Day Trippin in Chicago: What to do With 24 Hours in the Windy City

Day Trip in Chicago

When offered the opportunity to take a day trip to Chicago I could not pass it up! My boyfriend and I had never been to the Windy City, and I was very excited to finally explore the many Chicago staples I had been told about. Our only concern was what we were going to be able to do in a vast city such as Chicago-in only one day!

We ended up being pleasantly surprised by how much we packed into our day. At the end of the day, I realized how much easier our trip could have been if I had researched an Itinerary or Guide. So, I set out to write my own with one goal in mind-help anyone who only has 24 hours in Chicago and wants to make the most out of their time.

Visit the Bean at Millennium Park

The beautiful Millennium Park is probably one of the most visited places in Chicago. This park is home to one of Chicago’s most iconic landmarks, Cloud gate. This reflective structure is better known as “The Bean” and is one of the most photographed attractions in Chicago. Millennium Park also features Buckingham Fountain, which is one of the largest fountains in the United States. This fountain displays beautiful water shows during the warm seasons and sometimes even puts on light displays. Also, don’t forget to stop and admire the amazing sculptures and gardens while walking through the park. The best thing is all of this is free! There is no admission to the park so everyone can enjoy what it has to offer.

Experiences in Chicago

Eat Chicago Style Pizza at Giordano’s

In between sightseeing, enjoy delicious Chicago style deep dish pizza at one of the many famous pizza restaurants. We chose Giordano’s because it was walking distance from where we parked, and I had heard nothing but positive reviews about it. Expect to wait at least 30 minutes for the pizza to be made, but it is worth it! The pizza is fresh and delicious. There is no wonder why it is so famous. During the warmer seasons the restaurants get very busy, so expect a long wait with lines out the door during peak times. Giordanos offers takeout, but there is nothing like dining in the restaurant or out on the patio during the warmer seasons.

Experiences in Chicago

Take a Stroll through Grant Park

Grant Park is one of Chicago’s largest greenspaces. The park spans over 300 acres and is home to many Chicago staples such as the Shedd Aquarium and the Adler Planetarium. The park also includes Museum Campus, which is the site of the Art Institute of Chicago and the Field Museum of Natural History. One aspect of Grant park we loved was the art throughout the park. The Abe Lincoln statue and The Bowman statue are two of many statues and monuments we were able to experience while visiting, and they were amazing. The beautiful greenery, attractions, and art that Grant Park offers to visitors make it one of the best outdoor experiences in Chicago.

What to do With 24 Hours in The Windy City

Walk the Coast of Lake Michigan on Lakefront trail

Lakefront trail is an 18-mile long path that lines the coast of Lake Michigan. This path is used daily by many local joggers and cyclists because of its amazing views of Lake Michigan, and it is often the easiest way to travel through Chicago by avoiding city traffic. Lakefront trail passes through all four of Chicago’s major lakefront parks, including Millennium and Grant Park. We entered the path at Millennium Park behind Buckingham Fountain and were blown away by the spectacular views of not only the lake but Chicago landmarks such as the Navy Pier. Walking the trail was a unique experience that made me fall in love with Chicago.

Experiences in Chicago

Visit Maggie Daley Park

If you are visiting Chicago with children, let their imaginations run wild at Maggie Daley Parks Play Garden. This 3-acre playground has multiple play features that interconnect for easy access by the kids. The Watering Hole is a water feature for small children, and the Slide Crater features various slides and a suspension bridge for older kids. Combined with the other play features, the Play Garden creates a space that engages all of your child’s senses while keeping them entertained. The park also features a rock climbing wall, mini golf, and skating ribbon. Which were a few things we were unable to participate in because we visited in the offseason. We weren’t too disappointed because we know we will be back! Maggie Daley Park is connected to Millennium Park by a pedestrian bridge, making these fantastic parks only a short walking distance away from each other.

Experiences in Chicago

Our trip to Chicago may have been quick, but we were able to enjoy plenty of Chicago staples during our day. Even though we only had 24 hours in the Windy City, there was no lack of adventure and amazing experiences. I hope this guide will help anyone visiting Chicago with only a short amount of time, but a strong desire to see as much of what the city has to offer as possible!

If you have any suggestions for fellow travelers or tips for visiting Chicago, leave them in the comments below!

18 thoughts on “Day Trippin in Chicago: What to do With 24 Hours in the Windy City

  1. WineDivaa

    Hello! Thanks for this recommendations actually I visited Chicago once like that in a rush and visited the Millenium Park I had such a great time the only thing I didn’t do is to try a deep dish Pizza that means I should go back!

  2. Savannah

    Great guide! You packed a ton into what sounds like such a fun day. I loooove Chicago, though the last time I visited it was right after Christmas, and just about the coldest weather I’ve ever experienced. The aquarium was a welcome distraction from the frigid temps! Thanks for sharing and rounding up this great information. 🙂

    1. Arika Post author

      It was a great day! We will have to try the aquarium next time. It was also in the off-season that we visited, we were bummed we missed the light and water shows at the fountain! Another reason to return.

  3. Pat

    I haven’t been to America before but i am certain that one day my travel plans will lead me there. Who knows i might get to visit Chicago.
    Thanks for the post.

  4. Meghan Kleinschmidt

    Even though I only live about 30 minutes away from Chicago, I don’t get there too often. But Millennium Park is one of my favorite places to go. I love the fountains with the faces! Then we usually end up wandering around Macy’s and one of the lesser known museums Or historic buildings nearby. But the big museums are great too!

  5. Pat

    Seems like you can fit in quite a bit in 24 hours which is brilliant. hopefully when i visit America, Chicago will be amongst one of the places i will visit.
    Thank you for such an informative post.

    1. Arika Post author

      We were surprised at how much we were able to do. It was due to the fact that everything was in walking distance which was awesome!


Leave a Reply

Your email address will not be published. Required fields are marked *