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A Casual 30- something’s weekend guide to Chicago
If you want to explore the Chicago with an emphasis on music, food, and culture, check these spots out. Mix of local secrets and tourist favorites.
12 places

Monteverde Restaurant & Pastificio
Bar · Chicago, IL
THIS is the hottest Italian place in Chicago. While dinner reservations are booked months in advance, grab a lunch reservation for the same experience.

Cloud Gate
Bar · Chicago, IL
A.k.a. The Bean. Cool to take a selfie and then keep moving on.

360 CHICAGO
Bar · Chicago, IL
Honestly I chickened out with the Tilt, but the views were stunning at sunset.


Tre Dita
Bar · Chicago, IL
The new St Regis Hotel opened this one and only verified Tuscan restaurant in America. The Tiramisu was literally the best I have ever had.

Riverwalk
Bar · Chicago, IL 60601, United States
Stroll along the river and check out the architecture. Maybe stop for a beer or snack at one of the many food spots.

Kasama
Bar · Chicago, IL
It’s got a Michelin star. What further reason do you need to go!? Get here early — there’s always a super long line. The egg sandwich and chocolate cream brioche is wild.

Chicago Symphony Orchestra
Bar · Chicago, IL
IYKYK- This is one of the best orchestras in the world. Do yourself a favor and catch a concert and feel classy for the night.

Jazz Showcase
Bar · Chicago, IL
The best of the best jazz venue in Chicago. Tickets are super affordable and staff is very welcoming. Great spot for music lovers and culture seekers.

The Art Institute of Chicago
Bar · Chicago, IL
Cmon, it’s a classic. The impressionist gallery is out of this world.

Shoreline Sightseeing
Bar · Chicago, IL
The architecture river tour is informative and just the right length of time. Seeing Chicago from this angle provides a whole new perspective on what makes this city beautiful.

XOCO
Bar · Chicago, IL
Casual spot for tacos, margs, and chips. I recommend the Tortilla soup to warm you up on a windy chilly day.
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