Chicago packs its headline sights into a tight downtown grid: Millennium Park, the Art Institute and the Riverwalk sit within a few blocks of each other, and the lakefront museums are one short walk or bus ride south. The city is flat, the L train reaches almost everything else, and a river cruise is the fastest way to understand why the skyline looks the way it does. Most of what follows is either free or reachable on a single train fare, so you can plan around the weather instead of around distance.
The top 15, ranked
Ranked by how consistently each pick appears across official Chicago sources, the local destination marketing organization, and recent independent roundups.
- Top pick
#1Best for First stop downtown · #1 of 15Millennium Park
ParkThe LoopOpen daily, early morning to late eveningFreeChicago built this 25 acre park on top of a rail yard and filled it with work by big names: Anish Kapoor's mirrored Cloud Gate, Jaume Plensa's Crown Fountain with its video faces spitting water at kids, and Frank Gehry's ribboned Jay Pritzker Pavilion. Admission is free, the lawn hosts free summer concerts, and a footbridge carries you straight into Maggie Daley Park next door.
Local tipCome first thing in the morning or after dark if you want a photo at Cloud Gate without a crowd in the reflection.
- Top pick
#2Best for Art lovers · #2 of 15Art Institute of Chicago
MuseumThe LoopClosed Tuesdays$25 to $50Behind the bronze lions on Michigan Avenue sits one of the largest art museums in the country, best known for a French Impressionist collection deep enough to include Seurat's A Sunday on La Grande Jatte and Caillebotte's Paris Street, Rainy Day. American highlights include Hopper's Nighthawks and Grant Wood's American Gothic, while Renzo Piano's Modern Wing handles postwar work and connects to Millennium Park by footbridge.
Local tipThe museum is closed Tuesdays, so build the rest of your Loop day around that.
- Top pick
#3Best for Understanding the skyline · #3 of 15Chicago Architecture Center River Cruise
TourThe LoopCruises run in the warmer months$50 plusA trained docent narrates ninety minutes on the Chicago River while the boat threads the main branch and both forks, explaining why the skyline looks the way it does and how the river was reversed. You see the Wrigley Building, Marina City, the Merchandise Mart and dozens more from water level, which is the angle these buildings were designed to be seen from.
Local tipBook ahead for a late afternoon departure, when the light on the west facing towers is at its best.
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#4Best for The big view · #4 of 15Skydeck Chicago at Willis Tower
Observation deckThe LoopOpen daily year round$25 to $50The 103rd floor of Willis Tower puts you roughly a quarter mile above the Loop, with sight lines that reach across the lake toward Indiana and Michigan on clear days. The draw is The Ledge, a set of glass boxes that cantilever out from the building so you can stand on a transparent floor and look straight down at the street below.
Local tipBuy timed tickets online and go on a clear morning, because haze and low cloud can erase the view entirely.
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#5Best for Dinosaurs and world cultures · #5 of 15Field Museum
MuseumMuseum Campus and South LoopOpen daily except major holidays$25 to $50The Field is natural history on the grand scale, anchored by SUE the Tyrannosaurus rex, the most complete example of the species ever found, and Maximo, a cast of a titanosaur so long its neck reaches into the entrance hall. Beyond the dinosaurs there are walk through Egyptian tomb chambers, a hall of gems and meteorites, and Native North American galleries built with tribal collaborators.
Local tipThe Museum Campus is a long walk from the nearest L stop, so budget for a bus or a rideshare if you have small kids.
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#6Best for A free downtown stroll · #6 of 15Chicago Riverwalk
TrailThe LoopOpen dailyFreeA continuous pedestrian path runs along the south bank of the main branch of the Chicago River for a bit over a mile, from Lake Shore Drive west to Lake Street. The city built it in six themed blocks, so you pass a marina, a stepped river theater, floating gardens and a boardwalk, with cafes, kayak rentals and boat docks tucked under the bridges.
Local tipEnter down the stairs at Michigan Avenue or Clark Street, since not every bridge has a ramp to the lower level.
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#7Best for Rainy day with kids · #7 of 15Shedd Aquarium
AquariumMuseum Campus and South LoopOpen daily$25 to $50Shedd opened in 1930 in a domed beaux arts building on the lakefront and still centers on the Caribbean Reef, a circular tank you can walk all the way around. Newer wings add the Oceanarium, where beluga whales and dolphins swim against windows that frame Lake Michigan behind them, plus Wild Reef with its shark lagoon and Amazon Rising, which floods and drains on a yearly cycle.
