Must Visit Landmarks in Chicago and the Stories Behind Them

I have spent more late nights wandering the Loop than I care to admit, and every time I think I have seen it all, Chicago hands me another surprise around the next corner. The following guide collects the must visit landmarks in Chicago that I keep returning to, along with the small details that make each one feel like a conversation with the city itself. Think of this less as a checklist and more as a map drawn by a friend who keeps getting lost on purpose.

The Bean, Crown Fountain, and the Long View of Millennium Park

I was sitting on the big steps of the Pritzker Pavilion last Tuesday around 7 a.m., the only person awake besides a jazz drummer warming up somewhere under the trellis, when the Bean (officially Cloud Gate) caught the empty skyline and turned it into a wobbling silver painting. Millennium Park sits at 201 E. Randolph Street, right where Madison meets Michigan Avenue, and it is the most disorienting public space in the country because it somehow feels both futuristic and deeply old Chicago.

Cloud Gate was finished in 2006, designed by Anish Kapoor, and it weighs about 110 tons. Most people do not know that the surface is made of 168 stainless steel plates that were welded together on site and then sanded down five separate times to remove the seams. You can walk underneath it through a 12-foot tunnel and look up at a polished ceiling that is honestly stranger than the outside.

Crown Fountain, the two glass-block towers with the spitting faces on the east end, is the work of Jaume Plensa, and the locals know it as the only place in the Loop where your dog, your toddler, and a sunburned tourist can all be equally happy in July. Go before 9 a.m. on a weekday if you want photographs without crowds. The face on the south tower sticks its tongue out at 11:00 a.m. sharp on the hour, every hour, and most visitors never notice the schedule.

Local Insider Tip: "Stand on the south side of the Bean at sunrise. The whole sculpture turns into a giant mirror for the eastern towers, and you will have the place to yourself while the joggers loop past."

You do not just see Millennium Park, you sort of stumble into it, and that is part of why the must visit landmarks in Chicago feel so different from other big cities.

The Art Institute of Chicago and the Lions Out Front

I dragged a friend who hates museums through the Art Institute at 111 S. Michigan Avenue last winter, and she stayed four hours. The place is enormous, 300,000 square feet, with roughly 1.5 million objects, and it is the kind of institution that punishes you for trying to see everything in one go.

The two bronze lions at the entrance have been there since 1894, and they are officially named on the south side (you can read it on the plaque) and on the north side. Most people walk right past without noticing the names, which feels like a small Chicago secret even though 1.5 million people a year photograph them.

Inside, Grant Wood's American Gothic and Edward Hopper's Nighthawks are the two paintings that get the crowds, but I always send people to the little room with the Thorne Miniatures, 68 dollhouse-sized rooms tucked away on the lower level. The detail on those tiny models is the kind of thing that makes you forget you are in a museum in the middle of a major American city. The Modern Wing, designed by Renzo Piano and opened in 2009, is connected by the Nichols Bridgeway, a glass walkway that hovers over Monroe Street, and crossing it on a snowy day is one of my favorite small pleasures in Chicago.

Local Insider Tip: "Buy tickets online at least a day ahead, and pick a Thursday or Friday evening after 5 p.m. when the museum runs its extended hours. The Impressionist galleries empty out around 7 p.m. and you can stand in front of the water lily rooms without anyone breathing on you."

The Art Institute anchors the south end of Grant Park, and together with Millennium Park and the old library across the street, it forms the cultural spine of the city.

Grant Park, Buckingham Fountain, and the Museum Campus Connector

Buckingham Fountain sits in the middle of Grant Park at 301 S. Columbus Drive, and the first time I saw it in person, I had the same reaction as a kid on a school trip. The thing is 1.5 million gallons of water, originally donated to the city in 1927 by Kate Buckingham, and the main jet shoots 150 feet straight up. Every hour on the hour, the fountain does a 20-minute water show set to music, and at night it is lit in colors that change the whole surrounding skyline.

