There are so many ways to experience Chicago. If you’re craving a little extravagance to brighten the colder months, here’s our advice: indulge those desires.  

Perhaps you yearn to learn about the incredible buildings that house the secrets of the city skyline? Start by booking a private tour with the Chicago Architecture Center — their knowledgeable team can even customize a tour based on your interests.

Or maybe you’d prefer to see the top sights in comfort and style with Chicago Private Tours, which will supply you with a driver, a guide and a luxury vehicle. They offer some outlines for intriguing tour ideas, but they’ll also allow you to build specific must-see stops into each itinerary. 

Take a break from your touring with lunch at The Signature Room at the 95th, which offers a wildly impressive view of the surrounding metropolis from atop a skyscraper. Next, descend one level to visit TILT at 360 Chicago, where you’ll find a unique platform that extends out, giving you a thrilling perspective of the city from directly above. 

If you’re anxious about dining in the sky, opt for Travelle, an elegant restaurant on the second floor of the Langham that dishes out skillfully crafted cuisine to suit any palate.

Saks Fifth Avenue Chicago is already world renowned for luxury fashion and salon treatment. But for an extra-special retail therapy session, treat yourself to a personal shopper to help carry your bags, or schedule a special customized appointment before or after hours. 

You can also get your fix for the finer things at the world-famous, high-end Oak Street shopping district. As you explore these streets, you’ll find some of America’s most sought-after designers, brands and boutiques, including Hermès, CHANEL, Armani, and Christian Louboutin. Simply strolling down the sidewalk is an experience of understated sophistication. 

All that shopping can be hard work. Time to relax with a spa date. In the bustling heart of Chicago, you’ll find several magnificent hotels, all of which offer on-site sanctuaries for pampering — so make sure to consider the spa when selecting the night’s accommodations. 

Recognized by Forbes Travel Guide as a five-star hotel in its list of 2021 Star Award Winners and as one of the top five hotels in America by U.S. News and World Report for 2021, The Langham offers the perfect blend of comfort, convenience and modern style, and its Chuan Spa is an oasis of tranquility. As you indulge in a Chinese-style massage and wellbeing therapy, you’ll feel your body relax and your spirit reawaken.

For a soothing massage followed by facials and mani-pedis, book a session at the Waldorf Astoria Spa after checking into your room at the hotel. Guests can enjoy most of these services in-room, but if you visit the spa itself, you can experience luxurious treatments like a hydrating seaweed body wrap.

You’ll find The Peninsula Spa on the top floor of the famous Peninsula Chicago, another Forbes 2021 Star Award Winner and U.S. News and World Report top-five hotel for 2021. After enjoying a range of massage services, dive into the massive indoor swimming pool, surrounded by floor-to-ceiling windows that offer stunning views of the city.

An architectural marvel, the Four Seasons Hotel Chicago captures the essence of downtown Chicago with its refined style and energizing ambiance. Coincidentally, it was also given five stars in Forbes’ list of 2021 Star Awards Winners. At the spa, you can arrange a personalized treatment to suit your needs and preferences. Try their signature Magnificent Mile Massage, which offers a choice of several rejuvenating essential oil blends.

Now that you’re walking on cloud nine, it’s time to grab a light bite and a cocktail before tonight’s primary entertainment. Pops for Champagne will put you in the mood for an amazing night out. Enjoy some charcuterie or caviar while sipping your way through one of the hundred bottles of champagne and sparkling wine on the menu.

Now that you’re in the right mindset, reserve a table at BLVD Steakhouse, which is inspired by the glamor and luxury of Hollywood’s Sunset Boulevard. Select one of their private dining options for a truly unforgettable experience. Once you’ve soaked it all in, take your night to the next level with Broadway in Chicago Suite Service, where you’ll have access to a full private bar and a first-class attentive waitstaff.

What a day! Chicago may not sleep, but you still have to.

Take your time with room service in bed, then start the day with another retail therapy session on the The Magnificent Mile, where you’ll find world-class shopping at everything from major department stores to designer boutiques. Fancy an extra hand? Get extra help and expert style tips from personal shoppers at Bloomingdales or Nordstrom. 

The iconic 900 North Michigan Skyscraper rises from the epicenter of the Magnificent Mile. Explore the first seven levels of the 67-story building for a unique shopping experience — if you need inspiration, just ask one of their personal stylists to help create your new look.

If you’re a fine food aficionado, stop by Eataly Chicago, a creative Italian marketplace with an exceptional offering of delicacies and wine, a culinary educational center, and a diverse slate of boutique eateries.

Please don’t shop ‘til you drop — it’s time to stop for lunch. At Private Dining by Sepia, you’ll enjoy exquisite seasonal dishes prepared by award-winning chefs in a rustic, intimate setting. Or, if you’d prefer an immersive dining experience, book a table (brunch available Friday through Sunday) at Roister. You’ll see the talented chefs preparing your food in an up-close-and-personal setting, allowing you to observe their expert techniques as delicious aromas engulf you.

Spend the rest of your afternoon at a matinee performance at the Lyric Opera of Chicago. This stunning theatre is a hybrid of Art Nouveau and Art Deco architecture, so even when there’s no action on stage, you’ll find yourself gazing around in wonder.

