Chicago does not need much of an introduction, but it does reward a little planning. This city stretches 26 miles along Lake Michigan, packs in more than 200 neighborhoods, and somehow still feels walkable once you know where to start. Whether you have a weekend or a full week, the hardest part of visiting Chicago is narrowing down the list, not filling it.
We put together 35 things to do in Chicago that cover the icons, the neighborhoods, the food, and the parts of the city most first-time visitors miss entirely.
Quick Answer: The Best of Chicago at a Glance
Short on time? Start with Millennium Park and Cloud Gate (the Bean), take an architecture river cruise to understand how the city actually fits together, ride the Skydeck at Willis Tower for the view, and eat deep-dish pizza at least once even if you already have an opinion about it. From there, branch into a neighborhood that matches your pace: Wicker Park for shopping and bars, Hyde Park for museums and history, Pilsen for murals and Mexican food. If you want a fuller day of things to do and entertainment in Chicago, browse Giftory's Chicago collection for bookable tours, tastings, and activities that go beyond the standard tourist stops.
Sights & Sips Odyssey Cruise on the Chicago River
Chicago, Illinois
Iconic Chicago Sights Worth the Hype
Every big city has a list of things everyone tells you to do - here is the Giftory recommendations for what you should go out, do and see.
1. Millennium Park and Cloud Gate
Cloud Gate, better known as the Bean, sits in the northwest corner of Millennium Park and reflects the skyline back at you in a way photos never quite capture. Give it 20 minutes, then walk the rest of the park. Crown Fountain, two glass towers that project video portraits of Chicago residents and spit water from their mouths, is a few hundred feet away and is one of the few "attractions" in the city that costs nothing and delivers every time, especially with kids in the summer.
2. An Architecture River Cruise
Chicago's skyline makes a lot more sense once someone points out why it looks the way it does. A 90-minute cruise on the Chicago River, run by a guide who actually knows the buildings, covers the Great Fire, the invention of the skyscraper, and how Chicago engineers reversed the flow of an entire river. Boats leave from the docks near Michigan Avenue and Riverside Plaza. For an easy way to book one, Giftory's Chicago city tour collection lists several options, including a brunch cruise with bottomless mimosas if you want to make a late morning out of it.
Architectural Bottomless Mimosas Odyssey Brunch Cruise - Chicago River
Chicago, Illinois
3. 360 CHICAGO
360 CHICAGO, on the 94th floor of the John Hancock Center on Michigan Avenue, is the quieter alternative to the crowds downtown at Willis Tower, and the north-facing view over Lake Michigan and the Gold Coast is arguably the better angle in the city. Tilt, a moving glass platform that leans passengers out over the edge of the building, is the signature feature here, and it gives the Ledge at Willis Tower real competition. Tickets start around $34 for adults, and the shorter lines mean you can often walk right up without much of a wait, even on weekends. If you want to compare both views for yourself, Willis Tower's Skydeck, on the 103rd floor at 1,353 feet, is still the taller of the two, with general admission starting around $32.
360 CHICAGO Observation Deck Sip and View Experience
Chicago, Illinois
A few more sights worth working in if you have the time. Navy Pier, on the lake just east of downtown, holds a Ferris wheel, a stained-glass museum, and enough restaurants to cover a full evening. The Chicago Riverwalk, a paved path that runs beneath the bridges along the river's south bank, is one of the best free ways to spend a sunny afternoon downtown, with bars and kayak rentals built right into the wall. And the Chicago Cultural Center, a block from Millennium Park, has a Tiffany glass dome that rivals anything in a paid museum and does not charge admission.
Best Neighborhoods to Explore on Foot
Downtown Chicago is the postcard, but the neighborhoods are where the city actually lives. Each one has its own pace, and none of them require a car.
4. Wicker Park and Bucktown
These two adjoining neighborhoods on the near northwest side built their reputation on independent boutiques, vintage shops, and a music scene that helped launch Wilco and Liz Phair. Milwaukee Avenue is the main strip for shopping, and the side streets are full of well-preserved graystone houses worth a slow walk. Come hungry. This is one of the densest concentrations of good restaurants in the city.
5. Pilsen
Pilsen, southwest of downtown, is Chicago's Mexican American cultural anchor and one of the best open-air art scenes in the country. Murals cover entire blocks, particularly along 16th Street and Blue Island Avenue, and the National Museum of Mexican Art on 19th Street is free every day of the week. Pair a walk through the murals with tacos from one of the taquerias on 18th Street.
6. Hyde Park
Hyde Park, on the South Side, is home to the University of Chicago and a quieter, more academic version of the city. The Museum of Science and Industry sits at its northern edge, the Robie House shows off Frank Lloyd Wright's Prairie style, and the Obama Presidential Center is under development along the lakefront nearby. It takes about 25 minutes to reach by car or the Metra Electric line from downtown, and it is worth the trip for anyone interested in architecture or history.
