Grab your walking shoes, and become an urban adventurer. Long-time Chicagoan Robert Loerzel leads you on 35 unique walking tours in this comprehensive guidebook. Go beyond the obvious with self-guided tours through one of the nation’s most walkable cities, which is equal parts glamour and grit. Chicago’s diverse neighborhoods represent a melting potfrom Little Italy to Greektown, La Villita to the Ukrainian Village.
With this guide in hand, you’ll soak up history, political gossip, and architectural trivia. Find ethnic culture in Andersonville or high culture at the Art Institute. Listen to the blues on the South Side, or catch a ballgame on the North Side. Marvel at the Frank Lloyd Wright architecture in Oak Park or at nature’s masterpiece along Lake Michigan. There are tips on the best cafes, bars, and night spots. With humorous anecdotes, surprising stories, and fun facts to share with others, this guidebook has it all. Whether you’re looking for a walk on the beach or a slice of deep dish pizza, Walking Chicago will get you there. So find a route that appeals to you, and walk Chicago!
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The Magnificent Mile: Chicago’s Top Shopping
- Boundaries: Chicago River, Rush St., Cedar St., Lake Michigan
- Distance: 1.6 miles
- Difficulty: Easy
- Parking: Paid garages
- Public Transit: Use any of the CTA bus routes that stop on Michigan Ave. near Tribune Tower, or walk east from the Red Line’s Grand station.
The Magnificent Mile is nearly always bustling. The stores and restaurants are the main attraction on this 13-block stretch of North Michigan Avenue, but it’s also a prime spot for people watching and architectural sightseeing.
Its origins go back to the opening of Michigan Avenue’s bridge in 1920, which spurred construction north of the river. But then the Depression hit, stalling development. After Arthur Rubloff and William Zeckendorf bought much of the property along North Michigan Avenue, Rubloff unveiled his plan to create what he called the “Magnificent Mile” in 1947. That kicked off a retail boom.
The wealthy Streeterville neighborhood is east of Michigan Avenue, including Northwestern Memorial Hospital, Ann & Robert H. Lurie Children’s Hospital, and Northwestern University’s downtown campus. The River North neighborhood (Walk 9) is to the west.
Begin at Michigan Avenue and Illinois Street. The skyscraper at the northeast corner embodies the stylish architecture of the 1920s. It’s now the InterContinental Chicago Magnificent Mile, but the Chicago Shriners Club built the 42-story south tower in 1929 as the Medinah Athletic Club. Within four years, the Depression drove the club into bankruptcy. Architect Walter W. Ahlschlager borrowed elements from Egyptian, Greek, Celtic, Mesopotamian, medieval European, Gothic, and art deco styles. The hotel has a junior Olympic swimming pool on the 14th floor, where Olympian and Tarzan film star Johnny Weissmuller trained.
Walk north, and you’ll see an opening in the buildings where Michigan Avenue passes over Grand Avenuea reminder that the Magnificent Mile is one story above ground level here. Along the terrace west of Michigan, the Purple Pig serves pig’s tails and pig’s ears along with more typical porcine dishes like pork chops, ham, and bacon.
A building at 520 includes the Gwen hotelnamed after noted artist Gwen Lux, who sculpted mythological figures including Helios, Atlas, and Diana on the limestone panels above the entrance in collaboration with her then-husband Eugene Lux. This wall was salvaged from the McGraw-Hill Building, built in 1929 and demolished in 1998. The Shops at North Bridge, a four-level mall anchored by Nordstrom, fills a stretch north of the Gwen.
Farther north, one of the street’s boldest buildings is the Burberry store, completed in 2012, which looks like it’s encased inside a shiny black package featuring the clothing brand’s signature check pattern. At the northeast corner of Michigan and Erie Street, a nine-story-high mural shows people escaping from the Mag Mileclimbing up a ladder toward a circular portal, where trees and mountains are visible. “It’s an evocative view of a greener and unspoiled place,” Spanish artist Ignasi Monreal, who painted it in 2019, told the Curbed Chicago website.
Farther north, the Allerton Hotel is a rare Chicago example of North Italian Renaissance architecture. Completed in 1924, it was a residential “club hotel” catering to single young men with white-collar jobs. Near the top, a sign advertises the Tip Top Tap, a 23rd-floor lounge where Frank Sinatra and Bob Hope reportedly performed in the 1940s and 1950s. The Tip Top Tap hasn’t actually been open since the 1960s.
