After visiting some of the best cities in the world I honestly didn’t expect Chicago to compare… how wrong I was. Perhaps it was naive of me to think this, after all, Oprah does live there! But none the less, I was pleasantly surprised to find that Chicago was a city packed with some of the best food, culture, art and architecture.
I only spent a few days in Chicago, but made the most of my short trip. This itinerary is filled with ideas and inspiration in case you also find yourself trying to pack this huge city into 2 days.
Start your day by visiting Millennium Park, which is free to walk through. Depending on the time of year, you can easily spend hours walking through this park, which is home to the famous bean. Don’t rush through your time at Millennium Park or you could miss some of it’s other attractions like the Jay Pritzker Pavilion, Crown Fountain,Wrigley Square, Boeing Galleries, or Frank Gehry’s BP Bridge.
For lunch, try a famous Chicago hot dog (a beef frankfurter on a poppy seed bun, topped with yellow mustard, white onions, relish, a dill pickle spear, hot peppers, and tomato wedges). If hot dog’s aren’t your thing try a famous Chicago beef dip sandwich (thin slices of seasoned roast beef, on a Italian-style roll dipped in au jus).
If you’re looking for a classic Chicago experience, spend your afternoon at the Willis Tower, formerly known as the Sears Tower, the tallest building in the Western Hemisphere. For $22 USD per adult you can visit the Skydeck and feel your heart drop as you step onto the glass ledge and take in the spectacular Chicago views. Just beware that getting up to the Skydeck can take hours in line followed by a long wait to step onto the glass ledge.
If the Willis Tower doesn’t interest you, spend your afternoon at one of Chicago’s many museums, like the Art Institute of Chicago or the Shedd Aquarium, or just explore the fascinating streets in the downtown core. I enjoyed going into the lobby’s of the office buildings, where visitor’s are often welcomed to come in to view the history and architecture.
If you’re in Chicago for baseball season, you can even spend an afternoon at a baseball game rooting for one of Chicago’s 2 teams, The Cubs or the White Sox.
For dinner make sure you try some famous Chicago deep dish pizza. I loved Gino’s East, which had gluten free options.
Begin your day at Navy Pier, and enjoy walking up and down the pier and taking a ride on the ferris wheel or other carnival rides. There are a lot of good and quick restaurants in this area for lunch, at various price points.
Spend your afternoon walking up and down Michigan Avenue, one of the best streets to shop and take in the city. I’m not going to lie, I spent all my shopping money at Garrett Popcorn, which sells a Chicago classic, gourmet cheese and caramel popcorn (sound disgusting, tastes delicious), made famous by Oprah.
There are many famous restaurants in Chicago to try for dinner. If you’re looking for something unique venture uptown to Glenn’s Dinner, which was featured on the TV show Diners, Drive-Ins and Dives. Glenn’s Dinner is known for it’s delicious seafood, but also weirdly has EVERY cereal imaginable, which a lot of people were ordering for dinner!
Just before sunset, head back downtown and take an evening architecture river cruise. This was the highlight of my time in Chicago because the architecture of the buildings is world renowned and so unique. Although, you can take this tour during the day, the evening cruise allows you to see the city against the sunset. There are many different companies that offer this tour, and the price is approximately $45 USD per person.
Note: This tour is only available from April-November. Also, if you plan your tour in advanced, some of the tours have fireworks.
Chicago has a lot to offer and it’s nearly impossible to see it all in just 2 days, but hopefully with this itinerary as your guide you’ll feel like you really experienced this great city.
Have you been to Chicago? Let me know how you made the most of your time there in the comments below.