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July 5, 2019
Chicago, Illinois

Kylie & Brian

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    Our Guide to Chicago
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Our Guide to Chicago

Brian and Kylie's favorite things to do in Chicago.
Adler Planetarium

Adler Planetarium

1300 South Lake Shore Drive, Chicago, IL 60605

Brian proposed to Kylie right outside the Adler planetarium in front of an unbeatable view of the best skyline in the world (we might be biased). There is also the Field Museum and the Shedd Aquarium in this area.

Pequod's Pizza

Pequod's Pizza

2207 North Clybourn Avenue, Chicago, IL 60614

Lou Malnatis and Giardanos are the most popular spots for Chicago Deep Dish pizza, but Pequods is our favorite.

Garrett Popcorn Shops

Garrett Popcorn Shops

625 N Michigan Ave, Chicago, IL 60611

Kylie likes the Chicago Mix (two cheese and one caramel in one bite is the way to go!). Brian's dad, Dennis, likes Caramel only the best. There a multiple locations throughout the city.

London House Rooftop Bar

London House Rooftop Bar

85 East Upper Wacker Drive, Chicago, IL 60601

Our favorite rooftop bar, located right next door to the hotel.

The Game Room

The Game Room

12 South Michigan Avenue, Chicago, IL 60603

The Game Room is a bar located in the Chicago Athletic Association Hotel. It has a fun old-timey atmosphere with table games like bocce ball, fooseball, shuffleboard, chess, etc. There is also a great rooftop bar called Cindy's on the top floor of the hotel.

Wendella Boats

Wendella Boats

400 North Michigan Avenue, Chicago, IL 60611

Chicago Architectural tour on a boat! This is a great way to get to know the architectural history of Chicago and the boat stop is located right across the river from the hotel.

City Winery at the Chicago Riverwalk

City Winery at the Chicago Riverwalk

11 W. Riverwalk South, Chicago, IL 60601
, (312) 229-5593

Perfect spot to sit outside, have a glass of wine along the river, and enjoy the views!

Girl & The Goat

Girl & The Goat

809 West Randolph Street, Chicago, IL 60607

Amazing food. We recommend making a reservation months in advance.

The Second City

The Second City

1616 North Wells Street, Chicago, IL 60614

Chicago is known for its improv comedy clubs and Second City's star studded alumni include Tina Fey, Steve Carroll, and Mike Myers, to name a few.

360 Chicago (John Hancock Observatory)

360 Chicago (John Hancock Observatory)

875 Michigan Avenue, Chicago, IL 60611

Kylie prefers the views from John Hancock to Willis tower because you have a better vantage point of the city.

For all the days along the way
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