Hotels in Oakland

Where Skyscrapers Kiss the Shore: Discover Oakland's Urban Oasis

Discover Oakland, Chicago, a hidden gem that beautifully blends urban charm with lakeside serenity. Stroll along the picturesque shores of Lake Michigan, where stunning views of the skyline meet sandy beaches perfect for relaxation. Explore the vibrant local arts scene, featuring eclectic galleries and live music venues that reflect the neighborhood's rich cultural tapestry. Indulge in diverse culinary delights, from cozy cafes to trendy restaurants. With its inviting parks and community spirit, Oakland offers a unique escape for those seeking an authentic Chicago experience, all while reveling in the beauty of nature and city life.

Discover great hotels in Oakland

Oakland offers a variety of hotel accommodations, from comfortable mid-range options to luxurious stays. You'll find popular hotels with well-appointed rooms, convenient amenities, and unique charm, making it easy to enjoy your visit to this vibrant city. Whether you're seeking a cozy retreat or a stylish getaway, there's a perfect spot for you. Here are some of the most popular hotels with our travelers in Oakland:

1. Villa Dubois Guest HouseOpens in a new window: Villa Dubois Guest House is a 2.0-star guesthouse that offers a range of sports and recreation activities both onsite and nearby. For leisure travelers seeking active experiences, this property features fitness facilities in close proximity, creating an ideal environment for those looking to stay engaged during their stay. The positive sentiments highlight its welcoming atmosphere and the accessibility of various recreational pursuits, making it a comfortable choice for guests aiming to blend relaxation with activity.
2. Mccormick Place Guest HouseOpens in a new window: Mccormick Place Guest House is a charming 3.0-star guesthouse situated near a historical district, perfect for leisure travelers interested in cultural exploration. This property stands out for its scenic views and cultural activities available nearby, providing a distinctive experience for those who appreciate the rich tapestry of local history. Review sentiments emphasize the hotel's inviting ambiance and the proximity to fascinating sites, making it a delightful choice for travelers eager to immerse themselves in the local culture.
3. Amber InnOpens in a new window: Amber Inn is a 2.0-star hotel that caters to leisure travelers. It offers a delightful dining experience with an unspecified restaurant that features breakfast options and a continental breakfast, perfect for starting your day with a satisfying meal. The property also provides entertainment options including cable television, ensuring relaxation during downtime. Guests appreciate the hotel's convenient location near a metro station, facilitating easy access to the city’s attractions, creating a comfortable and enjoyable atmosphere for travelers seeking exploration and leisure.

Top locations to stay in Oakland

Staying near McCormick Place, Grant Park, and the University of Chicago offers diverse experiences in Oakland, Chicago, Illinois. McCormick Place is ideal for business and events, while Grant Park provides scenic views and vibrant nightlife. The University of Chicago boasts cultural attractions and beautiful architecture. For first-time visitors, staying near Grant Park is best for its central location and variety of activities.

1. Near McCormick PlaceOpens in a new window: Staying close to McCormick Place puts you in the heart of Chicago's vibrant urban scene. This area offers a fantastic blend of family-friendly attractions and stunning lake views. You can explore nearby shopping options like the Chicago Place Mall and enjoy scenic walks along the waterfront. Plus, with cultural attractions such as the Chicago Theatre and Cadillac Palace Theatre nearby, there's always something exciting going on.
2. Near Grant ParkOpens in a new window: Grant Park is a green oasis in the bustling city, perfect for those who appreciate a mix of nature and urban life. You'll find beautiful landscapes and the iconic Navy Pier just a short walk away. The park is also surrounded by top-notch shopping destinations, making it a great spot to unwind and indulge in retail therapy. With cultural venues and events frequently held in the area, you’ll always have something to enjoy.
3. Near University of ChicagoOpens in a new window: The University of Chicago area is a charming neighborhood that offers a unique blend of historic architecture and urban amenities. It's a wonderful place to explore leisurely, with nearby attractions including the Chicago Museum of Science and Industry. The area is also known for its serene parks and scenic spots, providing a peaceful retreat from the city buzz while still being close to shopping and cultural experiences.

