Here is what to do in Chicago like a local. Milions of people visit the city every year.
The breathtaking Chicago skyline viewed from Lake Michigan
Frank Sinatra wasn’t exaggerating when he crooned, “My Kind of Town, Chicago Is.” I grew up on the South Side, and no matter how many cities I’ve explored since, Chicago pulls me back like a gravitational force. The skyline, the lake, the neighborhoods, the food – there’s a particular electricity here that you simply can’t find anywhere else. This is my personal, no-fluff guide to the best Chicago has to offer – the places I’d take my own family, the spots I’d whisper to a trusted friend, and a few gems even longtime visitors miss.
Start your planning at Choose Chicago, the city’s official visitor bureau.
How to Get from the Chicago Airport to Downtown
The O’Hare Blue Line CTA station – your fastest and cheapest ride into the city
Let me save you the headache right away: don’t take a cab unless you enjoy watching your money disappear in gridlock. Chicago’s O’Hare Airport (ORD) sits about 30 minutes from the Loop on a good traffic day – which almost never exists on I-90. The Blue Line train terminus is right inside the airport, well-signed from baggage claim. Grab a one-way ticket at a kiosk or tap your credit card and you’re on your way for a fraction of the cab fare.
Depending on your hotel, hop off at Clark/Lake or State/Lake to connect to the Red, Green, or Brown lines. Flying into Midway instead? The Orange Line runs directly downtown from there. Bookmark this CTA System Map before you land – it’s the local’s bible for getting around.
Where to Stay in Chicago
Chicago’s hotel scene is as layered as its architecture – there’s something for every budget and personality. For my money, nothing beats staying in or near the Loop. You’re a short walk from nearly everything on this list, and you can feel the pulse of the city from the moment you step outside.
The iconic Drake Hotel neon sign on Chicago’s Gold Coast
If you want atmosphere with your thread count, the historic Drake Hotel on the Gold Coast is a timeless choice – I’ve stayed there more times than I can count, and it never loses its charm.
The ornate lobby of the Blackstone Hotel – one of Chicago’s most storied historic properties
The Blackstone Hotel is equally storied with a personality all its own, and the Palmer House Hilton (covered in its own section below) rounds out the trio of great historic downtown hotels. For something more budget-conscious, chain hotels near Millennium Park put you dead center for most attractions. Aim for a location near the Chicago River or Grant Park – you’ll be halfway between the northern and southern ends of the main sights, and your feet will thank you.
How Long Should You Stay in Chicago
I’ll be blunt: four days is the minimum. Three days will leave you feeling like you barely scratched the surface. The world-class museums each deserve a solid half-day minimum, and once you add in architecture tours, lakefront time, a deep-dish dinner, and a night out, you’ll be wondering where the week went. If you want to venture beyond the downtown core – to Oak Park, Wrigley Field, the Museum of Science and Industry, or the neighborhoods – plan for five to seven days. I once spent a full week playing tourist in my own hometown and still didn’t tick everything off my list.
Things to Do in Chicago: The Downtown Loop
Cloud Gate – “The Bean” – at Millennium Park
Every Chicagoan I know has a complicated relationship with The Bean. We roll our eyes at the tourist selfie swarms, but deep down, we love it too. Millennium Park is more than its most famous sculpture – the Jay Pritzker Pavilion hosts free summer concerts under a stainless steel canopy designed by Frank Gehry, and the Crown Fountain is pure summertime joy for kids and adults alike. Come on a weekday morning to actually enjoy it. In winter, the McCormick Tribune Plaza becomes an ice rink, and it’s one of the most magical scenes in the city.
The Willis Tower dominates the Chicago skyline
I’ll always call it the Sears Tower. Always. When it was completed in 1973, this 110-story giant held the title of world’s tallest building for approximately 23 years – until the Petronas Twin Towers in Kuala Lumpur surpassed it in 1996. The Skydeck on the 103rd floor is still the most exhilarating vantage point in the city. The star attraction is The Ledge – a glass box that juts out from the building’s side, giving you an unobstructed view straight down to the street below your feet. My palms sweat every single time, and I grew up here. Go early in the morning to beat the crowds and catch the city waking up beneath you.
The John Hancock Center rising above the Magnificent Mile
If Willis Tower has The Ledge, the John Hancock Center has the view. Completed in 1969, the 100-story tower is my personal favorite skyscraper in the skyline – its X-shaped exterior bracing gives it a character that’s unmistakably Chicago. When it was built, it was briefly the tallest building outside New York City. The observation experience offers sweeping 360-degree views, and on a clear day, you can see four states. My secret tip: skip the observation deck ticket and head up to the Signature Lounge on the 96th floor – buy a drink, grab a window seat, and enjoy the same view for the price of a cocktail.
