If you’re looking for a slice of history and charm in the bustling city of Chicago, then Old Town is the neighborhood for you. Nestled in the heart of the city, Old Town offers a glimpse into the past with its preserved Victorian-era architecture and quaint cobblestone streets. From its vibrant art scene to its thriving restaurants and shops, there is no shortage of things to discover and explore in this historic part of Chicago. So grab your walking shoes and get ready to immerse yourself in the rich heritage of Old Town Chicago.
History of Old Town
Founding and early settlement
Old Town, located on Chicago’s North Side, has a rich and fascinating history that dates back to its founding in the mid-19th century. Originally settled by German immigrants, this area was home to farms and orchards before the city began to expand. As more people moved to Chicago, Old Town became a popular destination for those seeking a quieter, more rural environment just outside the bustling city center.
Development and growth
In the late 1800s, Old Town saw a boom in development and growth. Victorian-style homes were built, giving the neighborhood its iconic charm and character. The population increased as people flocked to Old Town, attracted by the thriving businesses and bustling streets. This period of growth laid the foundation for the vibrant community that exists today.
Decline and revitalization
Like many urban neighborhoods, Old Town experienced a decline in the mid-20th century. As suburbanization took hold, many residents moved to the outskirts of the city, leaving behind vacant buildings and a struggling local economy. However, the 1960s brought a revitalization to Old Town, with artists and young professionals drawn to its historic architecture and cultural heritage. Today, Old Town stands as a testament to the power of community and preservation, with its historic buildings restored and its charm fully intact.
Architecture and Landmarks
Old Town Triangle Historic District
One of Old Town’s most notable architectural gems is the Old Town Triangle Historic District. This district is a designated Chicago Landmark and is renowned for its well-preserved and diverse architecture. The area features a mix of Victorian-era row houses, charming cottages, and elegant mansions, all nestled within a peaceful and tree-lined neighborhood. Taking a stroll through this historic district is like stepping back in time and offers a unique glimpse into Old Town’s past.
St. Michael’s Church
St. Michael’s Church, located on North Cleveland Avenue, is a prominent landmark in Old Town. This beautiful Romanesque-style church was built in 1869 and remains an active parish to this day. Its stunning stained glass windows, towering spires, and ornate interior make it a must-visit for architecture and history enthusiasts.
The Second City
No article about Old Town would be complete without mentioning The Second City. This world-renowned comedy club has been a staple of the neighborhood’s cultural scene since it opened its doors in 1959. Known for launching the careers of many famous comedians, The Second City continues to entertain audiences with its hilarious improv shows and sketch comedy. It’s a quintessential Old Town experience and a must-visit for anyone seeking a good laugh.
The Brewster Building
The Brewster Building, located on North Lincoln Avenue, is another architectural gem in Old Town. Built in the late 19th century, this historic structure features a striking combination of Romanesque and Queen Anne architectural styles. The building has a rich history, once serving as a residential hotel and later housing various businesses and artists’ studios. Today, it stands as a testament to Old Town’s architectural heritage and adds to the neighborhood’s unique character.
Cultural Institutions
Old Town School of Folk Music
The Old Town School of Folk Music is a beloved institution in the neighborhood. Since its founding in 1957, the school has been dedicated to preserving and promoting traditional music and dance. Offering a wide range of classes, concerts, and events, the Old Town School has become a hub for musicians and music enthusiasts alike. Whether you’re a seasoned musician or simply interested in learning more about folk music, this cultural institution is a must-visit in Old Town.
The International Museum of Surgical Science
For those with an interest in medical history, the International Museum of Surgical Science is a fascinating destination. Housed in a beautiful mansion on North Lake Shore Drive, this museum showcases a vast collection of medical artifacts, instruments, and artwork. Visitors can explore the history of surgery and gain a greater understanding of the advancements that have shaped modern medicine. With its unique exhibits and educational programs, the International Museum of Surgical Science is a captivating cultural institution within Old Town.
