I moved to Chicago seven years ago for a job I didn’t think I’d keep. The plan was simple: two years, three tops, then back to somewhere warmer. But this city has a way of anchoring you. It’s not just the skyline, though seeing the Sears Tower (I refuse to call it Willis) pop out of the fog on a fall morning still gets me. It’s the $6 Old Fashioned in Logan Square that would cost $20 in Brooklyn. It’s the tamale lady on the Blue Line platform at California station at 11 PM. It’s the way Lake Michigan turns a terrifying, electric blue in October when the trees along the lakefront go gold and the whole city looks like it was art-directed.
If I had to boil the best things to do in Chicago down to five, they’d be the architecture boat tour on the river, the Art Institute, a long walk along the lakefront, deep-dish pizza at Lou Malnati’s, and a full afternoon wandering a neighborhood like Pilsen or Wicker Park. But that’s the short version. Here’s the longer one, from someone who actually lives here.
Food Trucks and Sneksthe Stuff Everyone Tells You to See (and They’re Right)
I used to roll my eyes at tourists crowding around the Bean. Then I went at 7 AM on a Tuesday before work, and the entire plaza was empty, and the sculpture was catching the sunrise in this warped, pink-orange reflection of the skyline, and I stood there like an idiot for ten minutes. They’re right. Cloud Gate is the number one tourist attraction in Chicago and it earns it.
Millennium Park
Millennium Park is free and it wraps around the Bean in every direction. The Lurie Garden is quiet when the rest of the park is packed. The Crown Fountain spits water from giant LED faces and kids go absolutely feral for it in summer. The Jay Pritzker Pavilion hosts free concerts from June through August. Classical on Wednesdays, jazz on Thursdays, bigger acts on weekends. I’ve eaten tacos on the great lawn while listening to a full orchestra. That’s a normal Tuesday here.
Art Institute of Chicago
The Art Institute of Chicago is one of those museums that justifies its reputation. Nighthawks is here. American Gothic is here. Seurat’s Sunday on La Grande Jatte is here. The modern wing, designed by Renzo Piano, is worth visiting just for the building. I’d give it three hours. If you only have one, go straight to the Impressionist galleries on the second floor. They’re the reason people fly here from Paris and say “oh.”
Architecture Boat Tour
I’ve taken friends and family on this four separate times and I’m never bored. The Chicago Architecture Foundation runs a 90-minute cruise down the river narrated by trained docents who actually know the history. You float past Marina City (the “corn cob” towers that Wilco put on an album cover), the Tribune Tower, the Wrigley Building. The story of how the Chicago Fire led to the city basically reinventing modern architecture is genuinely fascinating. Book the CAF tour, not the party boats. Go in the afternoon for the best light.
Skydeck
The Skydeck at Willis Tower puts you on a glass ledge 1,353 feet above the street. Your brain knows the glass is safe. Your legs disagree. On a clear day you can see four states. Go when it opens at 9 AM. The afternoon wait can hit 90 minutes in summer and the line snakes through a gift shop, which feels like punishment.
Walk the Lakefront Before You Do Anything Else
Lakefront Trail
Here’s what I tell every visitor: before the museums, before the pizza, go walk the lakefront. Chicago has 26 miles of continuous public shoreline. No private beaches. No condos blocking the water. Just a path that runs from one end of the city to the other, with the skyline on one side and Lake Michigan on the other. Rent a Divvy bike (stations are everywhere, $1 to unlock) and ride from Navy Pier south to the Museum Campus. It takes about 20 minutes and the views are the reason you came.
North Avenue Beach
North Avenue Beach is where I go on summer Saturdays. The beach house looks like an ocean liner. There are volleyball courts, food stands, and a bar. Oak Street Beach is closer to downtown and more of a scene. Both are free. Both have that weird thrill of swimming in freshwater while skyscrapers watch you from a mile away. These are fun things to do in Chicago that cost nothing and feel like the city’s best trick.
The Food, Obviously
Chicago’s food scene doesn’t need me to hype it. It has 24 Michelin stars. But some of the best meals I’ve eaten here cost under $12, which is the part that doesn’t make the magazine covers.
Deep-Dish Pizza
Deep-dish pizza first, because you have to. Lou Malnati’s, butter crust, sausage. The Lincoln Park location has a shorter wait than downtown. Giordano’s is the other name people know and it’s fine, but I think Lou’s has more character in the crust. If someone tells you Uno’s is the “original,” it technically is, but it’s mostly a tourist operation now.