Continue basking in world-renowned culture at the Art Institute of Chicago, where you’ll marvel at iconic paintings by some of the world’s most celebrated artists in modern history, such as Van Gogh, Picasso, and Warhol. Book a private tour to gain a deeper appreciation for the stories behind the artworks.

It’s easy to work up an appetite while appreciating all that art and culture. Time to get dressed to the nines and book a car with Windy City Limousine so you can arrive at dinner in style. Regularly voted one of the best restaurants in the world, no luxury Chicago trip would be complete without sampling the multi-course tasting menu at Alinea. Booking ahead is absolutely essential.

Or, for a feast of the senses (as well as your palate), make a reservation at Truluck’s. The passionate staff will help you find the perfect wine pairing for the seafood-focused menu, and they’ll encourage you to be adventurous to maximize your experience. Gibson’s Steakhouse — a local favorite that’s famous for its generous portions and delightful atmosphere — is always an excellent choice, too.

Feel like switching it up from fine dining by taking things into your own hands? Try a private cooking class at The Chopping Block instead, which is perfect for passionate home cooks looking to experiment with gourmet ideas at home. The best part? You get to savor the fruits of your labor immediately.

If you’re looking to put your feet up and relax after dinner, we don’t blame you. For stogie lovers, simply browsing the extensive selection at the Biggs Mansion Cigar Lounge is a luxurious experience. Here you can puff a top-of-the-line cigar, or even secure a tour of the heritage home by booking ahead. 

Before retiring to the comfort of your room, sample the nightlight on Rush Street in the Gold Coast and toast the town. This beautiful district is home to some of Chicago’s most famous bars and upscale venues, all within easy walking distance — giving you all the makings for a memorable evening.

Even if it’s cold outside, it’s still warm on the wheel. Keep your premium experience going this morning at Navy Pier by booking a VIP Centennial Wheel gondola ride, which includes special perks like toasty heating, plush seating, and a glass-bottom for one-of-a-kind Chicago views. 

To bask in sheer opulence, wander around one of Chicago’s grandest residential 19th Century buildings: the Dreihaus Museum. Plan a private tour to learn about the landmark’s rich history as you admire impressive chandeliers, intricate furniture and jewel-studded possessions.

Lunch doesn’t get any more stylish than RL Restaurant, adjacent to Ralph Lauren’s flagship Chicago store. Feast on classic city-club cuisine, surrounded by leather chairs and portrait covered walls, while you relive the morning’s activities before you depart.

Now that you’ve experienced the finer aspects of the city, how about extending the getaway to Galena? The journey itself is part of the fun, with incredible views of the pastoral landscape as you traverse Northwest Illinois’ serene wooded hills. 

To unwind after the drive, take in a wine tasting at the picturesque Galena Cellars. Set in a charming 1840s farm granary building, this third-generation winery produces 40 wine varieties, and the Lawlor family will be only too happy to help you find your new favorite.

Ready for an elegant dinner? Peruse Goldmoor Inn’s seasonally crafted menu while you overlook the sweeping Mississippi River. You can even reserve a special seat at the Chef’s Table, where the chef and his staff will teach you about cooking techniques, show you how they prepare their ingredients, and offer samples of the evening’s specials. 

When the end of the night beckons, make your stay presidential! Originally called the Grant Hotel, Ulysses Suites offers historic, luxurious self-contained accomodations in a fitting tribute to our 18th President.

If the bed and breakfast experience is more your speed, what better place to rest for the night than one of America’s best B&Bs? This gem was voted the #1 B&B in the USA and #2 in the World by TripAdvisor in 2019 for a reason. For nearly 100 years, the four-story Jail Hill Inn served as Galena’s jailhouse. Today, it’s decorated with ornate gas fireplaces, features bubble massage tubs, and includes a wonderful reception of wine and cheese on arrival.

Those who prefer a quaint stay in the countryside will want to consider The Inn at Irish Hollow, which is located on 500 acres of picturesque, rolling hills and has been called “deliciously rustic” by the New York Times.

If you’re fantasizing about more pampering in the morning, check into Eagle Ridge Resort and Spa. In addition to traditional massage, facial and nail services, the spa offers an extended luxury body-wrap treatment — with this to look forward to, you can expect sweet dreams indeed.

Ease into the morning and leisurely prepare for your day — you’re in no hurry. An elegant lunch will be your first scheduled stop.

At Vinny Vanucchi's 'Little Italy,’ you’ll choose from a mouthwatering menu of made-from-scratch Italian dishes featuring recipes that have been handed down five generations. The cozy dining areas with traditional checkered tablecloths and imported artifacts will make you feel as though you’ve stepped into a different place and time.

Downtown on Galena’s Main Street, feel free to browse more than 125 independently owned shops and restaurants housed in original buildings from the 1800s. While you’re at it, pop into Blaum Bros. Distilling Co. to sample some top-shelf spirits. While it certainly differs from Chicago, Galena’s shopping district is home to those one-of-a-kind, bespoke artisan pieces that you can’t find anywhere else.

Does a fun-filled day among the vineyards sound more exciting? Then book a private shuttle with Galena Wine Tours. They’ll pick you up from wherever you’re staying, give you VIP access to Galena’s best wineries, and provide a luxurious wine tasting experience before returning you safely back to where you started.