Chicago Old Town Walking Tour, Chicago

Chicago Old Town Walking Tour (Self Guided), Chicago

Settled in 1850 by German immigrants, Chicago’s Old Town neighborhood is a popular destination for locals and visitors who cater to the entertainment venues, restaurants, pubs, coffee shops and boutiques – all of which have turned an area once referred to as the “Cabbage Patch” into an attraction that rivals Navy Pier, Wrigley Field and the Magnificent Mile.

Start your Old Town walking tour with a stroll down Wells Street for dining and entertainment, then make a turn towards the architecturally and culturally significant West Burton Place to see how artists and craftspeople of the Depression Era transformed what were then deteriorating 19th-century rooming houses into a series of unique and cohesive artist studio environments.

Next up is the excellent Chicago History Museum’s coverage of all aspects of the city’s history, starting with a model of a fort and expanding into modern territory (including insights into Chicago’s leading role in innovations and design), while right opposite stands the Second City Theatre – a place that launched the career of many great comics, and that remains rooted in improvisational games you can experience today.

Further along the way, don’t miss a visit to St. Michael’s Church and the close-by Midwest Buddhist Temple (a fixture in Old Town since 1944), both located in beautiful green and quiet surroundings.

Take a self-guided walk through this clean and safe neighborhood to fully understand Chicago as a city!
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Chicago Old Town Walking Tour Map

Guide Name: Chicago Old Town Walking Tour
Guide Location: USA » Chicago (See other walking tours in Chicago)
Guide Type: Self-guided Walking Tour (Sightseeing)
# of Attractions: 9
Tour Duration: 2 Hour(s)
Travel Distance: 2.6 Km or 1.6 Miles
Author: doris
Sight(s) Featured in This Guide:
  • Wells Street
  • West Burton Place Historic District
  • Chicago History Museum
  • Second City Theater
  • Olsen-Hansen Row Houses
  • Crilly Court
  • Menomonee Street
  • Midwest Buddhist Temple
  • St. Michael's Church
Wells Street

1) Wells Street

Wells Street is the main street of Chicago's Old Town area, between Division Street to the south and Lincoln Avenue to the north. The heart of the area would be the intersection of Wells Street and North Avenue, while on the southeast corner, stretching out from this intersection, one will find a fine neighborhood of historic townhouses (late 1800s to early 1900s) lined along three streets: Dearborn, State, and Astor.

Wells Street is home to a string of reliable restaurants and bars, but most here are more casual, with average prices lower than you'll find in River North or along the Magnificent Mile. NOOKIES (Mon-Sat: 6:30am–10pm; Sun: 6:30am–9pm) is the go-to place for brunch; always full of mainly locals and with extremely friendly staff. They have an excellent range of breakfast, lunch and dinner choices, and since portions are so generous, takeout boxes for leftovers are provided. When the weather warms up, there is even some limited outside seating. Another favorite local spot, the OLD TOWN PUB (Sun-Fri: 12pm–2am; Sat: 12pm–3am) has good prices, better than expected food/drinks, and a slight charm on the inside, but if looking for an Irish pub (who doesn't when in Chicago?), don't miss the perfectly located DECLAN'S, which purports to be the official bar of the University of Notre Dame.

On the 2nd weekend in June, the Old Town Art Fair and the Wells Street Art Festival become hot events for the neighborhood, showcasing exceptional work by local artists.
West Burton Place Historic District

2) West Burton Place Historic District

Developed in the late 19th century but renovated into an artists' colony in the 1920s and 1930s, the West Burton Place includes an eclectic and interconnected set of twelve main houses and five carriage houses. It's as if you had turned a corner and stepped into a slightly weirder world.