When you reach Chicago Avenue, go to the northwest cornerand the Water Tower, one of very few buildings around here that survived the Great Chicago Fire of 1871, when “the whole neighborhood, for blocks around, became a ‘sea of fire,’” according to a city report. Ever since, it has been a symbol of the Chicago’s rebirth. Built in 1869 and designed by William W. Boyingtonalong with the pumping station across the streetthe 182.5-foot-tall yellow limestone tower was a fancy disguise for an unglamorous piece of infrastructure: a standpipe that regulated water flowing from a crib two miles out into Lake Michigan. When Oscar Wilde visited Chicago in 1882, he called it a “castellated monstrosity.” The city now runs a gallery inside the Water Tower. The surrounding park, named Jane M. Byrne Plaza, is usually busy with pedestrians passing through and people relaxing in chairs. Horse-drawn carriages line up on Tower Court west of the plaza. The Loyola University Museum of Art is west of the plaza’s north end, inside Lewis Towers, a 1926 building that originally served as the Illinois Women’s Athletic Club.
Walk northeast through the plaza. At Pearson Street, go east across Michigan Avenue. Water Tower Place, a mall and 74-story high-rise, is on the northeast corner. Inside, eight stories of retail spaces encircle an atrium. Water Tower Place was a big deal when it opened in 1975, with as much retail space as the rest of North Michigan Avenue combined. And it remains popular today, with a Macy’s, the region’s only American Girl store, and more than 100 other shops, a dozen restaurants, and the Broadway Playhouse.
The Chicago Avenue Pumping Station is on the southeast corner of Pearson and Michigan. Walk through the first entrance on the building’s north side, entering a space where you can look through glass walls at the pipes and machinery. Turn left, walking east to the next room. The acclaimed Lookingglass Theatre Company has occupied the space to your right since 2003. Turn left, heading into a foyer with an information center for tourists, along with a library branch. Exit onto Pearson. Walk back west, then go south on Michigan.
Turn east on Chicago Avenue. On the street’s north side, a two-story limestone fire station with glossy red front doors houses the Chicago Fire Department’s Engine Company 98 and Ambulance 11. Built in 1902, it’s among of the city’s oldest active fire stations, with a design by Charles Hermann that complements the Water Tower. As you continue east, Seneca Park is on the street’s north side, including Deborah Butterfield’s 1990 sculpture Ben, a horse that looks like it’s assembled out of tree branches but is actually bronze.
At the next corner, turn north on Mies van der Rohe Way, entering the plaza in front of the Museum of Contemporary Art Chicago. Located here since 1996, the museum showcases post-1945 art in its large galleries. German architect Josef Paul Kleihues’s building has an aluminum facade and a limestone base, with a set of 32 wide steps leading up to the entrance. Large sculptures are sometimes displayed in the plaza. At the southeast corner, there’s a ground-level entrance to the gift shop, a trove of quirky oddities. At the northeast corner, doors lead into the MCA’s theater.
Go to the MCA’s north end, then turn east on Pearson, walking along Lake Shore Park. Turn north on Lake Shore Drive. After you pass Chestnut Street, look at the pair of box-shaped glass-and-steel residential high-rises at 860 and 880 N. Lake Shore. Completed in 1951 and known as the “Glass House” apartments, they were the first residential skyscrapers designed by Ludwig Mies van der Rohe, the influential German-born Chicago architect.
Turn west on Delaware Place. As you approach Michigan Avenue, the building originally known as the John Hancock Centernow called 875 North Michigandominates Delaware’s south side. When this 100-story skyscraper was completed in 1969, it was the world’s second-tallest building. Just east of the Hancock, there’s a small building called the Casino Club. This private club, which has been here since 1928, refused to sell its property in the 1960s, forcing Skidmore, Owings & Merrill’s architect Bruce Graham and engineer Fazlur Khan to rethink the original plan for building two skyscrapers on this block. Khan figured out a new way to construct a single tower tall enough to serve the project’s needs. Unlike all previous skyscrapers, this one is a giant tapered rectangular tube, supported by trusses on each side. The exterior structure is what holds up the 1,128-foot building, allowing for wide open spaces inside. Those huge X-shaped braces on the exterior enable “Big John” to resist the wind. The building’s elevators are said to be North America’s fastest, zooming up to the 95th floor in 38 seconds. The 360 Chicago observatory offers 360-degree views from the 94th floors. For an extra fee, visitors can enter the Tilt, a box on the building’s edge with floor-to-ceiling windows that slowly tilts to 30 degrees. The Signature Room restaurant is on the 95th floor, with a bar called the Signature Lounge one story up.
West of the skyscraper, Fourth Presbyterian Church is the oldest structure on North Michigan Avenue other than the Water Tower. Completed in 1914, it was designed by a leading architect of the Gothic revival style, Ralph Adams Cram, while Howard Van Doren Shaw designed the Tudor-style parish buildings around its courtyard.