The Second City Comedy Club
As mentioned earlier, The Second City Comedy Club is not only a landmark in Old Town but also a cultural institution. Founded as a small cabaret theater, it quickly became known for its satirical and cutting-edge comedy. Countless famous comedians, including John Belushi, Tina Fey, and Stephen Colbert, have honed their skills on its stage. Attending a show at The Second City is an absolute must for comedy lovers visiting Old Town.
Up Comedy Club
Located within The Second City building, Up Comedy Club offers a unique blend of stand-up, improv, and sketch comedy. With a diverse lineup of performers and a cozy atmosphere, Up Comedy Club provides an intimate setting for laughter and entertainment. Whether you’re a fan of well-known comedians or enjoy discovering new talent, this club is a great place to spend an evening in Old Town.
Entertainment and Nightlife
Wells Street
Wells Street is the heart of Old Town and offers a vibrant atmosphere for entertainment and nightlife. This lively street is lined with a variety of bars, restaurants, and shops, making it a popular destination for locals and tourists alike. Whether you’re looking for a cozy pub, a trendy cocktail bar, or a place to enjoy live music, Wells Street has something to offer.
The Second City Mainstage
For an unforgettable night of laughter, head to The Second City Mainstage. This iconic comedy club features hilarious shows that combine sketch comedy and improv. From political satire to pop culture parodies, the talented cast never fails to deliver side-splitting performances. Watching a show at The Second City Mainstage is a quintessential Old Town experience and is sure to leave you in stitches.
Zanies Comedy Club
If you’re craving more laughter, Zanies Comedy Club is another fantastic option in Old Town. This historic comedy club has been entertaining audiences since 1978 and has hosted many notable comedians over the years. With shows ranging from stand-up to improv, Zanies is the perfect place to catch both established and up-and-coming comedic talent.
Green Door Tavern
For a taste of Old Town’s history and a unique nightlife experience, Green Door Tavern is a must-visit. This historic establishment dates back to the Prohibition era, and its speakeasy past can still be felt within its walls. With its cozy atmosphere, vintage decor, and live music, Green Door Tavern offers a charming and nostalgic setting to enjoy a drink and unwind.
Shopping and Dining
Wells Street Market
Wells Street Market is an eclectic and bustling marketplace in Old Town. From boutique clothing stores to specialty food shops, this vibrant market offers a variety of shopping options. Whether you’re looking for unique fashion pieces, artisanal food products, or handmade crafts, you’re sure to find something that catches your eye at Wells Street Market.
Old Town Art Fair
The Old Town Art Fair is one of the oldest and most prestigious art fairs in the country. Held annually in the heart of Old Town, this event showcases the work of talented artists from around the world. Visitors can browse a wide range of art, including paintings, sculptures, photography, and jewelry. The fair also features live music, delicious food vendors, and a picturesque garden walk. It’s a fantastic opportunity to support local artists and immerse yourself in Old Town’s vibrant artistic community.
The Spice House
For culinary enthusiasts, The Spice House is a true treasure in Old Town. This beloved spice shop has been supplying chefs and home cooks with high-quality spices for over 60 years. From unique blends to exotic flavors, The Spice House offers an extensive selection that will elevate your culinary creations. Whether you’re a seasoned chef or a novice in the kitchen, a visit to this aromatic store is sure to inspire your taste buds.
The Fireplace Inn
The Fireplace Inn is a legendary restaurant in Old Town, known for its mouthwatering barbecue and warm hospitality. Established in 1969, this neighborhood institution has been serving up delicious ribs, wings, and other BBQ favorites for generations. The cozy atmosphere, complete with a fireplace, adds to the charm and makes it the perfect place to enjoy a hearty meal with friends and family.
Parks and Outdoor Spaces
Lincoln Park
Just east of Old Town lies Lincoln Park, a sprawling green oasis that offers a multitude of recreational opportunities. Spanning over 1,200 acres, this park features bike paths, walking trails, sports fields, and even a zoo. Whether you’re looking to take a leisurely stroll, have a picnic, or engage in outdoor activities, Lincoln Park provides a serene and picturesque backdrop to enjoy nature in the heart of the city.
