Little Italy Food Tour

Find the hidden gems and local characters of Chicago's original Italian enclave.


Chicago - Near West Side


*IMPORTANT NOTICE* Due to the COVID-19 pandemic, all Chicago Foodways tours are currently paused through April 30, 2020. We plan to resume our tour schedule as soon as we can safely and legally allow.

Please consider helping us out at this time by purchasing gift certificates for any future tour. Our gift certificates never expire and are always valid for a full-price tour, no matter if our prices increase in the future. Thank you!

Feast on a 6-course Italian meal from apertivo to dolce, as you walk through a charming 1870's neighborhood just beyond the Loop.

  • Visit eateries ranging from a rustic wine bar, a Mom & Pop deli, a lemonade stand, and an old school gem so hidden, it doesn't have a sign.
  • Meet sinners and saints through the stories of city hall corruption, bootleggers, wise guys and the patron saint of immigrants.
  • Conveniently located near United Center, UIC Pavilion, and Thalia Hall for a fun pre-game or pre-concert activity.

What You'll Experience:

Visit a great mix of Italian eateries including a wine bar, a deli, an old school red sauce joint and a streetside lemonade stand.

Davanti Enoteca

This rustic wine bar is consistently ranked in the best Italian restaurants of Chicago.


The modern bustling hub of Taylor Street is actually the oldest Italian restaurant in the city.

Tufano's Vernon Park Tap

This favorite of politicians, police and local sports stars is a gem so hidden, you won't find it unless you know to look for it.

Fontano's Subs

A fun and friendly side street hangout where you can find three generations of family on any given day.

Mario's Italian Ice

This sidewalk lemonade stand is a Taylor Street institution and a summertime destination for Chicagoans of all stripes.

Meeting Location and Tour Length:

Your tour guide will greet you inside of Davanti Enoteca, 1359 W. Taylor St. at the intersection of Taylor and Loomis.

We open with antipasti, working our way through pasta and meat courses before wrapping with one of the most old-school street food stands in Chicago.

Total walking distance is one and a quarter miles.  We walk at a leisurely pace.  All stops are handicapped accessible and all but the last location has a restroom available.

The tour finishes half a mile east of the starting point at Taylor and Carpenter.  The tour lasts 3 hours from start to finish.

Parking & Transportation:

- Valet parking at Davanti Enoteca is available for $8 (recommended)
- Ample metered parking is available on Taylor Street, however you will need to add value after 3 hours with parking app.
- No side street parking.
- Trains: short walk from Blue Line Racine stop or Pink Line Polk stop.
- Bus: #157 runs from Michigan Avenue to Taylor and Loomis.
- First time Lyft users receive a $5 credit when using CHICAGOFOODWAYS in the referral code.