Why Chicago Is the Best Friend Trip You’re Not Taking

I’ll happily admit my bias towards Chicago. It’s my chosen home and has been for more than seven years, so I will take any and every opportunity to explore it with my friends. Yet, when you look up “friend trip destinations,” it rarely makes the cut. Who says Chicago doesn’t have the glamor of New York City or Los Angeles? Or the culture and cuisine of New Orleans? Don’t get me wrong, I love all of those cities too, but when it comes to blowout friend trips, there is no place like the Windy City. 

Glancing down Michigan Avenue, shop windows glisten with wares galore. Iconic brand names zip by in a flash as your eye stops. Beneath the behemoth shadows of nearby skyscrapers dwells a building unlike any other. Its 182-foot height must have been the epitome of grandeur in 1869. Today, it shrinks in comparison to all around it, yet nothing shiny and new could diminish this ornate icon. The Chicago Water Tower – an astonishing work of Gothic Revival architecture with its carefully carved limestone – survived the Great Chicago Fire of 1871. It is the oldest building on the Magnificent Mile, its second life in the Second City exemplifying why Chicago is the ideal friend trip destination. 

Like the water tower itself, friendship is an act of resilience. It’s a beautiful, delicate thing that goes through years of joy, but sometimes has to go through fire too. This building has gone through seasons upon seasons of change, just as our long-term friendships do. Whether from childhood slumber parties or undergrad all-nighters to the tumultuous times and the precious moments throughout adulthood, our friends remain just as steadfast as that water tower. 

Just a stone’s throw from the Water Tower and Fourth Presbyterian Church is the magnanimous Four Seasons Chicago. Adorned with grey marble, this gorgeous hotel is the ultimate friends’ getaway headquarters. Gold accents peak out of every corner in this chic, luxurious accommodation. From the moment you step into the lobby, you are whisked up and away for a weekend of fun. Of all the hotels I’ve stayed in in Chicago, none have had better city views. 

My friend Noelle and I were downtown to see none other than Liz Callaway do a Stephen Sondheim tribute show at The Auditorium Theatre, but before that, we spent the day enjoying some of our favorite things. We grabbed a decadent breakfast at Wildberry Pancakes & Café, wandered over to Stan’s Donuts & Coffee for a coffee fix, and meandered Michigan Ave. We stumbled across an Epic Universe Installation by Universal Studios right before hitting the Chicago River. Random pop-up events are common in this city, but I’ll stop at them every time. 

When we returned to the Four Seasons, we went straight to the pool. The hotel’s indoor pool has a massive, circular skylight that floods the space with sun — a perfect way to enjoy the sunlight without being in the unforgiving Midwestern summer heat outside. It was precisely the peaceful moment we needed before our spontaneous trip to one of our favorite places – The Lincoln Park Zoo. I make everyone visit LPZ in part because it’s the second-oldest zoo in the country (founded in 1868), and because it’s one of the last that doesn’t charge admission. 

After the zoo, we couldn’t resist a room service opportunity. As Noelle and I are both kids at heart and on our way to see a performer whose voice epitomized so much of our childhoods, we ordered dinner a la the kids’ menu — whether you’re nine or 99, a gooey grilled cheese is always a good choice. We even got little teal plastic cups adorned with circus animals with our food. It’s the little details like that that make Four Seasons properties some of my favorites.  

Even if we wanted to go out to dinner, we would not have had the time. We crammed so much into our Saturday that there wasn’t a lot of time to spare before our show. Not to worry, though, we got ice cream after the show just to round out the day. 

While our city might be known for extreme weather, sports, deep-dish, hot dogs, and The Bear, we’ve got a lot more going for us than just those things. (No shade to deep-dish or Carmy; I love you.)

When you’re in downtown Chicago, there is so much to do. First-time visitors are always so surprised at the amount of stuff you can accomplish with just a few days in the Windy City. The Four Seasons is an ideal place to call home on your vacation, plus its centralized location makes it perfect to venture forth from. Just a few minutes’ walk away, you’ve got Water Tower Place – a mall with the Broadway Playhouse Theater right beside it. For blocks and blocks onward from there, you have Chicago’s premier shopping destination – the Mag Mile. That’s more than 450 stores in total! Heck, the city has over 250 theater companies, too. You’d need lifetimes to even get to it all. 

Even if you’re like me and not much of a shopper, Michigan Avenue is home to so much more. It’s not called the Magnificent Mile for nothing! From the Tony Award-winning Lookingglass Theatre Company to Architecture River Tours, you have so many opportunities to get to know Chicago. There’s even a haunted walking tour and pub crawl. Chicago is very, very haunted. As someone with a penchant for ghost stories, I’ll always be game for a good haunted tour. Also, as someone who is always at the theater, the tragedy of the Iroquois Theatre Fire always gets me. 

Staying around Michigan Ave or not, getting around the city is a breeze. Between the buses and the L, you can zip just about anywhere without hailing a cab. You can even explore some of the non-downtown neighborhoods to get to know the city a little better. Go cafe hopping in Wicker Park, thrifting in Logan Square, studying history in Bronzeville, or grab a bite in Pilsen. Our transit system is so easy to use, even if you’re not a city person. 

That means it’s even easier to appeal to everyone’s palates when it’s time to chow down — from fanciful delights at Girl & The Goat to fondue-deliciousness at Geja’s Cafe, or dig into the simplicity of Silver Spoon Thai. A bonus is that Silver Spoon, like many Chicago restaurants, is BYOB, so you can grab some vino from Spirits & Spice Chicago at Water Tower Place and bring it with you.

Having been to many of the places people recommend for friends' trips, usually with friends, Chicago is an underrecognized commodity. Besides the luxury spaces, world-class arts scene, museums, food, and everything in between, it’s abundantly friendly. The Windy City might be a little gruff at times, but it’s still Midwestern through and through. You need help finding the Red Line? Think you passed your destination? Just ask. Rarely will you find a major metropolis as friendly as this one. 

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