Hotels near Oak Street Chicago

Oak Street in Chicago offers a variety of hotel accommodations, ranging from luxury options to charming boutique hotels. Visitors can find some of the best hotels just steps away from the vibrant shopping and dining scene. Room rates vary widely, catering to different budgets. Whether you're looking for modern amenities or classic elegance, the area boasts a selection of options to enhance your stay in the Windy City. Enjoy the convenience of being close to attractions and public transportation. Here are some of the best hotels near Oak Street that our travelers love:

1. The Whitehall Hotel, BW Premier CollectionOpens in a new window: This 4.0-star hotel is conveniently located within a mile from Oak Street, making it an ideal choice for travelers seeking a blend of business and boutique experiences. The hotel features uniquely designed decor and artwork, providing a stylish atmosphere. It offers essential business amenities, including a Business Center and Meeting Room, ensuring a productive stay for business travelers. Additionally, this property is pet-friendly with specific policies for small pets and service animals, catering to those traveling with furry companions.
2. Waldorf Astoria ChicagoOpens in a new window: As a luxurious 5.0-star hotel situated within a mile from Oak Street, Waldorf Astoria Chicago is perfect for families and business travelers alike. With its Art Deco design, this hotel offers a range of business amenities, including a Conference Space and accessible Business Center. Families will appreciate the child-friendly features such as free cribs and onsite babysitting services. The unique decor and artworks further enhance the inviting atmosphere, making it a memorable stay for all.
3. Thompson Chicago, by HyattOpens in a new window: Located just under a mile from Oak Street, Thompson Chicago, by Hyatt is a 4.5-star establishment that combines luxury and pet-friendly accommodations. This hotel is tailored for business travelers, featuring a Conference Space and a Business Center. The property allows pets, with specific policies for small pets and service animals, ensuring that guests can travel with their beloved companions. The elegant design and upscale amenities provide a refined experience for those looking to unwind in style while still being close to the city's attractions.

A three-day trip to Oak Street offers a delightful mix of stunning beaches and lush parks, perfect for relaxation and outdoor activities. Visitors can enjoy shopping, wildlife watching, and various water sports, all set against a backdrop of beautiful natural landscapes, making it a must-visit destination for travelers. Here's a quick itinerary to make the most of your trip to Oak Street:

• Day 1: Begin your adventure on Michigan Avenue, known for its vibrant energy and iconic shopping. As you stroll down this Magnificent Mile, take in the stunning architecture and vibrant atmosphere. Next, visit the Holy Name Cathedral, where you can appreciate the beautiful stained glass and serene ambiance. Conclude your day at Water Tower Place, an impressive shopping destination offering a variety of stores, restaurants, and even an observatory to enjoy the city skyline.
• Day 2: Start your day at Navy Pier, a bustling hub of entertainment and dining. Enjoy a ride on the Ferris wheel for fantastic views of Lake Michigan. Afterward, head to Ohio Street Beach, where you can unwind on the sandy shores or take a refreshing swim. Wrap up your day by visiting the Ronald McDonald House near Lurie Children’s, a place dedicated to supporting families with children in need of medical care, where you can learn about their impactful work.
• Day 3: Your day begins in Millennium Park, home to the famous Cloud Gate sculpture. Take your time exploring the various gardens and art installations. Afterward, stroll through Grant Park, often referred to as Chicago's Front Yard, where you can enjoy beautiful landscapes and public art. Finish your day by walking along the Chicago Riverwalk, a scenic area lined with restaurants and pathways, offering stunning views of the city and a perfect place to relax as the sun sets.

1. Book for the cheapest times: The most affordable time to visit Oak Street is during January, February, and December, when hotel prices drop significantly. For a budget-friendly getaway, a stay of at least 2-3 days is recommended to fully enjoy the area’s main attractions, including the beautiful beach. This timing offers great value for money, making it an ideal choice for those traveling on a budget.
2. Look for last-minute deals on Hotels.com: For travelers seeking spontaneous adventures, last-minute deals to Oak Street can offer fantastic savings on hotel stays. To explore these offers on Hotels.com, head to the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections, where you might find discounted rates just before your trip. You could also enable email alerts or push notifications to keep informed about flash sales and exclusive promotions, helping you seize opportunities to save. With a variety of hotel options, reviews, and the potential for free nights, you’re more likely to find the perfect stay for your getaway.
3. Be flexible with dates: Hotel prices can fluctuate due to factors like the location, star rating, and season. As a result, being flexible with your travel dates could mean you may save on hotel expenses near Oak Street.
4. Consider your location: When booking on Hotels.com for your holiday, keep your location in mind. Staying closer to major attractions or city centers can offer convenience, but it usually tends to be more expensive. For more affordable options, consider hotels in less central areas or neighborhoods, striking a balance between cost and easy access to the places you want to visit.
5. Upgrade with One Key: Join Hotels.com's free One Key program and book your next stay near Oak Street. As a member, you can earn and use rewards points for hotel bookings. Progress through Blue, Silver, Gold and Platinum tiers to unlock various benefits like room upgrades when available, special discounts, and exclusive deals for members. Sign up today.

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.