The iconic bronze lion guards at the Art Institute of Chicago
I used to walk past those bronze lion statues on my way downtown as a kid, never fully grasping what treasure lay inside. The Art Institute of Chicago is, without exaggeration, one of the finest art museums in the world. Its Impressionist collection is breathtaking – Monet’s haystacks, Seurat’s pointillist masterpiece A Sunday on La Grande Jatte, and Picasso’s The Old Guitarist all live here. Go early or close to closing time to avoid the school groups and tour buses. The Modern Wing, designed by Renzo Piano, is architecturally stunning on its own terms.
The jaw-dropping Tiffany stained glass dome inside the Chicago Cultural Center
Directly across from Millennium Park sits one of the most underrated free experiences in the city. Walk inside the Chicago Cultural Center and tilt your head back – the world’s largest Tiffany stained glass dome glows above you like a cathedral made of light. The inlaid marble throughout the building is equally stunning, and rotating exhibitions, performances, and events fill the space year-round – all without spending a dime. Most tourists walk right past it. Don’t be most tourists.
The Adler Planetarium on the Museum Campus, with Lake Michigan behind
The first planetarium in the Western Hemisphere opened in 1930 on the lakefront, and I still remember the awe I felt on my first grade school field trip here – lying back in those reclining seats as the dome filled with stars. The Adler Planetarium has evolved dramatically since then, with immersive digital sky shows and exhibits on space exploration, telescope history, and astrophysics. The outdoor terrace also happens to offer one of the best unobstructed views of the Chicago skyline you’ll find anywhere. Arrive at opening time on weekdays to have the space almost entirely to yourself.
The neoclassical Shedd Aquarium on the Museum Campus
Of the three Museum Campus institutions, the Shedd Aquarium is the one that makes me feel like a kid again every single time. Built in 1930 with five million gallons of water, it was once the largest aquarium in the world. The Caribbean Reef exhibit is mesmerizing – fish of every conceivable color drift past you as if time has slowed down. The beluga whale and dolphin shows are crowd favorites, but for me, it’s always been about wandering the quieter gallery tanks alone, watching a pair of moray eels or an ancient-looking sea turtle glide past. Get there at opening – the crowds later in the day are intense.
The grand facade of the Field Museum of Natural History
The Field Museum is where you go to be humbled by the sheer scope of human and natural history. Mummies from ancient Egypt, gemstones that make you catch your breath, cultural artifacts from six continents, and Sue – one of the largest and the most complete T. rex skeleton ever discovered at approximately 90% intact – all under one neo-Classical roof. The museum’s collection tops 40 million specimens. I always head straight to the Ancient Egypt exhibit first, then loop back to spend time with Sue. Give yourself at least three to four hours, and buy your ticket online in advance to skip the box office line.
The Chicago River flows beneath its landmark bridges
If you do only one “touristy” thing in Chicago, make it this. The Great Chicago Fire of 1871 torched the city and, in a strange way, gave the world the modern skyscraper – because architects flooded in to rebuild, experiment, and push structural boundaries. The Chicago Architecture Center runs expert-guided boat tours aboard the First Lady that cruise the Chicago River, narrating the stories behind buildings both iconic and overlooked. For pure romance, try the combination river and lake cruise at sunset:
A Wendella boat cruising the Chicago River past Marina City – one of the most scenic rides in the city
The skyline lit gold at dusk, reflected in the water, is a sight I’ve never once gotten tired of.
The vibrant Chicago Riverwalk – the city’s beloved “Second Lakefront”
Locals call it the “Second Lakefront,” and it earns the title. The Chicago Riverwalk stretches along the south bank of the Chicago River from Lake Michigan west to Lake Street, filled with open-air restaurants, kayak rentals, a Vietnam Veterans memorial, outdoor seating, and live performances in summer. I love grabbing a cold drink from one of the riverside bars and watching the architecture tour boats glide underneath the lift bridges. It’s completely free to stroll, and in the evening, the string lights and reflected skyline make it one of the most atmospheric spots in the entire city.
The legendary blues club that keeps Chicago’s musical soul alive
Chicago Blues is not a genre – it’s a birthright. Without the electric blues that took root on Chicago’s South and West Sides in the 1940s and 50s, there would be no rock and roll as we know it. Buddy Guy’s Legends Bar in the South Loop is the city’s most celebrated blues venue, owned and occasionally performed in by living legend Buddy Guy himself. The atmosphere is thick with history, the music is always scorching, and the Louisiana food on the menu is a bonus nobody tells you about. Go on a weekend night and stand as close to the stage as you can.
