Old Town Chicago: A First-Timer’s Complete Guide (2026)

Love it? Please share it with a friend!

Last Updated: June 2026

The first time I wandered into Old Town, I was looking for a bar before a Second City show and ended up staying four hours. That’s just how this neighborhood works. One minute you’re browsing hand-ground spices at The Spice House, the next you’re on your third glass of wine at Old Town Ale House, listening to owner Bruce Elliot tell you about the night Anthony Bourdain sat right where you’re sitting. Old Town has that quality — it pulls you in and doesn’t let go.

Old Town is one of Chicago’s oldest neighborhoods, settled by German immigrants in the 1850s (they literally called it the Cabbage Patch) and later the epicenter of Chicago’s countercultural 1960s folk music scene. Today it’s an affluent, residential neighborhood with one of the city’s best entertainment corridors — comedy clubs, craft beer bars, Victorian brownstones, and boutique shops all layered on top of each other in a way that feels completely organic rather than manufactured.

If you’re visiting Chicago for the first time and wondering whether to bother with Old Town — yes, absolutely bother. Especially if you’re staying downtown: it’s 15 minutes on the CTA and a completely different energy from the Magnificent Mile.

🚆 Getting to Old Town Chicago

The Sedgwick station on the Brown/Purple Line is your best friend for Old Town. It drops you right at North Avenue and Sedgwick — one block from Wells Street and the heart of the action. From the Loop, it’s about 15 minutes on the train, and you won’t deal with parking. If you’re coming for a Second City show specifically, Piper’s Alley Self Park at 230 W. North Ave. is right next door, but rideshare is genuinely easier on weekend nights when the garage fills up. For the full rundown on the trains, see our Chicago CTA guide.

👉 Local Insider: If you’re doing an evening in Old Town — dinner on Wells Street followed by a show — take the CTA there and rideshare home after. Parking near Second City on weekend nights involves a lot of circling, and you’ll want to have a drink or two.

🎭 Comedy in Old Town: Second City & Zanies

Old Town is the comedy capital of Chicago — and arguably of North America. Two of the most important comedy venues in the world sit within two blocks of each other on Wells Street. If you visit Old Town and don’t see a show at one of them, you’ve missed the whole point.

The Second City

The Second City opened on December 16, 1959, and has produced more comedy legends than any other institution on earth. Bill Murray, Tina Fey, Stephen Colbert, Amy Poehler, Steve Carell, John Belushi, Gilda Radner, Dan Aykroyd, Chris Farley — the list goes on for pages. But here’s what makes Second City special as a visitor: the current casts are incredible, too. You’re not watching a museum piece. You’re watching tomorrow’s comedy stars in their first major gig, doing sharp, fast, brilliantly crafted comedy about things happening right now.

There are multiple stages in the building — the Chicago Mainstage (1616 N. Wells St., inside the stone arches) runs the polished, scripted-plus-improv revues. The e.t.c. Theater on the 2nd floor at 230 W. North Ave. showcases the next generation of talent in a slightly more experimental format. UP Comedy Club (3rd floor) hosts stand-up and special events. I’ve seen shows on all three stages and honestly loved each one — the e.t.c. Theater is often the most exciting because the performers are hungry and the writing is fresh.

👉 Pro Tips for Second City: Book mainstage weekend shows at least a week in advance — they sell out. Arrive 45 minutes before showtime; the house manager seats you based on arrival order. Bring a jacket — the theaters run cold. A full menu is available at your seat. Content skews adult.

Zanies Comedy Club

If Second City is the polished, institution-level comedy experience, Zanies is its rawer, scrappier cousin — and that’s a compliment. Open since 1978 at 1548 N. Wells St., Zanies seats about 120 people in a room that feels like the comedian is practically in your lap. The brick wall, the red sign, the cramped tables — it’s a proper comedy club the way they used to be. Jerry Seinfeld, Jay Leno, and Roseanne Barr all worked this room early in their careers.

The 2-drink minimum is real and expected — budget for it. Shows are 21+, so bring your ID. And do not buy tickets from resale sites; Zanies requires valid ID matching the original purchaser to enter.

👉 Local Insider: Second City and Zanies are two blocks apart on Wells Street. On a great night, you can grab dinner at Twin Anchors, catch a 7 p.m. show at Zanies, and walk to Second City’s late show — that’s a complete Old Town evening. See our full Chicago comedy guide for venues across the city.

