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Here's your plan for spray paint art, tasty fried chicken sandwiches, and live music vibes. Watch the video 👇

Channel your artsy side at a spray paint and sip class before grabbing fried chicken sandwiches and listening to live music at a Chicago institution. 

Artsy Grafitti Date Night

Unleash your creativity at Studio W.I.P., where you can take a graffiti class amidst Chicago's urban art scene.

Graffiti Class

⭐️ Studio WIP class guides are all local artists!

✅ Before you go 
• Tickets run $40/pp. Reservations go quickly, so book in advance: https://www.native312.events/
• All supplies included in ticket price
• Studio WIP is BYOB

💪Pro tips: 
• Wear clothes you don’t mind getting a little messy!
• You will leave the studio with a large canvas, so somewhere to stash for the rest of your evening may be helpful

Take a graffiti class at Studio W.I.P.

At Lucy's in Humboldt Park, enjoy a retro-themed meal with delicious burgers and spicy chicken sandwiches, plus indulgent giant milkshakes.

Fried Chicken Dining

Grab a bite at at Lucy's

End your date night at The California Clipper, a classic tavern with live music and a range of drinks. It's a lively spot for a night cap.

Live Music

✅ Before you go 
• Check out the website for information start times for nightly acts: https://www.californiaclipper.com/


Listen to music at The California Clipper

Here's your plan for a creative date night at a colorful art studio

with a delicious quick bite and final stop at a hidden music venue.

In Humboldt Park where you'll find this storefront

completely converted into an artist's playground.

After cheersing with some mocktails to the creative evening ahead,

you're guided through the entire process of spray painting.

There are stencils to create your masterpiece, but as you can see, I just went for it.

Next you'll venture a few blocks over to Lucy's fried chicken.

This retro-themed spot from Austin, Texas

features delicious hamburgers and spicy chicken sandwiches.

I personally love the giant milkshakes because sometimes we all deserve a treat.

Just across the street is the California Clipper where your

final stop is being transported to this classic Chicago tavern

bar with live music most nights of the week and

a diverse menu of both drinks and mocktails.

All you gotta do is find your next evening

to enjoy the sights and sounds of Humboldt Park.

Here's your plan for a fun-themed paint night with cocktails and creative vibes in Westmont. Watch the video 👇

Join Paint and Sip Bar at one of their themed paint nights across the Chicagoland area

Themed Paint & Sip 🎨

Unleash your creativity at SIP and Paint Bar in Westmont—enjoy two craft cocktails while you paint your own masterpiece at this self-guided themed event.

Paint & Sip Night

✅ Before you go
• Browse the calendar for upcoming paint nights https://www.sipandpaintbar.com/general-2-1
• Purchase your ticket on Eventbrite https://www.eventbrite.com/o/49788979153

💪 Pro tips
• This is a self-guided paint event! No paint instructor present. 
• A ticket comes with two (2) craft cocktails, blank canvas, instructions, and supplies (food purchased separately)

Purchase a ticket 🎫 

SIP and Paint Bar is a traveling paint party that hosts themed

paint and sip nights in restaurants all over the Chicago land area.

A purchase ticket guarantees your spot in the restaurant,

2 craft cocktails and the canvas with your supplies.

The paint and sip event is a self-guided experience,

so come ready to channel your inner artist.

the staff was great with great music and surprise giveaways.

Check out the link in the info section for details.

Here's your plan for tasting beers and cocktails at three breweries and one distillery in Chicago. Watch the video 👇

Stop at 3 breweries and 1 distillery in Ravenswood/ North Center! 

Malt Row Brewery Crawl 🍻

Enjoy a diverse selection of approachable craft beers at Begyle Brewing in North Center, Chicago—perfect for groups looking to start their brewery crawl adventure.

Brewery visit

✅ Before you go
• Begyle Brewing prides itself on offering a diverse and approachable selection of quality beer that brings people together. 

Begyle Brewing 

Experience traditional European-style beers at Dovetail Brewing in North Center, Chicago—specializing in unique sours and expertly crafted brews.

Beer Tasting

✅ Before you go
• Dovetail specializes in continental European styles and traditional methods. 

Dovetail Brewing 

Demo Brewing Company offers creative, unique brews in a converted garage space. Enjoy their Secondhand Store draft for a truly distinctive beer experience in Lake View.

Craft Beer Tasting

💪 Pro tips
• The secondhand store draft is delicious and different from anything I’ve ever had! 

Demo Brewing Company  

Sip creative cocktails or whiskey flights at Koval Distillery Tasting Room—enjoy outdoor seating, board games, and a lively, inviting atmosphere in Lake View.

Cocktail Tasting

✅ Before you go
• Visit the KOVAL tasting room for cocktails, flights, perfect pairs, light bites, international coffee drinks and more.

💪 Pro tips
• They have outdoor seating and board games! 

Koval Distillery Tasting Room

This Ravenswood brewery crawl is perfect to get a

group of friends together and hang out this summer.

where I got a cider because I don't usually do beer.

and from there we walked up north to Dovetail Brewing.

which I actually really ended up liking for a beer.

we walked another 2 blocks up to Demo Brewing.

I really loved the space because it's a converted garage.

their drinks were really good and unique here,

but they have amazing cocktails and you really just need to check it out.

Here's your plan for savoring Italian ice and frozen yogurt in Chicago's Lincoln Park. Watch the video 👇

A way to romanticize your summer day—one scoop of Italian ice at a time 🍦

Summer Scoop at Annette’s

Grab a creamy Italian Fro-Yo—half Italian ice, half frozen yogurt—at Annette's Italian Ice, a beloved Lincoln Park spot with fun flavors and cash-only charm.

Italian Ice & Froyo

Italian Fro-Yo
A perfect combination of Italian ice and frozen yogurt. Creamy and fruity unite.

My fav Italian ice flavors: Passion Fruit-Red Raspberry, Guava-Orange-Passion Fruit, Blueberry-Lemon

Note that it’s cash only! 💵

What should I get?

Enjoy a summer scoop at Annette’s Italian Ice, open daily until late—treat yourself to unique frozen flavors and stroll through lively Lincoln Park.

Italian Ice & Desserts

🗓️ Hours
Mon-Thurs, Sun: 12:00pm - 11:00pm
Fri & Sat: 12:00pm - 11:30pm

Note that it’s cash only! 💵

When can I go?

Annette's Italian Ice is a Chicago staple in Lincoln Park.

You order from a walk-up window and can taste as many flavors as you want.

where it's half frozen yogurt and half Italian ice.

You'll be right at the heart of Armitage here so you can grab your Italian froyo,

and window shop all the cute boutiques around.

Here's your plan for a restorative yoga class with stretches and meditation at Soul House, Chicago. Watch the video 👇

Take a yoga class at Soul House! Soul House is a yoga, healing, and teaching center in West Town. 

Soul House Experience 🧘☮️

Join a restorative yoga class at Soul House in Fulton Market, Chicago. Enjoy a serene studio with all props provided—just bring yourself and water!

Yoga class

✅ Before you go
• You can register for classes here: https://www.soulhousechicago.com/yoga-class-schedule

💪 Pro tips
• All you have to do is bring yourself and water! Everything else is provided free of charge. 

Yoga class at Soul House  

so come along with me while I check out Soul House in West Town.

The studio itself is absolutely beautiful.

They offer yoga classes and other types of meditation classes.

What I really loved is that you don't have to bring anything with you.

They had any kind of prop you can think of.

The class that I took was a restorative class,

you might even see the studio pop on your way out.