The iconic marquee of the Chicago Theatre on State Street
Built in 1921 for four million dollars, the Chicago Theatre is one of the most beautiful buildings in the city – and most people only ever see the outside. Step inside and you’re transported to another era of gilded excess and theatrical grandeur. In 1986, the theater was saved from demolition and fully restored to its original splendor. Today it hosts major performers from Jerry Seinfeld to Madonna. When Hamilton came through Chicago, I snagged last-minute tickets at a fraction of Broadway prices – that’s the Chicago theater advantage. Check what’s playing across the whole Theater District at Chicago-Theater.com.
Navy Pier extending into Lake Michigan
Built in 1916 and named for the WWI naval veterans, Navy Pier is Chicago’s most visited attraction – which is why locals have a love-hate relationship with it. But get past the crowds and there’s real joy here. The Ferris wheel is genuinely fun, the Chicago Shakespeare Theater is world-class, and the summer fireworks over the lake are something I’ve watched dozens of times without ever growing bored. The Children’s Museum is excellent for families. In winter, Winter WonderFest transforms the pier into a surprisingly magical holiday destination.
Michigan Avenue’s Magnificent Mile on a bright Chicago day
The Magnificent Mile runs a full mile along Michigan Avenue from Oak Street to the Chicago River, and it lives up to every syllable of its name. High-end boutiques, landmark hotels, and architectural gems line both sides of the boulevard. The Chicago Water Tower – one of the few structures to survive the Great Chicago Fire of 1871, having been built just two years prior in 1869 – stands quietly at the corner of Michigan and Chicago Avenue and now serves as an art gallery. My favorite time to walk the Mag Mile is during the Christmas holiday season, when over a million lights turn the entire boulevard into a glittering tunnel of light.
The iconic Marshall Field’s building – now Macy’s – on State Street
I refuse to call it Macy’s, and most Chicagoans feel the same way. Marshall Field’s on State Street is a civic monument dressed up as a department store. The 13-story building occupies an entire city block and features a 6,000-square-foot vaulted glass mosaic dome by Louis Comfort Tiffany – 1.6 million pieces of iridescent glass overhead while you shop. It was the first store to use escalators, the first to offer a bridal registry, and the first to provide revolving credit – now among the third-largest stores in the world. Grab lunch at the Walnut Room restaurant, especially in December when a 45-foot Christmas tree anchors the dining room. And before you leave, buy a box of Frango Mints – a Chicago institution since 1929.
The ornate lobby of the Palmer House Hilton
Even if you’re not staying at the Palmer House, you owe it to yourself to walk through the lobby. The gilded frescoed ceiling above the Empire Room bar is one of the most spectacular interior spaces in Chicago. Settle in for happy hour or afternoon tea at the Lockwood Restaurant, and absolutely order a brownie – they were invented right here in the Palmer House kitchens for the 1893 World’s Columbian Exposition, and the recipe hasn’t changed. The hotel was also the first in the city to install elevators and the first to offer electric light bulbs and telephones in guest rooms. History you can eat and drink.
Chicago-Style Deep Dish Pizza
Chicago pizza is not “pizza with extra stuff.” It’s an entirely different food category – a savory pie engineered for maximum cheese and sauce ratio. There are two camps: deep dish (open-topped, sauce on top) and stuffed (two layers of dough with cheese sandwiched inside).
A freshly baked deep dish at Pizzeria Uno – where Chicago deep dish was born
For the original deep dish, head to Pizzeria Uno or its sister Pizzeria Due – deep dish was literally invented there.
Giordano’s famous stuffed pizza – layers of dough, cheese, and sauce stacked sky-high
For stuffed pizza, Giordano’s is the gold standard, with multiple locations throughout the Loop.
A classic deep dish at Lou Malnati’s – whose legendary buttercrust has been perfected since 1943
A serious contender for best overall is Lou Malnati’s, whose buttercrust and family recipe date back to 1943. Order ahead – these pies take 45 minutes to bake properly.
Calder’s Flamingo sculpture in Federal Plaza – one of Chicago’s iconic public artworks
Chicago has been investing in public art since Picasso’s unnamed 50-foot Cor-Ten steel sculpture landed in Daley Plaza in 1967 – a gift the city didn’t quite know what to make of at first. Since then, Calder’s vivid red Flamingo, Chagall’s mosaic The Four Seasons, Miró’s Chicago, and dozens of other masterworks have turned the Loop into an open-air gallery. The South Loop around Columbia College is a dense canvas of murals and large-format street art. I recommend following the Chicago Architecture Center’s free public art map and just wandering – you’ll stumble onto something extraordinary around every corner.
