Hotels in Oakland

Oakland: Where Urban Skylines Embrace Serene Shores

Nestled on the shores of Lake Michigan, Oakland, Chicago, is a hidden gem that seamlessly blends urban vibrancy with natural beauty. This picturesque neighborhood offers stunning views of the skyline and tranquil beaches, perfect for sunbathing and picnicking. Nature lovers can explore lush parks and scenic waterfront trails, while art enthusiasts will appreciate the local galleries and vibrant street murals. With its rich cultural heritage and welcoming community, Oakland invites travelers to experience a unique blend of relaxation and urban excitement, making it an ideal destination for those seeking both adventure and serenity. For the best hotel rates in Oakland and to enhance your stay, be sure to check out Hotels.com's Last-Minute DealsOpens in a new window on travel.

Top locations to stay in Oakland

Oakland, Chicago offers vibrant attractions like Michigan Avenue, Navy Pier, and Soldier Field. Michigan Avenue is perfect for first-time visitors with its shopping and cultural landmarks. Navy Pier is great for entertainment and scenic views, while Soldier Field is a must for sports fans. Accommodations near these spots range from budget-friendly options to luxury hotels, with various amenities. Room rates vary by season, making it easy to find a suitable stay for your needs. Here are some of the best hotels in Oakland that our travelers love:

1. Near Michigan AvenueOpens in a new window: For shopping enthusiasts and city explorers, staying near Michigan Avenue means you're at the heart of Chicago's vibrant retail and cultural scene. This bustling area offers easy access to top attractions, dining, and entertainment. Consider Chicago Marriott Downtown Magnificent MileOpens in a new window, a 4.0-star hotel within a mile of Michigan Avenue, perfect for adventure and business travelers alike, featuring a business center and various recreational activities nearby. Another option is InterContinental Chicago Magnificent Mile, an IHG HotelOpens in a new window, a 4.5-star property situated in a historic building that caters to families and business guests, offering meeting facilities and amenities for children. For luxury and pet-friendly accommodations, The Gwen, a Luxury Collection Hotel, Michigan Avenue ChicagoOpens in a new window is an excellent choice, boasting a business center and comfortable amenities for both leisure and business travelers.
2. Near Soldier FieldOpens in a new window: A haven for sports fans, staying near Soldier Field puts you close to one of Chicago's most iconic venues. This area is perfect for those looking to experience the excitement of live sports. Residence Inn By Marriott MerrillvilleOpens in a new window is a 3.0-star hotel that welcomes pets and provides business amenities, making it a practical choice for travelers. If you're seeking adventure, Howard Johnson by Wyndham MerrillvilleOpens in a new window offers a 2.5-star rating and features a range of recreational activities nearby, along with accessible meeting spaces. Another solid option is Quality Inn Monee I-57Opens in a new window, a 2.5-star hotel that focuses on business travelers, equipped with essential business facilities.

Things to do in Oakland for first time

Three days in Oakland offer a perfect blend of urban vibrancy and natural beauty, with stunning beaches, picturesque lakes, and rolling hills. Enjoy activities like boating, hiking, and shopping, while taking in breathtaking sunsets that enhance the city's charm, making it a memorable destination for all travelers. Here's a quick itinerary to make the most of your trip to Oakland:

• Day 1: Start your adventure on Michigan Avenue, where you can explore the iconic shopping district renowned for its upscale boutiques and department stores. Just a short walk away, visit the Holy Name Cathedral, a stunning example of Gothic architecture that invites reflection and peace. After soaking in the beauty of the cathedral, head to Water Tower Place, an impressive shopping mall where you can enjoy a variety of dining options and perhaps catch a glimpse of the Chicago skyline from its observation deck.
• Day 2: Your day begins at Navy Pier, where you can enjoy rides, attractions, and beautiful views of Lake Michigan. From there, take a leisurely stroll to the Tribune Tower, a historic skyscraper known for its unique architecture and fascinating stone collection. Finally, unwind at Ohio Street Beach, a perfect spot to relax by the water and take in the breathtaking views of the Chicago skyline as the sun sets.
• Day 3: Kick off your day at Millennium Park, an urban oasis featuring the famous Cloud Gate sculpture, also known as The Bean. Next, wander through Grant Park, often referred to as Chicago's Front Yard, where you can enjoy a peaceful walk among gardens and fountains. Conclude your day with a scenic stroll along the Chicago Riverwalk, a vibrant waterfront promenade lined with restaurants, art installations, and stunning views of the city’s architecture.