People do not realize the fountain was inspired by the Latona Fountain at Versailles, and the architect was Edward Bennett. From the south end of Grant Park, you can look across the water and see the Museum Campus with the Field Museum, Shedd Aquarium, and Adler Planetarium, all sitting on a peninsula that juts into Lake Michigan like a ship. The view from the bridge between them, especially in October when the light goes amber, is one of the strongest arguments for visiting Chicago at all.

Local Insider Tip: "Skip the music show and go at 11 a.m. on a weekday in May. The wind off the lake is still cold, the fountain runs without the crowds, and the prairie dogs in the small petting area behind the rose garden are usually up."

If you only have time for one stretch of famous monuments Chicago offers, this east-facing axis is the one I would walk.

Navy Pier and the Honest Truth About It

I have a love-hate relationship with Navy Pier, and I think most Chicagoans do. It is at 600 E. Grand Avenue, jutting a full 3,300 feet into Lake Michigan, and on a Saturday in July it is genuinely one of the most crowded places in the city. I went last month on a Tuesday morning at 8 a.m. and had the whole thing almost to myself, which is when I finally started to appreciate it.

The pier opened in 1916 as a training center for the Navy during World War I, which is where the name comes from, and it was designed by Charles Sumner Frost, the same architect who did the LaSalle Street train station. Today it holds the Chicago Shakespeare Theater, a stained glass museum, an old-fashioned carousel, and a Ferris wheel that goes up 196 feet. The wheel is the best way to see the city in fifteen minutes, and most people do not know the cars are climate-controlled so you can ride in January without freezing.

My one real complaint is the parking situation. The lot fills up by 11 a.m. on weekends and the $35 flat rate hurts. If you drive, get there before 10 a.m., and if you do not, take the CTA bus 124 or just walk from the Mag Mile.

Local Insider Tip: "Skip the chain restaurants at the end of the pier and walk back toward the entrance. The small Mexican spot on the second level with the green awning has been there for twenty years and the al pastor is the real reason I keep going back."

Navy Pier is the kind of place that only makes sense if you time it right, and that timing is almost always earlier in the day.

Wrigley Field and the Oldest Scoreboard in the Country

I went to a Cubs game last September with a friend from out of town, and we got there at 11 a.m. for a 1:20 p.m. first pitch, which is the only correct move at Wrigley Field. The ballpark is at 1060 W. Addison Street, in the Lakeview neighborhood, and it opened in 1914, which makes it the second-oldest major league park in America.

The hand-turned scoreboard in center field has been manually operated since 1937, and the guys up there still flip the numbers by hand. The ivy on the outfield walls is original to 1937, when Bill Veach had it planted, and out-of-town scores are still reported by hand in the second deck. Most people do not realize the bleachers in center have obstructed view seats that are actually the most fun seats in the park because the bleacher bums are louder than the rest of the stadium combined.

The surrounding neighborhood, Wrigleyville, is loud on game days and sleepy on off days, and there is a cluster of bars on Clark Street that opens at 9 a.m. the morning of every home game. Murphy's Bleachers, right across from the main entrance, is where the diehards go before first pitch.

Local Insider Tip: "Buy tickets in the upper deck behind home plate, not the bleachers, for your first visit. The view of the ivy and the lake beyond the right field bleachers is the money shot, and you can move to standing room later if you want the bleacher energy."

The Cubs' 2016 World Series ended a 108-year drought, and even people who do not care about baseball felt something when it happened. Wrigley is one of those famous monuments Chicago fans treat like a member of the family.

The Magnificent Mile and the Water Tower That Survived the Fire

The Magnificent Mile runs along Michigan Avenue from the Chicago River up to Oak Street, and it is one of the most walked stretches of street in America. I have walked it more times than I can count, and I still detour to look at the old Water Tower at 806 N. Michigan every time.

