Michelle & Jake
Things To Do
Chicago's First Lady Cruises
The architectural boat tour is Jake & Michelle's #1 recommendation! In just 90 minutes, you'll get the best overview of Chicago’s architecture and its history.
Chicago Riverwalk
The Mariott Renaissance hotel is ON the river walk if you will be staying there. This 1.25 mile long path along the Main Branch of the Chicago River was completed in 2016 to transform the Chicago River into a recreational destination and weave the life of the River into the urban fabric of the city. We recommend grabbing a drink at City Winery on the river and taking in the views.
Big Bus Tours
Michelle and her mom did this one summer and really liked it. It's the easiest way to see all the top tourist attractions without needing to plan out transportation to each location.
Millennium Park
Get your picture with "the Bean" - an Iconic Chicago tourist attraction.
Navy Pier
Navy Pier is where you'll find the Centennial Wheel, Crystal Garden- indoor botanical garden, and where the boat tours will leave from. Check out Riva Crabhouse for seafood with a view, or visit Harry Caray's Tavern, Garrett's Popcorn, and Giordano's for a classic Chicago foodie experience.
Magnificent Mile
The Magnificent Mile offers the best shopping experience in Chicago with more than 460 retailers and three shopping centers. Check out Water Tower Place- home of the American Girl Doll store, and LEGO store.
360 CHICAGO
Experience breathtaking views from 360 Chicago, located atop the famed John Hancock building. Thrill seekers will especially love TILT - a moving platform that tilts you over Michigan Avenue from the 94th floor!
Skydeck Chicago
Step outside the tallest building in the Western Hemisphere and onto the Ledge on the top of the John Hancock building! At 1,353 feet in the air, the Ledge’s glass boxes extend out 4.3 feet from the Skydeck and overlooks up to four states.
Shedd Aquarium
One of the largest indoor aquariums in the country, Chicago's Shedd Aquarium houses over 32,000 creatures.
Adler Planetarium
Overlooking Lake Michigan, The Adler Planetarium creates space explorers out of everyone who visits. There are fun activities for guests of all ages.
Cindy's
Cindy's Rooftop Restaurant and open-air terrance offers panoramic views of Millennium Park, Lake Michigan, and the Art Institute of Chicago. Highly recommend making a reservation for brunch while you're in town.
The Northman Beer & Cider Garden
A dog-friendly beer garden with seating for more than 500. The drink list features dozens of ciders and beers, available on draft or by the bottle/can, and is accompanied by European-inspired gastropub fare, such as doner kebab sausages, pretzels, and baked Camembert cheese.
Lincoln Park Zoo
Chicago's free zoo- great for families with kids looking for a great outdoor activity a little bit outside of downtown in the Lincoln Park neighborhood.
Wrigley Field
Home of the Cubs! Wrigley is in the Wrigleyville/Lakeview neighborhood, a bit outside of downtown, but super easy to get to on the Red Line or via Uber/Lyft. Jake and Michelle both lived in Lakeview several blocks from Wrigley when they first moved to Chicago (and didn't know each other yet).