This is Why Everyone is Going to Chicago

Photo of tall buildings on the Chicago river.

I couldn’t help but wonder why everyone is going to Chicago? It seemed like so many people in my sphere either had been, or are thinking about, going to Chicago…but why? After a few minutes of research, I quickly learned Chicago is the 3rd largest city in the US, in the Top 5 of “America’s Best Sports Cities”, and is home to over 20 Michelin-starred restaurants.

With SO MANY fun things to do in Chicago in a weekend, it’s no wonder why my hun and I spent three days in the Windy City. Before we left, I did extensive research to find some of the top attractions and best things to do in the Second City and oh boy… this is why everyone is going to Chicago, Illinois!

1. Chicago Walking Tours

Downtown Chicago, “aka- “The Loop” are is an incredibly walkable part of town. I was easily within a quick 10-12 minute walk from nearly everything I wanted to see. In order to take advantage of the best of the city, I highly recommend at least one of the many walking tours to get yourself oriented within the Second City.

There are walking tours for: architecture, crime, Chicago food favorites, deep dish pizza, underground donuts, and even beer! Not only will you get great exercise, but you will be highly entertained, reduce your carbon footprint, and open your capacity to learn more about the history and culture of Chicago from a local. I suspect just walking around the city is one of the top reasons why everyone is going to Chicago.

Hun and I chose a Gangsters & Ghosts Tour. We walked with a historian to learn the true tales behind Chicago’s gangster past, think: Al Capone and other notorious Chicago gangsters of the 20’s, and tragic stories to learn why Chicago is named the “Second City”. Our guide Caleb was fun, friendly, and knew the city well. We listened to stories of the booze-smuggling tunnels underneath the city, saw Capone’s favorite spots, and learned the tragic tales behind some of Chicago’s well known ghost stories. Didn’t think Chicago had ghost stories? Neither did we, until we went on this amazing walking tour.

2. The Many Ways You Can Get on a Boat

The beautiful blue-green colored Chicago river runs throughout the entire city and onto the Mississippi river. The Chicago river once flowed into Lake Michigan but was reversed after a nasty sewage spill back in the late 1800s. How one is able to reverse an entire river’s water flow is beyond me, but boating on the Chicago river is a top reason why everyone is going to Chicago.

Take your time to soak up all the Chicago river (now without sewage) has to offer. Join a friend to rent a cycleboat or retroboat. Grab a drink and sit onboard the most popular Chicago attraction – the River Architecture Cruise. My hun and I picked this tour because: 1) I love all things art and design, and 2) it is excellent for photography! What better way to visually capture the city than from the vantage point of the river? The truth is there really is no better way!

There are many other types of boat rentals at your disposal based on your travel personality, such as yachts for the glamorous, party boats for the party people, and kayaks for the adventure seekers. There’s a little something for everyone on the Chicago River and another reason why everyone is going to Chicago.

3. The Food Scene is Absolute Fire

Bon Apetite once named Chicago the “Best Restaurant City in America.” With 7,300+ restaurants, 167 breweries (the most breweries of any metropolitan area in the nation), 20+ Michelin-starred restaurants, and 40 James Beard award-winning restaurants in the Chicagoland area, you really have to try very hard to find a bad meal. So yes, food…this is why everyone is going to Chicago!

What I found from my trip is there is delicious food at every price point. Whether you’re on a budget or ready to ball out, you can do so in this foodie city. Of course, you have to try the famous Chicago staples: a hot Italian Beef sandwich (dipped, with hot peppers, of course!), a Chicago-style hot dog (do NOT alter or add ketchup), Garret’s famous popcorn (listed as one of Oprah Winfrey’s favorite things), and Chicago-style deep-dish pizza.

I could go on and on about everything, but the pizza? Oh. My. Gosh! I admit I was skeptical about eating what I perceived to be thick, artery clogging, greasy pizza, but wow, I am so glad to be proved wrong! There is something magical in the light, yet crispy buttery crust of Lou Malnati’s deep-dish pizza. Lou’s father is said to have invented the deep dish, so this is why we chose this as our go-to pizza spot. Once the sizzling, fresh out the oven pizza arrived at our table and was artfully cut by our waiter, my palette quickly confirmed it was worth the 45 minute wait. I see exactly why everyone is going to Chicago after gobbling down my first slice! The deep-dish pizza competition and debate is fierce, but you can weigh in on the debate for yourself at Lou’s, Giordano’s, Unos’, Pequod’s, or a select few other notable establishments – you can thank me later.

4. Presence of Culturally Diverse Communities

Visitors to Chicago and locals alike recommend going outside of the downtown area into one of many culturally diverse communities. Chicago has rich history dating back hundreds of years and it would be remiss to not visit the communities that helped build this city.

