Truly the best way to experience Chicago. We've both taken the Architecture Tour multiple times, and every trip we've learned something new or noticed a detail we'd never seen before.

Ask any Chicagoan what a visitor should do, and they'll tell you to take the Architecture Tour. Every. Single. Time. It's the Malört of family-friendly activities.

The cruises last about an hour and a half and are led by knowledgeable docents who do an incredible job bringing the city's history and architecture to life. Boats depart throughout the day from the heart of downtown. We recommend buying tickets online ahead of time, as it's much easier than purchasing them in person.

Important: Be sure to book the Chicago River Architecture Tour, not the Lakefront Tour. The lakefront cruise is beautiful, but the river tour is the iconic Chicago experience.

If it's your first trip to Chicago—or even if you live here—go grab a Chicago-style hot dog. They're delicious, nutritious, and may be the closest thing we have to proof that the universe is fundamentally just.

Don't ask for ketchup.

Our advice is to visit whichever stand is closest to where you're staying, but if you're looking for recommendations, these are some of our favorites:

The Wiener's Circle – Delicious, legendary, NSFW

Red Hot Ranch – Technically a Depression Dog. Get the shrimp and the burger, too. (Rory's favorite.)

Gene & Jude's – A bit of a pilgrimage, but absolutely iconic.

Fatso's Last Stand – Another Chicago classic and a fan favorite. They have lots of other options as well.

One of, if not the best art museums in the country, the Art Institute of Chicago is absolutely worth fitting into your schedule. Wander through some of the most breathtaking collections in the world—but don't lose track of time.

Elizabeth was a longtime member of the Art Institute, and Rory happily mooched off her membership. We both especially love the Modern Wing.

Fun fact: The painting At Mouquin's features Rory's paternal great-great-grandmother, Jeanne Mouquin. The painting is currently on display at the Art Institute of Chicago.