Things to Do in Chicago: A Little Further Afield
The Chicago History Museum at the southern edge of Lincoln Park
At the southern tip of Lincoln Park sits a museum that’s been collecting the city’s stories since 1856. The Chicago History Museum holds a collection of roughly 22 million objects, from Mrs. O’Leary’s barn lantern – supposedly the spark of the Great Chicago Fire – to the actual L-train car from the city’s first elevated railway. Rotating exhibitions keep things fresh, and the permanent Chicago history galleries are among the most engaging in any American city museum. Sports fans: the Cubs and Bears exhibits alone are worth the trip.
The welcoming entrance to Lincoln Park Zoo
Free admission. Founded in 1868. Let that sink in. The Lincoln Park Zoo is one of the last major free-admission zoos in America, and it’s been a Chicago institution for longer than most nations have existed. I’ve been visiting since I was small enough to be carried in, and my favorites are still the same: the polar bears, the gorilla house, and the Farm-in-the-Zoo where city kids can interact with barnyard animals. The zoo sits inside Lincoln Park, about three miles north of downtown, and pairs beautifully with a bike ride on the Lakefront Trail.
North Avenue Beach with the downtown Chicago skyline behind
Chicago has 26 miles of lakefront and 24 beaches, and every neighborhood has its own favorite. Oak Street Beach is where you go to see and be seen. North Avenue Beach is where you go to actually relax. Rent a Divvy bike from any kiosk near the Drake Hotel, follow the Lakefront Trail north, and arrive at a wide, ocean liner-shaped beach house that looks like it washed ashore from Miami. The skyline views looking south from the water’s edge are the best in the city – better than any observation deck, and completely free. Paddleboards, lounge chairs, and cold drinks await.
Inside the legendary Second City theater – where comedy history is made every single night
The Second City launched the careers of Dan Aykroyd, Bill Murray, Tina Fey, Mike Myers, and Stephen Colbert – and it’s been doing it since 1959. An evening here includes sharp scripted material plus a completely improvised set based on audience suggestions, meaning no two shows are ever alike. Sitting in that room knowing you’re breathing the same air as some of the greatest comedy minds in history makes every performance feel electric. Take the Blue or Brown line to Sedgwick, and book tickets in advance – it sells out regularly.
Frank Lloyd Wright’s Home and Studio in Oak Park, Illinois
Take the Green Line west to Oak Park and step into the neighborhood that gave the world the Prairie Style of architecture. The Frank Lloyd Wright Home and Studio is where Wright lived and worked from 1889 to 1909, and it’s a masterclass in organic, human-scaled design. After the guided tour, pick up a self-guided walking map and spend an hour exploring the nearby streets – Unity Temple, the Laura Gale House, and dozens of other Wright-designed homes sit within blocks of each other. Budget half a day minimum; if you’re a design lover, plan for a full one.
The stunning greenhouse halls of the Garfield Park Conservatory
One of the largest and most beautiful conservatories in North America, the Garfield Park Conservatory is a warm, fragrant escape from a Chicago winter. Eight distinct greenhouse rooms hold everything from towering palm trees and ancient ferns to rare desert succulents. The permanent installation from glass artist Dale Chihuly – including his otherworldly Persian Lily Pads – turns the space into part museum, part garden dream. Ride the Green Line to the Conservatory-Central Park Drive stop. Admission is free most days, making it one of the finest free experiences the city offers.
The Museum of Science and Industry in Hyde Park
Worth a special trip to the South Side, the Museum of Science and Industry is one of the largest science museums in the Western Hemisphere. Where else can you descend into a full-scale replica coal mine, walk through the belly of a genuine WWII German U-boat captured in the Atlantic, and examine the Apollo 8 command module – all in the same afternoon? The interactive exhibits make this the top choice for families. My favorite seasonal event is Christmas Around the World, when 40 trees decorated by cultural groups from around the globe fill the main hall. Best reached by rideshare or taxi from downtown.
The ivy-covered outfield walls of historic Wrigley Field
There are newer, shinier baseball stadiums. There is no stadium with more soul than Wrigley Field. Built in 1914 and designated a National Historic Landmark in 2020, it sits in the heart of a residential neighborhood – no sprawling parking lots, no corporate campus, just a century-old ballpark surrounded by bars, rooftop bleachers, and a community that has grown up around its rhythms. Take the Red Line to Addison and walk one block. Even if you’re not a baseball fan, a game here on a summer afternoon – with the ivy-covered outfield walls, the hand-turned scoreboard, and the lake breeze – is one of the great American experiences.