Need ideas? I have a few for you! There’s a strong German community near Lincoln Square, Greektown near Westside, Polish community in downtown Chicago, Italian presence in Little Italy off Taylor Street, Mexican presence in Pilsen, and a lively Chinese presence in Chinatown near Cermak Road and Wentworth Avenue.

5. The Second City Improv comedy

Offers improv comedy shows and classes. The Second City is notably tied to launching large comedic legends like Tina Fey, Bill Murray, Steve Carell and many others. The show is great for adults, with kids ages 10+ allowed with an accompanying adult. Fair warning: parental discretion is advised, as some of the content may be more suited for adults.

6. Art Institute of Chicago

Founded in 1879, the Art Institute of Chicago is one of the most respected art museums in the world. The museum has over 300,000 artworks, is the 2nd largest museum in the US, and one of the top 20 largest museums in the world. You’ll find an extensive display of American art and impressionist collections (one of the biggest collections of Impressionist and Post-Impressionist art outside the Louvre in Paris!). There is photography, textiles, sculpture, more paintings, and more. Since art is high on my list of traveling activities, I can clearly see why everyone is going to Chicago based on my experience at the Art Institute of Chicago alone!

7. Excellent Theater Productions

Why is everyone going to Chicago? Well, if you can’t make it to NY for a Broadway production, go to Chicago! From Tony award-winning & Broadway productions to independent theaters, comedy, and sketch theater to fringe theater, there are over 250+ theater companies in Chicago. Why not grab a few friends, or just yourself , and make your way downtown to catch a spectacular theater production. Not sure which theater to go to? Get started with the Chicago tourism board’s theater district guide!

8. Prohibition Era Nostalgia: The Speakeasy

During Prohibition era, Chicago speakeasies popped up as a place for locals and mobsters alike to indulge in illegal alcohol consumption. Although nowadays speakeasies are less about illegal alcohol and more about an expertly crafted cocktail from top bartenders, you can still find secret speakeasies in Chicago.

9. Music & Dance Scene

Chicago hosts over 200 professional dance companies and has been tied to influential hip-hop artists (Kanye West, Chance the Rapper, Common, Lupe Fiasco, Twista). There are Summer Dance Festivals and many other opportunities to catch a ballet or other dance performance in the city.

10. Willis Tower Skydeck

The Willis Tower Skydeck sits atop of the twelfth-tallest building in the world. It’s also the second tallest building in North America and in the Western Hemisphere. The Willis Tower boasts excellent views of the city and is an Instagram favorite. Tickets are around $28/adult and  $22/youth; and are free for kids under 3 years old. Advanced, timed tickets are required, so I highly suggest snagging a morning slot and allow extra time for the really cool, interactive walk-through Chicago highlights exhibit.

11. Sporting Events

Forbes ranked Chicago one of the “Best Sports Cities” last year, taking the number four slot. You can catch all of the major leagues: Football (Bears), Basketball (Bulls), Baseball (Cubs + White Sox); and Hockey (Blackhawks). Not to mention the iconic Wrigley Field – one of the oldest National League ballparks in the U.S. has been home to the Chicago Cubs since 1916. Catch a game for a classic baseball experience or go on a tour of Wrigley field where you can walk the dugout, field, upper deck, and mote..

12. Navy Pier

Did you know the 1st ferris wheel came to Chicago during the World’s Columbian Exposition of 1893? Named after designer George Washington Gale Ferris Jr. the wheel meant to rival the Eiffel Tower in Paris. This was the reason why everyone was going to Chicago in the late 1800s and also why everyone is going to the Navy Pier in Chicago today.

At the Navy Pier, you attend both free events and paid attractions. Have fun trying your luck at one of the carnival-style games or carnival-style rides. Take advantage of the dining, dinner cruise, public artworks, fireworks, great shopping, and more!

13. All of the Museums

I mentioned the art museum, but there are many other opportunities to explore your interests in one of Chicago’s museums. Here’s a list to get you started:

  • Museum of Science and Industry
  • Field Museum
  • Chicago History
  • Surgical Museum
  • International Museum of Surgical Science
  • Shedd Aquarium
  • Adler Planetarium – look through ancient telescopes
  • American Writers Museum

14. Insanely Good Festivals

Lastly, Chicago is home to a number of festivals. There’s the Chicago Blues Festival (FREE!), Lollapalooza, Pitchfork, Gospel Music Festival, World Music Festival, and Jazz Festival. Not into music? Try the Taste of Chicago food festival or the popular Air and Water Show.

More of a visual learner? Check out my What to do in Downtown Chicago video!

These are the many reasons why everyone is going to Chicago! Of course there’s more to do and see in the city, but use this list as a starting place to plan your perfect Chicago itinerary!


Antoinette | Frolic & Courage

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