🏛️ Chicago History Museum

Founded in 1856 — making it Chicago’s oldest cultural institution — the Chicago History Museum is an underrated gem that most tourists walk right past on their way to Lincoln Park. That’s a mistake. The museum holds over 20 million artifacts and does an exceptional job telling the full story of Chicago: the Great Fire of 1871, the labor movement, the Great Migration, the 1968 Democratic Convention, the music scene, the architecture, the food.

The exhibit on the Great Chicago Fire alone is worth the visit — the reconstructed panorama and the sheer volume of artifacts from 1871 make the scale of that disaster viscerally real in a way a textbook never could. Budget 2–3 hours minimum, and if you’re traveling with kids, note that the museum can be reading-heavy for very young children.

👉 Pro Tip: Illinois residents get free admission on multiple days throughout 2026 — check the museum’s website for the current schedule before you go. Even at full price, it’s one of the better-value museums in the city.

🍺 Best Bars & Nightlife in Old Town Chicago

Wells Street between Division and North Avenue is one of Chicago’s best bar-hopping corridors — not because it’s flashy or trendy, but because it’s genuinely good. These are bars with history, personality, and regulars who’ve been sitting on the same stool for 20 years.

Old Town Ale House

If you visit only one bar in Old Town, make it this one. Open since 1958, the Old Town Ale House is everything a neighborhood bar should be: dark, slightly cramped, full of regulars, and covered in the owner’s paintings — a rotating gallery of politicians, celebrities, and neighborhood characters rendered in a style that is uniquely, unmistakably this place. Anthony Bourdain called it the best bar in Chicago. Roger Ebert called it “the best bar in the world that I know about.” The Second City cast and crew have been drinking here after shows for decades. Cash only, no pretension, pure Chicago.

The House of Glunz / Glunz Tavern

Part specialty wine and spirits shop, part tavern. The Glunz family has been in Old Town since 1888 — the tavern was restored by descendants of the original owner and feels like stepping into a different era. One of my favorite spots in the neighborhood for a glass of wine before dinner; the staff actually know what they’re talking about.

Happy Camper Old Town

Wood-fired pizza, good cocktails, and a lively atmosphere. The outdoor patio is one of the better dog-friendly spots on Wells Street. A solid choice for a casual meal that bleeds into drinks.

🍽️ Best Restaurants in Old Town Chicago

For the full rundown, see our guide to the best restaurants in Old Town. Here are the essentials.

Twin Anchors Restaurant & Tavern

A Chicago institution since 1954, Twin Anchors is famous for two things: the baby back ribs (fall-off-the-bone, slow-cooked, legendary) and the fact that Frank Sinatra used to eat here regularly when he was in town. The decor hasn’t changed much in 70 years — dark wood, Sinatra on the jukebox, old photos on the walls. It’s not the cheapest meal in Old Town, but it’s one of the most authentically Chicago experiences you can have. No reservations, so go early or embrace the wait at the bar.

Topo Gigio Ristorante

A beloved Old Town staple for classic Italian — pasta, risotto, wood-grilled meats, and a warm neighborhood feel. The outdoor patio on Wells Street is one of the best people-watching spots in the neighborhood on a warm evening. A good choice for a pre-show dinner at Second City or Zanies.

Nookies Restaurant

The go-to Old Town breakfast and brunch spot. A neighborhood institution known for massive portions, classic diner-style eggs and pancakes, and a comfortably unhurried pace. Great option if you’re starting your Old Town day in the morning before the History Museum.

🛍️ Shopping & Unique Stops in Old Town

The Spice House

You will smell The Spice House before you see it. This independent spice shop hand-grinds and blends hundreds of spices, herbs, and seasoning mixes, and the Old Town store has been a neighborhood anchor for decades. Free samples are encouraged — just walk in and start smelling jars. It’s one of the most distinctive shopping experiences in Chicago and the spice blends make excellent gifts that actually fit in your luggage.

The Fudge Pot

Handmade chocolate confections made in-store since 1963. The fudge, chocolate-dipped items, and old-fashioned candy shop atmosphere make it an irresistible stop — especially with kids. A true Old Town original.