5 tips to find a great Oakland hotel deal

1. Book for the cheapest times: The most affordable time to visit Oakland is during January, February, and December, when hotel prices drop significantly. For those traveling on a budget, a stay of at least 2-3 days is recommended to fully experience the city's highlights, including its beautiful beaches, impressive skyscrapers, and scenic lake. This makes it a great value for money for anyone looking to explore the vibrant attractions of Oakland.
2. Look for last-minute deals on Hotels.com: If you're looking for last-minute deals to Oakland, you're in luck! With a bit of exploration, you could find fantastic discounts on hotels just before your travel date. To uncover these offers on Hotels.com, head to the DealsOpens in a new window or Last-Minute DealsOpens in a new window section. You may come across great prices and exclusive discounts on a variety of accommodations. Additionally, consider enabling email alerts or push notifications from Hotels.com to keep informed about flash sales and special last-minute promotions, ensuring you stay in the loop for potential savings.
3. Be flexible with dates: Hotel prices can fluctuate due to factors like the location, star rating, and the time of year. As a result, being flexible with your travel dates could help you save on hotel expenses in Oakland.
4. Consider your location: When booking your stay on Hotels.com for your holiday, keep your location in mind. Staying closer to major attractions or city centers can be convenient, but it often comes with a higher price tag. For more affordable options, consider looking for hotels in neighborhoods that are usually less central. This way, you can strike a balance between cost and easy access to the places you want to visit.
5. Upgrade with One Key: Make your next reservation in Oakland and be a part of Hotels.com's free One Key program, which enables members to take advantage of reward points for hotel bookings. Progress through the tiers of Blue, Silver, Gold and Platinum to unlock advantages like room upgrades when available, discounted rates, and exclusive offers for members. Start earning reward points now.

What to eat in Oakland

Here are some must-try dishes in Oakland, Chicago, Illinois, United States of America:

• Chicago-style hot dog: A quintessential Chicago treat, the Chicago-style hot dog is a beef frankfurter served in a poppy seed bun, topped with yellow mustard, chopped onions, sweet pickle relish, a slice of tomato, a pickle spear, and sport peppers, all without ketchup. This iconic dish symbolizes the city’s vibrant street food culture and is often enjoyed at local hot dog stands, making it a spontaneous and convenient choice for tourists and locals alike.
• Italian beef sandwich: The Italian beef sandwich is a beloved Chicago classic, featuring thinly sliced, seasoned roast beef served on an Italian roll, often topped with giardiniera (a spicy pickled vegetable mix) or sweet peppers. This flavorful sandwich is typically dipped in the savory beef juices, creating a rich, messy experience that is perfect for sharing during casual gatherings or enjoying on the go.

Best time to go to Oakland

Oakland experiences its lowest average temperature in January, at 25.7°F (-3.5°C), while July is the hottest month, with an average temperature of 73.4°F (23.0°C). June is typically the wettest month. If you’re looking to soak up the lively atmosphere in Oakland, June, September, and October are the peak months to visit, bustling with fellow travelers. During this peak period, the weather is mostly sunny, accompanied by light rainfall. However, if you prefer a more relaxed experience, January, November, and December are perfect for a quieter getaway, marked by light rainfall and mostly sunny to mostly cloudy conditions.