The tower is the only public building in the burned district that survived the Great Chicago Fire of 1871, and it was built in 1869 from Joliet limestone. Locals know it as a kind of civic talisman. The tiny Pumping Station next to it, finished in the same year, is now a gallery for the City of Chicago's photography collection, and the exhibits are free.

Down the street, the Wrigley Building is the white terra cotta tower at 400-410 N. Michigan, completed in 1924, and at night the entire facade lights up. Across the river, the Tribune Tower is a 1925 Gothic revival skyscraper made of actual stones embedded into the exterior walls, fragments from the Great Wall, the Parthenon, the Great Pyramid, and over 100 other world sites. You can walk right up to the wall and find them.

Local Insider Tip: "Skip the brand-name flagships and walk into the alley right behind the old Water Tower. There is a tiny European-style courtyard with a coffee bar that has been there since 1998, and the owner still pulls the shots himself."

The Mag Mile is the place where Chicago architecture announces itself, and the Water Tower is the reminder that all of it rose from ashes less than 200 years ago.

Willis Tower Skydeck and the Ledge You Can Step Out On

I went up the Willis Tower (you can call it the Sears Tower, most Chicagoans still do) last year with my parents, who were visiting from out of state, and the Ledge still made my dad grab my arm. The building is at 233 S. Wacker Drive, and it was the tallest building in the world from 1973 to 1998, when it was surpassed by the Petronas Towers.

The Skydeck is on the 103rd floor, and the Ledge consists of four glass boxes that extend 4.3 feet out from the building at 1,353 feet in the air. I am not scared of heights, but looking straight down through the floor of the box while tourists next to me were losing their minds was something else. The original construction used 76,000 tons of steel, and the building has 108 floors total.

Local Insider Tip: "Go at sunset, but buy the Flex Pass ticket that lets you re-enter. Watch the sunset, leave, grab a drink at the bar in the lower level of the building, and come back an hour later when the city is fully lit. The second visit feels like a different city."

From the Skydeck you can see four states on a clear day, which is the kind of claim that sounds like marketing but is actually true because the curvature of the lake and the flat prairie make it possible.

The 606 / Bloomingdale Trail and the Elevated Park

The 606 is the city's elevated linear park, and it is one of the most underrated Chicago architecture and urbanism projects in the last twenty years. It runs 2.7 miles along a former rail line on the northwest side, roughly along Bloomingdale Avenue between Ashland and Ridgeway, and it opened in 2015.

I run on the 606 at least twice a week. It used to be a freight rail spur, and the entire length has been converted into a multi-use path with twelve access points. From up there you can see the old Milwaukee Avenue corridor, the CTA Blue Line running below, and rooftops of Chicago you would never see from the street. The trail connects four neighborhoods, Bucktown, Wicker Park, Logan Square, and Humboldt Park, and the trailhead at the west end is near the actual Bloomingdale Line mural project, a long wall of public art.

The parking is the main headache. The metered spots on the side streets fill up by 9 a.m. on Saturdays, and I have circled for twenty minutes more than once. The best move is to take the Blue Line to the Western stop and walk two blocks north.

Local Insider Tip: "Ride the trail end to end at golden hour in October. The trees on either side turn colors at slightly different times, and there is a small clearing near the western ramp that frames the downtown skyline perfectly."

The 606 is what Chicago does best: takes a piece of forgotten industrial infrastructure and turns it into public space.

Robie House and the Prairie Style Origin Story

Frank Lloyd Wright's Robie House sits at 5757 S. Woodlawn Avenue, in the Hyde Park neighborhood on the South Side, and it is the single most important residential building in American architecture. It was finished in 1910, and it is the textbook example of Prairie Style, low-slung, horizontal lines, overhanging eaves, ribbon windows, geometric ornament.

I took the tour last spring with a group of architecture students, and the guide pointed out details I had missed on three previous visits. The 174 leaded glass art glass windows are all original, and the central fireplace in the living room is the literal heart of the house, with every major room radiating out from it. The whole building is around 9,000 square feet, and the brick on the exterior was custom-made to match the color of the prairie soil.

