A Self-Guided Tour for The Most Beautiful Places in Chicago
Meredith Francis
December 6, 2023
Retrace Geoffrey Baer’s footsteps with these self-guided tours of the locations featured in The Most Beautiful Places in Chicago and The Most Beautiful Places in Chicago 2.
We’ve arranged the tour by geographical area, so you can try one or all of them. (Just select the “layer” on the map of which tour you want.) Some are made for walking, others are best enjoyed by transit or car. These are just our recommended directions – if you know a better route or need to reverse the order, go for it! We’ve linked to info about each of the locations, so if you’re a know-before-you-go kind of person, we’ve got you covered.
A note about entering some locations: Some of these beauties are schools, places of worship, or private businesses, so you will not necessarily be able to enter them. Some locations offer their own tours, so be sure to check out their business hours if you’re interested in that.
Some tips for having fun: Build in time for a meal in the neighborhood, bring a friend and a camera, and take a moment to stop and rest in some of the parks to take in the beauty of Chicago.
Michigan Avenue and The Loop
This quintessential downtown tour is walkable if you’ve got the stamina, the right set of shoes, and want to build in stops to rest and grab a bite to eat.
Starting point: 875 North Michigan Avenue (formerly known as the Hancock Center)
Address: 875 N. Michigan Ave.
Why it’s beautiful: The architects who designed the Hancock Center pioneered a new structure that allowed buildings to be taller. Its tapered structure and the X’s that create the exterior cross bracing have made it an iconic part of Chicago’s skyline since 1969. Plus, Geoffrey Baer showed us that the view from the top is stunning even in bad weather.
Stop 2: InterContinental Chicago
Address: 505 N. Michigan Ave.
Why it’s beautiful: Look up at its limestone facade, which contains detailed relief sculptures in a pseudo-Mesopotamian motif.
Getting there: Located at Michigan Avenue and Illinois Street, InterContinental Chicago is about a 15-minute walk south down Michigan Avenue from the Hancock Center. You could also hop the 146, 147, or 151 CTA bus for a quick ride.
Stop 3: Tribune Tower
Address: 435 Michigan Ave.
Why it’s beautiful: Tribune Tower was built as part of a competition to create the most beautiful building in the world. Its neo-Gothic details and flying buttresses are reminiscent of a cathedral.
Getting there: This is an easy one! It’s just a block south of InterContinental Chicago.
Stop 4: Marina City and AMA Plaza (with a bonus glimpse of The St. Regis Chicago)
Address: See from the corner of E. Wacker Dr. and State St.
Why they’re beautiful: What’s not to love about Marina City’s corn cob appearance? Just east of the curving lines of Marina City is Ludwig Mies van der Rohe’s modernist building, AMA Plaza, which embodies the principle that “less is more."
Getting there: To get the best look at Marina City and AMA Plaza, head south down Michigan Avenue. At the DuSable Bridge, look east towards the lake for the wavy outline of The St. Regis Chicago and cross the river on the DuSable Bridge. Walk west on Wacker Drive and head to the corner of State Street for a nice, straight shot of the buildings across the river. It’s about a 10-minute walk from Tribune Tower.
Stop 5: Chicago Cultural Center
Address: 78 E. Washington St. (You can enter on Randolph St., too.)
Why it’s beautiful: The interior of the Chicago Cultural Center has two breathtaking domes: Preston Bradley Hall’s Tiffany glass dome, and The Grand Army of the Republic Hall and Rotunda, which was restored to its former glory in 2022.
Getting there: From your spot at State Street and Wacker Drive, walk south to State and Randolph, then walk east on Randolph until you reach the Chicago Cultural Center. It’s about a 10-minute walk. It’s free to enter.
Stop 6: Millennium Park
Address: 201 E. Randolph St.
Why it’s beautiful: There’s something beautiful for everyone here: Cloudgate (a.k.a. The Bean), the Frank Gehry-designed Pritzker Pavilion, Crown Fountain, Lurie Garden, and more.
Getting there: Millennium Park is just across Michigan Avenue from the Chicago Cultural Center.
Stop 7: Macy’s Tiffany Mosaic Ceiling
Address: 111 N. State St. (State and Washington)
Why it’s beautiful: Imagine what it was like to stand under this Tiffany mosaic in the original Marshall Field’s in 1907. There are over one million pieces to this gem.
Getting there: You’ll want to aim for the building’s entrance on State and Washington, which is less than a 10-minute walk from the Bean. You’re in the right place if you head toward the make-up counters. If you want a stunning, up-close look at the mosaic, take the elevators up to the 5th floor.
Stop 8: Reliance Building
Address: 1 W. Washington St.
