Book the best 5 Star Luxury Hotels in Chicago

Top 5-Star Hotels in Chicago – VIP Perks & Luxury Experiences

Chicago is appealing in many ways, but its bold architecture, vibrant neighborhoods, and sumptuous food make it quite a draw. From shopping on the Magnificent Mile to coasting boat rides along the Chicago River, it's the perfect place for a comfortable and memorable stay. You could be here for business, art, or the views. Whatever the case, Chicago's best five-star hotels offer quality spacious spaces and the service to match.

You can enjoy the scenes and many perks when you book with PrivateUpgrades, which comes with access to exclusive travel benefits at leading luxury hotels in Chicago. That includes free suite upgrades, daily breakfast, a 100 USD hotel credit to explore more amenities, and personalized service each time you stay.

Book now with PrivateUpgrades to access and enjoy all these perks and more!

VIP Perks at the Best 5-Star Hotels in Chicago

When you book through PrivateUpgrades, you get these amazing benefits throughout your stay.

• Complimentary Suite and Room Upgrades – Constant upgrades to boost your views, provide more space, or premium categories when available
• Daily Breakfast for Two – Begin every morning with a full, free breakfast at the hotel’s restaurant
• 100 Dollar Hotel Credit – Spend it on quality dining experiences, in-room services, or spa treatments.
• Early Check-in and Late Check-out – Flexible arrival and departure times for a convenient schedule.
• Special Member Promotions – Seasonal and promotional offers, extra nights to your stay, and not available elsewhere.
• Personal Travel Support – Expert hands to help you choose hotels and book, all tailored to your experience.

See exclusive Hotel Offers in Chicago

Where to Stay – Chicago’s Best Luxury Hotels & Resorts

• The Loop and Millennium Park – Stay close to popular attractions, such as the Art Institute and Cloud Gate. While The Loop itself has few luxury options on PrivateUpgrades, The Peninsula Chicago is nearby and offers refined service, an indoor pool, and spacious rooms just a short walk from the park.
• Magnificent Mile and River North – Shop, dine, and appreciate the eye-catching architecture of Michigan Avenue, and the river views of The Langham Chicago. Enjoy afternoon tea and a serene wellness floor steps away from the city’s energy.
• Gold Coast – This is another historic area offering quieter streets, classic charm, and access to Oak Street Beach. Stay at Waldorf Astoria Chicago and enjoy larger suites, marble bathrooms, and spa treatments on-site.
• West Loop and Fulton Market – Known for modern restaurants, galleries, and converted warehouses, it's the perfect destination for a more modern and local vibe. It's ideal for a boutique hotel stay and doubles as a place food lovers will enjoy.
• Lakefront and Streeterville – Stay by the water for a natural feel near Navy Pier and the lakefront trails. A suitable location for travelers who want beautiful views, fresh air, and fast access to the beach or a jog by the lake.

Top 5 Luxury Hotels in Chicago You Can Book with PrivateUpgrades

• Waldorf Astoria Chicago – Features include spacious suites, a full spa with modern equipment, and private terraces in the Gold Coast.
• The Langham Chicago – Set in a landmark Mies van der Rohe building, it's an excellent location with sweeping river views and a luxury wellness club.
• Park Hyatt Chicago – Just off the Magnificent Mile, get ready to stay in stylish rooms and a rooftop terrace overlooking the famous Lake Michigan.
• The Peninsula Chicago – Classic Chicago elegance equipped with the latest features, such as a rooftop spa, indoor pool, and much larger suites just off the Magnificent Mile.
• The Ritz-Carlton Chicago – Rich lakefront location boasts a modern fitness center, expansive views, and direct access to premier shopping and dining.

Luxury Experiences in Chicago

• Lake View Suites and Rooftop Cocktails – Admire the mesmerizing skyline and lake views from the comfort of your private balcony or rooftop lounge.
• Private Architecture Boat Tours – Cruise the river with your guide offering unique directions to help you see the city from a new angle.
• Wellness and Spa Days – Recharge at convenient hotel spas that offer full treatments, steam rooms, and quiet lounges.
• Fine Dining in the West Loop – Book a table at one of the city's posh restaurants or order a chef’s tasting menu delivered straight to your suite.
• Art and Culture Walks – Visit amazing locations like The Art Institute and the Museum of Contemporary Art, or take a guided walk through captivating local galleries.

Find the Best Luxury Hotels in Chicago

Why Book with PrivateUpgrades?

• Exclusive Hotel Offers: Gain access to complimentary nights, privately negotiated rates, and seasonal specials offered at the top five-star hotels in Chicago.
• Handpicked Luxury Hotels: Book with confidence, as our experts have done all the homework to select the city’s finest hotels, known for their exceptional service, location, and quality.
• VIP Benefits with Every Stay: First-class treatment, including room/suite upgrades, breakfast, and hotel credit, is automatically added to every reservation.
• Expert Travel Support: Our team helps tailor your stay to your needs, providing personalized suggestions and handy support at every step.

Join for Free & Access Exclusive Chicago Hotel Offers

Frequently Asked Questions About Luxury Hotels in Chicago

What are the best five-star hotels in Chicago available through PrivateUpgrades?

The best choices include Waldorf Astoria Chicago, The Langham Chicago, and Park Hyatt Chicago.

What perks do I get when I book with PrivateUpgrades?

Benefits include free Room Upgrades, Daily Breakfast for two, a 100 USD Hotel Credit for added fun, and Flexible Check-in and Check-out. You also receive access to special offers.

Can I find hotels near the lake or with city views?

Absolutely. Hotels like The Langham and Park Hyatt Chicago offer beautiful views of the river, skyline, or Lake Michigan.

Are there spa hotels in Chicago?

Yes. You can relax in various top-tier spas, including the Waldorf Astoria Chicago, which features a full-service spa and wellness center with treatments available every day.

How do I book a hotel in Chicago with PrivateUpgrades?

Sign up for free, select your preferred hotel, and complete your booking to access all membership perks.