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Cicely & Ross

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    Things To Do

Things To Do

Architecture Boat Tour

Architecture Boat Tour

In our opinion, this is the best way to see downtown Chicago. Be sure to grab a drink or a bite to eat along the Riverwalk afterward!

The Lakefront Trail

The Lakefront Trail

The Lakefront Trail offers views of Lake Michigan and the city skyline, making for a beautiful walk or bike ride. There's plenty of beach and greenspace for sitting, too. :)

Mott St

Mott St

This is probably our #1 go-to restaurant in our neighborhood (Wicker Park). Get the burger...and the mushrooms...and the stuffed cabbage.

Small Cheval

Small Cheval

Skip the famed Au Cheval and head here for an equally delish burger. The Old Town location is just an 8-min walk from Claridge House Hotel.

MFK

MFK

This special spot serves up phenomenal Spanish small plates and refreshing cocktails. We went here on our first date — and the night we got engaged. :)

Mon Ami Gabi

Mon Ami Gabi

If you're staying in Lincoln Park and fancy something French — go here! We love their patio in the summertime.

Old Town Ale House

Old Town Ale House

This is Chicago's favorite dive bar, famously frequented by the likes of Bill Murray, Michael Shannon, and Anthony Bourdain. Perhaps more famously, it's where Ross and Cicely first met! Beware: this is a true dive. Cash-only, made-up prices and not a cocktail menu in sight.

Estereo

Estereo

Gotta be one of our favorite spots for drinks in the Summer! If you like Latin-American cocktails, definitely don't miss it. We recommend visiting the original Logan Square location on Milwaukee Ave.

The Up Room at The Robey

The Up Room at The Robey

Venture to this rooftop bar in Wicker Park for the very best views of the city. It opens at 5, we recommend getting there early as seats fill up quickly!

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