Chicago's great attractions are built things, and the dates read like a timeline: Holy Name Cathedral from 1874, Our Lady of Sorrows Basilica (out at 3121 West Jackson Boulevard) from the same year, the Chicago Theatre from 1921, Buckingham Fountain from 1927, the Civic Opera House from 1929, Willis Tower from 1971, the Harris Theater from 2003, and Cloud Gate from 2004. Several carry formal protection. The fountain, the theatre and Navy Pier are all Chicago Landmarks, and the cathedral is listed on the National Register of Historic Places. This list is for the visitor who wants the city's real architecture and public spaces, and who will skip the souvenir circuit. We've mixed the obvious names with places of worship that most itineraries leave out, including Mosque Maryam on South Stony Island Avenue. Go in any order, but do go to all twelve.
-
1 Willis Tower
233 South Wacker Drive, Chicago, IL 60606The skyscraper that sets the scale for the whole Chicago skyline
Willis Tower, dating from 1971, stands at 233 South Wacker Drive in the 60606 postal area: every other building in town ends up measured against it. Resist the urge to treat it as one photo snapped from the pavement, because a skyscraper of this size looks different from every approach, and walking up Wacker shows you the whole silhouette before you end up underneath it. Before you go, check the tower's own site, willistower.com, which is the authority on what you can see inside and when. Come late in the day, when the office crowd has gone and the street goes quiet enough for you to stand still and take in the height.
Dates from 1971
-
2 Cloud Gate
11 North Michigan AvenueA public art sculpture that hands the city back to you as a reflection
The city shimmers across the curved surface of Cloud Gate at 11 North Michigan Avenue, a public art sculpture that turns everyone who walks up to it into part of the composition. It dates from 2004, which puts it among the younger landmarks on this list, but it has earned its place. Skip the midday scrum at the front, where everyone lines up for the same photo, and walk underneath and around to the far side, where the distortions get stranger and the crowd thins out. Early morning is the best time, before the selfie lines form, when you can see your own reflection without twenty strangers in it.
Dates from 2004
-
3 Buckingham Fountain
301 South Columbus Drive, Chicago, IL 60605A fountain from 1927 that holds Chicago Landmark status
Buckingham Fountain at 301 South Columbus Drive, in the 60605, has been part of the city since 1927 and holds Chicago Landmark status. Don't give it a quick look through a car window. Walk all the way round the basin, find the side the wind is blowing away from, and give the water a few minutes. It is a fountain, plain and simple, and it needs neither an exhibit nor a ticket desk to justify the visit. The Chicago Park District keeps the official page, and that is where to check whether the water is running before you plan an evening around it.
Dates from 1927 · Chicago Landmark
-
4 Chicago Theatre
175 N. State Street, Chicago, IL 60601A former movie theater from 1921, now a live theater with Chicago Landmark status
At 175 North State Street, in the 60601, the Chicago Theatre has stood since 1921, opening as a movie theater before settling into its current life as a live theater, with Chicago Landmark status. Skip the anonymous modern halls that could be in any city. Book a seat here and the building becomes part of the evening, not just the box around it. Even without a ticket, the State Street frontage deserves a proper pause rather than a glance on your way past. Take in the details, then decide whether to come back after dark for a show.
Dates from 1921 · Chicago Landmark
-
5 Navy Pier
600 East Grand Avenue, Chicago, IL 60611An amusement pier with Chicago Landmark status
Navy Pier, at 600 East Grand Avenue, 60611, is an amusement pier that also holds Chicago Landmark status, though it is not worth the full day some itineraries give it. We'd treat it as a long walk and a breath of air, taking a ride or two if the mood strikes, then leaving before the arcade noise wears you down. The landmark status is the part most people miss, so slow down for the pier's structure and not just the attractions bolted onto it. What runs changes with the season, so check navypier.com before you go and plan the visit around something you want to see.
Chicago Landmark
-
6 Holy Name Cathedral, Chicago
730 North Wabash AvenueA Catholic cathedral from 1874 listed on the National Register of Historic Places
Holy Name Cathedral has stood at 730 North Wabash Avenue since 1874, a Catholic cathedral listed on the National Register of Historic Places that gets fewer sightseers than its history deserves. Slip in on a weekday between services, when the interior is quiet and you can sit for ten minutes without feeling like an intruder. Check Mass times on holynamecathedral.org before you go, so you arrive respectfully and don't walk in halfway through a service. Think of it as a working church that happens to be a landmark, not a museum that happens to hold services.
