oakland. This eco-certified 4-star hotel is ideal for nature enthusiasts and business travelers alike. With multiple meeting rooms, an accessible business center, and conference spaces, it caters to all your professional requirements while maintaining an eco-friendly approach. The hotel’s prime location allows guests to explore the beauty of Chicago’s natural surroundings, making it a perfect blend of business and leisure. Enjoy stylish accommodations and exceptional service in a setting that prioritizes sustainability.

Where to stay near Oakland

Oakland, a vibrant neighborhood in Chicago, offers a perfect blend of family-friendly fun and urban charm. Explore its beautiful outdoor spaces, perfect for picnics and leisure walks. With its great location, you can easily venture into nearby San Francisco for a day of exploration. Experience the welcoming atmosphere filled with friendly people and enjoy the diverse vibes that make Oakland an ideal destination for both relaxation and adventure.

• Chicago: As a vibrant metropolis, Chicago is a must-visit destination for travelers seeking a blend of culture, history, and urban excitement. Nestled along the shores of Lake Michigan, the city boasts a rich array of attractions, including world-class shopping districts, bustling entertainment arenas, and renowned educational institutions. Visitors will find themselves immersed in a family-friendly atmosphere, with outdoor activities aplenty during the warmer months. Key highlights include iconic landmarks like the Willis Tower and Millennium Park, making Chicago a hub for city-themed adventures.
• Downtown Chicago: Located a mere 5 miles from Oakland, Downtown Chicago is a bustling neighborhood that pulses with energy and excitement. This area is perfect for families and outdoor enthusiasts alike, offering a wealth of shopping options, vibrant theaters, and spectacular views of the skyline. The summer months see a peak in visitors, drawn to attractions such as the Chicago Riverwalk and Navy Pier. Whether you're catching a show or exploring the local dining scene, Downtown Chicago is a lively hub for city exploration and leisure.
• North Kenwood: Just 0.6 miles from Oakland, North Kenwood offers a charming neighborhood experience with a mix of cultural and recreational opportunities. Known for its family-friendly vibe, this area invites visitors to enjoy its arts centers, educational venues, and entertainment facilities. With a backdrop of beautiful parks and access to nearby sports facilities, North Kenwood is an ideal spot for those looking to blend relaxation with adventure. Don't miss the local events at the convention center, which showcase the neighborhood's vibrant community spirit.

Things to do near Oakland

Oakland offers a variety of activities perfect for families and outdoor enthusiasts. You can enjoy arena entertainment, explore educational and recreational areas, and savor delicious meals at local restaurants. Don't miss the opportunity to visit event venues, embark on photo tours, and take advantage of outdoor seating for a relaxing experience. Whether you're here for leisure or business, Oakland has something for everyone.

Shopping

For a great shopping experience in Oakland, visit Chicago Place Mall, just 5 miles away, offering a vibrant atmosphere. Also, explore the 900 North Michigan Shops, 5 miles from Oakland, for entertainment and family-friendly vibes. Don’t miss Maxwell Street Market, only 4 miles away, for local finds and a bustling atmosphere.

Recreation

Catch a game at Wrigley Field, where the electric atmosphere and sports vibes create an unforgettable experience. For tranquility, explore Northerly Island Natural Area, perfect for relaxation and enjoying nature. Don't miss the House of Blues Chicago for lively music and entertainment, adding to your vibrant getaway.

Adventure

For adventure in Oakland, explore the Salt Creek Trail, a scenic hiking trail located 12 miles away, perfect for outdoor enthusiasts. Alternatively, head to Rainbow Falls Waterpark, situated 24 miles from Oakland, offering thrilling water attractions and family-friendly entertainment.

Nightlife

In Oakland, the Chicago Theatre offers a romantic atmosphere with cultural performances just 5 miles away. Film Row Cinema, located 3 miles from Oakland, provides a cozy movie experience. For adventure seekers, Amazing Chicago's Funhouse Maze, also 5 miles away, delivers thrilling arcade excitement.

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 accommodation prices are lower. Monday is the best day for budget stays, while Saturday tends to be the most expensive. Use Expedia to compare prices, book packages that include flights and activities, and join the One Key membership for exclusive discounts. Additionally, take advantage of Oakland’s public transport system for affordable travel, and seek out free activities like parks and local events to make the most of your visit without breaking the bank.

• 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 preferences, such as your budget, desired location, and preferred hotel type. To find the best prices and deals, arrange the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your Oakland hotel reservation with your flights and activities through an Expedia package.
• Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Oakland

Oakland is perfect for family, outdoor, and business-themed vacations, offering a range of attractions. Visitors can explore urban parks, historic houses, and art museums, catering to those seeking culture and a vibrant city experience. Whether you're traveling with family or looking to immerse yourself in local history and art, Oakland has something for everyone.

• McCormick Place: A premier event and conference venue located 2 miles from Oakland, McCormick Place offers a bustling atmosphere ideal for business travelers and professionals. With its state-of-the-art facilities, it hosts a variety of trade shows and conventions, making it a hub of innovation and networking.
• Grant Park: Situated 4 miles from Oakland, Grant Park is a sprawling urban oasis perfect for families and outdoor enthusiasts. Enjoy beautiful landscapes, recreational activities, and cultural events, all while soaking in the vibrant city vibes of Chicago.
• University of Chicago: Just 2 miles from Oakland, the University of Chicago boasts stunning architecture and rich history. Explore its beautiful campus, engage with cultural institutions, and soak up the scholarly atmosphere that this historic university offers.

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.

The nearest major airports for your trip to Oakland

Traveling to Oakland, Chicago, offers convenient access via two major airports. Chicago O'Hare International Airport (ORD) is located 19 miles away, with nearby accommodations such as the Loews Chicago O'Hare Hotel and Hyatt Regency O'Hare Chicago, both within 2 miles. Meanwhile, Midway International Airport (MDW) is closer at 8 miles, featuring luxury options like the Trump International Hotel & Tower Chicago and Nobu Hotel Chicago, both around 8-9 miles away. For those considering Chicago Executive Airport (PWK), it sits 25 miles from Oakland, with comfortable stays available at the Hilton Chicago/Northbrook, just 1 mile away. Each hotel offers easy transportation access to their respective airports.