OLD TOWN

Steeped in history and full of charm, Old Town is one of Chicago’s most beloved neighborhoods. Known for its Victorian-era architecture, tree-lined streets, and lively entertainment scene, Old Town perfectly blends historic character with modern conveniences.

The neighborhood is home to some of the city's best comedy clubs, independent boutiques, and neighborhood taverns, contributing to its warm, community-focused vibe. Located just minutes from downtown, Old Town is an ideal spot for those looking to enjoy a blend of culture, history, and urban living.

Whether you're exploring Wells Street’s vibrant nightlife, catching a show at The Second City, or strolling through its picturesque residential streets, Old Town offers a dynamic urban experience.

Pet Friendly - Old Town

ROAMING GUIDE

Old Town offers a variety of housing options, from charming walk-ups and vintage brownstones to modern apartments with city views. The neighborhood’s central location and historical appeal make it one of the most desirable places to live in Chicago.

Average Rents

Studio: $1,800 - $2,600
1-Bedroom: $2,400 - $3,800
2-Bedroom: $3,800 - $5,500
3-Bedroom: $5,500 - $8,000+

Shopping & Retail

Fleet Feet Sports – A go-to spot for running shoes, athletic gear, and local races.
Fudge Pot –Longtime candy counter doling out handmade sweets & specializing in custom items for any occasion.
The Spice House – A historic shop selling high-quality spices, herbs, and blends for home cooks and chefs.
Piper's Alley Mall – Landmark shopping mall offers a variety of retail shops, restaurants & a cinema.

Nightlife & Bars

The Second City – Chicago’s legendary comedy club where stars like Tina Fey and Steve Carell got their start.
Zanies Comedy Club – One of the oldest stand-up comedy clubs in the country, featuring top-tier comedians.
The Old Town Ale House – A classic dive bar filled with local charm, strong drinks, and political satire artwork.
Benchmark – A lively sports bar with a two-story patio and great weekend crowds.

Dining & Cafe

Twin Anchors – A historic, no-frills spot serving some of Chicago’s best barbecue ribs since 1932.
The Vig – A stylish gastropub with great cocktails and an inviting atmosphere.
Nookies: A cozy neighborhood diner serving classic American comfort food and all-day breakfast in a welcoming setting..
La Fournette – A cozy French bakery offering authentic pastries, bread, and light breakfast options.
Kamehachi - Kamehachi: A beloved Old Town sushi spot serving fresh, high-quality Japanese cuisine in a stylish setting

Public Transportation & Accessibility

Old Town is extremely walkable and bike-friendly, with easy access to downtown and nearby neighborhoods.

The CTA Brown and Purple Lines (Sedgwick Station) and Red Line (Clark/Division) provide quick commutes to the Loop and beyond. Multiple bus routes, including the 22 Clark, 36 Broadway, and 156 LaSalle, make getting around a breeze. The neighborhood is also steps from Lake Shore Drive, North Avenue Beach, and the Chicago Riverwalk, offering scenic walking and biking routes.

Roaming Around: A Weekend in Old Town

Friday Night: Enjoy dinner at Twin Anchors, then catch a comedy show at The Second City. Wrap up the night with a drink at the legendary Old Town Ale House.
Saturday: Start with coffee and a pastry at La Fournette, then explore the boutique shops along Wells Street. In the afternoon, take a walk along the Lakefront Trail or visit Washington Square Park before heading to Benchmark for a lively night out.
Sunday: Take your pup for a morning walk, then grab brunch at The Vig. Spend the afternoon exploring Lincoln Park Conservatory. Finish off the weekend with a relaxing drink at J. Parker, the rooftop bar overlooking the park and lake

ROAM WITH ROVER

With its quiet residential streets, pet-friendly patios, and easy access to green spaces, Old Town is an excellent neighborhood for pet owners

Parks & Outdoor Spaces

Washington Square Park – A peaceful green space with shaded benches and walking paths, great for leashed strolls.
Lakefront Trail – Just a short walk away, perfect for scenic jogs and long walks with your pup.
Lincoln Park – One of Chicago’s largest and most iconic parks, offering miles of walking trails, open green spaces, and dog-friendly areas.
Lincoln Park’s South Field Dog Park – A dedicated off-leash area within Lincoln Park where dogs can run and play freely in a safe, fenced-in environment