Why it’s beautiful: If you saw this building in the 19th century, it would have been a marvel – all that glass on a skyscraper?! It was unfathomable in those days.
Getting there: The Reliance Building is caddy-corner from Macy’s, on the southwest corner of State and Washington.
Stop 9: Sullivan Center
Address: 9 E. Madison St.
Why it’s beautiful: Hidden in the black, ornamented cast-iron entrance of the Sullivan Center, you can find the initials L. H. S., which the architect, Louis Henry Sullivan, left as a kind of signature on his work.
Getting there: Walk one block south from the Reliance Building toward State and Madison.
Stop 10: The Rookery
Address: 209 S. La Salle St.
Why it’s beautiful: Famed architects Burnham and Root designed this building, and then Frank Lloyd Wright gave its stunning, light-filled lobby a makeover in 1907. You can walk in and see the lobby for yourself.
Getting there: Walk two blocks south of the Sullivan Center, then head west on Adams Street and walk three more blocks toward La Salle Street. It’s about a 10-minute trip.
Stop 11: Manhattan Building
Address: 431 S. Dearborn St.
Why it’s beautiful: One of the city’s early skyscrapers, the Manhattan Building has some fun details in its facade: Spooky faces that peer down at the sidewalk below.
Getting there: Exit onto Adams Street, walk two blocks east towards Adams Street, then walk south on Dearborn. The building is just north of Ida B. Wells Drive, and it should take about 10 minutes to walk there from the Rookery.
South Loop and Near South Side
This tour features two beautiful parks and is ideal for a nice, sunny afternoon. If you’re driving, we recommend using the GPS on your phone. There are many routes between locations
Starting Point: Harrison Street and Wabash Avenue (Wabash Arts Corridor)
Why it’s beautiful: If you walk south down Wabash Avenue starting at Harrison Street for several blocks, you’ll notice murals all over the place that make up the Wabash Arts Corridor. They transform basic downtown parking lots and the sides of buildings into colorful works of art.
Stop 2: Glessner House
Address: 1800 S. Prairie Ave.
Why it’s beautiful: This impressive structure is a time capsule for Chicago’s opulent Gilded Age. If you want to go inside, according to the Glessner House website, they are open for tours on Wednesday, Friday, and Saturday at 11:30 am, 1:00 pm, and 2:30 pm.
Getting there: If you’re into a long walk, this is a 30-minute walk from Harrison and Wabash. You can also head a block east to Michigan Avenue and hop the 3 King Drive bus or the 4 Cottage Grove bus south. Get off at 18th Street and walk east.
Stop 3: Second Presbyterian Church
Address: 1936 S. Michigan Ave.
Why it’s beautiful: This South Loop church has beautifully restored stained glass windows, some of which are Tiffany glass.
Getting there: This is just a 5- to 10-minute walk around the corner on Michigan Avenue. Head west on 18th Street, then south toward Cullerton Avenue.
Stop 4: Ping Tom Memorial Park
Address: 1700 S. Wentworth Ave. (access entrance via 19th Street)
Why it’s beautiful: This riverside park was designed by landscape architect Ernie Wong, who took inspiration from the nearby Chinatown neighborhood.
Getting there: There isn’t much of a transit option here, so be ready to walk about 15 minutes. You’ll walk west down Cullerton Avenue, and then southwest on Archer Avenue. Then, you’ll turn right (walking north) on Wentworth Avenue. You’ll walk west down 19th Street until you reach the entrance of Ping Tom Park, which is tucked away on that street!
Stop 5: Pui Tak Center
Address: 2216 S. Wentworth Ave.
Why it’s beautiful: This Chinatown mainstay has ornate, terra-cotta panels on its facade and pagoda-inspired towers. Pro-tip: Head to Chinatown’s oldest bakery nearby for a snack break.
Getting there: You can leave Ping Tom Park the way you entered, heading toward Wentworth Avenue. Walk south down Wentworth until you pass under the Chinatown gateway, and the building will be on your right. The walk should take less than 10 minutes.
Stop 6: Palmisano Park
Address: 2700 S. Halsted St.
Why it’s beautiful: This is another Ernie Wong-designed park, and features a beautiful quarry-turned-pond as its showpiece.
Getting there: It’s about a 25-minute walk southwest down Archer Avenue, then south down Halsted Street. You can also hop the 62 Archer bus toward Harlem and get off at the Halsted Orange Line station and then walk down Halsted Street.
South Side
As architecture critic Lee Bey points out in The Most Beautiful Places in Chicago 2, the architecture of the South Side is often overlooked, despite the area being large and populous enough to be a city within a city. There’s a big geographic area to cover in this tour, so this one is probably best done via car or in parts. If you’re driving, we recommend using the GPS on your phone. There are many routes between locations, so we’ve just given the estimated drive time.
