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  • Writer's pictureMegan MacNee

Your Ultimate Guide to Exploring Chicago for the First Time

One of my favorite business trips this summer was to Chicago, the Windy City. While it wasn't my first visit, I hadn't been in over 20 years, so it might as well have been.


Chicago is a bustling metropolis known for its rich history, stunning architecture, and mouthwatering cuisine. If you're visiting for the first time, you're in for a treat. Here's a curated list of must-do activities that will make your first time in Chicago an unforgettable experience.


Take a Food Tour to Try the Classic Bites

First-time visitors to Chicago often have one thing on their minds: the food. Chicago is famous for its deep-dish pizza, beef sandwiches, Chicago dogs, and more but there's so much more to explore. Kickstart your culinary adventure with a food tour that takes you on a gastronomic journey through the city's diverse neighborhoods. Don't miss the chance to eat these classic bites!


There are many companies providing quality tours, but I thoroughly enjoyed my experience with Bobby's Bikes Hikes.


Go See a Game at Wrigley Field

Chicagoans are passionate about sports, and the iconic Wrigley Field is the perfect place to immerse yourself in the city's sports culture. If it's baseball season don't miss a Chicago Cubs baseball game, the electric atmosphere and camaraderie of the fans are bound to leave a lasting impression. If not, don't worry you can still take a tour of the historic park.


Architecture Boat Tour

Chicago is often referred to as the birthplace of modern architecture, and it's not hard to see why. To truly appreciate the city's architectural marvels, hop on an architecture boat tour along the Chicago River. Learn about the history and design of iconic skyscrapers like the Willis Tower (formerly known as the Sears Tower) and the John Hancock Center.


I chose this as part of my Chicago City Pass. I don't always get one when I travel but if I'm hitting enough big tourist items they can absolutely be worth it!


Discover Chicago's Premier Museums

While in Chicago, don't miss the chance to explore its renowned museums. The Field Museum offers a journey through natural history, while The Art Institute of Chicago houses iconic masterpieces. For marine enthusiasts, the Shedd Aquarium showcases captivating aquatic life. These world-class institutions provide a glimpse into the wonders of art, history, and the natural world, making them essential stops during your first visit to Chicago.


Museum tickets are another great reason to grab a City Pass.


Crime/Ghost Walking Tour

If you have a taste for the eerie and mysterious, consider joining a crime or ghost walking tour. Explore the darker side of Chicago's history as you visit haunted locations and learn about notorious criminals and unsolved mysteries that still send shivers down the spine.


Eat Your Way Through Top Chef

Chicago's culinary scene has gained worldwide recognition, and you simply can't visit without indulging in some exquisite dining experiences. Head to Girl & the Goat, an award-winning restaurant by Top Chef winner Stephanie Izard, where you'll savor inventive dishes made from locally sourced ingredients. Rose Mary, by Joe Flamm another must-visit spot and was my favorite meal in Chicago, it offers a Mediterranean-inspired menu in a charming setting.


Watch Some Improv

Chicago is the birthplace of improvisational comedy, and catching an improv show is a must-do. The city is home to renowned comedy clubs like The Second City and iO Theater, where you can witness talented comedians perform hilarious, unscripted acts that will keep you in stitches.


Explore Millennium Park and See "The Bean"

Millennium Park is an urban oasis in the heart of Chicago, offering a delightful blend of art, architecture, and nature. Stroll through the park's lush gardens, enjoy outdoor concerts, and be sure to marvel at "Cloud Gate," affectionately known as "The Bean." This iconic sculpture reflects the city's skyline and makes for an excellent photo op.


Sail or Cruise on Lake Michigan

Lake Michigan, one of the Great Lakes, provides a stunning backdrop to the Chicago skyline. To appreciate the city from a different perspective, consider taking a sailing or cruise excursion on the lake. Whether you opt for a leisurely sailboat ride or a thrilling speedboat tour, you'll be treated to breathtaking views of the city's skyline against the shimmering waters of Lake Michigan.


Making Your First Time in Chicago a Memorable Visit

Your first time in Chicago promises an array of experiences that will leave you enchanted with the city's diverse culture, remarkable architecture, and culinary delights. Whether you're exploring Millennium Park or indulging in gourmet cuisine, you'll find that the Windy City has a unique charm that's sure to captivate your heart.


So whether it's for a work trip or just another adventure, pack your bags, prepare your taste buds, and get ready to make unforgettable memories on your first time in Chicago. It's a city that will leave you longing for more, ensuring that you'll return for another adventure in the future.

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