Whether you're headed to iconic sites like the Bean, the Picasso structure or Navy Pier, or to quieter parts of the city like the North Side’s Andersonville, Chicago keeps the good times rolling.
But with all the experiences on offer, how do you know where to start? Listen to the locals, of course. Here are the 10 best ways to experience Chicago like those who know it best – before you know it, you'll be exploring the Windy City like a pro.
1. Attend a game
Chicago's home to the Chicago Cubs (at historic Wrigley Field) and Chicago White Sox (MLB), Chicago Bears (NFL), Chicago Bulls (NBA), Chicago Sky (WNBA), Chicago Blackhawks (NHL), Chicago Fire FC and Chicago Red Stars (NWSL) – it’s safe to say this is a sports town.
On any given day, you'll find a sporting event happening, with fans filling up arenas, stadiums and bars and rooting for their favorite players.Plus, Chicago is one of the rare cities with a long legacy of championships, so don't miss out on the magic—and maybe even the disappointment—of cheering on the hometown team.
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2. Dive into Chicago’s cocktail scene
The Violet Hour is 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 are open for business. Once you cross the threshold, the lights dim, and sound hushes behind towering velvet curtains that open to reveal an upscale cocktail bar. Be sure to keep your phone on silent and dress as if you’re meeting the parents to ensure admittance.
If you can’t get enough of Chicago’s speakeasies, add The Drifter and Lady Bird to your list. The Drifter is located on the lower level of River North’s iconic Green Door Tavern,the city’s oldest drinking hole. Find the entrance en route to the bathroom behind a bookshelf. And the best part? Vaudeville shows play every hour (expect to pay a cover).
Lady Bird is nestled in the basement of the Hoxton, located in the West Loop. The low-lit bar features live music (jazz, soul and rock) Thursday through Saturday and evokes feelings of 1960s glam.
The best times to visit Chicago
3. Find Chicago's magic
Four of the most prominent magicians in the industry reside in Chicago, and Midwest Magic–the world’s largest magic shop – is located in the nearby suburb of Franklin Park. It’s no wonder the city has become a hub for a burgeoning magic scene.
In the Loop, spectators can get dolled up for an intimate night of magic with Dennis Watkins, a third-generation magician, at the opulent Palmer House Hilton; dress well, as cocktail attire is encouraged. If you prefer something more laid-back, head north to the Chicago Magic Lounge.
In true magical fashion, the entrance is disguised – as a laundromat. A wall of washers swings open to reveal a host ready to guide you to an auditorium show or the bar, where the bartenders serve up close-hand magic alongside delicious drinks.
4. Groove to the blues and rock
In Chicago, no genre is as iconic as the blues – the 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, such as Buddy Guy's Legends, where the icon himself still takes the stage, or Rosa's 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 cool little clubs hosting edgy indie bands slouch on many a street corner.
5. Shop local in Chicago neighborhoods
Chicago is a collection of vibrant neighborhoods– to really experience the city like a local, leave the Loop, avoid Michigan Avenue and support local shops that reflect the city’s make-up.
Andersonville sits on the North Side and has Swedish roots. The Clark Street passage between Foster and Bryn Mawr is littered with nostalgic shops that give off Wes Anderson vibes, while Wicker Park and Bucktowntailor their scene to local hipsters and young families.
If you continue south to Little Village, you'll find a predominantly Mexican community that's the city’s highest shopping district. Pop into Comercio Popular to shop from unique artisans and catch events imported straight from Mexico.
End your retail tour in Hyde Park, home to Michelle and Barack Obama (when they’re in Chicago). The Silver Room is a must – this Black-owned store features various products that place Black culture and Black artisans at the forefront.
6. Dine at award-winning restaurants
Over the years, Chicago's reputation as a culinary destination has flourished. The James Beard Awards arrived in Chicago in 2015, with plans to stick around until 2027, largely thanks to local chefs such as Grant Achatz, Stephanie Izard, Bill Kim and Carlos Gaytan.
For high-end dining, head to the West Loop and take your pick of top culinary artists, Beard winners and Michelin-starred chefs. Joe Flamm’s Rosemary, an Italian-Croatian restaurant, is one of the city’s hotspots, while Swift & Sons fits the power dining crowd, and Beatrixdelivers top-notch brunch.
For anyone looking to splurge, book a reservation at Next for their Chicago 1933 World’s Fair-inspired meal.
For more low-key, budget-friendly fare, head to the Athenian Room in Lincoln Park for the chicken kalamata (a Tina Fey favorite), Oasis in the Loop (located in the back of a jewelry shop) or Aguascalientes in Little Village.