Local tipTimed entry sells out on summer weekends, so reserve a slot before you leave your hotel.
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#8Best for Families on the lakefront · #8 of 15Navy Pier
LandmarkNear North and StreetervilleOpen daily, shorter hours in winterFreeNavy Pier runs more than half a mile out into Lake Michigan and costs nothing to walk, which makes it the easiest free afternoon on the lakefront. The Centennial Wheel turns near the middle, the Chicago Children's Museum and the glassed Crystal Gardens sit indoors for bad weather, and boat docks along the south side send out everything from tall ship sails to speedboat runs.
Local tipFireworks go off over the water on summer nights, and the free viewing spots along the south dock fill up early.
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#9Best for A free half day · #9 of 15Lincoln Park Zoo
ZooLincoln Park and Old TownOpen daily year roundFreeOne of the last free zoos in the country has been on this spot since 1868, tucked into Lincoln Park about three miles north of the Loop. More than 170 species live here, including gorillas and chimpanzees in the Regenstein Center for African Apes, lions in the restored Kovler Lion House, and a working barn at Farm in the Zoo that small kids tend to like best.
Local tipAdmission is free but parking is not, so take a bus up Stockton Drive or walk in from the Lakefront Trail.
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#10Best for Baseball and the blocks around it · #10 of 15Wrigley Field
Historic siteLakeview and the North SideGames and tours on scheduled datesVariesBaseball has been played here since 1914, which makes this the second oldest ballpark in the major leagues, and it still has hand turned numbers on the center field scoreboard and ivy growing on the outfield brick. Even without a ticket the neighborhood is worth an hour, since bars and rooftop bleachers on Waveland and Sheffield look right into the park.
Local tipCheck the Cubs schedule before you plan the day, because ballpark tours run on a different pattern when there is a game.
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#11Best for Hands on science · #11 of 15Griffin Museum of Science and Industry
MuseumHyde Park and the South SideOpen daily except major holidays$25 to $50The old Palace of Fine Arts from the 1893 world's fair now holds a science museum big enough to park a Boeing 727 and a captured German U-boat indoors. Kids gravitate to the U-505 submarine, the Great Train Story model railroad and the storm rigs in Science Storms, while adults tend to linger over Colleen Moore's Fairy Castle, a jeweled dollhouse built in the 1930s.
Local tipThe submarine walkthrough needs a separate timed ticket, so pick that up as soon as you arrive.
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#12Best for Skyline views and sky shows · #12 of 15Adler Planetarium
MuseumMuseum Campus and South LoopOpen most days, check the calendar$25 to $50America's first planetarium sits at the tip of Northerly Island, which means the walk out to it delivers the postcard view of the skyline across the water. Inside are domed theaters running live sky shows and immersive space films, plus galleries of antique telescopes, sundials and navigation instruments that trace how people mapped the sky before photographs existed.
Local tipWalk out on the lakefront path east of the building for the classic head on photograph of the downtown skyline.
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#13Best for A free hour of beauty · #13 of 15Chicago Cultural Center
LandmarkThe LoopOpen daily, closed holidaysFreeThe city's former central library, finished in 1897, is now a free civic art space with rotating exhibitions, free lunchtime concerts and a marble staircase worth the climb on its own. Preston Bradley Hall on the third floor holds what is billed as the largest Tiffany stained glass dome in the world, and the north side has a second dome in the Grand Army of the Republic rooms.
Local tipGo up to the third floor first, since Preston Bradley Hall is sometimes closed for private events later in the day.
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#14Best for Summer afternoons · #14 of 15North Avenue Beach and the Lakefront Trail
BeachLincoln Park and Old TownOpen daily, lifeguards in summer season onlyFreeChicago has miles of public beach inside the city limits, and this is the busiest stretch, backed by a boathouse shaped like an ocean liner and lined with volleyball courts all summer. The paved Lakefront Trail runs right behind it, giving walkers, runners and cyclists a separated path with the skyline rising to the south the whole way.
Local tipLifeguards work a set season between late May and early September, and swimming outside that window is not supervised.
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#15Best for A night out · #15 of 15The Second City
TheaterLincoln Park and Old TownShows most nights$25 to $50Modern American sketch comedy essentially starts in this Old Town building, which has been sending performers to Saturday Night Live and beyond since 1959. Three stages run most nights, including the Mainstage revue and the UP Comedy Club, and the short improv set that follows the Mainstage show is often thrown in for free.
Local tipSeating is filled by arrival order in some rooms, so show up early if you care where you sit.
Where things cluster
A quick orientation so you can group stops instead of crossing Chicago twice.
