Chicago is the perfect city for a weekend getaway. It’s a lakeside metropolis with beautiful skyscrapers to rival New York, and a thriving artistic scene. Chicago has made many significant cultural contributions over the years, not least their famous (and somewhat divisive) deep dish pizza. The huge range of cultures present in Chicago make it a vibrant and interesting place to spend a weekend, and I love that the locals are so friendly, down-to-earth and genuinely passionate about their city. Chicago holds particular appeal for luxury travelers because of the fantastic shopping and of course, a great choice of 5 star hotels to rest your head in after you’ve shopped ‘til you dropped. Here’s how to spend a luxurious weekend in Chicago, Illinois.

Weather in Chicago

Chicago is known as the windy city, so wrap up warm. When checking the forecast for your trip, remember that average temperatures don’t tell the whole story. The wind makes it feel a lot colder, so bring plenty of winter gear if you’re visiting from October – March.

For the rest of the year, I’d still advise bringing a jacket. This applies even in the summer, but keep it light so you can carry it around if you want to take it off.

Best Luxury Hotels in Chicago 

The Waldorf Astoria

Chicago’s Parisian-inspired Waldorf Astoria hotel is an excellent choice for a luxury getaway. From the moment you step through the doors and see the Chanel-inspired chandelier hanging in the lobby, you’ll know that you’ve arrived somewhere special. Each room has a fireplace as standard, which is just the ticket on those cold Chicago days, as is a dip in the indoor heated swimming pool. The Waldorf Astoria also welcomes dogs under $30lbs for a $75 charge, which is perfect if you can’t bear to part with your pooch for the weekend. 

The Peninsula 

The Peninsula is a truly exceptional hotel. It’s plush, opulent decor will charm you in an instant and the service is exemplary. The staff do everything they can to take care of your every need (and want.) Fitness fanatics love the state-of-the-art fitness centre, replete with brand new Peloton bikes and a half-Olympic swimming pool. And after all that hard work in the gym, it’d be wrong not to indulge in the champagne and chocolates in the minibar, no? If that doesn’t tickle your fancy, there are also four excellent in-house restaurants, too, from casual to upscale. 

The Peninsula is especially enchanting at Christmas. The hotel goes all-out with holiday decorations and during the winter months there’s an ice skating rink on the roof. It really is the most wonderful time of the year when you stay here. 

The Langham 

Conde Nast declared this award-winning hotel as one of the top hotels in the world, so prepare for the ultimate luxury experience. The Langham exudes class and style with its light, airy yet lavish design. With excellent facilities, five-star service and excellent restaurants that are destinations in their own right, The Langham is a fine choice of hotel for a luxurious weekend in Chicago. During the holiday season, I highly recommend that you experience their festive afternoon tea. It’s guaranteed to put you in the Christmas spirit. 

Best Restaurants in Chicago 

Alinea

You never know quite what you’re going to get at Alinea, but you always know it’ll be memorable. What will appear on your plate next is anyone’s guess, but it will definitely be innovative, expertly crafted and unlike anything you’ve eaten before. I don’t want to give away too many spoilers, as that’s all part of the fun at Chicago’s most exciting upscale restaurant. However, I will say that if inhaling your dessert from a helium balloon sounds fun to you, you’ll love this crazy place. 

Spiaggia 

Critics and customers don’t always agree, but Spiagga is beloved by both. This upscale restaurant reinvents traditional Italian desserts and dishes in the most remarkable way. If food is an art – and I think many would agree that it is – then Spiagga is an exemplary gallery. The vibe here has grown more relaxed in recent years and jeans and t-shirts are now acceptable attire to dine in… but when you have the opportunity to dress up, why not take it? This is a luxurious weekend in Chicago, after all. 

Oriole 

With two Michelin stars, an evening at Oriole will surely be one of the highlights of your luxurious weekend in Chicago. The cooking here is minimalist and the decor is informal, which sets you at ease. It’s not about fancy frills at Oriole, it’s about great quality gourmet food that makes you want to savor every bite. 

Things to do in Chicago 

Noble Art Tours 

Chicago has a fantastic art scene and one of the best ways to experience this is on a carefully curated Noble Art Tour. You can enjoy private VIP guided tours of all of the city’s artistic highlights, such as the Chicago Art Institute and the Chicago Architecture Biennial. These tours are tailored to you and you’ll learn so much more this way. 

Magnificent Mile 

The Magnificent Mile is Chicago’s premier upscale shopping area. It’s a shopping paradise for those who enjoy the finer things in life. The area is densely populated with some of the world’s best luxury department stores and boutiques, including: 

• Bloomingdales
• Saks Fifth Avenue
• Nordstorm 
• Neiman Marcus 
• Cartier
• Armani
• Chanel
• Burberry
• Saint Laurent
• Tom Ford
• Gucci
• Prada
• Jimmy Choo
• Louis Vuitton 
• Christian Louboutin
• Tiffany & Co
• Max Mara
• Omega
• Rolex 

I’d say “magnificent” is pretty apt, wouldn’t you? A luxurious weekend in Chicago is definitely not complete without a marvelling at the Magnificent Mile. 

A VIP Ride on the Centennial Wheel 

The Navy Pier’s Centennial Wheel is an iconic Chicago landmark, not to mention one of the best ways to enjoy stunning aerial views of the city. A VIP glass-bottomed gondola offers you a luxurious (and slightly hair raising, if you’re scared of heights) experience. 

Take a Helicopter Tour 

A helicopter tour is always a special experience. You can really get a unique appreciation of Chicago’s beauty as you soar across the skies. I also find that a helicopter tour helps you get the most out of the city when you’re short on time. It’s a luxurious win-win. 

A Night at the Lyric Opera 

Chicago’s lyric opera puts on spectacular shows night after night. The beautiful Art Nouveau and Art Deco building makes attending a show feel particularly lavish, and the performances will take your breath away. 

For more on US city breaks, why not check out my guides to New York, Miami and Austin?