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Planning Your Trip

You may come to Chicago on business, but it’s likely you will find yourself exploring the city beyond the office. From the namesake windy weather and lakefront location to the walkable neighborhoods and urban beach, Chicago requires planning when it comes to packing.

Business Travel

You’ll want to be prepared for windy conditions when navigating business meetings, so here is what bring to make sure you always look buttoned-up and ready instead of windswept and unsteady.



  • A thick scarf that protects your neck and face from the Lake Michigan swirls is a vital addition to your suitcase. Those with color or pattern can enliven your business basics.
  • Layer up for Midwest weather. Men can wear a V-neck sweater over a tie and a button-down shirt under a coat, while women can button up a cardigan over a long-sleeve shirt.
  • In summer, male business travelers can still bring their signature suits but might want to reassess their footwear. Fashionable wingtips that can be worn without socks are a staple of Chicago summers.  
A city skyline is reflected in a large metal sculpture

Exploring the City

The amazing neighborhoods of this city all deserve a visit. From the upscale Magnificent Mile to the eclectic streets of Wicker Park, there are plenty of restaurants, boutiques and coffee shops that you should be ready for.  


  • For women, check out the best shopping spots on North Michigan Avenue in ankle boots with a bit of flair (like studded heels). This shoe choice is a perfect way to navigate this city without losing style points.
  • The trails along Lake Michigan are a runner’s dream. Running shoes and a beanie or ear muffs to protect against wind are a smart idea. In winter, running gloves are also a practical item.
  • Pack the ventilated light ski jacket that you would normally only bring to the slopes. When you’re trying to explore a city like Chicago, best to have coat prepared for it all.  
View across a large lake toward a city skyline

Weekend Getaway

A light, organized bag is the first step toward the perfect weekend in Chicago. Be sure to bring a few essentials so you can spend the weekend exploring and relaxing.




  • A convertible tote bag is a great idea. Whether you’re browsing shops along Magnificent Mile or picking up take-away growlers from local breweries like Half Acre Balmoral brewery, it’s best to have a bag that can carry it all.
  • The weather in this lakeside metropolis can be unpredictable, so bring light layers such as fleece cover-ups, light down jackets and silk long johns in case the temperatures drop.
  • Even if the Midwest weather won’t reciprocate, bring something bright and colorful to shine some light on a dreary day. Remember, the Chicago Cubs are the most beloved team in the area; their colors are bright red and blue.  

Don’t Forget

If you’re a golfer, bring along your clubs and golf gear. The city offers an abundance of excellent courses, including Olympia Fields to the south, where two U.S. Opens, two PGA Championships and the 2017 Women’s PGA Championship, among others, have been played, and Cantigny Golf Club in nearby Wheaton, which is often ranked among the best courses in the Midwest.  

Michelin-starred restaurants, renowned museums, private architectural tours and spa treatments are among the must-reserve experiences for a romantic couple’s getaway to Chicago, Illinois.

Dining Reservations

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Begin your dining adventures at Torali Italian – Steak at The Ritz-Carlton, Chicago. The fresh, house-made pastas and prime and dry-aged meats are served in a gilded setting rippling with Jazz Age chic; retreat to the adjacent bar or rooftop lounge for post-dinner cocktails. And be sure to reserve a table at Parachute, Chicago’s most sought-after restaurant, from a former “Top Chef” contestant, that serves inventive Korean fusion, from pork belly and baked potato bing bread to bibimbap with burdock root and ganjang.  

Day Trips

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Head one hour north to Milwaukee — this old brewery town has gone through a cultural revival in the last few years, and its downtown now boasts numerous microbreweries along with farm-to-table eateries serving local craft beers. It has also become a mecca for festivals, including Summerfest, the world’s largest music festival. Also, make sure to stop by the Harley-Davidson Museum to see the oldest-known Harley in the world.     

Museum Tickets and Cultural Sights

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Right next to The Ritz-Carlton, Chicago is the Museum of Contemporary Art, which has a permanent collection of more than 2,500 pieces of art spanning movements from the 1920s to the present and also boasts a 300-seat Wolfgang Puck café. The Field Museum is a Chicago must-see; a remnant of the World’s Fair in 1893, it is one of the largest natural history museums in the world and has exhibitions on dinosaurs and mummies. And don’t forget to go to Millennium Park to snap a photo in front of the city’s famous silver bean.   


Book a seat on the Chicago Architecture Foundation River Cruise, a top-rated experience where certified volunteer tour guides give you the history behind more than 50 buildings along the Chicago River. Then get an up-close look at the work of legendary architect Frank Lloyd Wright on walking tours of the many Chicago homes and buildings he designed. Reserve tours through the Frank Lloyd Wright Trust, which maintains five Wright-designed buildings throughout the city.

Chicago is a place where one can see the highlights during a quick weekend getaway or spend time exploring its niche offerings, from cuisine and improv comedy to architecture and art. The hotel’s experts have curated itineraries for those seeking all-encompassing and focused experiences.

24 Hours in Chicago

With so many attractions so highly concentrated in downtown Chicago, it’s very possible to experience the soul of this great American city in one day, from the top of the tallest skyscraper to the Lake Michigan shoreline, and the best of the museums, shops, restaurants and historic landmarks in between. Of course, you’ll need to make some tough decisions, like deep-dish or stuffed pizza? Jazz music or improv comedy? Or plan a second visit pronto. 


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A Culinary Tour

Chicago’s culinary scene has exploded in the past decade, leaving in its wake a tantalizing selection of top-notch eateries, restaurants and bars at seemingly every turn. The city’s trademark cuisine is a delightful mash-up of classic Midwestern comfort foods, many with an ethnic twist, and cutting-edge gastronomy prepared by award-winning chefs. 




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