- The LoopMillennium Park, the Art Institute, the Riverwalk and Willis Tower sit inside a walkable grid ringed by the elevated tracks, and almost every train line stops here.
- Museum Campus and South LoopThe Field Museum, Shedd Aquarium and Adler Planetarium share one lakefront peninsula just south of Grant Park, close enough to walk between in a few minutes.
- Near North and StreetervilleNavy Pier, the Magnificent Mile shopping strip and the tallest lakefront towers fill the blocks between the Chicago River and Lincoln Park.
- Lincoln Park and Old TownA free zoo, a conservatory, a long city beach and the comedy clubs of Old Town sit inside or beside the biggest park on the North Side.
- Lakeview and the North SideWrigley Field anchors a neighborhood of bars, music rooms and taquerias about six miles north of downtown, with the Red Line running straight to it.
- Hyde Park and the South SideThe 1893 world's fair grounds in Jackson Park, the University of Chicago campus and the Griffin Museum of Science and Industry cluster along the southern lakefront.
Make it a day
The Loop, the river, then the lake
Start at Millennium Park for Cloud Gate and Crown Fountain, then cross the footbridge into the Art Institute of Chicago for a couple of hours. Walk north to the Chicago Riverwalk for lunch at water level and catch an architecture river cruise from the dock near the Michigan Avenue bridge. Finish with the elevator up to Skydeck Chicago at Willis Tower, or keep walking east along the river to Navy Pier for the wheel and the lake breeze.
Downtown Saturday, neighborhoods Sunday
Give Saturday to the Loop and the lakefront: Millennium Park, the Art Institute, the Riverwalk, an architecture cruise, and the Chicago Cultural Center on the way back. On Sunday head north for Lincoln Park Zoo, a stretch of the Lakefront Trail past North Avenue Beach, and a Cubs game or a ballpark tour at Wrigley Field, then a late show at The Second City in Old Town. Swap in the Field Museum or the Griffin Museum of Science and Industry if the weather turns.
Map
Best time to visit
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Late spring through early fall is when the lakefront, the Riverwalk and the boat cruises are all running, with warm days and long evenings from May into September. July and August are the hottest and busiest months, so June and September give you similar weather with shorter lines. Winter is genuinely cold and windy off the lake, but the museums, the Cultural Center and the observation decks stay open and are far quieter.
Chicago things to do FAQ
Parking, timing, cost, and weather answers for a smoother visit.
How many days do you need in Chicago?
Two full days covers the Loop, the lakefront museums and one neighborhood. Three days lets you add the South Side, a ballgame and a proper sit down dinner without rushing anything.
What is the best free thing to do in Chicago?
Millennium Park, the Chicago Riverwalk, Lincoln Park Zoo, the Chicago Cultural Center and the entire lakefront, including North Avenue Beach and Navy Pier, all cost nothing to enter.
Is a bundled attraction pass worth buying?
If you plan to visit three or more of the big ticket sights such as the Field Museum, Shedd Aquarium, Skydeck Chicago and the Griffin Museum of Science and Industry, a bundled pass usually beats buying separately. For one or two stops, buy direct from the venue.
How do you get around Chicago without a car?
The CTA runs eight rail lines plus a dense bus network, and the Blue Line connects O'Hare to downtown around the clock. Get a Ventra card or tap a contactless card, and walk or bike the lakefront for anything near the water.
Which museum should you pick if you only have time for one?
Choose the Art Institute of Chicago for art, the Field Museum for dinosaurs and world cultures, or the Griffin Museum of Science and Industry if you are travelling with kids who want to touch things.
Is Chicago walkable for visitors?
Downtown is flat and gridded, and the Loop, Millennium Park, the Riverwalk and Navy Pier all link up on foot. Anything beyond that, including Wrigley Field, Hyde Park and Lincoln Park Zoo, is a short train or bus ride.
Keep planning
Use these nearby guides to extend your Chicago trip with a different pace and a clear next stop.
Photos via Wikimedia Commons. Credits: Raidarmax, Ken Lund from Reno, Nevada, USA, Beyond My Ken, Traveler100, Daniel Schwen, Wikimedia Commons contributor, SecretName101, Setiawan Soekamtoputra, Banpei at English Wikipedia, chascarper from Chicago, U.S.A., Knarfol at de.wikipedia, TonyTheTiger at English Wikipedia (Original text: en:User:T, The original uploader was DS1953 at English Wikipedia., Marc Heiden – User: (WT-shared) Gorilla Jones at wts wikivo.