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Yo Sunday Funday!  That’s not a saying for nothing, hello!  In this post, Sunday in The City : 3 Fun Off-Beat Suggestions from your local fave Chicagoan, moi 🙂

places to walk chicago

What I love about any city are the locals, their delish food and their neighborhoods.

In this post, sharing 3 suggestions of what to do in the city.  Hoping to expand the boundaries of Chicago culture beyond gold coast, old town & lincoln park.

What to do in Chicago?

Sunday in The City : 3 Off-Beat Suggestions from a Local

1.  Sunday after a crazy night out?

This one’s for you!  Taking it to Lakeview for the yummiest of comfort foods (I’m talking next level for the past 20yrs) at Southport Grocery & Cafe, followed by a matinee up the block to the Music Box Theater.

sunday in the city

what to do in chicago

  • Southport Grocery & Cafe : Their bread pudding pancakes can cure any ailment.
    • I love their breakfast sandwich (everything homemade including the sausage)
    • OMG the grilled poundcake is everything
    • pick up a bag of drizzle pretzels for the movie
  • Cafe Tola : If you can’t get into Southport Grocery (it happens!) pop into Cafe Tola for a couple of their empanadas.  YUM.    
    • love their chicken tinga, guava & cheese and nutella banana empanadas.
    • love their drink menu.  I’m a big fan of their spicy mocha 👅
  • El Mercado : If lines are too long at Cafe Tola (happens!  It’s the city, we got choices) walk down the block to the Mercado for their homemade empanadas.  They’re owned by the same family of Tango Sur, Argentinian steakhouse, and Bodega both directly next door.   El Mercado is the OG on the street, so.
    • love the corn, the spinach and the eggplant.
    • large assortment of alfajores
  • Music Box :  Bonus to have such a charming historic theater in Chicago. 
    • art-house cinema 
    • 2 theaters with lounge & garden space

2.  Sunday with friendzzz

sunday in chicago

sunday in the city

what to do one day in chicago

This little trifecta triangle is always a hit with the gf’s.  Start with a yummy bite and great local vibes at Milk & Honey, then across the street to sister stores Penelope & Gemini and lastly down a couple of blocks east to Ruby Room for tarot readings, crystals and all things for your soul ❤️.  Happy to say, all these fab local places have been around for over 2 decades now!

  • Milk & Honey : yum yum yumminess since 2002!  Anything on the menu, everything in the pastry case.  Full stop.
  • Penelope’s & Gemini : sister shops, you can’t go to one and not the other!  Fun vibes, clothing, shoes & accessories for both him & her (and baby!  At Penelope’s!).  Best place for gifts too!
  • Ruby Room : best assortment of decks, crystals, incense.  Can also book a reading / healing.

3.  Sunday Inspiration :

sunday in the city

This little section south on Ashland is the newbie neighborhood :)).   They’ve been sprouting & evolving and taking on it’s own design-centric life these couple of years.   So fabulous.  Period.  Check this list of locals!

Home :

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Food :

In this post, I’m sharing Chicago neighborhoods, best off-beat things to do in Chicago from a local and what to do on a Sunday in the city.


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is sharing her unique personal style from a 50+, p.o.c  p.o.v  along with easy stylist tips, style inspirations & essentials, travel stories with recommendations and best of all, overall good vibes, self care & wellness.  
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