Top 10 Things to Do in Chicago

No matter what kind of holiday atmosphere you want to roll with, the Windy City can make it happen.

Whether it’s a break filled with famous sites like the Bean, the Picasso structure or Navy Pier, or a quieter trip to cooler parts of the city like North Side Andersonville, Chicago makes for a good time.

But with so much on offer, where to start? Be sure to listen to the locals. Here are 10 great ways to experience Chicago the best it can be – before you know it, you’ll be exploring the Windy City like a pro.

1. Take yourself to a ball game.

When you consider the fact that the city is home to the Chicago Cubs (at historic Wrigley Field), the Chicago White Sox (MLB), the Chicago Bears (NFL), the Chicago Bulls (NBA), the Chicago Sky (WNB A) is the house of With the Chicago Blackhawks (NHL), Chicago Fire FC and the Chicago Red Stars (NWSL), it’s safe to say this is a sports town.

On any given day, you’ll find a sporting event taking place, with fans filling arenas, stadiums and bars, rooting for their favorite players. Plus, Chicago is one of those rare cities with a long championship legacy, so don’t miss out on the magic of cheering on the hometown team.

Planning Advice: Tickets for big games sell out fast, so buy well in advance if there’s a particular one you want. Accommodation prices also go up at the best of times – book ahead to avoid disappointment.

2. Dive into Chicago’s cocktail scene.

gave The Violet Hour It’s said to be the birthplace of craft cocktails in Chicago, and no visit is complete without a drink at one of the city’s original speakeasies.

Look for a yellow light to mark the bar’s entrance – if the light is on, they’re open for business. Once you cross the threshold, the lights dim, and sound is heard behind soaring velvet curtains that open to reveal an upscale cocktail bar. Make sure you put your phone on silent and dress like you’re meeting a parent to ensure entry.

If you can’t get enough of Chicago’s speakeasies, add on. Drifter And Lady Bird on your list. The Drifter is located on the lower level of the famous River North. Green Door Tavern, The city’s oldest drinking hole. Find the entrance behind the bookcase on the way to the bathroom. And the best part? Vaudeville shows every hour (expect to pay cover).

The ladybird lives in the basement. Hoxtonin the West Loop. The dimly lit bar offers live music (jazz, soul and rock) from Thursday to Saturday and evokes feelings of 1960s glam.

3. Find the magic of Chicago.

A few famous magicians live in Chicago in industry, and iIt’s no wonder that the city has become the center of a growing occult scene.

In the loop, spectators can prepare for an intimate night of magic. Dennis WatkinsA third-generation mage, in Amir Palmer House Hilton — to dress well, as Cocktail attire is encouraged. If you prefer something more relaxed, head north. Chicago Magic Lounge.

In true magical fashion, the entrance is disguised – as a laundromat. A wall of washers opens up to reveal a host ready to guide you to an auditorium show or bar, where bartenders serve delicious drinks as well as sleight of hand.

Planning Advice: The Magic Lounge hosts a family matinee show every other Sunday that welcomes everyone aged five and over. Perfect for the whole family!

4. Groove to Blues and Rock

In Chicago, no genre is as popular as the blues — electric blues, to be exact. When Muddy Waters and friends plugged into their amps in the 1950s, guitar grooves reached new decibel levels. Hear it in clubs around town, e.g Legends of Buddy Guywhere the icon itself still takes the stage, or Rosa Lounge, where the vibe is a bit more down and dirty. The blues paved the way for rock and roll, so it’s no surprise that many street corner cool clubs host great indie bands.

5. Shop local in Chicago neighborhoods.

Chicago is a A collection of vibrant neighborhoods –to Truly experience the city like a local, head past the Loop, avoid Michigan Avenue and support local shops that reflect the city’s makeup.

Andersonville sits on the North Side and has Swedish roots. The Clark Street corridor between Foster and Bryn Mawr is lined with vintage shops that feature Wes Anderson voices. Wicker Park and Bucktown Localize their view Hipsters and young families.

If you head south toward Little Village, you’ll find a predominantly Mexican community that is the city’s largest shopping district. I pop Popular Commerce To buy from unique artisans and catch live imported events Mexico.

End your retail tour in Hyde Park, home of Michelle and Barack Obama (when they’re in Chicago). gave The Silver Room Essential – This black-owned store features a variety of products that champion black culture and black artisans.

6. Dine at an award-winning restaurant.

Over the years, Chicago’s reputation as a culinary destination has grown. The James Beard Awards arrived in Chicago in 2015, with plans to stay until 2027, thanks in large part to local chefs like Grant Achatz, Stephanie Izzard, Bill Kim and Carlos Gayton.

For high-end dining, head to the West Loop and take your pick of top culinary artists, beard winners and Michelin-starred chefs. Joe Flame’s RosemaryAn Italian-Croatian restaurant, one of the city’s hotspots, while Swift & Sons Power Dining fits the crowd, and Beatrix Provides an upscale brunch.

Whatever splurge you want, book it. next For their unique dining experiences.

For more low-key, budget-friendly fare, head to Athenian room I Lincoln Park For Chicken Kalamata (one tina per favorite), Oasis In the Loop (located at the back of the jewelry store) or Aguascalientes in a small village.

The best free things to do in Chicago

7. Make the most of Millennium Park.

In the vibrant heart of Chicago, Millennium Park The whimsy shines with public art. Go ahead, walk under Anish Kapoor’s Cloud Gate – aka “The Bean” – and touch its silvery smoothness. Let the human gargoyles of Jaume Plensa’s Crown Fountain shower you with water to cool off in the summer or youUnwrap a blanket from the shell of Frank Gehry’s Silver Band as the sun sets, as beautiful live music fills the twilight air.

Planning Advice: Check out the schedule of free summer concerts in Millennium Park. Jazz and world music on Mondays and Thursdays, and Classical music on Wednesday, Friday and Saturday.

8. Take a tour

Want to know all the secrets of the Windy City? Take a guided tour to uncover little-known facts and all sorts of Chicago tidbits that will help you win trivia night. Operated by River Cruises Chicago Architecture Foundation Popular with architecture enthusiasts. It now operates during the day and at sunset with indoor and outdoor seating.

If you want to explore. Chicago neighborhoods more fully, Book a tour Run by the city’s TikTok Historian. Sherman “Della” ThomasJoe makes a charming excursion with his company through Bridgeport/Stockyard, Bronzeville or Pullman/Roseland Chicago Mahogany Tour.

9. Laugh out loud at local comedy shows.

A group of pranksters began performing deliberately improvised skits in a Chicago bar half a century ago, and Voilà – Improv comedy was born. Another city Still nurtures the best in the biz, though many other improv theaters also operate with booze-fueled propositions that get audiences rocking.

The city’s 200 theaters have powerhouse drama groups such as Hollywood star-studded Steppenwolf And heaps of fringe, outrageous “off the loop” companies, e.g The neo-futurists.

How to Get Around Chicago

10. Navy Pier

Off the skyline and into the blue of Lake Michigan, half a mile long Navy Pier It is one of the most visited attractions in Chicago. Its charms revolve around cool breezes and sweet views, especially from the spinning, 196-foot-tall Ferris Wheel. Hi-tech rides, splash fountains, giant boats and greasy snacks blow the minds of youngsters.

Live music, Shakespearean theater and spectacular firework displays keep everyone else entertained. A smart renovation has included public plazas, performance spaces, art installations and free cultural events.