An Afternoon Downtown: What to Do, Eat, and See

By Kelly Pawlak

Planning a trip to downtown Chicago can be overwhelming at times because there is so much to do! From parks to fine dining and everything in between, Chicago is the ideal place to spend an afternoon with friends or family.  Here’s your guide on what to do, eat, and see! 

You are going to want to make sure you start the day off with a full stomach. You won’t regret making Yolk the first stop of the day. This creative breakfast, brunch, and lunch stop has options everyone in your group will love. Try the breakfast mac ‘n’ cheese for something savory and exciting, or go for the banana nut bread french toast for something sweet and delightful. Yolk has multiple locations throughout the city making it accessible no matter where your day in the city starts off.

Once you are fully energized, make your way to Skydeck Chicago located at the top of the Willis Tower. This thrilling experience allows you to view Chicago from 1,353 feet above. For a truly exhilarating experience, step out onto The Ledge— a glass box that allows you to see the streets of the city directly below your feet. If that does not sound like your thing, you can still see up to 50 miles out and four different states from the Skydeck’s windows.

After you have viewed the city from above, explore it in one of the best ways possible— by foot. Walk up and down the city’s streets to experience its vast culture and lively atmosphere. If fun and games are your thing head in the direction of Maggie Daley Park for a round of mini-golf or to roller skate around the ribbon. If you would prefer to spend the afternoon shopping, the Shops at North Bridge is the place for you. No matter where you decide to go, you’ll pass by some of the city’s great shops, architecture, and art. 

You might be getting hungry after all of this exploring. If you are looking for a snack to hold you over until dinner, stop by one of the many Garret’s Popcorn shops located throughout the city. You can’t go wrong with the world-famous Garret mix— a mix of sweet caramel popcorn and savory cheddar cheese popcorn that will have you licking your fingers and wanting more. Don’t forget to take a bag home for later!

After an eventful afternoon experiencing Chicago’s iconic sights and sounds, you’re going to need some dinner. Whatever you have a taste for, Chicago most likely has it. If you’re looking for an interactive dining experience, Safehouse Chicago is your place. This spy-themed restaurant sends guests on a mission as soon as they arrive and treats all of its detectives to a mouthwatering meal. Of course, you can never go wrong with one of 4 Star Restaurant Group’s many restaurants including Frasca, Smoke Daddy, Crosby’s Kitchen, Remington’s, Ella Elli, or Tuco and Blondie.

Your afternoon in Chicago is going to fly by and before you know the sun is going to set over Lake Michigan. This is a sight you don’t want to miss, and there is no better place to watch the sunset than Navy Pier. Relax at the end of the pier or grab a drink at Offshore Rooftop for an unforgettable way to end your day in Chicago.

If you’re looking to get out on the water, hop on board with Entertainment Cruises for a sunset or late night cruise! Departing directly from Navy Pier, Entertainment Cruises has several cruise options great for different group sizes and all ages.

With so much to do in downtown Chicago, you might be thinking- “I want to spend more than an afternoon here!” Luckily, nobody’s stopping you! Start planning your perfect Chicago getaway today.