🗓️ Perfect Day in Old Town: Suggested Itinerary

Morning (10 a.m.–Noon): Start at Nookies for a proper Old Town breakfast — big portions, no rush, quintessentially neighborhood. From there, walk one block south to the Chicago History Museum and plan to spend 2–3 hours. The Great Fire exhibit is unmissable, and the exhibits on Chicago’s role in American labor and civil rights history are genuinely moving.

Afternoon (2–5:30 p.m.): Walk back up Wells Street and let the afternoon meander. The Spice House is a must-stop — even if you don’t buy anything, walking in and experiencing the smell is a genuine sensory moment. Grab chocolate at The Fudge Pot two doors down. Stop into House of Glunz for a glass of wine and let the staff talk you through what they’re excited about. This is the best way to experience Old Town — unhurried, on foot, peeking into shops.

Evening (5:30 p.m.–close): Get to Twin Anchors by 5:30 p.m. to beat the wait. Order the ribs. After dinner, walk two blocks south to Second City or Zanies for your 7 p.m. show. Post-show, Old Town Ale House is right there and it’s the perfect way to end the night — dark, unpretentious, genuinely Chicago.

📅 Best Time to Visit Old Town Chicago

Season	What to Expect	Best For	Crowds
Spring (Mar–May)	Warming up, patios opening, the neighborhood coming back to life	Walking, patio dining, comedy with smaller crowds	Moderate
Summer (Jun–Aug)	Peak season; Wells Street Art Festival in June; full patio season	Everything — Old Town at its best	High
Fall (Sep–Nov)	Comfortable temps, beautiful tree colors, strong comedy programming	Walking, museum visits, shows without summer crowds	Moderate
Winter (Dec–Feb)	Cold, but the bars and comedy clubs are warm and lively	Second City, Zanies, cozy bars, the History Museum	Low

The Wells Street Art Festival (typically the second weekend of June) is one of the city’s best outdoor events — local and national artists set up on Wells Street for two days of art, live music, and food. If your trip overlaps with it, build your schedule around it. Check oldtownchicago.org for 2026 dates.

🐾 Visiting Old Town Chicago with Dogs

Old Town is one of the more dog-friendly neighborhoods in Chicago — the residential character, wide sidewalks, and proximity to Lincoln Park make it easy to bring your dog along for most of the day.

Lincoln Park: Directly adjacent to the eastern edge of Old Town, Lincoln Park is one of the city’s premier dog-walking destinations. The park runs along the lakefront with miles of paved paths and designated off-leash areas. From the Sedgwick CTA station, it’s about a 10-minute walk east to the park.

Dog-friendly bars and patios: Happy Camper (1209 N. Wells St.) has an outdoor patio that typically welcomes leashed dogs. Old Town Pour House (1419 N. Wells St.) has outdoor seating — call ahead to confirm dog access. Topo Gigio’s outdoor patio is a good option for a meal with your dog in warmer months. Always call ahead on the specific day, as patio access depends on weather and staffing.

What to skip with dogs: The comedy clubs, the History Museum, and most indoor venues don’t allow dogs. Plan your dog time around the outdoor portions of the day — Lincoln Park in the morning or afternoon, then leave your dog at the hotel for the evening comedy show.

🐾 Local Insider: The residential blocks just west of Wells Street — North Park Avenue, Crilly Court, and the Old Town Triangle streets — are some of the most beautiful and dog-friendly walking blocks in Chicago. Victorian-era homes, tree-lined sidewalks, and almost no tourist foot traffic. A morning walk through those streets with a coffee from one of the Wells Street cafés is genuinely lovely.

♿ Accessibility Guide: Old Town Chicago

Old Town is reasonably accessible for most visitors, though some older venues require advance planning.

• Getting there: The CTA Brown/Purple Line Sedgwick station has elevator access. The Red Line Clark/Division station also has elevator access and is about a 10-minute walk to the south end of Old Town. CTA buses (routes 36, 72, 156) serving the neighborhood are accessible.
• Sidewalks: Wells Street and North Avenue have paved sidewalks with curb cuts. The residential blocks can be uneven in places due to tree roots and older pavement — be aware if using a wheelchair or mobility device.
• Chicago History Museum: Fully ADA accessible. Accessible parking on Stockton Drive ($10 with museum validation). Accessible restrooms on each floor.
• The Second City: Accessible entrance at 230 W. North Ave. (not the 1616 N. Wells St. entrance). Elevator access to all stages. Companion seats in every theater. Assistive listening devices available on request — contact customer service in advance at (312) 337-3992.
• Zanies Comedy Club: Located in a vintage 1978 storefront — call ahead at (312) 337-4027 to discuss accessibility needs before attending.
• Restaurants and bars: Most ground-floor Wells Street restaurants are at street level with accessible entries. Older buildings like Twin Anchors and Old Town Ale House may have entry steps — call ahead at (312) 266-1616 (Twin Anchors) if accessibility is a concern.

