A Long Weekend in Chicago, Illinois

Check into your hotel and then get out and explore! The perfect way to start a Chicago city trip is by taking one of the Architectural Boat Tours down the river. You’ll get the lay of the land, learn about the history of the city and get to see the amazing architecture from the water. There are many options of tour companies, and you can’t go wrong! Some tours stay just on the river, but if you want to spend a little more time on the water, check out a tour that does the river and lake, especially if you are arriving around sunset.

After the tour, I recommend having dinner at one of the Chicago staples—Gibson’s Bar and Steakhouse, Hugo’s Frog Bar & Fish House or one of the many deep dish pizza places. My personal favorites are Lou Malnati’s and Gino’s East.

The second day is a great day for more exploration, so get out on foot and check out Millenium Park. Here you will find the famous Cloud Gate, otherwise known as “The Bean”, interactive fountains, gardens and a great green space for kids to run around while you relax and enjoy the sites. Depending on the season, there could be a skating rink, live music, free events and more.

After a day of exploring, check out the Chicago sports scene and catch a game! Between the Chicago Bears, Bulls, Blackhawks, Fire, Cubs and White Sox, you have plenty of options depending on your sport of choice. If you’re there during the baseball season, I highly recommend spending the afternoon in Wrigleyville before or after a Cubs game at Wrigley Field.

Start your day by strolling along the riverwalk or riding the Ferris wheel at Navy Pier. From there, rent bikes and venture up Lake Shore Drive towards Lincoln Park. I recommend stopping at The Lakefront Restaurant for coffee, lunch, or a cocktail for views of the lake and city. While in Lincoln Park, check out the Lincoln Park Zoo (bonus, it’s free to enter 365 days a year!).

After a morning of biking and exploring, spend your afternoon shopping on The Magnificent Mile. Here you will find over 430 different retailers, from the big-name brands to the small boutiques and stores within all budgets.

Chicago has a great nightlife scene, so I recommend checking out a comedy show at Second City (where a lot of Saturday Night Live alums got their start!) or seeing some live music at one of the many theaters and venues. I love heading to Uptown for live jazz at the Green Mill Cocktail Lounge or a show at the Riviera Theater.

Exploring the many different neighborhoods in Chicago is one of the best things to do! Start your day by going up to the top of the John Hancock Building or the Willis Tower for great views, and then hop on the L or in a rideshare and head to one of the many unique neighborhoods. I love the West Loop for great food, Wrigleyville for all things Cubs or the artsy Ukrainian Village and River North. At some point in your day, make sure you get a classic Chicago Hot Dog or an Italian Beef sandwich, you won’t be disappointed!