Caroline & Michael
Things To Do
Skydeck Chicago @ Willis Tower
A suspended clear glass observation box on the 103rd floor of the Willis Tower (Sears Tower, as the locals call it) with views extending to four states. This is TERRIFYINGLY hard to trick your brain to walk out onto, and a must do for visitors.
Wendella Tours & Cruises
Seeing the city from the river is truly one of the best experiences you will have here, while also learning some incredible facts about Chicago architecture: its the birthplace of the modern skyscraper! Caroline and Mikey have been on COUNTLESS boat tours, every one of them is unique.
Yolk - South Loop
Caroline's favorite breakfast in the city. They have a new pancake every month that rarely disappoints. Pro tip: the line is always VERY long - join the Yelp waitlist via their website to get in line beforehand, and it will tell you when you should expect to arrive.
Cloud Gate (The Bean)
You cannot come to Chicago and not stand under the bean. Don't let the locals convince you that it isn't cool.... it is indeed very cool.
Michigan Avenue
Michigan Avenue AKA "The Magnificent Mile" is home to the fancy strip of shopping in the city, in addition to the largest Starbucks in the world and many historic landmarks. We recommend starting at the Wrigley building just north of the river, and heading north from there.
360 CHICAGO
360 Chicago is an observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000ft up. It has panoramic views of the city in all directions and should not be missed for thrill seekers!
Field Museum
The Field Museum is incredible, the building is beautiful, and the lawn out front with skyline views is amazing. The Field Museum is massive; it is of the largest museums in the world and at any given time it only has 3% of its inventory on display, so the exhibits change often. The Field Museum also houses Sue, the largest and most intact T-rex ever discovered.
Giordano's - North Rush Street
While there are multiple Giordano's locations in the city, the North Rush Street location was the original restaurant, and also gives you a sneak peak of the neighborhood Caroline and Mike live in. Trust us when we say, you'll want Giordano's deep dish while in town, and not Lou Malnati's. You're welcome.
Chicago Riverwalk
The Riverwalk is a 1.25 mile long path spotted with restaurants and seating areas for river views and people watching. This was in Mike and Caroline's very first neighborhood after moving to Chicago, so every single dog walk took place up and down the Riverwalk.
The Chicago Theatre
The Chicago Theatre is a landmark for its large, iconic sign. This street has many plays and shows at all times and are worth the watch if you have a night available!
Buckingham Fountain
This is a tourist attraction in Chicago, surrounded by skyline views and easy access to observe Lake Michigan near a marina. The water will be turned back on post-winter in May, so fingers crossed for a warm month so that it is running for your visit!
Lincoln Park
Lincoln Park is a massive park area consisting of many free activities (online reservations required) including: a gorgeous conservatory, a zoo, access to the beach, and a large farmer's market on Saturday's. You will lose track of time wandering this large park and enviable neighborhood. PS this is where Mike proposed to Caroline!
Oak Street Beach
A beachfront with skyline views, what more could you ask for?! This is a short walk from Mike and Caroline's home, and a very familiar playground for Phoebe and Penny. While it may not be the ideal season, visit this beach for our reasoning of calling Chicago a "beach town" (we're serious!!).