Hotels near Oak Street Chicago

Where Waves Embrace Oak: A Coastal Haven of Adventure and Charm

Nestled along the shores of Lake Michigan, Oak Street in Chicago is a vibrant blend of urban charm and coastal relaxation. Famous for the picturesque Oak Street Beach, visitors can bask in the sun, take refreshing dips, or enjoy leisurely strolls with stunning skyline views. The nearby Magnificent Mile boasts upscale shopping and dining, making it a luxury lover’s paradise. With its mix of chic boutiques, inviting cafes, and cultural attractions, Oak Street is perfect for both romantic getaways and family adventures. Experience the best of city life and lakeside bliss in this enchanting Chicago gem.

Discover great hotels near Oak Street

Oak Street in Chicago offers a variety of hotel accommodations, from budget-friendly options to luxurious stays. You'll find comfortable rooms close to Oak Street Beach, making it easy to enjoy the sun and sand. Whether you're seeking a cozy getaway or a stylish retreat, there's a perfect fit for every traveler. Here are some of our travelers' favorite hotels near Oak Street:

1. Thompson ChicagoOpens in a new window: This elegant 4.5-star hotel offers a luxurious retreat for travelers seeking a refined experience in a vibrant urban setting. With amenities including a Business Center and Conference Space, it caters to those who appreciate convenience and comfort. The hotel’s pet-friendly policy enhances its appeal, allowing guests to enjoy their stay with their furry companions. Visitors appreciate the upscale atmosphere and thoughtful touches that elevate their experience, making it a perfect choice for those looking for a sophisticated getaway.
2. Waldorf Astoria ChicagoOpens in a new window: As a premier 5.0-star hotel, this property is a haven for adventure seekers and business travelers alike. It features a range of exciting amenities, such as accessible Business Centers, Conference Spaces, and Meeting Rooms, alongside opportunities for outdoor activities like boating, kayaking, and hiking in the nearby area. Guests are drawn to the exquisite design and upscale offerings, including curated experiences that promise an unforgettable stay. This hotel is ideal for those who desire both luxury and adventure in their travel experiences.
3. The Whitehall HotelOpens in a new window: This charming 4.0-star hotel stands out as a boutique gem, perfect for travelers who appreciate distinctive design and a welcoming atmosphere. With uniquely designed decor and artworks, it creates a memorable setting that enhances the overall experience. Business amenities such as Meeting Rooms and a Business Center cater to the needs of discerning professionals. Guests often praise the hotel's artistic flair and intimate vibe, making it an exceptional choice for those seeking a stylish and comfortable retreat in Chicago.

Things to do near Oak Street

Oak Street invites travelers to explore its stunning beaches, where sun-soaked shores meet inviting waters perfect for swimming and sunbathing. Nature enthusiasts can discover nearby parks and forests, ideal for hiking and wildlife spotting. After a day of outdoor fun, indulge in boutique shopping and lively dining options that make for a memorable getaway.

• Navy PierOpens in a new window – Experience the vibrancy of Navy Pier, a bustling jetty that stretches out into Lake Michigan. Explore its lively atmosphere, with various attractions, restaurants, and shops that make it a hub for both relaxation and excitement. Don’t miss the chance to take a ride on the iconic Ferris wheel for stunning views of the Chicago skyline and the shimmering lake. Enjoy the beaches nearby, where you can soak up the sun or take a stroll along the waterfront.
• Michigan AvenueOpens in a new window – Stroll down Michigan Avenue, known for its striking architecture and vibrant energy. This famous street offers a mix of high-end shopping, local boutiques, and dining options, making it ideal for a leisurely afternoon. Marvel at the historic buildings and vibrant public spaces, perfect for people-watching. Whether you’re grabbing a coffee or exploring art installations, Michigan Avenue is a lively spot that captures the essence of Chicago.

5 tips for savvy savings when booking a hotel near Oak Street

1. Book for the cheapest times: The most affordable time to visit Oak Street is during January, February, and December, when hotel prices are lower. For those looking to explore the area's significant landmarks, cultural sites, and historical attractions, staying for at least 2 to 3 days is recommended. This duration provides a great value for money, allowing visitors to experience shopping, dining, and family-friendly activities while enjoying the local culture. If you're on a budget, these months could offer an even better deal as prices might drop even more.
2. Look for last-minute deals on Hotels.com: To discover last-minute deals to Oak Street, 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 can keep you informed about flash sales and special promotions, helping you save money on your stay. Additionally, the Smart ShoppingOpens in a new window tool available via the app allows you to compare hotel prices and amenities, ensuring you’re more likely to see the best options. If prices drop or rooms become available, you’ll be among the first to know, making it easier to book a budget-friendly getaway.
3. Be flexible with dates: Prices may fluctuate depending on factors like the hotel's location, star rating, and the time of year. Being flexible with your travel dates could help you save on your stay near the Oak Street hotel. If you're interested in a unique experience, boutique hotels often provide a more personalized touch and may offer better value. When you book through Hotels.com, we’ll inform you if the price for your chosen dates is higher or lower than the average. If the price is on the higher end, we’ll suggest alternative dates that could help you find a better deal.
4. Consider your location: Staying near 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 at hotels in less central areas or neighborhoods, where you can find a better balance between cost and accessibility to the places you want to visit. Exploring independent hotels a bit further out can also lead to a more authentic and usually more affordable experience.
5. Become a Member: Join for free and start planning your next stay near Oak Street! As a member, you'll save on over 100,000 hotels globally with exclusive member prices. Enjoy the benefits of tier progression, including perks like complimentary room upgrades (subject to availability) and food and beverage discounts at select VIP Access properties. Don't miss out on these fantastic offers—sign up today!

What to eat near Oak Street

Here are some must-try dishes near Oak Street, Chicago, Illinois, United States of America:

• Chicago-style Hot Dog: A quintessential Chicago dish, this hot dog is served on a poppy seed bun and topped with mustard, onions, relish, a pickle spear, tomatoes, and sport peppers, but never ketchup! It’s a vibrant street food experience, often enjoyed at local stands or casual eateries, reflecting the city’s love for bold flavors and fresh ingredients.
• Italian Beef Sandwich: A Chicago specialty, this sandwich features thinly sliced beef, simmered in savory juices, and served on a crusty Italian roll. It’s typically topped with giardiniera or sweet peppers, making each bite a flavorful delight. Often enjoyed at local delis, this dish represents the city’s rich immigrant history and communal dining culture, perfect for a quick yet satisfying meal.

Best time to go to Oak Street

Oak Street 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 tends to be the wettest month. The peak travel months to visit Oak Street are June to August, which see a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by light rainfall. In contrast, January, February, and April are ideal if you're looking for a calmer vacation, marked by light rainfall and mostly sunny to mostly cloudy conditions.