Starting point: Liberty Baptist Church
Address: 4849 S. King Dr.
Why it’s beautiful: Liberty Baptist Church has a beautiful, bold, parabola-shaped roof that recalls its postwar, modernist roots.
Stop 2: KAM Isaiah Israel
Address: 5039 S. Greenwood Ave.
Why it’s beautiful: This Byzantine-style synagogue in Hyde Park serves as the house of worship for Chicago’s oldest Jewish congregation.
Getting there: It’s about a 5-minute drive to Kam Isaiah Israel from Liberty Baptist Church.
Stop 3: Jackson Park’s Bobolink Meadow
Address: 6401 S. Richards Dr. (This is the address for the Jackson Park Driving Range, which shares a parking lot with Bobolink Meadow).
Why it’s beautiful: Jackson Park, the location of the 1893 World’s Columbian Exposition, is also a haven for more than 250 species of birds, and the Bobolink Meadow makes for a great birdwatching spot.
Getting there: There’s a parking lot south of the meadow near the driving range. The entrance to the path is at the north end of the lot. It’s about a 10-minute drive from Kam Isaiah Israel.
Stop 4: South Shore Cultural Center
Address: 7059 S. South Shore Dr.
Why it’s beautiful: This Mediterranean Revival building sits on beautiful public park property right on the lake.
Getting there: The South Shore Cultural Center is about a 5-minute drive from the Bobolink Meadow parking lot.
Stop 5: Steelworkers Park
Address: E. 87th St. at Lake Michigan
Why it’s beautiful: This repurposed park has ore walls that are now climbing walls, and a sculpture by artist Roman Villarreal that honors the steel mill families who built their lives in the neighborhood.
Getting there: Steelworkers Park is as far east as you can go on 87th Street, about a 10-minute drive from the South Shore Cultural Center.
Stop 6: Bowen High School
Address: 2710 E. 89th St.
Why it’s beautiful: Bowen High School is a twin to the North Side’s Schurz High School, and both were designed by prairie school architect Dwight Perkins, departing from the “Dickensian” school design of the past.
Getting there: This is less than a 10-minute drive from Steelworkers Park. Obviously, this is a high school, so you won’t be able to enter! You can admire the architecture from 89th Street.
Stop 7: Chicago Vocational High School
Address: 2100 E. 87th St.
Why it’s beautiful: This art moderne-style building has relief sculptures carved into its facade that celebrate the trades taught at the school.
Getting there: This is a 5-minute drive from Bowen High School. Again, it’s a high school, so you won’t be able to enter.
Stop 8: Lavezzorio Community Center
Address: 7600 S. Parnell Ave.
Why it’s beautiful: Studio Gang designed this community center that has a striking exterior with visible layers of differently shaded concrete.
Getting there: This is about 15 minutes from Chicago Vocational High School. This is a functioning center for foster children and families, so you’ll only be able to admire Jeanne Gang’s architecture from outside.
West Side
This tour, with gorgeous parks and stunning houses of worship, is a little bit more spread out and zig-zags around the West Side, so you’ll need a car or transit for this one. Just a heads up before you go: Transit will take longer on this one since you’re zig-zagging and often switching buses! There are many routes between locations, so we’ve just given the estimated drive time.
Starting point: Humboldt Park (The Boathouse)
Address: 1301 N. Humboldt Dr.
Why it’s beautiful: You could spend hours exploring the green spaces of Humboldt Park, but some of the buildings have classic Chicago charm, including its Prairie-Style, open-air boathouse.
Stop 2: Sts. Volodymyr & Olha Ukrainian Catholic Church
Address: 739 N. Oakley Blvd.
Why it’s beautiful: This church has a shining gold dome, a colorful mosaic over its entrance, and a bright, elaborate interior if you’re able to visit when it’s open.
Getting there: It’s about a 10-minute drive from the Humboldt Park Boathouse, or 25 minutes on transit, south on the 94 California bus and east on the 66 Chicago bus.
Stop 3: Our Lady of Sorrows Basilica
Address: 3121 W. Jackson Blvd.
Why it’s beautiful: This renaissance revival basilica has an expansive, barrel-vaulted ceiling, and the nave contains ornate gold-leaf panels.
Getting there: This one is another 10-minute drive. It’ll take about half an hour on transit. You can take the 49 Western bus south and then the 126 Jackson bus west.
Stop 4: Garfield Park (Field House)
Address: 100 N. Central Park Ave.
Why it’s beautiful: Garfield Park’s Spanish baroque revival field house has a beautiful scallop-shell dome and is adorned with gleaming gold leaf. If you have the time and energy, make a reservation to visit the nearby, Jens Jensen-designed Garfield Park Conservatory.