Frequently Asked Questions About Old Town Chicago

What is Old Town Chicago known for?

Old Town Chicago is best known as the home of The Second City comedy club — the legendary stage that launched Tina Fey, Bill Murray, Stephen Colbert, Amy Poehler, and dozens of other comedy legends. Beyond comedy, Old Town is celebrated for its Victorian-era architecture, the Wells Street bar and restaurant corridor, the Chicago History Museum, and a genuine neighborhood feel just 1.5 miles from the Loop.

How do I get to Old Town Chicago?

The easiest way is the CTA Brown or Purple Line to Sedgwick station, which drops you right in the heart of Old Town on North Avenue. From downtown (the Loop), it’s about 15 minutes by train. The Red Line Clark/Division stop is a 10-minute walk to the south end of the neighborhood. Rideshare also drops off easily on Wells Street.

Is Old Town Chicago safe?

Yes — Old Town is one of Chicago’s safest neighborhoods. It’s an affluent, heavily residential area with active streets, well-lit commercial corridors, and consistent foot traffic day and night. The Wells Street corridor from Division to North Avenue is busy with restaurants and bars most evenings. Standard urban awareness applies, as with any major city neighborhood.

Do I need to book Second City tickets in advance?

Yes — especially for weekend mainstage shows, which sell out regularly. Book at least a week in advance at secondcity.com. Tickets start around $30 and go up depending on the show and stage. All seating is general admission assigned by the house manager based on arrival time — arrive 45 minutes early for the best seats.

What is the best time to visit Old Town Chicago?

Summer (June–August) is peak season with full outdoor dining and events like the Wells Street Art Festival in June. Fall (September–November) offers comfortable temperatures and fewer crowds. Old Town is genuinely worth visiting year-round — the comedy clubs and bars run year-round regardless of weather, and the History Museum is open Tuesday through Sunday.

What are the best restaurants in Old Town Chicago?

The standouts are Twin Anchors (1655 N. Sedgwick St.) for legendary baby back ribs since 1954; Topo Gigio (1516 N. Wells St.) for classic Italian; Broken English Taco Pub (1400 N. Wells St.) for creative tacos; Happy Camper (1209 N. Wells St.) for wood-fired pizza; and Nookies (1746 N. Wells St.) for an excellent breakfast or brunch.

Are there dog-friendly spots in Old Town Chicago?

Yes — Old Town is dog-friendly, particularly for outdoor activities. Lincoln Park (directly east of the neighborhood) is one of Chicago’s best dog-walking destinations with off-leash areas. On Wells Street, Happy Camper and Old Town Pour House have outdoor patios that typically welcome leashed dogs. Always call ahead to confirm patio access for the specific day of your visit.

Is Old Town Chicago accessible for visitors with mobility needs?

Old Town is reasonably accessible. The CTA Sedgwick station has elevator access. The Chicago History Museum is fully ADA accessible. The Second City’s accessible entrance is at 230 W. North Ave. with elevator access to all stages and assistive listening devices available. Some older bars and restaurants may have steps — call ahead for specific venues. The Wells Street commercial corridor has paved sidewalks with curb cuts.

---

Old Town is the kind of neighborhood that doesn’t announce itself — it just quietly delivers one of the best urban experiences in Chicago. The comedy is world-class, the bars have actual soul, the history is genuinely fascinating, and you can do the whole thing on foot in a neighborhood that looks the same as it did 50 years ago. If you only have time for one neighborhood off the tourist path, make it Old Town.

Planning more time in Chicago? Check out our complete Chicago comedy guide for every venue across the city, our CTA guide for navigating Chicago by train, and our best things to do in Chicago guide for the full citywide picture.

Love it? Please share it with a friend!