Dates from 1874 · National Register of Historic Places listed place
-
7 Chicago Temple Building
West Washington Street, Chicago, IL 60602A church building from 1924 in the 60602 postal area
The Chicago Temple Building on West Washington Street, in the 60602, is a church building dating from 1924, and most people walk straight past it, assuming it is just another downtown block. Don't make that mistake. Give the facade a proper look, and consider what it means for a congregation to have kept a home among the city's commercial streets for this long. Visiting arrangements are set by the church itself, so check chicagotemple.org for when the doors are open to visitors before you plan a stop inside.
Dates from 1924
-
8 Civic Opera House
20 North Wacker Dr, Chicago, IL 60606An opera house dating from 1929
The Civic Opera House at 20 North Wacker Dr, 60606 is an opera house that dates from 1929, and if you are going to hear opera in this city, it should be here, not in a hotel ballroom at a cut-price night. Dress up a little, arrive early enough to take in the building before the lights go down, and stay for the walk out afterwards along Wacker. Even if opera isn't your thing, the building is worth seeing from the street. Check the season and ticketing on civicoperahouse.com well before your trip, since the best nights go first.
Dates from 1929
-
9 Harris Theater
205 East Randolph Street, Chicago, IL 60601A theater dating from 2003, the modern counterpoint to the city's older stages
The Harris Theater at 205 East Randolph Street in the 60601 is a theater that dates from 2003, so you get a modern hall rather than a gilded relic, and that is the reason to come. It holds its own against the big touring houses when what you want is an evening that feels chosen and not sold to you, and the programming tends to reward a little curiosity. Browse the calendar on harristheaterchicago.org, pick something you wouldn't book at home, and give it a night. Pairing it with one of the older stages on this list gives you two very different Chicago evenings.
Dates from 2003
-
10 Chicago Water Tower
806 North Michigan Avenue, Chicago, IL 60611A water tower recognised as a contributing property on the National Register of Historic Places
The Chicago Water Tower at 806 North Michigan Avenue, 60611 opens at 10:00 on weekdays, closes at 19:00 Monday to Friday, and keeps shorter weekend hours of 10:00 to 17:00 on Saturday and Sunday. It is a water tower and a contributing property on the National Register of Historic Places, and that is enough reason to stop. Skip the shopping detour most visitors tack on: the tower is why you are on this stretch of Michigan Avenue, so give it your full attention and not a hurried photo between store windows. Weekday afternoons give you the longest window to wander in at your own pace.
National Register of Historic Places contributing property
Hours: Mo-Fr 10:00-19:00; Sa,Su 10:00-17:00
-
11 Our Lady of Sorrows Basilica
3121 West Jackson Boulevard, Chicago, Illinois 60612A Catholic church dating from 1874
Our Lady of Sorrows Basilica, at 3121 West Jackson Boulevard, 60612, is a Catholic church that dates from 1874, and most visitors to Chicago never make the trip out here. We think they lose out. There are no tour groups working their way through this one, no crowd at the entrance, and if you want to experience a church on its own terms, this is where to come. Sit at the back, let your eyes adjust, and give the building the quiet it asks for. Check ols-chicago.org for service times before you set out, so you arrive when the doors are open and nobody is mid-ceremony.
Dates from 1874
-
12 Mosque Maryam
7351 South Stony Island Avenue, Chicago, IL 60649A mosque on South Stony Island Avenue, a place of worship most Chicago itineraries never reach
Mosque Maryam at 7351 South Stony Island Avenue, 60649, is a mosque that rounds out a list otherwise dominated by downtown names and older churches, and it asks something different of you than the usual stops on a Chicago visit. Don't treat it as a quick photo opportunity. It is a place of worship first, and seeing it properly means doing a little preparation: check the official site, noi.org, before you go, dress modestly, and let the people who use this building every day take the lead. The trip to this address will tell you more about Chicago than another hour in the shopping district.
Last verified by automated review (v1.7.2_nonsight1017-1015-1839-20261017072551) on . What is automated review?