Dog Friendly, 4-Star, Luxury Hotels in Oak Park IL

A premier Chicago hotel steps away from upscale shopping, fine dining, the theater district, and Millennium Park. Revitalize in one of the 520 guestrooms and 40 suites featuring unique amenities.

Staypineapple Chicago, An Iconic Hotel, is a distinguished establishment located in the heart of the Loop, offering an exceptional experience for luxury-seeking guests. Upon arrival, visitors are welcomed with refined decor, outstanding service and a range of carefully considered amenities that contribute to the hotel's esteemed reputation. Guestrooms feature a harmonious blend of modern and classic styles, with plush bedding, spacious bathrooms and numerous conveniences such as complimentary in-room coffee and tea, high-speed Wi-Fi and the exclusive Naked Experience with cozy robes and individual duvets. Guests are also invited to indulge in the exquisite culinary offerings at Atwood, the hotel's award-winning restaurant specializing in seasonal American cuisine and handcrafted cocktails. For a more relaxed dining experience, Staypineapple offers Afternoon Delights and Quick Bites & Bevvies to cater to a variety of cravings.

The Royal Sonesta Chicago River North provides a luxurious retreat in a prime location near popular attractions like Michigan Avenue, Navy Pier and Millennium Park. Guests can enjoy upscale accommodations, a heated indoor pool, rooftop sundeck and state-of-the-art fitness center. The hotel offers on-site dining at CBR, serving American cuisine and craft cocktails, and over 8,000 square feet of versatile meeting and event spaces with stunning city views. Additional amenities include an indoor heated pool, outdoor sundeck and convenient parking options, ensuring a comfortable and enjoyable stay for all.

A complete transformation of the Gold Coast's famed Ambassador East Hotel and its historic Pump Room restaurant. Its 285 spacious and oversized guest rooms and suites are individually furnished with taste and superb functionality.

A luxurious hotel situated among the tree-lined streets in the heart of Chicago. Oak Street’s boutiques, The Magnificent Mile, Lake Michigan, Museum of Contemporary Art are just a few minutes away.

An historic Chicago building filled with character, now open in downtown Chicago, just a few minutes from Mag Mile.

Α luxury hotel on the world-famous Magnificent Mile, redefining the boutique hotel experience in downtown Chicago.

The stylish Pendry offers 364 luxurious rooms and suites to choose from, all with modern amenities and features. Guests are also spoiled for choice when it comes to drinking and dining while the hotel's 24-hour fitness center is perfect for those who want to keep up with their exercise regime while away from home.

Located in the heart of the city on Michigan Avenue the hotel embraces the iconic architecture within Chicago, the redesign highlights historical elements of Louis Sullivan's intricate sketches and the Chicago School's building materials.

One of the finest historic downtown Chicago hotels offering luxury accommodations and the perfect place if you want to explore the Magnificent Mile.