We love and appreciate the progression of time as we move through this increasingly modern, high tech world. We also find comfort in the old, the familiar. There are places scattered throughout the city that truly feel like Chicago from back in the day. Despite all of the changes throughout the decades, some institutions have managed to preserve an old world feel that’s delightfully nostalgic.  Check out our list of some of those spots — of course we’re partial to our NBHD neighborhoods! 

Book Now to reserve a room & indulge in a “Taste of old Chicago” staycation! 


Tufano’s Vernon Park Tap: Chalkboard menu, casual, delicious, family owned. Don’t miss the chef statue near the bar – it has been there since the 50’s along with photos of visiting friends and celebs that line the walls. Standout dishes: Eggplant or Chicken Parm, Garlic Shells and Broccoli, Lemon Chicken & Potatoes, Porkchops w/ Peas + Fettuccine Alfredo! 

Pompei: Delicious + inexpensive Italian food that has been family owned since 1909! They’re known for rectangular pizza, beef angelo strudel, fresh pastas (that you can often watch them make), lemon knot cookies – the list goes on. Be sure to check out the daily specials. And don’t miss the Pepper & Egg sandwiches. Final thought: Marie’s Salad has the best [family secret] dressing! 

Mario’s Italian Lemonade: A summertime classic for purely delicious Italian ice since the 1950’s. Fun fact: John Belushi worked here when he was in high school. Still family run and has not changed since opening day. 

Hull-House Museum: Chicago’s first social settlement from the late 1800’s was not only the private home of Jane Addams and other Hull-House residents, but also a place where immigrants of diverse communities gathered to learn, eat, debate and acquire the tools necessary to put down roots in their new country. The Museum is comprised of two of the settlement complex’s original thirteen buildings: the Hull-Home and the Residents’ Dining Hall. 

Pillar of Fire Statue: This statue marks the suspected location of Mr. and Mrs. O’Leary’s former property and the alleged starting point of the Chicago fire (c. 1871). Today, the property is occupied by the Robert J. Quinn Fire Academy. However, one can still view the “Pillar of Fire,” a bronze sculpture by Egon Weiner commemorating the event outside the fire academy.


Kingston Mines: Calling all Blues lovers! This is THE spot for some serious Chicago Blues – it’s the largest and oldest Blues club in Chicago (opened in 1968)! 

Chicago Pizza & Oven Grinder: Most famous for their ‘pizza pot pies’ — you can only imagine the oozing cheese + soft bread that they’ve been churning out since 1971. They also have ‘grinders’ – think of a delicious, hot sub sandwich. Their one and only location is a few minutes down Clark Street in a historic building. 

Athenian Room: If you’re a Lincoln Park local, you’ve probably been to the Athenian Room 1,000 times since it opened in the early 1970’s. Some of the best Greek food in the city – burgers, chicken and gyros galore. 

The Wiener’s Circle: This has been THE spot for a Chicago dog since the early 1980’s. Cheese fries and a real deal Chicago hot dog is really all you need. This is also your go-to late night snack spot. 

Wrigley Field: You can feel the history and nostalgia upon entry! The home of the Chicago Cubs [2016 World Series Champs] was built in the early 1900’s! It has of course been updated, but the old school feel is solid and ever lasting. 


The Green Mill (Uptown): This is the ultimate place to hear great jazz in Chicago. The Green Mill opened in the early 1900’s and has QUITE a fascinating story. Too long to tell here but just go, experience, listen & read. 

Margie’s Candy Shop (Bucktown): This place has seriously delicious treats/ice cream and an old-timey, fun vibe. It has been rocking since the early 1920’s – even Al Capone and The Beatles couldn’t resist their sweets! 

J.P. Graziano (West Loop):  Many consider these subs to be the best, old school Italian subs in town. Family owned since the 1930’s, J.P. Graziano has everything from subs made on the spot to a great selection of Italian grocery staples. 

Alamo Shoes (Andersonville): Walking into this store will make you feel like a kid again. There is something about the preserved 1970’s vibe and the layout that is classic, timeless and straight up cool. 

About The Neighborhood Hotel:

The Neighborhood Hotel was founded by travel enthusiasts who enjoy spaces that inspire, comfort and fuel. Each suite is well equipped for short and longterm stays (i.e. kitchenettes, laundry, etc.). The Neighborhood Hotel aims to transform old buildings with cool history into well outfitted apartment style hotels that honor the old while representing the now. The vibe is fresh + fun with rooms that are stocked to support everyone from the homebody to the adventurer. The Neighborhood Hotel serves as a basecamp for the explorer and a sanctuary for the traveler who needs to recharge, reset or just chill.The suites are simple + clean punctuated by accents that bring the right amount of pop. The Neighborhood Hotel has locations in: Lincoln Park, Little Italy, West Loop (2025 opening), New Buffalo, MI and Grand Beach, MI.

We've got news. Great news.
Coming Soon:
The Neighborhood Little Italy
Where welcome drinks come in the form of bold espresso + crisp prosecco. We can't wait
Chi? [Who]
The Neighborhood Hotel
Cosa? [What]
Warmth, bellezza, history. The cornerstones of Italian culture that The Neighborhood Little Italy captures in its third + largest location with 35 suites (Studio - 2 bedrooms).
Quando? [When]
Spring/Summer 2023
Dove? [Where]
In the heart of Little Italy! Here, you're nestled in a neighborhood with an old world feel that seamlessly welcomes the new and modern. Plus, the most bustling parts of the city are just a stone's throw away and easily accessible on foot/public transit! Places like: The Illinois Medical District + Fulton Market + West Loop + UIC + The United Center + the Loop.
Perché? [Why]
To experience fun, adventure, and comfort!
Come? [How]
Our buildings have stories ingrained in the walls (in a non-creepy way) - stories that are meant to be told and shared. The Neighborhood Little Italy was formerly the National Italian American Sports Hall of Fame which honored the greatest Italian-American athletes, broadcasters, and sports workers to benefit athletics in the United States. Once again, we've fallen for a space outfitted with cool history + architecture. Grateful to all of the hard workers and supporters who are turning another NEIGHBORHOOD HOTEL vision/dream into reality!
The Neighborhood Little Italy building design
Rebel House is nailing the design. Soaring ceilings give way to chic urban lofts with sophisticated Italian villa vibes. the top floor's outdoor terraces feature captivating views of the city and the piazza across the street. La vita é bella.
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