Discover Where to Enjoy Best Pizza & Wine Date in Chicago

You can’t go wrong with a pizza and wine combo, but you can go wrong with the restaurant. Tip: Stay away from rowdy sports bars on your first date! We are very particular when choosing date spots, therefore, this list is short and sweet. 

homeslice-chicago.jpg

HOMESLICE | LINCOLN PARK

Homeslice gets an overall grade of an A+ for atmosphere, food, and drinks. The rustic decor makes you feel like you’re in a log cabin nestled in a ski resort. The outdoor back patio has bright Italian lights, heat lamps, cozy patio seating, and a gutted silver bullet trailer available for seating. They have the best gluten-free pizza I’ve personally ever had. Plus, they serve their Moscow Mule just right and necessarily out of a copper mug (which you can buy for $10). 
Address: 938 W Webster Ave, Chicago, IL 60614
Website: http://www.getsomehomie.com

quartino-chicago.jpg

QUARTINO PIZZERIA & WINE BAR | NEAR NORTHSIDE

Quartino is a great spot for grabbing a Neapolitan thin-crust pizza and a carafe of wine for two. This bustling downtown venue serves authentic regional Italian food and an atmosphere perfect for a date night.
Address: 626 N State St, Chicago, IL 60654
Website: https://www.quartinochicago.com

More City Guides

Discover Boston: History, Culture, and Things to Do

Discover Boston: History, Culture, and Things to Do

Dating in Boston should feel natural. It’s a city full of accomplished, intelligent, ambitious people — professionals, academics, innovators, and ...
Matchmaking Services in Seattle for Busy Professionals

Matchmaking Services in Seattle for Busy Professionals

Dating in Seattle should feel exciting. It’s a city full of accomplished, intelligent, ambitious people — tech leaders, creatives, healthcare ...
Why Dating in Washington DC Feels So Hard (Even for Successful People)

Why Dating in Washington DC Feels So Hard (Even for Successful People)

Dating in Washington DC should be easy. It’s a city full of accomplished, intelligent, ambitious people — attorneys, entrepreneurs, executives, ...
Romantic Couple’s Guide to NYC

Romantic Ultimate Couple’s Guide to NYC at Christmas (2026)

Let’s be real for a second. When you picture a romantic Christmas in New York, your mind probably goes straight ...
Portland Romantic Date Ideas You’ll Love

Portland Romantic Date Ideas You’ll Love Together

Look, you can find a list of Portland's "top 10 attractions" anywhere. But that’s not how you connect with a ...
Best Nashville Date Spots, Views & Music

Best Nashville Date Spots: Coffee, Views & Music

Alright, look. Throw the other guides out. Seriously. If you're planning a trip to Nashville with your partner, and you ...
A Perfect Summer Date Night in NYC: Heathers: The Musical Edition

A Perfect Summer Date Night in NYC: Heathers: The Musical Edition

Looking to impress your date in the city that never sleeps? This summer, skip the usual and turn your evening ...
London’s Most Romantic Night Out and Dinner Plan

London’s Most Romantic Night Out and Dinner Plan

If you’re looking to impress someone special or simply enjoy a night out in one of the world’s most romantic ...