Top 5 Things to do in Chicago – A Guide

April 29, 2025

Folks usually talk about New York or LA, but I feel Chicago's where the real magic is. It's a city that offers you a skyline and a beach. If you're a guest, or if you do live here and need to re-fall in love with this city, here's our Top 5 recommended Things to do in Chicago. So keep reading.

1. Eat Deep Dish Pizza (the Right Way)

Talking about things to do in Chicago, let's begin with pizza because, why not? It's Chicago! But a word of caution - not everyone does deep dishes correctly. Some are simply just tourist traps. You don't need that, right! Here's the thing: deep dish is not your regular pizza you eat every day. It's rich, it's saucy, and it'll leave you a cheese coma victim. Done well? It's heaven!

Our Suggestions -

• Pequod's (Lincoln Park) – its crust is almost legendary.- crunch-chewy in all the right places!
• Lou Malnati's – Miss at your own risk! Their farm fresh veggies are something to die for!

Pro tip: Don't have a deep dish before walking 10 blocks. You'll be sorry.

2. Walk (or Bike) the Lakefront Trail

There are not many spots on this planet where you can find yourself standing out at a large skyline, and also looking out at a beautiful lake. Chicago has that kind of magic. The Lakefront Trail circles Lake Michigan for 18 miles, and no, you don't have to bike the entire distance. Just put on your running shoes and take in the lakesite's breathtaking scenery.

What you'll notice:

• Beaches
• Boats gliding across the water
• Locals jogging, rollerblading, or taking their dog out for a stroll
• The beautiful blue skyline

3. Check out the Art Institute (Yes, Even If You "Don't Like Museums")

Let's get one thing straight: you don't have to be some art hipster to appreciate the Art Institute of Chicago. We have seen people who "don't understand art" actually getting inspired. The museum boasts some heavy-hitters such as:

• Pitchfork-inspired American Gothic, such as the farmer and his daughter
• On the Island of La Grande Jatte, a lazy Sunday afternoon
• Massive modern and contemporary art

Even the interior architecture has a full vibe. It's right in the middle of Grant Park, close to the lion statues that everyone loves. Take your time and Wander around.

4. Explore a Neighborhood That Isn't Downtown

Visiting the neighborhood is the next item on the list of things to do in Chicago. This is where Chicago becomes interesting. The city's real heart is in its neighborhoods. Every neighborhood is different, each with its own feel, character, and tiny culture. The best thing about Chicago is that it's not just one city. It's made up of 77 tiny microcities.

Places to visit-

• Pilsen: inventive tacos, colorful murals, and a thriving creative scene. Don't miss Thalia Hall and the National Museum of Mexican Art.
• Andersonville: charming, walkable, and teeming with tiny stores. Ideal for a laid-back afternoon.
• Chinatown – Slurp down noodles, purchase weird snacks, and walk through the red gate with your bubble tea.

Since you are in Chicago USA, you can also visit the Lone Star State, Texas for another memorable experience. Do read - Things to Do in Austin: Your Guide to Texas’ Coolest City

5. Catch Live Music or a Community Show

Chicago is a music town. Sure, big concerts at United Center or Grant Park are lots of fun, but the real treasure is the tiny, eclectic, gritty-around-the-edges clubs.

Some of our favorites:

• The Green Mill (Uptown) – A retro-themed jazz club that was a favorite of Al Capone's back in the day. Jazz live, dark, every night - a lifetime of experience.
• Kingston Mines – Blues, baby. Two stages, nonstop, and a crowd that actually enjoys being there.
• Schubas Tavern – Larger indie bands, very cozy atmosphere, and a great burger just a hop, skip, and jump next door at Tied House.

Honorable Mentions (Because Five Isn’t Really Enough Right)

Few special mentions on the list of things to do in Chicago are as follow-

• Don't ask about the Garrett Popcorn Mix (cheese + caramel). Simply eat.
• Skydeck at Willis Tower or 360 CHICAGO – Do it for the views if you get your kicks from that head spinning skyline-high action.
• Wrigley Field The atmosphere here is electrifying, even if you're not a Cubs fan. On game day, the entire neighborhood is like a block party.

Final Thoughts

As per latest data , the travel and tourism industry in the United States is predicted to grow to $3.1 trillion by 2034. Chicago may be a bit rough around the edges but it's got heart and character at the right palace that one gradually uncovers. You may get hailed on, you may have to stand in line for pizza, you'll inevitably be mystified by the weather. But somewhere along the way between that initial view of skyline vista and your third street taco in Pilsen, you'll begin to fall in love with Chicago . This city will seep into your bones in the best possible way - It's authentic and it's brash. When it comes to things to do in Chicago, the city has plenty to offer. So wait no more, wear a sweatshirt and sunglasses, and let the city surprise you. Get in touch with us right now to reserve your unforgettable vacation to Chicago!