Getting there: It’s a 6-minute drive from Our Lady of Sorrows. Or, you can grab the 126 Jackson bus heading west for a few minutes and get off at Central Park Avenue. There, you’re already in the park. The field house is a mile north.
Stop 5: Laramie State Bank
Address: 5200 W. Chicago Ave.
Why it’s beautiful: This West Side building, which was once a bank, has a bold, mustard-colored facade with interesting terra-cotta details.
Getting there: It’s a 15-minute drive to Laramie State Bank from the Garfield Park Field House. You can also hop on the Green Line at Conservatory-Central Park toward Harlem/Lake, get off at Laramie, and walk about half a mile north on Laramie.
Stop 6: Columbus Park (Refectory)
Address: 5701 W. Jackson Blvd.
Why it’s beautiful: Jens Jensen considered this park his masterpiece. It has a stunning natural area that mimics a glacial ridge among a natural prairie landscape, so although the park’s water elements appear to be natural, they are actually man-made.
Getting there: If you’re aiming for the refectory, Columbus Park is about a 10-minute drive from Laramie State Bank. There’s a parking lot on S. Golf Dr. To take public transit, it’ll take a little over 20 minutes going west on the 66 Chicago bus, and then south on the 85 Central bus to get off at Jackson.
Stop 6: Unity Temple
Address: 875 Lake St.
Why it’s beautiful: The sturdy exterior of Frank Lloyd Wright’s Unity Temple gives way to its light and airy interior. (You need to schedule a tour to see the interior.)
Getting there: It’s about a 15-minute drive from Columbus Park to Unity Temple in Oak Park. To take transit, be prepared to walk a bit. You can walk north on Central Avenue, and then take the Green Line toward Harlem/Lake and get off at Oak Park.
North Side
This tour of the North Side proves that beauty can be found in the smallest of details. This one also covers a large area, so it is also probably best done via car or in parts! A couple of the locations are also only open in warmer months, so this would be a spring, summer, or early fall adventure.
Starting point: Carl Schurz High School
Address: 3601 N. Milwaukee Ave.
Why it’s beautiful: Schurz High School is a twin to the South Side’s Bowen High School, and both were designed by prairie school architect Dwight Perkins, departing from the “Dickensian” school design of the past.
Stop 2: El Centro
Address: 3390 N. Avondale Ave.
Why it’s beautiful: The clever design of this NEIU building blocks out the sound of the nearby expressway, and its structure plays with color and light.
Getting there: El Centro is less than a 10-minute drive from Schurz High School.
Stop 3: Reebie Storage
Address: 2325 N. Clark St.
Why it’s beautiful: The terra-cotta facade of this Lincoln Park storage building features colorful designs, depicting scarab beetles, snakes, flowers, and other Egyptian motifs.
Getting there: It’s a 20-minute drive to Reebie Storage in Lincoln Park. Your next stop is just a 10-minute walk from Reebie storage, so we recommend parking for stop 3 and 4.
Stop 4: Alfred Caldwell Lily Pool
Address: 125 W. Fullerton Pkwy.
Why it’s beautiful: This small, slightly hidden garden is a quiet respite from the bustle of Lincoln Park and has been restored to landscape architect Alfred Caldwell’s original vision. Note: It’s only open during warmer months.
Getting there: This is a 10-minute walk east down Fullerton from Reebie Storage. It’s easy to miss the gate, which is just past Stockton Drive on the south side of the street.
Stop 5: Elks National Memorial
Address: 2750 N. Lakeview Ave.
Why it’s beautiful: With its ancient Roman-inspired architecture, this building looks like a memorial out of Washington, D.C. Note: It’s only open from mid-April through mid-November.
Getting there: This is less than a 5-minute drive from the lily pool, or less than a 20-minute walk.
Stop 6: Indian Land Dancing
Address: Foster Avenue Underpass at DuSable Lake Shore Drive
Why it’s beautiful: A local public art group worked with Chicago’s Native American community to incorporate their stories on this mural, which is made up of ceramic tile, paint, sculpted cement, mirror mosaic, and photo transfer tile.
Getting there: This is a 10-minute drive north up DuSable Lake Shore Drive. There’s a parking lot east of the Foster exit, and then you can get out and walk to the underpass to explore the mosaic.
Stop 7: Baháʼí House of Worship
Address: 100 Linden Ave.
Why it’s beautiful: The exterior of this house of worship looks like it’s made of elaborate lace, but is really made of concrete infused with crushed quartz to give the building an added shimmer.
Getting there: This will be your longest journey, but with a spectacular, intricate finale. It’s about 30 minutes north to Wilmette from the Indian Land Dancing mosaic.
