What Are the Coolest Things to Do in Chicago

What Are the Coolest Things to Do in Chicago

The coolest things to do in Chicago are the architecture river cruise, the Willis Tower Skydeck with The Ledge, a guided food tour through downtown, kayaking the lakefront at Ohio Street Beach, and a night out in the blues and speakeasy scene. Each one shows you a different face of the city: the buildings, the height, the food, the water and the after-dark rhythm. Do at least two of them and you have seen the Chicago that people move here for.

Cool is a moving target, so this page sticks to things with a track record: experiences that are consistently the most booked and best rated in the city, plus a few that locals defend harder than tourists discover. The list is deliberately mixed between the Loop, the lakefront and the neighborhoods, because Chicago rewards visitors who leave downtown at least once.

Start with the river. Chicago is the city that invented the skyscraper and then, in a feat of engineering bravado, reversed its own river to protect the lake. The boat tour is the fastest way to understand what you are looking at, and the guides on the good ones are trained docents who can name the architect of nearly every tower you pass. For a deeper dive into that world, our Chicago architecture boat tour guide compares every operator, route and departure point side by side.

Which Experiences Are the Most Worth Your Time?

If you only do three things, make them the architecture river cruise, the Skydeck at Willis Tower, and a food tour. The cruise covers dozens of buildings in about an hour, the Skydeck puts you on a glass ledge above Wacker Drive, and the food tour feeds you deep dish, Italian beef and a brownie in one three-hour walk. Together they cost less than a single night in a nice hotel and they cover the city's three obsessions: architecture, height and food.

The river cruise is the one activity that shows up on almost every visitor's list, and the reviews explain why. The classic version runs 1 to 1.5 hours from a dock near Michigan Avenue, and the commentary is the point: you learn why the Tribune Tower looks like a gothic cathedral crashed into a modern street, and why the Marina City towers are locally called the corncobs. Book the first departure of the morning if you want the best light for photographs and the smallest crowds on deck.

The Skydeck is the second half of the height equation. The Ledge, the glass boxes that extend out from the top of Willis Tower, is the photo that ends up on everyone's feed, and the general admission price starts at $32 for adults and $24 for children ages 3 to 11, with under 3s free, per the Skydeck's own ticket page. If you would rather compare the two observatories before you commit, our Skydeck versus 360 Chicago comparison breaks down price, view angle and wait times.

Food tours are the third pillar, and Chicago earns them. This is a city with a legitimate claim on deep dish pizza, the Italian beef sandwich and the Chicago style hot dog, and a guided walk lets you try all three without gambling on a random restaurant. The three-hour versions move between downtown spots on foot, so wear comfortable shoes and arrive hungry.

What Are the Coolest Free and Cheap Things to Do?

The coolest free things in Chicago are Cloud Gate in Millennium Park, the Lakefront Trail, the Chicago Cultural Center's Tiffany dome, and the free Loop highlights walking tour, which runs on tips. Add the riverwalk, Lincoln Park Zoo, which charges no admission, and the city's museum free days for Illinois residents, and you can fill two days without buying a single attraction ticket. Chicago is unusually generous for a big American city.

Cloud Gate, the sculpture everyone calls the Bean, is free to walk around, touch and photograph, and the city's own Millennium Park pages confirm the park is open daily. The Chicago Cultural Center is the sleeper: a former library building with the largest Tiffany glass dome in the country, open to the public at no charge, and most tourists walk past it without ever going in.

The Lakefront Trail is 18 miles of paved path along Lake Michigan, and it is the single best free experience in the city on a summer day. You can walk a short stretch between Oak Street Beach and North Avenue Beach, or rent a kayak at Ohio Street Beach and see the skyline from the water, which is the coolest angle in the city that does not involve a crowded tour boat.

The free walking tours are worth singling out. Two tip-based walks operate in the Loop, both run by guides who work for tips alone, and the Loop highlights version covers the famous buildings and public art in about two and a half hours. Our free walking tours in Chicago guide covers schedules, routes and how much people actually tip.

One caution that saves out-of-state visitors money and confusion: the famous museum free days here are an Illinois residency benefit, not a general one. The Field Museum is free for Illinois residents on Wednesdays, the Art Institute runs free evenings for Illinois residents, and Shedd gives Illinois residents free days while Chicago residents get a fixed discounted rate. A visitor from another state pays full price on those same days. Our free museum days in Chicago guide lists exactly who qualifies where.

What Should You Do in Chicago at Night?

The coolest things to do in Chicago at night are a river and lake cruise past the lit skyline, a blues club on the South Side or in River North, a speakeasy crawl, and the view from 360 Chicago after dark. The night skyline cruise is the standout: the buildings read completely differently lit up, and the 1.5-hour version costs from $50. Chicago's after-dark scene is genuinely distinctive, not just bars with the lights turned down.

Blues is the city's musical signature, and the clubs are the real thing: small rooms, veteran musicians and a door charge that has not lost touch with reality. Do not expect a ticketed tourist product here, the blues and jazz coach tour exists but the scene is best entered directly at the clubs. Our Chicago blues and jazz clubs guide names the rooms worth the cab fare.