Here’s the thing nobody tells you: locals don’t actually eat deep dish that often. The pizza Chicagoans eat on a Tuesday night is tavern-style, thin crust, cut in squares. Pat’s Pizza on Lincoln Avenue. Vito & Nick’s on the South Side. About $14 for a large. No line. No 45-minute wait for your food to bake. Just pizza.
Italian Beef
Italian beef is the food Chicagoans argue about more than pizza. Al’s #1 Italian Beef on Taylor Street claims the original. You order it dipped (the whole sandwich dunked in jus) with hot giardiniera. You will destroy your shirt. It’s worth it. Johnnie’s Beef in Elmwood Park is another popular pick, and people drive 30 minutes to eat there, which tells you something.
Hot Dogs
Chicago-style hot dogs have seven toppings and a rule: no ketchup. Mustard, green relish, onion, tomato wedges, pickle spear, sport peppers, celery salt, on a poppy seed bun. Portillo’s is the chain that visitors know. For something more local, Jim’s Original on Maxwell Street has been open since 1939 and the Polish sausage is just as good as the hot dog.
Tacos in Pilsen and Little Village
Walk into any taqueria on 18th Street or 26th Street. I like Birrieria Zaragoza for birria tacos. Cash only, there’s a line on weekends, and the consommé they serve on the side could fix a bad day.
Garrett Popcorn
The Chicago Mix is caramel and cheese popcorn mixed together. It sounds wrong. It isn’t. The Michigan Avenue location always has a line, but it moves fast and the smell alone is worth standing in it.
The Neighborhoods That Make This City
Chicago has 77 neighborhoods. The Loop is where tourists stay, but the neighborhoods are where the city actually lives. When people ask me what to do in Chicago beyond the obvious, I always say: pick two or three neighborhoods and just wander.
Pilsen
Pilsen is on the Lower West Side and its home to one of the largest Mexican-American communities in the Midwest. The murals alone justify the trip. Almost every wall along 18th Street has one. Some are political, some are personal, some cover entire buildings. The National Museum of Mexican Art is here, it’s free, and it’s one of the best small museums I’ve been to anywhere. The bakeries sell pan dulce for a dollar.
Wicker Park
Wicker Park is where I spend most of my free time. Good coffee shops (Ipsento 606 is my go-to), vintage stores, a music venue called the Empty Bottle that books bands I’ve never heard of and somehow they’re always good. Small Cheval has one of the better burgers in the city. The six-way intersection at Damen, Milwaukee, and North is chaotic and loud and full of people and I love it.
606 Trail
The 606 trail connects Wicker Park to Logan Square along 2.7 miles of abandoned elevated rail line. Think of it as a longer, less crowded version of New York’s High Line. It’s great for walking, running, or biking, with public art and murals along the route. On a spring evening the views from up on the old rail bed feel almost cinematic, the western sun hitting the brick buildings on both sides. I run on it twice a week and I still notice new details.
Logan Square
Logan Square is a bit further northwest and a bit more relaxed. The actual square has a beautiful eagle monument and the streets around it are lined with greystones, which are Chicago’s version of brownstones but built with Indiana limestone. Lost Lake is a tiki bar here that’s been on “best bars in America” lists multiple times. The cocktails are genuinely excellent and the interior feels like you teleported to a Polynesian beach bar in the 1960s.
On certain days, if the wind is right and you’re walking through the West Loop, you’ll catch the smell of the Blommer Chocolate Company. It’s been roasting cocoa beans on the same block since 1939. The whole neighborhood smells like brownies at 8 AM. It’s one of those small, weirdly specific things that makes this city feel like home.
Hyde Park
Hyde Park is on the South Side, about 20 minutes from downtown on the Metra. The University of Chicago campus looks like Hogwarts. The Museum of Science and Industry is here, and it’s one of the best things to do in Chicago if you like spending five hours looking at a captured German U-boat, a coal mine simulation, and a Boeing 727 hanging from the ceiling. I’ve been three times and haven’t seen everything. Obama’s house is in the neighborhood too. You can’t go in, but people walk by.
Chinatown
Chinatown is small compared to New York’s, but the food is real. Take the Red Line to Cermak-Chinatown and walk south on Wentworth. Dim sum at Phoenix before 11 AM on weekends, or you’ll wait 45 minutes. The bakeries sell egg tarts for $1.50 and they’re perfect.
