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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.

Ritz Carlton Hotel image
Ritz Carlton Hotel image
Planning Your Trip
What To Pack

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.

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. 

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.  

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.

Looking up at two tall buildings
Looking up at two tall buildings
Planning Your Trip
What To Reserve

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.

Ritz Carlton Hotel image
Ritz Carlton Hotel image
Planning Your Trip
Itineraries

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.