Best free things to do in Chicago
7. Millennium Park
In the playful heart of Chicago, Millennium Park shines with whimsical 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 down in summer or unfurl a blanket by Frank Gehry's swooping silver band shell as the sun dips, when wine corks pop and gorgeous music fills the twilight air.
8. Take a tour
Want to know all the Windy City's secrets? Take a guided tour to uncover lesser-known facts and all sorts of Chicago information that will help you win Trivia Night. The river cruise run by the Chicago Architecture Foundation is popular with architecture buffs; it now runs during the day and at sunset with indoor and outdoor seating.
If you want to exploreChicago's neighborhoods more fully,book a tour run by the city’s TikTok Historian Shermann “Dilla” Thomas, who leads fascinating walks through Bridgeport/Stockyard, Bronzeville or Pullman/Roseland with his company Chicago Mahogany Tours.
What Is a Chicago-Style Hot Dog?
9. Laugh out loud at local comedy shows
A group of jokesters began performing intentionally unstructured skits in a Chicago bar a half-century ago, and voilà – improv comedy was born. Second City still nurtures the best in the biz, though several other improv theaters also work from booze-fueled suggestions that the audience hollers up.
Among the city's 200 theaters are powerhouse drama troupes such as Hollywood-star-laden Steppenwolfand heaps of fringey, provocative "off-Loop" companies, such as The Neo-Futurists.
How to get around Chicago
10. Navy Pier
Stretching away from the skyline and into the blue of Lake Michigan, the half-mile-long Navy Pier is one of Chicago’s most visited attractions. Its charms revolve around the cool breezes and sweet views, especially from the vertigo-inducing, 196ft-tall Ferris wheel. High-tech rides, splash fountains, big boats and greasy snacks blow the minds of young ones.
Live music, Shakespearean theater and whopping fireworks displays entertain everyone else. A smart renovation has added public plazas, performance spaces, art installations and free cultural programming.
FAQs
What is the number 1 attraction in Chicago? ›
Navy Pier. Chicagoans, out-of-towners and suburbanites love the downtown pier that extends into Lake Michigan. Once used by the military, it's now Chicago's largest tourist attraction. You can just walk up and down the pier, taking in skyline and lake views.
What is there to do off the beaten path in Chicago? ›- Visit Treehouse Cat Cafe. ...
- Take A Trip To Oz. ...
- Conquer Your Fear Of Heights. ...
- Check Out Woolly Mammoth Antiques And Oddities. ...
- Enjoy A Drink At The Violet Hour. ...
- View A Collection Of Miniature Rooms. ...
- Check Out The Wabash Art Corridor. ...
- Visit The World's Largest Tiffany Glass Dome.
The best sightseeing, shopping, and dining and the most interesting architecture are found in Chicago's city center, and this is where most visitors will want to stay. The city center encompasses the famous Magnificent Mile and areas of the waterfront, which are particularly popular in summer.
How many days in Chicago is enough? ›How many days do you need in Chicago? 3 to 4 days should be enough to see the top attractions in Chicago. However, depending on your interests and travel style, you can certainly spend a week in Chicago exploring the area and main tourist attractions.
Is 2 days in Chicago enough? ›Short answer – no – there is soooooo much to do and see in the city that 2 days in Chicago won't even come close to enough to see it all! However, I have found that 2 days in Chicago is definitely more than enough time to see all the highlights and to get a good introduction to the city.
How many days should I visit Chicago? ›3-5 days is enough time to visit Chicago. For seeing the top tourist attractions and exploring some different areas, 3 days in Chicago is enough, just know your days will be packed.
What is secret Chicago? ›Secret Chicago is the ultra-shareable online guide to news, events, and things to do in Chicago. From hidden bars and restaurants to fascinating museum exhibitions and how to make the most of the city, Secret Chicago highlights the very best our vibrant city has to offer.
Is Chicago Cultural Center free? ›The Chicago Cultural Center offers FREE events, performances and exhibitions year-round.
Where does the Riverwalk in Chicago start? ›The Chicago Riverwalk runs along historic Wacker Drive from Lake Michigan west to Lake Street, with access at street level from each major intersection.
Does Chicago have a cat cafe? ›Welcome to the Tree House Humane Society Cat Cafe – a place to meet cool cats, drink great coffee, and connect with friends. All the cats in our Cafe Lounge are 100% adorable and 100% adoptable! Make a reservation today–all ages welcome!
