New Yorkers are loyal to the core, which means other U.S. cities can be a hard sell.
But if you’re a city lover looking to spend a weekend doing NYC things outside of NYC, Chicago is the place for you! It’s even dubbed the “Second City” amongst midwesterners due to its impressive cultural attractions, vibrant food scene, and other features it shares with New York.
Now, before the hair stands on the back of your neck, hear us out: although they’re more different than not, NYC and Chicago have a surprising amount of similarities in terms of attractions and things to do.
That’s why we’re breaking down 5 reasons you shouldn’t sleep on the Second City, along with insider tips on where to stay to make the most of your eventual visit.
1. It’s home to dozens of world-class museums
If your ideal trip involves traversing a city’s museum scene, stop what you’re doing and book a flight to Chicago ASAP.
Trust us when we say Chicago is the closest it gets to NYC’s museum game on this side of the Mississippi. With both the Art Institute of Chicagoand the Field Museum ranking in the top five for their respective categories, you can’t go wrong planning a visit dedicated entirely to the city’s world-class cultural institutions.
Plus, Chicago has two legs up on NYC with its impressive Shedd Aquarium and Adler Planetarium. Both attractions feature breathtaking lakefront views and are geared towards visitors of all ages. Get up close and personal with a beluga whale at the Shedd, then come face-to-face with the cosmos at Adler Planetarium’s observatory – all on the same campus!
🏨Where to stay: Palmer House, a Hilton Hotel’s Adler Planetarium Package is the perfect way to make the most of your visit to Chicago’s many museums. Just two blocks from the Art Institute of Chicago, enjoy overnight accommodations and up to four general admission digital passes to Adler Planetarium.
2. There’s an incredible food scene
Much like New York, the Chicago food scene is wide-reaching and diverse. Spend one weekend in Chicago and you can try everything from cozy Eastern European pierogis to amazing Indian cuisine, authentic Italian beef sandwiches to some of the best soul food you’ve ever tasted…the list goes on.
And while you’ll find no shortage of mom-and-pop shops in Chicago’s many ethnic neighborhoods, there are also over 20 Michelin star restaurants to indulge in something more upscale during your trip.
Now you might be wondering, “Why would I take a trip to Chicago when I can basically eat any food I want in NYC?” To which we say, it’s good to branch out!
Every city’s food scene is different from the next due to unique, regional spins on traditional recipes, which means you have the potential to fall in love with a classic dish all over again. And remember: Chicago is more affordable, so you can try more food for less money than you would in NYC.
🏨Where to stay: For easy access to some of the best dining in Chicago, book your stay at LondonHouse Chicago, Curio Collection by Hilton. You’ll be right on the Magnificent Mile and within easy travel distance from major downtown foodie hubs.
3. You can finally settle the New York vs. Chicago-style pizza debate once and for all
Speaking of food, let’s address the elephant in the room: deep-dish pizza.
If you spend your life defending New York-style pizza but haven’t actually tried legit, Chicago-style deep-dish, you’ve got no skin in the game. By taking a trip to the Windy City and tasting deep-dish pizza on-site, you can finally defend your honor with factual evidence, and enjoy an objectively good pie in the process!
And don’t worry – if, for some reason, you do enjoy deep-dish more than New York-style, your secret’s safe with us. We’re just glad you’ll have enjoyed yourself.
🏨Where to stay: If you need to be within a few blocks of amazing pizza at all times, first of all, we understand and agree. Hilton Chicago is located on Michigan Ave. near several South Loop staples, including Lou Malnati’s and Gino’s East.
4. Its parks offer a true urban oasis
Even if you have a favorite “quiet escape” in NYC, there’s always a looming awareness of the chaos that will ensue once you’re back in the concrete jungle. Not to mention the inescapable crowds of tourists looking for the same peaceful retreat.
Chicago’s greenspace is more sprawling and less tourist-heavy than NYC’s, making it easier to get lost in nature. So if you love the vibe of an urban oasis but can’t stand the crowds that usually come with it, the Windy City’s parks are the perfect escape for you.
🏨Where to stay: The luxurious Waldorf Astoria Chicago is an excellent, centrally located choice for exploring the city’s greenspace from the picturesque Gold Coast Historic District.
5. You can experience its robust theater district
When you think of theater, Broadway most likely comes to mind. But that doesn’t mean you should sleep on the Second City’s theater district!
The Chicago Theatre District is a hub for both world-class shows and novelty productions. Visitors have access to anything from large-scale musicals to tiny, avant garde comedy works, giving you an opportunity to enjoy either big-budget productions or something more intimate in the bustling city center.
So while yes, New York theater has the upper hand in terms of prestige, Chicago institutions have more creative freedom to host diverse selections of shows. It’s definitely worth the trip if you want to experience up-and-coming productions you can’t find anywhere else.
🏨Where to stay: theWit Chicago, a Hilton Hotel is your best bet for making the most of the Chicago Theatre District. It’s located in the heart of the neighborhood, giving you doorstep access to dozens of shows!
So what are you waiting for? It’s time to find out for yourself whether Chicago really is “the Second City” after all.