Walk north on Michigan. The 900 North Michigan Shops mall is anchored by Bloomingdale’s. The Palmolive Building, a 1929 art deco skyscraper designed by Holabird & Root, stands at the southeast corner of Michigan and Walton Place. This was the Playboy Building from 1965 to 1989, housing the magazine’s editorial and business officeswith nine-foot-high illuminated letters at the top, spelling out “PLAYBOY.” Installed in 1930, an aerial beacon named for aviator Charles Lindbergh was atop the building, with an arc light rotating 360 degrees and projecting a beam into the night sky, reportedly visible from as far away as Cleveland. The light was shut off in 1981 when neighbors complained. In 2007, the light began shining again, every night from 8 p.m. until midnight, but with a modificationnow its beam is directed in an arc over Lake Michigan. The building’s Palmolive name was restored after new owners converted it into condos.
Farther north, the Drake Hotel dates back to 1920. The Italian Renaissance-style building was designed by architects Benjamin Marshall and Charles Fox. The hotel’s Coq d’Or bar has been serving liquor since a day after Prohibition was lifted in 1933. The Palm Court is famous for its afternoon tea, a ritual that Diana, Princess of Wales, participated in during her stay in 1996. In the Cape Cod room, you can see the spot on the wooden bar where Joe DiMaggio and Marilyn Monroe carved their initials.
Across the street, Spiaggia has been acclaimed by many critics as Chicago’s best Italian restaurant for more than three decades. For a less pricey meal, try the adjacent Cafe Spiaggia. Continue north on Michigan, crossing Oak Street. As you approach the pedestrian tunnel under Lake Shore Drive, pause to look back at the Drake’s northern face, with the Palmolive Building and its beacon towering up behind itand farther back, the Hancock overshadowing both. Go through the tunnel under Lake Shore Driveemerging on the sands of Oak Street Beach, a great spot for looking at Lake Michigan and vistas of Chicago.
To depart, use one of the many bus routes that stop at Michigan Avenue and Delaware Place.
Points of Interest
- InterContinental Chicago Magnificent Mile 505 N. Michigan Ave., 312-944-4100, cchicagohotel.com
- The Purple Pig 500 N. Michigan Ave., 312-464-1744, thepurplepigchicago.com
- The Gwen hotel 521 N. Rush St., 312-645-1500, thegwenchicago.com
- Shops at North Bridge 520 N. Michigan Ave. 520 N. Michigan Ave., 312-327-2300, theshopsatnorthbridge.com
- Allerton Hotel 701 N. Michigan Ave., 312-440-1500, warwickhotels.com/allerton-hotel-chicago
- Chicago Water Tower 806 N. Michigan Ave.
- Loyola University Museum of Art 820 N. Michigan Ave., 312-915-7600, luc.edu/luma
- Water Tower Place 835 N. Michigan Ave., 312-440-3580, shopwatertower.com
- Lookingglass Theatre 821 N. Michigan Ave., 312-337-0665, lookingglasstheatre.org
- Museum of Contemporary Art Chicago 220 E. Chicago Ave., 312-280-2660, mcachicago.org
- 875 North Michigan (John Hancock Center) 875 N. Michigan Ave., 875northmichiganavenue.com; 360 Chicago Observation Deck Chicago, 888-875-8439, 360chicago.com
- 900 North Michigan Shops 900 N. Michigan Ave., 312-915-3916, shop900.com
- Drake Hotel 140 E. Walton Pl., 312-787-2200, thedrakehotel.com
- Spiaggia 980 N. Michigan Ave., 312-280-2750, spiaggiarestaurant.com
- Oak Street Beach 1000 N. Lake Shore Dr., 312-742-3224, chicagoparkdistrict.com/parks-facilities/oak-street-beach
Table of ContentsAcknowledgments
- Michigan Avenue at the Chicago River
- The Loop, Part 1
- The Loop, Part 2
- The Loop, Part 3
- Millennium Park & the New Eastside
- Grant Park
- The Museum Campus & Northerly Island
- The Chicago Riverwalk
- River North
- The Magnificent Mile
- Near South Side
- Hyde Park & Kenwood
- Jackson Park & South Shore
- Wolf Lake
- West Loop
- Little Italy & Vicinity
- Beverly & Morgan Park
- Garfield Park
- The 606
- Humboldt Park
- Wicker Park & Vicinity
- Logan Square
- The Gold Coast & Old Town
- Lincoln Park
- Lake View
- The Lakefront from Addison to Foster
- Andersonville & Uptown
- Rogers Park
- Lincoln Square & Nearby
- North Branch Trail
Appendix: Walks by Theme
About the Authors