Is it better to stay in The Loop or Magnificent Mile in Chicago? ›
Should I stay in the Loop or Magnificent Mile? If you enjoy shopping, nightlife, and dining, you'll prefer staying at the Mag Mile. That way, you get to experience the vibrancy and people of Chicago. Contrastingly, if you don't fancy shopping, dining, or nightlife and prefer a quiet life, you'll enjoy the Loop.
What is the safest part of Chicago to stay in? ›What is the safest part of Chicago to stay in? The safest parts of Chicago to stay in are The Loop, Lincoln Park, Lakeview, and River North (west of The Magnificent Mile). Although it's always best to be careful no matter where in Chicago you are.
Which area is best to stay in Chicago? ›- River North, great for nightlife. ...
- Magnificent Mile, luxury area. ...
- Old Town, nice area where to stay in Chicago. ...
- Lincoln Park, good area for families. ...
- Theater District, best Chicago neighborhood for theater aficionados. ...
- Lakeview, welcoming area to stay in Chicago. ...
- Airport area.
Johnnie's Beef
The Italian beef is perhaps the most iconic sandwich in all of Chicago. Although it's hotly contested, a large chunk of people think the best one is found at Johnnie's Beef out in Elmwood Park. Order it the traditional way: Topped with spicy giardiniera or sweet peppers, and dipped in jus.
1. Chicago Deep-Dish Pizza at Lou Malnati's. If there's one Chicago food that's the best known, it's deep-dish pizza. Composed of a thick crust, zesty tomato sauce, personalized toppings and a behemoth layer of cheese, the Chicago deep-dish dares to be different.
What breakfast foods is Chicago known for? ›A proper Midwestern brunch is hearty and filling. We're in the middle of the country surrounded by farms so that means we're all about meat and potatoes. You'll see a plate of eggs –any style, your bacon, sausage, hash browns and toast or pancakes.
What is the best month to visit Chicago? ›The perfect time to visit Chicago is between either April and June or September and early November. You might prefer to visit the Windy City during other times of the year, but these are the times that appeal to most based on optimal weather, crowds, and things to do.
Is Chicago expensive to visit? ›You should plan to spend around $221 per day on your vacation in Chicago, which is the average daily price based on the expenses of other visitors. Past travelers have spent, on average, $37 on meals for one day and $29 on local transportation. Also, the average hotel price in Chicago for a couple is $305.
Is there a free trolley in Chicago? ›Navy Pier Free Trolley
Navy Pier Free Trolleys operate seasonally. Check schedules and track trolleys in real time.
- Figure out which Chicago airport is the cheapest to fly to.
- Take the L train from the airport.
- Use Chicago's public transit system to get around.
- Hop on a water taxi.
- Visit in spring or fall to save money.
- Consider staying at a hostel.
Is a weekend in Chicago enough? ›
Chicago is a vibrant city that feels very alive, and with the perfect 3 days in Chicago itinerary, it's possible to sample the best of the city in a long weekend! The city is always on the move, and there isn't an hour in the day that you won't find at least 10 unique and adventurous things going on around town.
Should you have a car in Chicago? ›No, especially if you're visiting the city just for a short while. The city's trains and buses will get you just about anywhere. In fact, a lot of people are living in Chicago without a car, relying mainly on public transport.
How do people dress in Chicago in October? ›Chicago Fall Weather
It is generally a good idea to pack a substantial jacket or coat like the shearling style we recommend in our guide as it does get cool at night, even in the early months of fall. A stylish sweater dress is a good packing choice for nice dinners out in the city.
Chicago is a large city but easy to navigate by walking, taxi, and public transportation. Plan to explore Chicago by neighborhood to cut down on transportation time and make the most of car or bike rental days.
Why is Navy Pier in Chicago famous? ›The Pier played an important role in World War I.
It soon played an important role in military preparations, housing soldiers' barracks, a Red Cross station, and even a detention center for draft dodgers. In 1927, to honor those who had served in World War I, the Pier got a new name: Navy Pier.
North Avenue Beach is one of Chicago's most popular beaches with locals and visitors alike, thanks to its spacious sands, cool beachfront bars, and convenient location near other top attractions (like the nearby Lincoln Park Zoo).
How do people get around in Chicago? ›...
Taxi
- Yellow Cab Chicago.
- Flash Cab.
- Checker Taxi Chicago.
- City Service Taxi.
- Uber.
- Lyft.
- Haunted History Tours at Lincoln Park Zoo. ...
- Reflections on 1919 with Eve L. ...
- Chicago Tech Career Fair: Exclusive Tech Hiring Event. ...
- Sweeney Todd. ...
- BHB INVEST. ...
- Comedians You Should Know (CYSK) ...