On the block's southeastern side, the neighborhood's Victorian mansions are largely overtaken by an eruption of Art Deco and Art Moderne-style architectural fantasy, with the stark white Theophil Studios sporting large circular windows. The real highlight, however, is the sprawling Carl Street Studios, loosely modeled on the Montmarte studios in Paris by one of the most versatile Art Deco artists/craftsmen, Edgar Miller. Behind its quirky brick wall is a maze of tile-studded sidewalks, carved wooden doors and staircases, narrow passages, stained glass windows, and a pair of courtyard gardens with koi ponds!
Chicago History Museum

3) Chicago History Museum (must see)

Set on a beautiful piece of land near the Lincoln Park Zoo and the lakefront, this institution traces Chicago's rich history, beginning with its first explorers and settlers, through the city's development, to major events in modern-day Chicago. The interior is a mix of vintage and modern, with everything kept pristinely clean and tidy. It's an easy-in/easy-out museum, great to wander about for a couple of hours without the jostling crowds.

Many people may not know that the Chicago History Museum has one of the largest costume and textile collections (50,000 pieces) in the country, dating from the 18th century to present day. It also has an incredible collection of artifacts and original paintings that are unique to Chicago and US history, including the bed that Abraham Lincoln died in, slave shackles from Civil War time, original paintings by Norman Rockwell; a restored turn-of-the-century train car and many other fascinating objects. For sports fans, there is a display of some of the famous athletes in Chicago history, including Ernie Banks, Michael Jordan, Dick Butkus, Mike Ditka, Bobby Hull, and Stan Mikita.

As a side note, the 2nd-floor exhibits are more entertaining than those on the ground floor. Since most of the museum's exhibits are not interactive, there may not be a lot of appeal for little kids; however, there's a special area set aside just for them, with activity-based learning.

Opening Hours:
[Museum] Mon, Wed-Sat: 9:30am-4:30pm; Tue: 9:30am-9pm; Sun: 12-5pm
[Research Center] Tue-Fri: 1-4:30pm; Sat: 10am-4:30pm
[Café] Mon-Sat: 9:30am-3pm; Sun: 12-4pm
Second City Theater

4) Second City Theater (must see)

Old Town's biggest claim to fame, this comedy club is known for first-class acts who made it to the big screen: names like Mike Myers, Bill Murray, John Belushi and Tina Fey grace the foyer of fame.

Culturally relevant and hilarious, the place is usually packed and generates a good atmosphere, though one should definitely be prepared for a fair amount of profanity and left-leaning political content. Some parts contain a little bit of audience-participation improvisation; in fact, the third and final act (going around 10:30pm) is just that and no ticket is necessary to attend as the cast tries out new comedy material. Seats are otherwise considered first-come, first-served, so be sure to get in 20-30mins prior if you want the full show, or spend some extra to reserve seats on the rail.

Note that besides the Second City Theater, the complex also houses the Black Orchid Supper Club, a Sony Multiplex, as well as restaurants and a Starbucks. The theater's mainstage entrance features stone arches with faces originally from the Adler and Sullivan-designed Garrick Theater.

To visit one of Chicago's favorite dive spots, head to the OLD TOWN ALE HOUSE (Mon-Fri: 3pm–4am; Sat: 12pm–5am; Sun: 12pm–4am) known mainly for its proximity to Second City and the cast's inclination to hang out there after shows. The interior resembles a pub from decades past and is decorated with random paintings. It's packed on weekends, and loud, but that's what makes it so fun.

Opening Hours:
Mon-Thu: 10am-9pm; Fri: 10am-12am; Sat: 11am-12am; Sun: 11am-8pm
Olsen-Hansen Row Houses

5) Olsen-Hansen Row Houses (must see)

Primarily used in residential architecture, the Queen Anne style was highly influential in Chicago from the mid- to late 1800s. Here, as well as in other American cities, the name does not reflect a historical period or a specific formulaic style; instead, the look of the buildings is hybrid, mixing Classical, Tudor, Victorian, and Colonial elements together.