Seward Park
Seward Park is a hidden gem nestled in the heart of Old Town. This small neighborhood park offers a peaceful respite from the hustle and bustle of city life. With its serene atmosphere, well-manicured lawns, and colorful flowers, Seward Park is a great place to relax and unwind. It also features a playground, making it a popular destination for families with young children.
La Salle Language Academy Park
La Salle Language Academy Park is a charming pocket park located near the La Salle Language Academy, a local elementary school. This park offers a lush green space, colorful playground equipment, and a basketball court, providing ample opportunities for outdoor recreation. Whether you’re looking to enjoy a picnic, play a game, or simply soak up the sun, this small park is a peaceful oasis within Old Town.
The Midwest Buddhist Temple
The Midwest Buddhist Temple, located in Old Town, offers not only a place of worship but also a serene outdoor space known as the Peace Garden. This peaceful oasis features beautiful landscaping, a tranquil koi pond, and traditional Japanese architecture. Visitors can wander through the garden, meditate, or simply find solace in the serene surroundings. The Midwest Buddhist Temple and its Peace Garden provide a unique cultural experience that is worth exploring in Old Town.
Annual Events and Festivals
Old Town Art Fair
The Old Town Art Fair, previously mentioned in the Shopping and Dining section, is a highly anticipated annual event in Old Town. Held in June, this two-day fair attracts art enthusiasts from near and far. In addition to showcasing stunning artwork, the fair also features live music, delicious food vendors, and a garden walk. It’s a festive celebration of creativity and community that should not be missed.
Wells Street Art Festival
The Wells Street Art Festival is another beloved annual event in Old Town. Held in July, this street festival showcases the work of over 200 artists. Visitors can explore a wide variety of art, including paintings, sculptures, jewelry, and photography. The festival also offers live music, food vendors, and activities for children, ensuring there is something for everyone to enjoy.
Old Town Halloween Parade
When fall rolls around, Old Town comes alive with its annual Halloween Parade. This festive event invites community members of all ages to dress up in their spookiest costumes and join in the Halloween fun. The parade features floats, marching bands, and a lively atmosphere that is sure to get everyone in the Halloween spirit.
Old Town Food Truck Social
For food lovers, the Old Town Food Truck Social is a delicious event that takes place in August. This food truck festival brings together a curated selection of Chicago’s best food trucks, offering a wide range of cuisines and flavors. From street tacos to gourmet burgers, visitors can sample a variety of dishes while enjoying live music and a vibrant atmosphere.
Historic Homes and Residences
Clarke House Museum
The Clarke House Museum, located just outside the official boundaries of Old Town, is a historic gem worth visiting. Built in 1836, it is the oldest surviving structure in Chicago and showcases the city’s early architectural history. Visitors can take a guided tour of the house and learn about the lives of the Clarke Family, who were prominent early residents of Chicago. The museum provides a fascinating glimpse into Chicago’s past and serves as a reminder of the rich history that surrounds Old Town.
The Noble-Seymour-Crippen House
The Noble-Seymour-Crippen House, also known as the Charnley-Persky House, is a stunning example of modern architecture in Old Town. Designed by renowned architects Louis Sullivan and Frank Lloyd Wright, this house is considered a masterpiece that showcases their innovative design principles. While not open for regular tours, the exterior of the house is a sight to behold and stands as a testament to the architectural brilliance that can be found in Old Town.
The Richard H. Driehaus Museum
The Richard H. Driehaus Museum, located just outside the boundaries of Old Town, is a must-visit for architecture and design enthusiasts. Housed in a stunning Gilded Age mansion, this museum showcases the opulence and grandeur of the late 19th century. Visitors can explore the beautifully restored interiors, adorned with luxurious furnishings and decorative arts. The museum also hosts exhibitions and educational programs that explore the history and significance of this extraordinary period.
