A Casual 30- something’s weekend guide to Chicago

A Casual 30- something’s weekend guide to Chicago
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Chicago, IL

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.

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12 places

Tre Dita 05

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 06

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 07

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.

Jazz Showcase 09

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.

Shoreline Sightseeing 11

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 12

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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