Speakeasies are the other after-dark signature, a nod to the Prohibition years when this city was famously wetter than the law allowed. Several basement and back-door bars keep the theme honestly, and a guided speakeasy tour bundles the history with the drinks so nobody has to find the unmarked doors alone. The Chicago speakeasies guide lists the best of them.

For the night view, the river and lake cruise is the move. The buildings along the Chicago River are lit to be seen from the water, and the skyline from the lake at night is the view that makes people understand why locals put up with the winters. If you prefer height to water, 360 Chicago on Michigan Avenue stays open into the evening, and the TILT ride leans you out over the street below. The wider set of guides lives on Best Things to Do in Chicago.

Which Neighborhoods Are Worth Leaving Downtown For?

The coolest neighborhoods to visit are Wicker Park and Bucktown for independent shops and restaurants, Pilsen for murals and Mexican food, Chinatown for the food walk, and Lakeview and Wrigleyville for the ballpark and the bar scene. Each is 15 to 30 minutes from the Loop on the CTA, where a train ride costs $2.50 and a transfer within two hours is free. Staying only downtown means missing the Chicago that Chicagoans actually live in.

Wicker Park and Bucktown are the default answer when locals are asked where to eat or drink outside downtown. The two neighborhoods blend into each other along Milwaukee Avenue, with vintage shops, record stores and one of the densest collections of good restaurants in the city. Pilsen is the art answer: a Lower West Side neighborhood with murals on many blocks, the National Museum of Mexican Art, and a food and walking tour that is one of the best rated in the city.

Chinatown is the easiest neighborhood detour, a straight Red Line ride south from downtown, and the food scene rewards a guided walk if you do not know which storefront to pick. Our Chinatown guide covers the restaurants and the timing.

Getting to any of these is cheap. The CTA fare table shows the 'L' train at $2.50 a ride with free transfers, and a 1-day unlimited pass at $5, per transitchicago.com. That pass pays for itself on the third ride of the day.

How Do You Fit the Coolest Stuff Into a Short Trip?

For a two-day trip, spend day one on the downtown core: the architecture cruise in the morning, Millennium Park and the Bean at midday, the Skydeck or 360 Chicago before dinner, and a blues club or speakeasy after dark. Spend day two outside downtown: a food tour or a neighborhood like Wicker Park or Pilsen, then the lakefront before you leave. Two days is enough for the greatest hits, and three lets you breathe.

The single biggest planning decision is whether to buy a pass. The Chicago CityPASS costs $144 for adults and $114 for children and bundles five attractions, including the Skydeck and Shedd Aquarium, at a stated saving of up to 50 percent against combined box-office prices, per CityPASS's own comparison page. If your list includes three or more of the bundled attractions, the math usually works. If you are mostly here for tours and food, skip the pass and book experiences individually.

Timing matters more than most guides admit. The architecture cruise is best on the first morning departure, the lakefront is best on a weekday morning before the crowds, and the observatories are best either at opening or after sunset, when the lines thin. Winter is a different city: the cruises scale back, the lakefront gets brutal, and the museums and food scene carry the trip. Our Chicago in winter guide covers the cold-weather version of this list honestly.

For the fuller versions of these plans, see our one day in Chicago itinerary and our two days in Chicago itinerary, which sequence the same experiences against real opening hours and transit times. This site, bestthingstodoinchicago.com, exists to answer exactly these questions without padding.

The trio below is the short version of this whole page: the cruise, the deck and the food tour, the three experiences that define a first visit.

Common Questions About the Coolest Things to Do in Chicago

what are the coolest things to do in chicago

The architecture river cruise, the Willis Tower Skydeck with The Ledge, a guided food tour, kayaking the lakefront at Ohio Street Beach, and a night in a blues club or speakeasy. Those five cover the buildings, the height, the food, the water and the after-dark scene, which is the full range of what makes Chicago distinct.

Is the architecture river cruise really worth it?

Yes, and it is the single most reviewed experience in the city, with the classic version rated 4.8 by thousands of guests. The commentary is what separates it from a plain boat ride: trained guides explain the buildings, the reversed river and the design history as you pass.

What is the coolest thing to do in Chicago for free?

Cloud Gate in Millennium Park, the Chicago Cultural Center's Tiffany dome, the Lakefront Trail and a tip-based free walking tour of the Loop. Lincoln Park Zoo also charges no admission. Museum free days exist but are limited to Illinois residents, so out-of-state visitors should not plan around them.

What should you do in Chicago at night?

A river and lake cruise past the lit skyline, a blues club, a speakeasy, or 360 Chicago after dark. The night cruise is the standout because the buildings are lit to be seen from the water, and the 1.5-hour version runs from $50.

How many days do you need for the coolest stuff?

Two days covers the greatest hits: the cruise, the Skydeck, Millennium Park, a food tour and one night out. Three days lets you add a neighborhood such as Wicker Park or Pilsen and a lakefront afternoon without rushing.

Is Chicago cool in winter too?

Yes, differently. The cruises scale back and the lakefront gets genuinely cold, but the museums, the food tours, the speakeasies and the blues clubs all run through winter. Dress for it and the city rewards you with shorter lines everywhere.