In our opinion, this is one of the best ways to see how beautiful Chicago really is. We recommend the "Architecture River Tour" via Shoreline Sightseeing: https://shorelinesightseeing.com/. Boarding from Michigan Avenue is most common but departing from Navy Pier would be great as well.
We believe exploring the West Loop is a must! Here are some of our favorite places to grab a bite to eat or a cocktail: Au Cheval, Parlor Pizza (Great for bigger groups), Bar Siena, Girl & The Goat, Formento's, and Beatrix, Haymarket (beer), The Aviary (cocktails), Lone Wolf, Goose Island Fulton Street Brewery.
For those that have a deep dish craving, we recommend Lou Malnati's or Giordano's.
Here are some of our favorites: Field Museum, Shedd Aquarium, Art Institute of Chicago, and the Museum of Science and Industry.
Is it really a trip to Chicago without a picture of "The Bean" in Millennium Park?
Chicago's Lakefront Trail is an 18-mile paved path that follows the Lake Michigan shoreline on the city's eastern edge. Great for walking, running, biking, and of course excellent skyline views.