Don’t get me wrong – the views from the Willis Tower are amazing, and the fireworks at Navy Pier are a sight to see, but there’s a lot more to the amazing city of Chicago worth exploring than what you’ll find in tourism brochures. After moving to Chicago two years ago and hosting visitors every month since, bringing my loved ones to The Bean and museums got old pretty quickly, so I realized it was time to get creative.
Living and working in the heart of the city, I've found more unique ways (with the help and brainpower of my awesome coworkers) to entertain my guests, and I think it’s about time I share these hidden gems. Below is a collection of distinct – yet authentically Chicago-esque – activities to enjoy on your own or with a crew. If you ever have some free time in beautiful Chicago, I highly recommend all of the activities and restaurants below.
It’s not an amazing trip if you haven’t stuffed yourself with Chicago’s best. You’ve heard about our deep dish pizza and Chicago-style hot dogs, but be sure to grab a delightful bite at one of these restaurants, all located within walking distance of the One North office.
1. Gilt Bar
Some love this spot because of the hidden speakeasy in the basement. Others are obsessed with the full bar that still allows you to bring your own bottle of wine with no corkage fee. Gilt Bar is my favorite restaurant because of the food. I have never had anything on the menu I didn’t love. Managed by Hogsalt, the same company who owns other famous joints including Au Cheval and Green Street Smoked Meats, Gilt Bar is definitely somewhere you can’t miss next time you are in town.
2. Siena Tavern
Homemade pastas and pizzas – do I need to say more? This Italian restaurant always finds itself winning awards like Best New Restaurant, Hot Spots in America and Best Event Venue. A few of my favorite items on the menu are the burrata and the butternut squash tortellacci. They also have a great outdoor patio that is a must during the summer.
3. Doc B’s
Located near all of the shopping on the Magnificent Mile, Doc B’s is a great place to stop and take a break. They have an amazing happy hour every weeknight from 4-6pm. With features like drafts and wine by the glass for $3, it’s hard to pass up. If you’re hungry, you can’t go wrong with the Grilled California Artichokes, hand-crafted salads or the Gelato Cookie Sandwiches.
Stuff for a Small Squad:
Need to keep the kids busy? Looking to treat yo’self? Trying to plan a memorable date night? Whatever the occasion, I guarantee smiles, excitement and memories with these unique activities.
1. Scavenger Hunt
If you sometimes dream about being Nicholas Cage from National Treasure, this one is for you! When purchasing the hunt on your phone, you will receive access to over 20 questions which will direct you all over downtown Chicago. Not only will this work your brain by having you solve crosswords and look for clues, but you will also get some exercise by traveling over two miles throughout the city.
2. Wrigley Field Tour
Known for its famous ivy, hand-operated scoreboard and rooftops, the Friendly Confines is a great place to learn more about Chicago. During this 90-minute tour, you'll learn fun facts to impress your friends with later.
3. Architectural Tour by Kayak
Chicago architectural tours are one of the most popular attractions for both visitors and residents, but why not make it more fun by learning the fun facts from the river? Discover what the stars and stripes mean on the Chicago Flag and learn about the clock on the Wrigley Building. If you have a few hours on a nice day, I highly recommend this activity.
Bring the Whole Crew:
It can be tough to keep big groups busy. Sure, you could go bowling, but why not think outside the box? Get creative with these Chicago activities made for parties of 10 or more, perfect for family retreats and employee bonding.
1. A Cooking Class
Ever wanted to learn how to make your own salad dressing? Or make pasta from scratch? The ladies of One North all learned this when we signed up for an awesome outing at Wooden Spoon. This three hour event allows you to choose your menu, bring your own wine and taste delicious food that you make yourself.
2. Room Escape Adventure (Zombie Included)
Voted the number one team building activity in Chicago, Room Escape Adventures challenges teams to follow clues and solve puzzles in an effort to escape the room in under an hour. Can your team do it?
Take the game of lacrosse, throw in square basketball hoops, put all of the players on bumper cars, and you’ve got Whirlyball. Whether you’re looking to escape the cold or just trying to embrace your inner child, whirlyball is bound to be a blast.
There are so many things to eat, learn and explore in Chicago. I have had a blast discovering the spots above and I hope you enjoy them as much as I have. Welcome to the Windy City!