Traveler's Blog

“An Insider’s Guide to Chicago”- A Day In Roscoe Village

We continue our series  “Insider’s guide to Chicago” with A Day In Roscoe Village, written by our Chicago neighborhood guy, blogger Elliott DiTusa.

Having spent the past six years in Chicago, I’ve had the opportunity to explore some of Chicago’s many hidden gems. With over 200 neighborhoods, Chicago has an endless amount of places to explore even if you’re a well-seasoned local.  As a traveler in Chicago, figuring out what to see in a short amount of time can be a challenging process. In a series of posts, I will highlight how you can spend a day visiting some of my favorite neighborhood restaurants, shops, bars, and sights.

9:30 am

Roscoe Village, home to my first Chicago apartment, is a quiet Northside neighborhood steps from the Paulina Brown Line Spot. Located in the heart of Roscoe Village on Roscoe Street sits my all-time favorite breakfast spot in the city, Victory’s Banner. Inspired by Indian Spiritual Master Sri Chinmoy, Victory’s Banner features Chinmoy’s artwork wall to wall, books of his poetry, and if you’re lucky, running videos of Chinmoy’s incredible feats of strength. Above all else, Victory’s Banner has downright delicious breakfast food and a friendly staff committed to Chinmoy’s spiritual expression. Make sure to try their Satisfaction-Promise egg dish (Two eggs scrambled with spinach, pesto, sun-dried tomatoes, and feta) and a cup of their delicious, and endless, chai tea.

11:30 am

Alongside Victory’s Banner on Roscoe Street are a number of antique shops, vintage stores, and boutiques that are well worth a visit. Some favorites to look out for are Shangri-La Vintage and the great neighborhood record shop Village Records. Further down Roscoe on Paulina is another boutique shop called Bazar.

1:00 pm

A true Chicago original, Hero’s Submarine Shop has been serving fresh, simple sandwiches for over 30 years. Located on the corner of Western and Addison across from Lane Tech College Prep, this tiny sub shop is cash only and very much old-school. For a true Chicago experience, order a scoop of homemade giardiniera (a condiment of spicy pickled peppers and vegetables) on your sandwich.

2:30 pm

Further East on Roscoe Street is a dimly-lit tavern with a beer list longer than a Chicago Winter, Four Moon Tavern. Four Moon boasts some great Chicago brews such as Half Acre’s Daisy Cutter, Revolution’s A Little Crazy, 5 Rabbit’s 5 Vulture, and the exceedingly rare Local Option’s Top Fuel. In addition to their beer, they also have good comfort food and a laid-back atmosphere that fits the neighborhood perfectly

4:00 pm

Looking for a 90 year-old bakery to soak up your afternoon beer? You’re in luck. Down the street from Four Moon, located on Lincoln Avenue is the landmark Dinkel’s Bakery. Family owned and operated since 1922, Dinkel’s offers fresh cakes, donuts, cookies, and bread.

6:00 pm

A few blocks from Roscoe Village, located near the intersection of Southport and Grace, is a Chicago treasure that still goes unnoticed and unused by locals. Dubbed as “Chicago’s year-round film festival,” the Music Box Theatre plays the newest acclaimed independent and foreign films as well as cult favorites (Pee-Wee’s Big Adventure, The Big Lebowski, etc.), midnight movies every weekend (Rocky Horror Picture Show, The Room, etc.), and classic films (Chinatown, The French Connection, etc.). The inside of the Music Box is wonderfully preserved and it is a must see for any cinema aficionado. Don’t take my word for it; here is what the late-great Roger Ebert once wrote:

“The Music Box is the largest surviving first run movie palace in Chicago. It is deeper than it is wide, and has an arching ceiling where illusory clouds float and stars twinkle. Many shows are preceded by music on the organ.


8:30 pm

To end the night, head about one block north on Southport and dine at Tango Sur. This BYOB, Argentine steak house is perfect for a late dinner. With generous portions and a dimly-lit hip atmosphere, make sure to bring a great bottle of wine and enjoy the scene.

Combine a Roscoe Village outing with one of our Weekend Escapes to Chicago , designed by Russ at DiTusa Travel Group.  Our Weekend Escapes include luxury accommodations at one of our  gorgeous Virtuoso hotels -which means you get all of the exclusive perks and amenities!  Contact Russ today.

-Elliott DiTusa