- Wednesday Night Standup Comedy at Laugh Factory Chicago.
For information about professional photography permits in the Chicago Cultural Center, contact Lara Ziemba at lziemba@mbres.com, personal photos are always allowed.
Can you eat in the Chicago Cultural Center? ›Of course you can! There is a large room w/tables on the first floor near the Randolph St entrance.
What is the culture of Chicago? ›
The culture of Chicago, Illinois is known for the invention or significant advancement of several performing arts, including improvisational comedy, house music, blues, hip hop, gospel, jazz, and soul. The city is known for its Chicago School and Prairie School architecture.
Is the Navy Pier free? ›Navy Pier is free and open to the public year-round. Before you visit, be sure to familiarize yourself with our hours and admission policies, directions, and parking information.
Is the river walk free? ›The River Walk is a public park and is free to visit.
How long does it take to do the Chicago Riverwalk? ›Explore this 2.7-mile out-and-back trail near Chicago, Illinois. Generally considered an easy route, it takes an average of 47 min to complete. This is a very popular area for running and walking, so you'll likely encounter other people while exploring.
How long is the life of a cat? › Where is the largest cat cafe? ›Give Purrs a Chance, Berkley Springs, West Virginia
The cafe is located in a huge two-story Victorian house, making it the largest cat cafe in the nation!
Chicago is home to an estimated 200,000 feral cats, and since 2007, the primary duty for managing that population has fallen to people like Mendoza.
Why is Navy Pier in Chicago famous? ›The Pier played an important role in World War I.
It soon played an important role in military preparations, housing soldiers' barracks, a Red Cross station, and even a detention center for draft dodgers. In 1927, to honor those who had served in World War I, the Pier got a new name: Navy Pier.
Visiting Chicago is absolutely worth it. Chicago has top-tier attractions, shopping, restaurants, and more. The city also offers visitors incredible city and waterfront scenery.
What is the best time to visit Chicago? ›The perfect time to visit Chicago is between either April and June or September and early November. You might prefer to visit the Windy City during other times of the year, but these are the times that appeal to most based on optimal weather, crowds, and things to do.
Why do people visit Chicago? ›
And it's a city with a legacy – its home to comedy star-maker The Second City; electrified blues (it started here!); five Tony Award-winning theaters; championship sports teams; one of the most inclusive LGBTQ+ communities in the country; the largest collection of Impressionist and Post-impressionist art outside the ...
Is Navy Pier free to get in? ›Navy Pier is free and open to the public year-round. Before you visit, be sure to familiarize yourself with our hours and admission policies, directions, and parking information. To skip the ticket lines for events and attractions, buy tickets online before you arrive.
How far is the Magnificent Mile from Navy Pier? ›How far is it from Magnificent Mile to Navy Pier? The distance between Magnificent Mile and Navy Pier is 1 miles.
Is there free parking at Navy Pier? ›There isn't any designated free parking at Navy Pier. If you're looking to save some money, you may find a cheaper garage or lot a little further away from the pier.
What is the famous street in Chicago? ›Michigan Avenue is a major thoroughfare that runs north-south through downtown Chicago. Along North Michigan Avenue – between Oak Street and the Chicago River – lies the Magnificent Mile. This 13-block stretch is home to more than 450 retailers and is one of the world's most iconic shopping districts.
What is the cheapest month to visit Chicago? ›The Quick Answer
If you want something in-between, coming in March-May or September-October means fewer crowds, average prices, and still plenty to see and do!
Short answer – no – there is soooooo much to do and see in the city that 2 days in Chicago won't even come close to enough to see it all! However, I have found that 2 days in Chicago is definitely more than enough time to see all the highlights and to get a good introduction to the city.
Is 3 days enough in Chicago? ›How many days do you need in Chicago? 3 to 4 days should be enough to see the top attractions in Chicago. However, depending on your interests and travel style, you can certainly spend a week in Chicago exploring the area and main tourist attractions.
Is New York or Chicago better? ›Based purely on statistics, New York is a much safer city than Chicago. According to a scale compiled by BetterPlaces, Chicago scored 49.9 for violent crime and 46.3 for property crime. New York, in comparison, scored 28.2 for violent crime and 24.9 for property crime.
What are people from Chicago called? ›a native or inhabitant of Chicago, Ill.
Is it worth staying in downtown Chicago? ›
The Loop. Downtown/The Loop is undoubtedly the most famous neighbourhood and the best area to stay in Chicago for first-timers. Home to the city's business district, this area of Chicago is packed with skyscrapers, lively theatres, and picturesque architectural landmarks.