Food and Drink Experiences Worth Building a Day Around
Chicago's food reputation is not overstated, but it also is not just deep-dish. Build a day around eating and you will come away with a better sense of the city than any single museum could give you.
7. Deep-Dish and Beyond: A Chicago Pizza Tour
Yes, you should eat deep-dish. Lou Malnati's and Giordano's are the household names, but Pequod's, with its caramelized cheese crust, has the strongest local following. Just as important, and often skipped by first-timers, is Chicago's other pizza style: tavern-cut, a thin, cracker-crisp pie cut into squares instead of slices, best found at neighborhood spots like Vito & Nick's on the South Side. If you would rather have someone else plan the route, a guided Chicago food tour will hit several stops in one afternoon so you are not stuck choosing just one.
Self-Guided VIP Deep Dish Pizza Tour of Chicago
Chicago, Illinois
8. Food Halls and Market Crawls
Time Out Market Chicago, in the Fulton Market district, packs a dozen well-known local chefs into one building with shared seating, which makes it an easy way to sample a lot of the city's food scene in one visit without committing to a single restaurant. The French Market, tucked inside the Ogilvie Transportation Center downtown, is a smaller, more local option with produce stands, bakeries, and lunch counters that fill up fast on weekdays. If you would rather cook than just eat, Giftory's cooking classes in Chicago collection has hands-on options that pair well with a market visit.
BYOB Fresh Pasta from Scratch Cooking Class in Chicago
Chicago, Illinois
9. Rooftop Bars with Skyline Views
Chicago has more rooftop bars than most cities its size, largely because the skyline gives every single one a built-in view. LondonHouse, near the river and Michigan Avenue, has one of the best angles on the skyline for the price of a cocktail. Cindy's, on top of the Chicago Athletic Association Hotel facing Millennium Park, gets busy at sunset for good reason. Book ahead in summer. Walk-ins are a gamble after 6pm on weekends.
Two more worth knowing about. The city's hot dog and Italian beef culture deserves its own stop, ideally at a no-frills counter like Portillo's or Al's #1 Italian Beef, where you order at the register and eat standing up. And for wine drinkers, the West Loop's cluster of wine bars, many of them wedged between the neighborhood's better-known restaurants, make for a low-key way to spend an evening without a reservation.
Things to Do in Chicago for Couples and Date Night
Chicago is a genuinely good date city, mostly because so much of it involves a view. A sunset architecture cruise checks that box directly, timed so the skyline lights up right as you're finishing the tour. For something less scenic and more playful, Second City, the improv theater that trained a long list of Saturday Night Live alumni, runs shows nightly in Old Town and rarely disappoints. And if you want a night that feels like a small secret, several of Chicago's speakeasy-style cocktail bars, including one hidden behind a phone booth in a hot dog stand, require a bit of searching to even find the entrance, which tends to make for a good story afterward.
Chicago Date Night for two
Chicago, IL
Things to Do in Chicago with Kids and Family
Chicago's museum campus alone could fill a full family trip, and the lakefront gives kids somewhere to burn off energy between stops.
Shedd Aquarium, right on the lake, is one of the largest indoor aquariums in the world and worth the full day if your kids are into marine life. General admission for Chicago residents runs about $20, with pricing higher for out-of-town visitors, so it is worth booking ahead online. Next door, the Field Museum's dinosaur skeletons, including Sue the T. rex, are the kind of thing kids talk about for years afterward. Navy Pier's Centennial Wheel and Chicago Children's Museum make for an easier, lower-effort afternoon if you are traveling with younger kids who need shorter activities and more breaks. And Lincoln Park Zoo, one of the few free zoos left in the country, is an easy add-on if you are staying near the North Side.
For a broader set of ideas beyond Chicago specifically, Giftory's guide to fun things to do with families covers activities that travel well no matter which city you're in.
Outdoor and Lakefront Activities by Season
Chicago's relationship with its lakefront changes completely depending on the month, and knowing which season you're visiting in changes what is actually worth doing.
Summer on Lake Michigan
North Avenue Beach, with its boat-shaped beach house, is the city's default summer hangout, and it gets loud and crowded on hot weekends, in a good way if that's your thing. The Lakefront Trail, an 18-mile paved path running the length of the city, is one of the best free ways to see Chicago by bike, and Divvy, the city's bike-share system, has docking stations every few blocks along the route. For a different kind of summer view, a helicopter tour over the skyline and lakefront gives you a sense of just how far the city actually stretches, something that's hard to grasp from the ground. Giftory's helicopter tour over Chicago collection covers a few length and route options if you want to add one to a summer trip.
