This is something we recommend to everyone who hasn't tried it out before. An architectural river tour is the best way to see Chicago's beautiful skyline and learn some interesting facts along the way! This is not only for people who are interested in architecture, it is an amazing tour regardless! TIP: Book through Groupon or a similar service for discounted tickets.
The Bean, officially named "Cloud Gate", sits in Millennium Park in downtown Chicago. This is a beautiful location to head to on a walk and continue meandering towards the lakefront, or for towards shopping along the famous "Mag Mile".
Museum Campus is a 57-acre park along the shore of Lake Michigan. It holds Adler Planetarium, the Shedd Aquarium, the Field Museum, Soldier Field, and the most iconic view of the Chicago skyline in the city. Whether you're visiting any of the museums or not, this is a great place to walk and take pictures!
Magnificent Mile is Chicago's "premier commercial district." If you're looking for luxury shopping, this is the place to go. It's a very lively area with massive storefronts (5 story Burberry flagship) and restaurants (1 of 6 Starbucks Roastery Reserves in the world) along the mile itself. Rush and Division is another shopping district a short walk north, with more storefronts and slightly more accessible brands.
Chicago is known for its food! If you're looking for deep dish we recommend Pequod's! Other Chicago food staples like Italian Beefs sandwiches and Chicago Dogs can be found at a ton of different restaurants in the city, however Devil Dawgs is great! We recommend opening Google Maps on your phone and finding a highly rated restaurant within walking distance--it hasn't steered us in the wrong direction yet!