Andersonville
Andersonville is a quiet North Side neighborhood with Scandinavian roots and a strong LGBTQ+ community. It has the kind of independent bookstores, bakeries, and coffee shops that make you consider moving. Women & Children First is one of the best feminist bookstores in the country.
The Museums (and Which Ones Are Worth the Money)
Chicago’s museums are not an afterthought. Several of them are legitimately world-class, and a couple are good enough that I’ve gone back five or six times.
Field Museum
The Field Museumon the Museum Campus is enormous. SUE, the largest and most complete T. rex skeleton ever found, has her own room now. The exhibitions on ancient Egypt and the Americas are excellent. I’d give it two to three hours. It can feel overwhelming if you try to see everything in one visit, so pick two or three sections and go deep.
Shedd Aquarium
The Shedd Aquarium is right next door. The Caribbean Reef exhibit is the centerpiece, a 90,000-gallon circular tank where you stand surrounded by sharks and sea turtles and stingrays gliding past at eye level. It’s one of the best things to do in Chicago if you’re traveling with kids, but I’ve been as an adult without children and it’s still mesmerizing. Tickets are steep ($42 for all-access) and the summer lines are long. Go on a weekday morning.
Museum of Science and Industry
The Museum of Science and Industry in Hyde Park is a full-day thing. They have a captured German U-boat from World War II that you can walk through. An actual Boeing 727 hanging from the ceiling. A simulated coal mine. A mirror maze. I spent five hours there once and when I checked my phone I couldn’t believe how much time had passed. Take the Metra Electric train from Millennium Station. Fifteen minutes.
For something weirder, the International Museum of Surgical Science in Gold Coast is a mansion full of medical artifacts dating back centuries. Antique surgical instruments, an iron lung, a jar of gallstones. It’s strange and fascinating and almost never crowded. Twenty bucks to get in. My mom loved it, which says something about my mom.
Lincoln Park Zoo
The Lincoln Park Zoo is free and open year-round. It’s not the San Diego Zoo. It’s smaller and older. But it’s in the middle of one of the most beautiful parks in the city, and you can wander through on a Wednesday afternoon without paying a cent. The Regenstein Center for African Apes is the standout exhibit. I’ve watched gorillas in there for longer than I’d admit to anyone.
After Dark
This is where Chicago quietly beats most American cities, and it’s one of the reasons the things to do in Chicago for adults list is longer than you’d expect.
- Blues: Chicago invented electric blues. Buddy Guy’s Legends in the South Loop is the famous one. Buddy himself still plays there sometimes. Kingston Mines in Lincoln Park is grittier, louder, and open until 4 AM on weekends with two stages running simultaneously.
- Jazz: The Green Mill in Uptown has been a jazz club since the 1920s. Al Capone drank there. The booths, the neon sign, the low tin ceiling haven’t changed much. I’ve gone on random Tuesday nights and heard musicians who’d headline anywhere in New York.
- Comedy: Second City is where Tina Fey, Steve Carell, and Bill Murray got their start. The main stage shows are polished. The smaller improv rooms are cheaper, messier, and often funnier. The iO Theater and Laugh Factory are also excellent.
- Rooftop Bars: Chicago does these well in summer. The LondonHouse rooftop at Michigan and Wacker has the best view in the city, straight down the river with the Wrigley Building glowing next to you. Drinks are $18 to $22, but the view is free with your drink. Cindy’s on top of the Chicago Athletic Association overlooks Millennium Park and it’s the kind of place where you accidentally stay for three hours.
Sports, if That’s Your Thing
Wrigley Field opened in 1914 and still has the original hand-turned scoreboard. Even if you don’t care about baseball, the atmosphere is worth it. Bleacher seats start around $25 for weekday Cubs games. The surrounding neighborhood, Wrigleyville, turns into a block party when there’s a game.
The White Sox play on the South Side at Guaranteed Rate Field. Cheaper tickets, better stadium food, less touristy. The United Center on the West Side hosts the Bulls and the Blackhawks. Michael Jordan’s statue outside is a free photo op even if you can’t get game tickets.
The Seasons Matter
Chicago is a different city depending on when you visit.
Summer
Summer is the peak. Free concerts at the Pritzker Pavilion, Lollapalooza in late July, packed beaches, outdoor patios on every block. It’s the best version of Chicago, and everyone knows it, so hotel prices reflect that.