The Green Mill – a Chicago jazz institution since 1914
If Buddy Guy’s is the throne room of Chicago Blues, the Green Mill in Uptown is its jazz equivalent – and it has considerably more criminal history. The original saloon on this site dates back to at least 1907, but the current Green Mill Gardens building was constructed in 1914 and quickly became Al Capone’s preferred Prohibition-era haunt. The original art nouveau bar curves through the space, leather booths line the walls, and live jazz fills the room every single night of the week. This is not a tribute or a tourist trap – it’s a working jazz club that has barely changed in a century, and it’s the real Chicago. Take the Red Line to Lawrence.
National Museum of Mexican Art – Pilsen Neighborhood
The National Museum of Mexican Art – the cultural heart of Pilsen
Most tourists never make it to Pilsen, which is exactly why you should. Chicago’s most vibrant murals blanket nearly every building in this neighborhood, telling stories of migration, community, resilience, and pride. At the center of it all is the National Museum of Mexican Art – the only nationally accredited museum in America dedicated entirely to Mexican and Chicano art and culture. Its permanent collection spans 3,000 years of Mexican civilization, with approximately 12,000 physical works and 6,000 digital works. Admission is free. Afterward, walk the surrounding streets, grab a meal at any of the neighborhood’s excellent taquerias, and follow the Pilsen Mural Guide to discover art around every corner.
When Is the Best Time to Visit Chicago?
Honestly? Any time – and I mean that. Summer is peak season: the lakefront buzzes, free outdoor concerts fill Millennium Park and Grant Park, and the city runs at full voltage. But summer also brings the biggest crowds and hotel prices to match. Spring and fall are ideal for pleasant temperatures and thinner tourist crowds. And winter – famously brutal, gloriously underrated – offers dramatically lower hotel rates, a surprisingly festive holiday atmosphere, and an authenticity that the summer swarms can’t touch. Bundle up, follow the heated pedestrian bridges over the Chicago River, duck into cozy neighborhood bars, and experience the city the way actual Chicagoans live it.
For the most current events and seasonal programming, always check Choose Chicago before your trip.
This guide covers the Chicago I grew up knowing and loving – from the skyline views I’ve seen a hundred times to the jazz clubs and neighborhood museums that remind me why this city, above all others, will always feel like home.
| Place | Official Website |
|---|---|
| Choose Chicago (Visitor Bureau) | choosechicago.com |
| O’Hare International Airport | flychicago.com |
| CTA Transit Map | transitchicago.com |
| Drake Hotel | thedrakehotel.com |
| Blackstone Hotel | marriott.com |
| Adler Planetarium | adlerplanetarium.org |
| Buddy Guy’s Legends | buddyguy.com |
| Chicago 360 (John Hancock) | 360chicago.com |
| Chicago Art Institute | artic.edu |
| Chicago Cultural Center | chicagoculturalcenter.org |
| Chicago River Architecture Tour | architecture.org |
| Chicago Riverwalk | chicago.gov/riverwalk |
| Giordano’s Pizza | giordanos.com |
| Lou Malnati’s Pizza | loumalnatis.com |
| Pizzeria Uno | pizzeriauno.com |
| The Chicago Theatre | msg.com/chicago-theatre |
| Field Museum | fieldmuseum.org |
| Magnificent Mile | themagnificentmile.com |
| Marshall Field’s (Macy’s) | macys.com |
| Millennium Park | chicago.gov/millenniumpark |
| Navy Pier | navypier.org |
| Palmer House | palmerhousehiltonhotel.com |
| Shedd Aquarium | sheddaquarium.org |
| Willis Tower Skydeck | theskydeck.com |
| Chicago History Museum | chicagohistory.org |
| Frank Lloyd Wright Studio | flwright.org |
| Garfield Park Conservatory | garfieldconservatory.org |
| Green Mill Cocktail Lounge | greenmilljazz.com |
| Lincoln Park Zoo | lpzoo.org |
| Museum of Science and Industry | msichicago.org |
| National Museum of Mexican Art | nationalmuseumofmexicanart.org |
| North Avenue Beach | chicagoparkdistrict.com |
| Second City | secondcity.com |
| Wendella Boat Tours | wendellaboats.com |
| Wrigley Field | mlb.com/cubs/ballpark |