The Fifty/50 Chicago

Multi-level eccentric bar

Sydney from Chicago

About me I am a Chicago native best defined for my curiosity and willingness to explore. I value uniqueness and quality, which attributes to my appreciation for the city and for the entertainment it provides. With a close-knit set of friends and family nearby, I am often exploring the areas around me with peers by my side. Whether it’s through travel or leisure activities, I am...
""The Fifty/50" in Chicago offers an array of comfort food classics with a special twist. I must say, this restaurant has the best wings in the city..."

The Fifty/50 offers an array of comfort food classics with a special Chicago twist, making it the perfect place to visit on any occasion for a taste of the famed city.

Located in the heart of the city’s Wicker Park neighborhood, the upscale sports bar houses three floors, each offering ample seating space surrounded by contemporary, eclectic furnishings. With over 20 flat-screen TVs and a spacious outdoor patio, Fifty/50 is my go-to spot for any and all sporting events (but be prepared to be distracted by the breaded spicy garlic chicken wings - they hold the title of the best wings in the city, making it a welcomed distraction).

Each individual floor offers a unique setting, from casual booth seating on the first floor to lively, game day gathering spots on the higher floors. Though the modern ambiance draws people in, it’s the outstanding food that keeps people coming back. 50/Fifty is best known for its award-winning chicken wings, but it's the 3-type cheddar and creamy bechamel blend on the cheese waffle fries that keeps me an addicted local patron.

028-beach-bar-1
Bars
021-spoon-and-fork-1
Restaurants

This week 25% off

with the code fall25

*on our yearly membership

Chicago Spotter Sydney

About me I am a Chicago native best defined for my curiosity and willingness to explore. I value uniqueness and quality, which attributes to my appreciation for the city and for the entertainment it provides. With a close-knit set of friends and family nearby, I am often exploring the areas around me with peers by my side. Whether it’s through travel or leisure activities, I am always looking for the next opportunity to discover my surroundings and enjoy the entertainment and livelihood I find. Why Chicago? Having lived in Chicago my entire life, I am a p...

About this spot

2047 W Division St

8 chicken wings:

USD

12

7734895050

Oct 2, 2025

Our Chicago City Guide

Find your way with 116 Insider Tips from our Local Spotters

Discover hidden gems and all our locals’ favourites! Get full access to our Chicago guide.

Loved it? Join us!

Loved this Spot?Join your international community. Share your favs and become part of our international community!

Nice place right!? There’s so much more to discover:

Discover all other hidden gems in Chicago

TARY Coffee House

Kazakh specialty cafe

There are many unique food options to try on their menu like Bylamyk porridge with raspberry jam, Baursak (fried dough bites) or Truffle Mushroom Soup.

020-coffee-cup-1
Coffee & tea
021-spoon-and-fork-1
Restaurants
024-burger-1
Snacks

by

Lydia

Schultz

Nov 19, 2025

Old Town Ale House

Famed dive with historic roots

" Old Town Ale House" is one of my favorite spots to enmesh myself in the history, art, and unique company found in Chicago.

028-beach-bar-1
Bars

by

Sydney

Epstein

Nov 19, 2025

Monk's Pub

Craft beer bar in the Loop

Monk’s Pub is a cozy, monastery-inspired bar in the Loop serving a wide variety of beers and hearty pub fare — an unexpected escape from the downtown rush.

028-beach-bar-1
Bars

by

Sophie

Amado

Nov 18, 2025

Orso's

Italian bistro in Old Town

Orso’s in Old Town is a cozy, old-world Italian gem with house-made pasta, live piano, and a charming patio—perfect for date nights or celebrations.

021-spoon-and-fork-1
Restaurants

by

Sophie

Amado

Nov 18, 2025

Middlebrow

Natural wine meets fresh bread

I am always stunned by Middlebrow's appetizers, including "the big salad," which includes seasonal vegetables topped with plenty of pepper and shredded cheese.

021-spoon-and-fork-1
Restaurants

by

Sophie

Amado

Nov 17, 2025

PIZZ'AMICI

Tavern-style pizza

Tavern-style pizza takes the crown at PIZZ'AMICI — thin, crispy crust, cozy vibes, and big local love since they moved from apartment to restaurant in 2024.

021-spoon-and-fork-1
Restaurants

by

Sophie

Amado

Nov 17, 2025

Vito + Nick's

Breaking Chicago pizza stereotypes

Vito & Nick's doesn't make typical Chicago pizza: it's the thin crust that reigns supreme here. I drive out of my way to get there, but it's worth it.

021-spoon-and-fork-1
Restaurants

by

Sophie

Amado

Nov 17, 2025

Reggies Chicago

Bar with music and shuttles

Reggies Chicago is a grunge bar, concert venue, and shuttle hub with great eats, Sox game packages, a beach bar and unique events like a pancake art show.

028-beach-bar-1
Bars

by

Sophie

Amado

Nov 17, 2025

The 606

Quiet nature path

The 606 (aka the Bloomingdale Trail) in Chicago is a repurposed walking trail on a disused piece of L train track. In my opinion, it's a piece of art.

017-plant-1
Relaxing

by

Sophie

Amado

Nov 17, 2025

Luft Balloons

Decorating Chicago with balloons

Luft Balloons in Chicago isn't just a balloon shop – it's a female-operated & owned business that makes balloon sculptures specifically for marches...

026-thrift-shop-1
Shopping

by

Sophie

Amado

Nov 14, 2025

Little Madrid

A bit of Spain in Chicago

Little Madrid in Chicago feels so European, it's surprising — trust me, I've spent some time in Madrid myself. Great place for a date or coworker night.

021-spoon-and-fork-1
Restaurants

by

Sophie

Amado

Nov 14, 2025

Rice'N Bread

Cozy Korean restaurant

Rice'N Bread in Chicago is a special spot for dinner or even pre-gaming a baseball game, a Korean restaurant that always makes my day. Try the bibimbap!

021-spoon-and-fork-1
Restaurants

by

Sophie

Amado

Nov 13, 2025

Heading to Chicago?

116 Insider Tips from our local Spotters

Authentic Stories by Real People

Escape the Crowd & Travel Slow 🐌

... for just €9.99

Chicago app Home
Chicago app Home
Chicago app Map
Chicago app Home

0 Insider Tips from our local Spotters

116 Insider Tips

✓ Escape the Crowds

✓ Find Spots nearby

✓ Authentic Stories

... for just €9.99

City guides by those who know the city in and out!

Our Locals' Favorite Bars

Our team loves Chicago

Get to know our other Spotters from Chicago

As featured on:

New-York-Times
the-guardian
mashable
the-sunday-times
[paywall_activator]
false
0
false
71
Made with the 💚 of 496 Spotters.
Filters