Things to do near Oakland

Oakland offers a vibrant mix of stunning beaches, serene lakes, and rolling hills, inviting travelers to explore its natural beauty. Enjoy sunset strolls along the shore, indulge in local shopping, or take part in thrilling activities like boating and hiking through lush parks. It's a diverse destination that caters to all interests!

• Navy PierOpens in a new window – Experience the lively atmosphere at Navy Pier, a vibrant jetty that stretches out into Lake Michigan. Here, you can stroll along the waterfront and take in breathtaking views of the city’s iconic skyline. Enjoy a variety of attractions like the Ferris wheel, which offers stunning panoramas, or grab a bite to eat at one of the many restaurants overlooking the water. This is an ideal spot to relax on the beach, take a leisurely walk, or simply soak up the sun while enjoying the lively ambiance.
• Michigan AvenueOpens in a new window – Walk down Michigan Avenue, the bustling thoroughfare known for its impressive skyscrapers and vibrant energy. Dive into a shopping spree at some of the city’s best stores, or explore the unique architecture that lines the street. With a backdrop of beautiful lake views, it’s a perfect place to capture memorable photos. Don’t forget to pause and enjoy the local street performances that often take place, adding to the lively atmosphere of this iconic avenue.

5 tips for savvy savings when booking a hotel in Oakland

1. Book for the cheapest times: The most budget-friendly time to visit Oakland is during January, February, and December, when hotel prices tend to be lower. To truly appreciate the city's historical and cultural landmarks, it's recommended to stay for at least 2 to 3 days. This duration allows visitors to explore various attractions, including family-friendly sites, dining options, and beautiful urban scenery, as well as enjoy the stunning sunsets over the lake. By planning your trip during these months, you can experience Oakland's vibrant culture while still keeping your travel expenses in check.
2. Look for last-minute deals on Hotels.com: To discover last-minute deals to Oakland, visit the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections on Hotels.com, where you may find discounted hotel rates as your travel date approaches. Enabling email alerts or push notifications from Hotels.com can keep you informed about flash sales and special promotions, helping you take advantage of potential savings. Additionally, the Smart ShoppingOpens in a new window feature allows you to compare hotel prices and amenities, so you're more likely to find the best options available. By staying updated on price changes and availability, you can seize the opportunity for a spontaneous getaway.
3. Be flexible with dates: Prices can fluctuate based on factors like the hotel's location, star rating, and the time of year, so being flexible with your travel dates may help you save on your stay in an Oakland hotel. If you're interested in unique accommodations, boutique hotels often provide a more personalized experience and can sometimes offer better value. When you book through Hotels.com, we'll inform you if the price for your chosen dates is above or below the average. If the price is on the higher end, we’ll recommend more budget-friendly dates to help you find the best deal.
4. Consider your location: Staying closer to major attractions or city centers can be convenient, but it often comes with a higher price tag. For more budget-friendly options, you might want to look for hotels in less central areas or neighborhoods, striking a balance between cost and accessibility to the sights you want to see. Independent hotels located a bit further out are usually more likely to be affordable and can offer a more authentic experience.
5. Become a Member: Join our membership for free and start planning your next stay in Oakland! Enjoy exclusive member prices and save on over 100,000 hotels worldwide. As a member, you’ll advance through tiers quickly and unlock exciting perks, including complimentary room upgrades (when available) and discounts on food and beverages at select VIP Access properties. Don’t miss out on these fantastic benefits—sign up today!

Best time to go to Oakland

Oakland has a varied climate due to its size, so the best time to visit depends on the region and your preferences for weather and crowds. June, September, and October are the peak travel months in Oakland, attracting a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by light rainfall. On the other hand, January, November, and December tend to be quieter times to visit, marked by light rainfall and mostly sunny to mostly cloudy conditions.