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  • Writer's pictureJuliet Weller

Spotlight on...Chicago

Several years ago when a friend informed me that he and his girlfriend were going to Chicago on vacation, I rolled my eyes, scrunched my nose and said, "Chicago? Why??" Silly me. Fortunately, I've learned a thing or three since then. Chicago might not be the first place that comes to mind when you think of a vacation destination, but maybe I can change that. Turns out it's a really fun place, full of history, sights, food, activities, lore, culture, arts and architecture...all the stuff of a great vacation, right? So let's dig in.

Start your exploration during a fascinating 90-minute architectural river cruise and discover how the Great Fire of 1871 paved the way for the birth of the skyscraper. Continue your discovery with one of the Windy City's greatest highs - the 360 Chicago Observation Deck atop the former John Hancock Center. It offers breathtaking panoramic views of Chicago from 1,000 feet above the famed Magnificent Mile. The observation deck is also the home of TILT – Chicago’s highest thrill ride. What a way to start off your vacation!


Your entree to the city could be a private tour designed to hit some of Chicago’s must-see spots; a ride along Michigan Avenue and The Loop to see incredible Chicago architecture like the aforementioned Hancock building, and of course the Willis Tower (formerly known as the Sears Tower) with it’s iconic view of the city. Take a spin past Wrigley Field. Also for sports fans, the United Center (where the Bulls and the Blackhawks play) and Soldier Field (home of da Bears); the Museum of Science and Industry from the 1893 World’s Fair for history buffs, and the Navy Pier for families. If photography is your passion, one of the best photo-ops in the city is at Promontory Point.


Ready for the ultimate day out in Chicago? This tour combines two of my favorite Chicago experiences, Chicago Culture & Architecture and Classic Bites in River North for one epic Chicago adventure! Start your tour under the dazzling marquee of the Chicago Theater (you might recognize the neon sign from the movie musical Chicago), then head off into the bustling city towards the Chicago Pedway. This unique feature of Chicago is used by locals and commuters daily to move about the city in a network of underground tunnels. Once back above-ground near City Hall, stop inside to see the classic interior design and architecture, then for a sweet treat and a local tradition: Chicago-style popcorn. Stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Britannica Building and the Willis Tower.

From there, hop on the ‘L’ train or a water taxi on the Chicago River (depending on the weather and time of year). Either option offers a uniquely local Chicago experience. Take an afternoon stroll through the beautiful lakefront parks along Michigan Avenue to picturesque Millennium Park and get your photos with the Bean sculpture. You’ll have built up a good appetite by now so catch the ‘L’ train up to the River North neighborhood, the original Chicago foodie destination for any (or all) of these: Chicago-style hot dog; world-famous Chicago deep-dish pizza; and that classic Chicago sandwich, the Italian beef.


There are tours designed to hit some of Chicago's must-see TV & movie filming locations such as the action-packed Dark Knight, the 90’s classic romantic comedy My Best Friend’s Wedding, and the fantastic Ferris Bueller’s Day Off, one of my personal faves. Others: locations from the thriller The Fugitive, avoid a pileup on Lower Wacker Drive (from The Blues Brothers), see the Chicago Fire Academy, (Chicago Fire), Out in the suburbs you can find Kevin McAllister’s house from Home Alone, grab a drink at Emmit’s Pub, like Linus did in Ocean’s 11, or relive the 90’s and check out the Rainbo Club and Biograph Theatre, from High Fidelity.


The Art Institute of Chicago is one of the oldest and largest museums in the country. The gorgeous building is home to around 26,000 works, which includes an impressive collection of Impressionist and Post-Impressionist pieces of art. An art expert will guide you along to Warhol’s Four Mona Lisas, Picasso’s Old Guitarist, and other world-renowned masterpieces. Along with the art, you will learn about the museum’s history and the wealthy patrons that turned an artistic dream into a reality.

If Chicago has never been on your 'to visit' list, add it now. In fact, a 'must visit in 2021' list is in order, don't you think? I've got one going.

'til next week.


Did you miss any of my blog posts? They are all here.


I create expertly designed, transformative vacations for people who crave immersive travel. If you’re too busy to take time to plan the details of your own well-deserved escape, don't know where to begin, or are longing to make unforgettable memories with those you love, then don’t wait another day. Let's talk.

-Juliet Weller, Founder

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