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Here's your plan for a cozy dinner and dessert followed by live jazz at a hidden Chicago gem. Watch the video 👇

Indulge in dinner and dessert at the back bar of a steakhouse before listening to jazz music.


Cozy Date Night at a Hidden Gem Jazz Bar

Enjoy a special dinner and cocktails at the back bar of Carson's Steakhouse in Streeterville, Chicago.

Dinner at Carson's

✅ Before you go 
• Aim to get to dinner ~1.5 hours before your show starts

💪Pro tip: 
• Head to the back bar for their special drink menu

Eat dinner at Carson's

Visit Winter's Jazz Club in Streeterville, Chicago, to experience intimate jazz performances. A perfect date night spot to cuddle up and enjoy amazing musicians.

Jazz Music

✅ Before you go 
• Get tickets in advance here: https://www.wintersjazzclub.com/

🚶‍♀️Transportation:
• 2 minute walk from Carson’s

Listen to jazz music at Winter's Jazz Club

I have the most romantic date night for you as these cold Chicago nights approach.

You'll indulge in a yummy dinner and then cozy up at a hidden jazz club.

Carson's Steakhouse may be a popular restaurant,

it's way more intimate and they have a special cocktail menu.

I had a delicious gingerbread old fashioned and it paired really nicely

with dinner and dessert. Right next door is one

of Chicago's best hidden gems and I promise you

it's actually a hidden gem. Winter's Jazz Club is

the perfect spot to cozy up with your date.

There's just something about the jazz music that makes this place extra romantic.

I was in awe of these amazing musicians. Now it's your turn to grab a date and get cozy!

Here's your plan for a hilarious Japanese-inspired comedy showdown with food and drinks in Chicago. Watch the video 👇

Head to Batsu for an insanely funny night!

Chicago’s Most Entertaining Show

Catch BATSU! in Old Town—an unpredictable, hilarious Japanese-inspired comedy show where losers face silly punishments. Grab food, drinks, and join in the fun with friends!

Comedy game show

✅ Before you go
- get tickets here: https://batsulive.com/chicago/

💪 Pro tips
- get the headband so you can 3 rounds of sake throughout the show! 
- there’s a restaurant in the same building below the show that looked delicious!! 

See a Batsu show 

This is your nudge to go to one of Chicago's most entertaining shows.

It's a Japanese inspired comedy show where comedians compete in

different rounds and then the losers get punished in just

At no point during the show did I know what was about to happen next.

It was just so funny and so entertaining.

Here's your plan for spray paint graffiti class in Uptown, then enjoy tasty Thai next door. Watch the video 👇

Head to uptown to make your own graffiti art then grab Thai after. 

Graffiti Girls Afternoon 

Get creative at Studio WIP in Uptown with a 90-minute BYOB spray paint graffiti class, including stencils and instructor guidance for all skill levels.

Spray Paint Class

✅ Before you go
- book a class here: https://www.native312.events

💪 Pro tips
- it’s BYOB! 

Take a spray paint class 

Enjoy a delicious Thai lunch at Dib Sushi Bar and Thai Cuisine in Truman Square, with walk-ins welcome for a laid-back, flavorful meal.

Thai Lunch

✅ Before you go
- nothing! Walk ins welcome 


Grab a late lunch 

Here's your plan to take a spray paint graffiti

class and then cozy up with delicious Thai afterwards.

The instructor will walk you through everything.

They'll give you stencils and they'll tell you what to do,

Here's your plan for exploring a huge thrift store with clothes, salt & pepper sets, and hidden treasures. Watch the video 👇

Thrifting at a “living museum for the community, rooted in the very soul of Hermosa” 

Chicago’s Vintage Vault 🛍️

Thrift for treasures in a massive vintage wonderland at Beyond Grandma’s House in Hermosa—explore rooms packed with clothes, decor, books, and unique collectibles.

Thrift Shopping

✅ Before you go

Treasure Hunting Hours:
Thursday: 2:00 PM – 6:00 PM 
Friday: 1:00 PM – 5:00 PM
Saturday: 10:00 AM – 4:00 PM
Sunday: 1:00 PM – 5:00 PM

💪 Pro tips

Where to Park

You can usually find spots along:
> Keystone Ave (right in front of the shop)
> Belden Ave or Fullerton Ave (just around the corner)

Shopping at Beyond Grandma’s House 

I was in this thrift store for hours and I still didn't see everything.

Come with me to check out Beyond Grandma's Thrift,

where they have literally anything you can think of.

you'll be amazed at just how much stuff they can fit in here.

and found the pair of these snakeskin boots that I absolutely fell in love with,

they have a salt and pepper collection that is their pride and joy,

Check out beyond Grandma's house for an incredible day of thrifting.

Here's your plan for festive drinks, comfort food, live music, and pinball fun in Chicago. Watch the video 👇

Classic Holiday Pub🎄

Enjoy festive décor, craft cocktails, live music, and comforting Irish fare at Chief O’Neill’s Pub, a beloved Avondale spot perfect for a cozy holiday night out with friends.

Festive drinks & comfort food

✅ Before you go
• Tables fill up quickly during the holidays, so make sure to book your reservation in advance https://www.chiefoneillspub.com/reservations

💪 Pro tips
• There’s plenty of street parking nearby 
• Order one of their craft cocktails
• Visit during their Sunday brunch or live Irish music session on Sunday evening 

Chief O’Neill’s Pub 

Enjoy a huge variety of beers or NA drinks, play pinball (bring quarters!), and chill in a relaxed, friendly taproom. Bring or order your own snacks!

Craft Beer Tasting

✅ Before you go
• Make sure to bring quarters for the pinball machine! 

💪 Pro tips
• They have some snacks for purchase but you can bring your own snacks or order delivery right to the taproom 


Revolution Brewing

This is your sign to plan a festive night out with friends this holiday season.

Chief O'Neill's Pub has been around for over 25 years,

and their holiday decorations are up from Halloween

They also have delicious craft cocktails,

The shepherd's pie and french fries with ranch,

They have live music on Sundays and various

drink and food specials throughout the week,

like half-price wine bottles on Wednesday.

once you've gotten your fill of holiday magic,

which is less than a 10 minute walk away for a nightcap or two,

and non-alcoholic drink options in a chill atmosphere.

the staff will also have a movie playing in the background,

and you should definitely make sure to take advantage of their pinball machines.

festive friends to join you on this holiday adventure.