Along with Crilly Court (1885), the elaborate Olsen-Hansen Row Houses (1886) on West Eugenie Street are fine expressions of Queen Anne style. Although only five of the original twelve houses remain (No. 164 was the Norwegian-born architect's own residence), their turrets, various window styles, irregular roof-lines, Victorian porches, and combinations of building materials and colors typify the most exuberant design of the period.
Sight description based on Wikipedia.
Crilly Court

6) Crilly Court

Built in 1885 by real-estate developer Daniel Crilly, the Crilly Court's row houses, with their turrets and bay windows, are one of the finest examples of Queen Anne style in Chicago, creating what is now one of the city's quaintest streets. On the court's west side stand two-story stone row houses, while on the east side is a four-story apartment building, the names of Daniel Crilly's four children – Isabelle, Edgar, Eugene, and Erminie – carved above the doors.

The development's renovation in the 1940s included creating private courtyards and installing wrought-iron balconies, which give the complex a charming New Orleans-like atmosphere. This redevelopment, in turn, initiated the renewal of the greater Lincoln Park neighborhood soon after.
Menomonee Street

7) Menomonee Street

Menomonee St. lies in the heart of the Triangle Historic District, a delightful area of narrow tree-lined streets with picturesque houses and quite a few interesting shops and restaurants.

A walk along this street will give a good idea of what the Old Town community looked like before the Great Chicago Fire of 1871. Most of the area's original houses were small cottages with lightweight wooden frames and, as such, were reduced to ashes; however, the reconstructed ones located at Nos. 325–45 were built in the same style and with the same materials. Also of note, the whitish-gray dwellings at No. 348 and 215, on the edge of the street, are rare surviving examples of the one-room “fire relief” shanties built for people made homeless by the fire. These structures, costing the city about $100 each, were transported on wagons to a burned-out lot, providing instant lodging.

Walking east to Sedgwick Street, you will find one of Chicago's oldest taverns – MARGE'S STILL (Mon-Thu: 4:30pm–12am; Fri: 11:30am–1am; Sat, Sun: 10am–1am). From outside in and inside out, the place looks great; one you'll want to walk into and spend a lot of time in if you can. Great beer selection, too, and their "world-famous" pot pie is no joke, either!
Midwest Buddhist Temple

8) Midwest Buddhist Temple

Buddhism varies quite a bit by nationality, sect, ethnicity, and geography. This is a Buddhist temple of the "Pure Land" sect, founded by Japanese-Americans fleeing the growing scapegoating racism of the American West during WWII. The American Midwest was relatively more tolerant, but some of the idiosyncrasies of this sect's practices also contributed to blending in with a minimum of conflict.

The temple is set up more like an American Protestant Church with Japanese architectural influence (primarily expressed in the combination gable and hip roof), rather than a traditional Japanese mainstream temple – you keep your shoes on and sit in Western-style pews, Sunday morning services are conducted by ministers instead of monks, Dharma talks mimic homilies or sermons, the opening chant is the only Japanese for the English services, and some of the hymns are actually Protestant traditional hymns with adjusted words.

A visit to this temple is especially recommended to those interested in comparative religion, anthropology, immigration history, cross-cultural studies, and members of any other Buddhist group.

Look for the Ginza Holiday Festival on the 2nd week of August, the annual fundraiser featuring delicious Terriyaki chicken, goods for sale, and fantastic entertainment with Taiko drums.
St. Michael's Church

9) St. Michael's Church

By tradition, if you can hear St. Michael's bells, you are in Old Town. Owing to its thick, redbrick walls, this 19th-century Bavarian-style church, founded by German immigrants, was one of only six buildings to 'survive' the path of the 1871 Great Chicago Fire. Although there is a small memorial dedicated to Catholic war veterans on its grounds, the church has become a haven for the local Puerto Rican community.

Adorned with a large four-faced clock, the bell tower has five bells, each weighing between 2,500–6,000 lbs (or 1,1–2,7 t). Visitors can also view the beautiful, colorful baroque interior with tall, thin stained-glass (Mayer) windows, frescoes, a carving depicting The Last Supper (purchased from the 1893 World's Columbian Exposition), a working Kilgen pipe organ, and five painted altars illustrating St. Michael, flanked by archangels Raphael and Gabriel, casting Lucifer from heaven.

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