The Globe Getter

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How to Spend 3 Days in Chicago

Though I've been to more than 30 countries throughout my travels, my coverage of the U.S. is admittedly not as significant. So, I've been on a personal mission to see more U.S. cities this year, one of them being Chicago.

I've visited many of the major cities in America multiple times and yet I had never been to Chicago, until now. Thanks to a great deal with JetBlue, I got the opportunity to go there with my sister for a long overdue, jam-packed and fun 72 hours.

For anyone visiting the Windy City for the first time, particularly during warmer months, here's how to spend three days in Chicago:

Day 1

  • Start your Chicago adventure with my favorite way to explore most new cities: walking. Walk along the Chicago River, window shop (or actually shop) on the Magnificent Mile, stop for some Garrett Mix® at Garrett Popcorn (which originated in Chi-Town), go to the top of the John Hancock building or just wander and take in the sights of the city.
  • For lunch, you have no choice but to try Chicago's famous deep dish pizza. I promise it's worth it, plus you did all that walking so it's okay. The places people often mention are Lou Malnati's, Giordano's, Gino's East and Pequod's. I tried Lou Malnati's Chicago Classic pizza with lean sausage and extra cheese on their trademarked Buttercrust. Not going to lie, I wish I had more room in my stomach to eat more than I did. It was so freakin' good.
  • After your pizza, spend the afternoon at one of Chicago's many museums, like the Art Institute of Chicago or the Museum of Contemporary Art Chicago. There are plenty to choose from, so visit as many as you'd like.
  • Take some downtime before heading to the popular West Randolph Street area for dinner and drinks. A few restaurants to try: Au Cheval, Maude's Liquor Bar and my personal favorite, Girl and the Goat. It's hands down one of the best restaurants I've ever visited. In fact, my sister and I loved it so much, we went twice in three days (worth it). Just make sure you make reservations way in advance if you want to go during prime hours.

Day 2

  • Start your day with the Chicago Architecture River Cruise (there are several vendors – I decided to book through Viator). It's a relaxing and beautiful way to see Chicago's many fascinating buildings while learning a few fun facts, like why the Chicago River is the unique greenish color that it is. If you board the 75-minute cruise from Navy Pier, you'll be able to explore that area before or after the cruise.
  • Since you stuffed yourself silly yesterday, head to Beatrix for a more health-conscious lunch. This restaurant, which has two locations, has some great heart-healthy options available, like the supernatural chopped salad, quinoa and turkey burgers and their selection of fresh-squeezed juices.
  • After lunch, walk over to Lake Michigan to stroll along the water, go for a swim or just relax at one of the lake's beaches. There are many cities around the world that are situated along the water, but Chicago's prime position next to Lake Michigan feels different and somewhat more appealing. This could be due to the fact that it was a gorgeous sunny day when I visited and being at Lake Michigan felt like the epitome of summer. The point is, you should take some time to step away from the hustle and bustle of the city to visit the lake. 
  • In the evening, head to Second City for an improv or comedy show, but make sure you buy your tickets in advance! This place has seen the likes of Tina Fey, Amy Poehler, Horatio Sanz, Steve Carrell and so many other famous funny people. 

Day 3

  • Visit Millennium Park to walk around the area and see the famous Cloud Gate sculpture and Crown Fountain. There's also rock climbing for anyone looking to get super active, as well as a beautifully designed amphitheatre that I imagine must be amazing when an event is taking place (I visited in the morning, so it was empty).
  • For lunch, check out Brown Bag Seafood Co, a fun and cutely decorated spot that lets you "design" your meal. You're provided with several seafood options that you can customize how you'd like — as a sandwich, salad, tacos, straight up or in a powerbox. Then you add on your side (also customizable), grab a drink and you're good to go.
  • In the afternoon, take a trip to the Lincoln Park Zoo, which, by the way, is completely FREE (woot woot!). You can easily spend hours here and never get bored.
  • End your third day, and your overall trip, with a special meal, whether it's a super fancy venue like Alinea, more of Chi-Town's delicious pizza or something else that's sure to be fantastic. Chicago is an amazing food city, so come prepared to eat.

A big thanks to everyone who gave this Chicago first-timer some great recommendations! I had such a fun time in Chicago and can't wait to return and explore more of the city.

Have you ever been to Chicago? What's your favorite thing to do there?