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Here's your plan for sipping tarot-themed cocktails and enjoying live burlesque performances. Watch the video 👇

Trust me on this one. Go to the Drifter to sip on a rotating menu (all on tarot cards) and enjoy nightly acts and burlesque performances. 

🃏Tarot Cocktails and Burlesque Speakeasy 🃏

Experience unique cocktails and burlesque at The Drifter in Chicago’s River North, where a tarot card-based drink menu and vibrant performances guarantee an unforgettable night.

Tarot Cocktails

✅ Before you go
• No reservations! We waited upstairs for our table to be ready for a good minute. I promise it’s worth the wait. 

💪 Pro tips
• You can keep your table for 90 minutes. Plan accordingly 

Give everyone FOMO at The Drifter

Everyone has been to Green Door Tavern. But what about the basement Speakeasy?

The Drifter is the place to witness elaborate performances while

sipping on cocktails from a nightly rotating Tarot menu.

This is one of those places that you'll never get the same experience

twice. If you're lucky enough to see “Port of Desire” on the menu,

I'm not showing much of the interior right now because

Grab your friends and get over there tonight.

Wednesday nights are even better with live jazz music & signature cocktails at the Shedd Aquarium 

$30 Jazzin’ at the Shed 🎺

Enjoy live jazz, cocktails, and fireworks at the Shedd Aquarium every Wednesday night this summer, with full exhibit access included.

Live Jazz & Cocktails

✅ Before you go
• Ticket link: https://www.sheddaquarium.org/tickets?event_id=29

💪 Pro tips
• Wednesdays, May 28 through August 27, 2025
• Adults $29.95 and children (3-11) $24.95

Visit on a Wednesday

and enjoy the Shed Aquarium's classic Jazzing at the Shed Wednesday series.

we were able to explore all the exhibits the shed has to offer,

but with the beautiful addition of live jazz music and signature drinks.

and the best part in the summer is that you get to watch the fireworks from the patio.

Here's your plan for enjoying live comedy shows at The Den Theatre in cozy Wicker Park. Watch the video 👇

Looking for something fun to do at night? Laugh it up at The Den!

Comedy Shows at The Den Theatre 

Catch hilarious live comedy shows at The Den Theatre in Wicker Park. Grab tickets for upcoming performances and enjoy a night full of laughter!

Comedy Show

Visit  https://thedentheatre.com/calendar?view=calendar&month=08-2025 to grab tickets for the next few months!

Get your tickets

The Den Theater is one of my favorite spots for live comedy in Chicago.

I saw Gabby Bryant here and she was so funny and

it was such a good set in a super cozy venue.

They've got comedy shows happening all the time and in this September,

So whether you're planning a fun night out or you just want to switch it up,

The Den always has something worth checking out.

Here's your plan for grabbing giant Chicago-style pizza slices and tasty local favorites. Watch the video 👇

Bacci Pizza is home to Chicago’s famous giant slice — bigger than your head and under $7. Open late, serving classic thin crust with that perfect fold, it’s a must-try local staple that’s been feeding the city for over 25 years. Fast, filling, and full of flavor — Bacci hits every time.

The Giant Slice You Can’t Skip in Chicago 🔥

Grab a giant, foldable pizza slice at Bacci – a local legend for late-night eats. Order online for fast, satisfying Chicago-style comfort food at multiple city locations.

Pizza by the slice

✅ Before you go
• Check out their multiple locations across the city

💪🏾 Pro tips
• Order ahead online – Skip the wait at baccipizza.com or through delivery apps.

	Find your closest location. 

Grab a legendary giant pizza slice at Bacci Pizzeria on Taylor Street in Little Italy—it's bigger than your head and delivers on flavor. Try their whole menu too!

Eat giant pizza slice

Bacci is known for their giant slices, but don’t sleep on the rest of the menu — they’ve got wings, salads, sandwiches, deserts, and more. I tried the deep dish pizza, chicken sandwich, tiramisu, and Italian ice, and it ALL hit so hard. 

Try the giant slice – It’s what they’re known for (and yes, it’s bigger than your head).

They are well known for servicing Chicago jumbo slices since '96.

From slices bigger than your plate to deep dish,

they don't hold back on portions or flavor.

I pulled up for a slice and ended up eating the whole menu.

keeping Chicago happy one jumbo slice at a time.

Here's your plan for tacos, shopping local, and rooftop cocktails on Chicago’s North Side. Watch the video 👇

Grab tacos from a no-frills spot then sip cocktails at a trendy rooftop bar on the North Side (plus stop into a funky retail shop).

Rooftop Bar + Hidden Gems in Ravenswood 🌮

Enjoy delicious, crispy Al Pastor tacos at La Amistad—a cozy, hidden gem in Lincoln Square that's perfect for a BYOB taco night.

Eat tacos

✅ Before you go
• They’re BYOB, but there’s a liquor store about a block away!
• My boyfriend has celiac disease and has eaten here about a million times with no issues (though I’m not 100% sure of their allergy practices, I know the chips are NOT safe from cross-contact so we usually avoid those!)

💪 Pro tips
• Get the Al Pastor tacos, thank me later!

Grab tacos from La Amistad

Shop for unique, locally made gifts and art at Ponnopozz—a vibrant boutique perfect for creative finds and supporting independent makers in Lincoln Square.

Gift shopping

✅ Before you go
• Fun fact: everything in the shop is from a local, independent maker or a small company!

💪 Pro tips
• They used to host classes at their old space so keep an eye out on their IG/newsletter to see what’s in store for this new location 👀

Browse around Ponnopozz

Sip creative cocktails with friends on Arriba Rooftop in Lincoln Square. Enjoy a relaxed North Side vibe with drinks and city views—perfect for summer evenings outdoors.

Rooftop Cocktails

✅ Before you go
• They do offer food (if you’re in the mood for $7 tacos…) but it’s not the same menu as Farm Bar on the ground floor (no outside food allowed)

💪 Pro tips
• Ask to pay with your server - the QR code payment method charges an extra 3%

Sip cocktails on the Arriba Rooftop

who said all rooftop bars have to be downtown?

Here's your plan to get tacos from a no-frills spot,

then grab drinks at a rooftop on the North Side.

I think this place is the definition of a hidden gem.

Their Al Pastor tacos are my favorite in the city.

I just love all the little crispy charred bits

and their rice hits so good every. single. time.

I'm not going to gatekeep this spot anymore,

I think it's time everyone knows about it.

we popped into this funky little shop that's new to the street.

though they have completely different menus.

Arriba’s cocktail menu is a good mix of creative

classics and summer staples like this guava daiquiri.

Share this plan with someone who loves a good rooftop moment