The Potawatomi Hotel
Located in the heart of Old Town, The Potawatomi Hotel is a historic building that has been converted into a boutique hotel. Originally built in 1891, this architectural gem offers a unique blend of vintage charm and modern amenities. The hotel’s elegant facade, intricate detailing, and luxurious interiors make it a beloved landmark in Old Town and a popular choice for visitors seeking a historic and comfortable stay.
Transportation and Accessibility
CTA Red Line
Old Town is well-connected to the rest of Chicago via public transportation, making it easily accessible for both residents and visitors. The CTA Red Line provides convenient access to Old Town, with the North/Clybourn and Sedgwick stations serving as the nearest stops. From these stations, it’s a short walk to the heart of Old Town, where you can explore all the neighborhood has to offer.
CTA Brown Line
In addition to the Red Line, the CTA Brown Line also provides access to Old Town. The Sedgwick station, located near the southern border of Old Town, offers a convenient gateway to the neighborhood. Whether you’re coming from downtown or other parts of the city, the CTA Brown Line offers a reliable and efficient mode of transportation.
Nearby expressways
For those traveling by car, Old Town is easily accessible via nearby expressways. The Kennedy Expressway (I-90/94) and the Eisenhower Expressway (I-290) provide direct routes to and from the neighborhood. Additionally, Lake Shore Drive (US-41) runs along the eastern edge of Old Town, offering scenic views and quick access to downtown Chicago.
Biking and walking
Old Town is a pedestrian-friendly neighborhood, making it a great place to explore on foot or by bike. The neighborhood’s tree-lined streets, historic architecture, and charming shops are best experienced at a leisurely pace. For those who prefer biking, Divvy bike-sharing stations can be found throughout Old Town, providing a convenient and eco-friendly way to get around.
Visiting Old Town
Accommodation options
When visiting Old Town, there are several accommodation options to choose from. Whether you prefer luxury hotels, cozy bed and breakfasts, or modern boutique hotels, there is something to suit every preference and budget. The Potawatomi Hotel, mentioned earlier, is a charming boutique hotel with a historic ambiance. Additionally, there are several national hotel chains in the area that offer comfortable and convenient lodging options.
Public transportation
As mentioned earlier, Old Town is well-served by public transportation. The CTA Red Line and Brown Line provide easy access to the neighborhood, making it convenient to explore other parts of the city as well. Additionally, bus routes run through Old Town, providing further options for getting around. For those traveling from other parts of the country or the world, nearby airports such as O’Hare International Airport and Midway International Airport provide easy access to Old Town.
Suggested itineraries
To make the most of your visit to Old Town, here are a few suggested itineraries:
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Start your day with a visit to The Second City and catch a matinee show. Laugh the afternoon away with top-tier improv and sketch comedy performances.
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Next, explore the Old Town Triangle Historic District and admire the stunning architecture that gives this neighborhood its charm. Take a leisurely stroll and imagine what life was like in the 19th century.
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Pop into The Spice House and stock up on unique spices to bring back home or to enhance your own culinary creations.
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Head to Lincoln Park and enjoy a picnic or a bike ride along the lakefront. Take in the beautiful views and explore the park’s many attractions, such as the Lincoln Park Zoo or the Alfred Caldwell Lily Pool.
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In the evening, make your way to Green Door Tavern for some cozy ambiance and delicious comfort food. Enjoy a meal and revel in the historic ambiance of this Prohibition-era gem.
Safety precautions
While Old Town is generally a safe neighborhood, it’s always important to take necessary precautions when exploring any unfamiliar area. Here are a few safety tips to keep in mind:
- Be aware of your surroundings and trust your instincts.
- Keep your belongings secure and be mindful of pickpockets in crowded areas.
- Stick to well-lit streets and well-traveled routes, especially at night.
- Take note of emergency contact numbers and know the locations of nearby police stations or hospitals.
- If traveling alone, share your itinerary with a trusted friend or family member.
- Stay connected and have a fully charged phone in case of emergencies.
By following these simple safety guidelines, you can ensure a pleasant and worry-free visit to Old Town. Enjoy your time exploring this historic neighborhood and all it has to offer!