Fall
Fall is my favorite. The lakefront trees turn orange and gold, the crowds thin out, and you can actually get a dinner reservation. The Chicago Marathon in October runs through dozens of neighborhoods and it’s fun to watch even if running isn’t your thing.
Winter
Winter is brutal. I’m not going to lie. The wind off the lake at negative 10 feels like a personal attack. But the Christkindlmarket in Daley Plaza is genuinely charming (hot spiced wine, wooden market stalls, crowds of people in massive coats), and the museums are empty. Hotel prices drop hard. If you can handle the cold, you’ll have the city to yourself.
Spring
Spring is chaos. Seventy degrees one day, snow the next. Cherry blossoms bloom in Jackson Park around late April if the timing cooperates. The patios reopen and Chicagoans emerge from hibernation like bears who just discovered cocktails.
Practical Stuff
The “L” train covers most of the city and a day pass is $5. For neighborhoods, rent a Divvy bike. Uber and Lyft work fine. You don’t need a car unless you’re leaving the city.
Three full days is the minimum to see the highlights. Four to five lets you explore neighborhoods without feeling rushed. I’d spend day one on the lakefront and downtown (Millennium Park, Art Institute, boat tour), day two in the museums, and day three in two or three neighborhoods.
A lot of the best things to do in Chicago are free. The lakefront. Millennium Park. Lincoln Park Zoo (open year-round, no admission fee). The 606 trail. Street art in Pilsen. Free concerts in summer. The CityPASS ($94 for adults) bundles five major attractions at about half off if you’re planning to hit the Skydeck, Shedd Aquarium, and Field Museum.
What to Skip (or at Least Manage Expectations)
Navy Pier is on every list. The Ferris wheel is fun, the lake views are great, kids love it. But the food inside is overpriced chains and on summer weekends the crowds are miserable. Go for the Centennial Wheel ride, then leave and eat literally anywhere else.
The Magnificent Mile is Michigan Avenue’s shopping district and it’s fine if you need a Zara or a Nike store, but you can do that anywhere. The architecture is worth a walk, but don’t spend half a day shopping here unless that’s specifically what you came for.
And a note on safety, since people always ask: Chicago has neighborhoods with high crime rates, but they’re far from where tourists go. Every place I’ve mentioned in this guide is safe. Downtown, the lakefront, Lincoln Park, Wicker Park, Logan Square, Pilsen, Hyde Park, Chinatown, Andersonville. Use normal city common sense. Don’t flash valuables. Keep your phone in your pocket on the L. Stay aware of your surroundings. Same rules as New York or any other big city.
Day Trips if You Have Extra Time
Starved Rock State Park
It is 90 minutes southwest. Eighteen canyons, seasonal waterfalls, easy-to-moderate trails along the Illinois River. It’s one of the popular places for Chicagoans to escape the city on a weekend.
Indiana Dunes National Park is
Indiana Dunes National Park is about an hour southeast. Sandy beaches on the southern shore of Lake Michigan, dune hikes, and good birding. It became a national park in 2019 and it’s still quieter than it should be.
Galena, Illinois
Galena, Illinois is 2.5 hours west. Brick streets, 19th-century buildings, wineries, antique shops. Ulysses S. Grant lived here before the Civil War. It’s the kind of small town that makes you briefly consider leaving Chicago before you remember you’d miss the tamales.
A Few Things People Always Ask Me
What should you not miss in Chicago?
The architecture boat tour. Full stop. If you do one paid activity, make it that. After that: the Art Institute, a lakefront walk, and deep-dish at Lou Malnati’s. Four things, one day, and you’ll get why people love this city.
So, what’s the number one attraction?
Cloud Gate, the Bean, the giant reflective blob in Millennium Park. Everyone goes. Everyone takes the same photo. And somehow it’s still worth it, especially before 8 AM when you’ll have it to yourself.
What’s the least touristy thing worth doing?
Walk around Pilsen on a Saturday. Eat birria tacos, look at the murals, visit the National Museum of Mexican Art (free), and grab pan dulce from a bakery. Zero tour groups. Better food than anything on Michigan Avenue.
Are there areas I should avoid?
The tourist areas, lakefront, and neighborhoods I mention in this guide are all safe. Chicago does have high-crime areas, but they’re far from where visitors go. Use normal city awareness and you’ll be fine.