Winter in Chicago (Christkindlmarket and Ice Skating)
Winter in Chicago is genuinely cold, but the city leans into it rather than shutting down. Christkindlmarket, a German-style holiday market in Daley Plaza, runs from mid-November through Christmas Eve and fills the plaza with mulled wine, ornaments, and food stalls. Ice skating at Millennium Park's McCormick Tribune Ice Rink is free to enter, with a modest fee for skate rental, and typically runs from late November through early February, weather depending. Dress for it. Chicago wind off the lake in January is not something a light jacket handles well.
Museums and Culture Beyond the Art Institute
The Art Institute of Chicago gets most of the attention, and it deserves it, but the city's museum scene runs much deeper than one building on Michigan Avenue. The Museum of Science and Industry, in Hyde Park, has a real captured German U-boat and a coal mine you can walk through, which makes it one of the more hands-on science museums in the country. The Museum of Contemporary Art, near the Magnificent Mile, rotates challenging, current exhibitions and is a good stop for anyone who wants something less encyclopedic than the Art Institute. The National Museum of Mexican Art in Pilsen, mentioned above, is free and covers everything from folk art to contemporary political work. And the DuSable Black History Museum, on the South Side near Washington Park, was one of the first museums in the country dedicated to African American history and culture, with a permanent collection that traces Chicago's specific role in that history.
Best Day Trips and Under-the-Radar Spots Near Chicago
If you have an extra day, or you've already covered the city center and want something different, a few spots outside downtown are worth the drive. Starved Rock State Park, about 90 minutes southwest, has waterfalls and canyon trails that look nothing like the flat prairie most people picture when they think of Illinois, and it's especially good in spring when the falls are running high. Galena, closer to three hours northwest near the Wisconsin and Iowa borders, is a well-preserved 19th-century town with antique shops and Ulysses S. Grant's former home, and it makes a good overnight if you want to get out of the city entirely. Milwaukee, about 90 minutes north, is close enough for a day trip and has its own strong beer and museum scene if you want a second city on the same trip.
Closer to downtown, an escape room is a good option for a rainy afternoon or an evening you'd rather spend indoors with a group. Chicago has a dense cluster of them, many built around Prohibition-era or Old West themes that fit the city's history, and they typically run 60 minutes with a small group.
How Much Does It Cost to Visit Chicago? Budgeting Tips
Chicago can run expensive or reasonable depending on how you plan it. A downtown hotel room typically runs $150 to $300 a night depending on season, with prices climbing in summer and around major conventions.
Chicago Charm: 2-Night Hotel Experience
Chicago, IL
Food ranges widely: a deep-dish dinner for two runs $40 to $60, while a hot dog and fries at a neighborhood counter costs under $10. Most major attractions, including the Skydeck, Shedd Aquarium, and the Field Museum, sit somewhere between $20 and $40 per adult, and combo passes like Chicago CityPASS can save money if you're planning to hit three or more of them. The single best way to cut costs is to lean on free options: the Riverwalk, Millennium Park, Lincoln Park Zoo, the Chicago Cultural Center, and Pilsen's murals cost nothing and easily fill a full day on their own.
Best Time of Year to Visit Chicago
Late May through early October is Chicago at its best, with warm weather, a full calendar of outdoor festivals, and long daylight hours that make the lakefront usable well into the evening. September is a particular sweet spot: the summer crowds thin out, hotel rates ease up slightly, and the weather often stays warm enough for the beach. December brings Christkindlmarket and holiday lights downtown, which is worth the cold if you dress for it. January and February are Chicago's harshest months, with wind chills that regularly drop below zero, and are best avoided unless you specifically want the off-season rates and don't mind spending most of your time indoors.
FAQ: Things to Do in Chicago
How many days do you need in Chicago?
Three full days covers the essentials: downtown and Millennium Park on day one, a neighborhood and food-focused day two, and a museum or day trip on day three. A weekend works if you're willing to move fast, and a week gives you room to add neighborhoods and day trips without rushing.
Is Chicago walkable for tourists?
Downtown and the neighborhoods just outside it, including Wicker Park, Lincoln Park, and the Gold Coast, are very walkable. The 'L' train covers longer distances well, including trips to Hyde Park and O'Hare, and a Ventra card works across trains and buses.
What is Chicago known for?
Deep-dish pizza, the Bean in Millennium Park, its architecture and skyline, blues and jazz clubs, and being the birthplace of modern improv comedy through Second City.
Is Chicago expensive to visit?
It can be, especially downtown hotels in summer, but a huge amount of the best stuff, including the Riverwalk, Millennium Park, and Pilsen's murals, is free. A budget traveler can see a lot of the city for the cost of transit and food alone.
What should first-time visitors not miss?
Cloud Gate, an architecture river cruise, one deep-dish pizza dinner, and at least one neighborhood beyond downtown. Those four cover the range of what makes Chicago worth visiting.