Hyde Park itself is worth the trip. The University of Chicago is right there, the Oriental Institute has a 40-ton statue of a winged bull at the entrance that is free to see, and the neighborhood has a different feel from the rest of the city, quieter, older, more like a small Midwestern town inside Chicago.

Local Insider Tip: "Book the interior tour, not the exterior one, and ask the guide about the second floor. The balcony off the master bedroom faces the Midway Plaisance, and the view is what Wright designed the whole horizontal line of the house to frame."

Robie House is one of the historic sites Chicago architecture fans treat with the same seriousness as the Eiffel Tower, and it earns it.

Garfield Park Conservatory and the West Side Glasshouse

If you have already done Millennium Park and you want a quieter green space, the Garfield Park Conservatory at 300 N. Central Park Avenue is the move. I go there when the city gets loud. It is one of the largest conservatories in the country, covering about 4.5 acres under glass, and it sits on the west side, in a neighborhood most tourists never make it to.

The building was designed by Jens Jensen and opened in 1908, and it has eight display rooms, a permanent collection of about 600 plant species, and a few hundred more that rotate seasonally. The Fern Room, the Aroid House, and the Palm House are the three I go back to. The show room changes every season, and the Fall Flower Show in October is a thing I plan my year around.

Local Insider Tip: "Go on a Tuesday, when school groups are in session but the public crowds have not arrived. The staff horticulturists are usually walking the floor and will tell you what is about to bloom. Bring a notebook. I have gotten better plant advice here than from any nursery."

Garfield Park connects to the rest of the West Side through a long boulevard system, and the conservatory anchors one of the largest park districts in the city.

Historic Pullman and the Company Town

Pullman is a neighborhood on the far south side, around 111th Street, and it is the only National Monument in Chicago. I went there on a Saturday last summer and ended up spending four hours. The town was built in 1880 by George Pullman as a company town for the workers of his railroad sleeping car company, and it is one of the most intact planned industrial communities in the country.

The factory complex, now the Pullman National Monument since 2015, is open for tours, and the rows of worker housing, the Hotel Florence, the Market Hall, and the Greenstone Church are all still there. The strike of 1894, which started at this factory and spread across the country, is the kind of labor history that shaped the rest of American industry.

The neighborhood is also a real working community, not a museum, and the small diner near 111th and St. Lawrence has been there for thirty years. The corned beef hash is the real local deal.

Local Insider Tip: "Take the Metra Electric line to the 111th Street station from Millennium Park, it is about thirty minutes and you avoid the drive. The tour guide at the visitor center is a former Pullman worker, and his version of the 1894 strike is the version you want."

Pullman is the most under-visited of the famous monuments Chicago claims, and that is exactly why it is worth the trip.

When to Go and What to Know

Chicago summers are wonderful but extremely crowded, especially at Navy Pier and Millennium Park. The shoulder months of May, early June, September, and October have the best weather and the smallest crowds, and they are when the city actually feels like itself. Winter is brutally cold but has the best hotel prices, and the Magnificent Mile lights up for the holidays in late November.

CTA is the way to move around. A single ride is $2.50, a day pass is $5 for unlimited rides (downloaded as a Ventra ticket), and a 7-day pass is $20. The L goes almost everywhere you need to go, and the buses fill in the rest. Parking downtown averages $30 to $50 a day in garages, and street parking is mostly permit-based.

For food, get a Chicago-style hot dog at Portillo's (no ketchup, ever, this is a civic rule), a deep dish pizza at Lou Malnati's or Pequod's, and an Italian beef at Johnnie's Beef in Elmwood Park. The skyscraper canyons along the river are best seen from the Chicago Riverwalk, which is free and runs the entire west bank of the main stem of the river from Lake Street to Lake Michigan.

Frequently Asked Questions

Is it possible to walk between the main sightseeing spots in Chicago, or is local transport necessary?

The Loop, Millennium Park, the Art Institute