The Haute Seeker

How To Experience Chicago In 24 Hours: A One Day Itinerary

Have you ever wondered what you could do in Chicago in one day? Perhaps you’re a local looking for some new ideas to get to know your city better, or perhaps you’re a traveler with a one-day layover.

Discover the city’s top attractions and exciting activities, perfect for both locals and tourists, all within a one-day period. With this step-by-step guide to 24hrs in Chicago, you’ll be sure to have an unforgettable adventure.

Start Your Journey in Streeterville

The best game plan has you starting north and working your way down the city throughout the day. There are a ton of historical landmarks and fantastic cafes in this neighborhood. We recommend grabbing a quick coffee or bite to eat as you wander through Magnificent Mile and do some window shopping.

Learn Chicago History during a Mob Tour

While you’re in Streeterville, why not join a mob boss tour to learn some interesting Chicago history? These tours are anywhere from 1-2 hours long and have stops along the way to see historical landmarks. It’s another great way to get around and see the city.

Explore the Chicago Riverwalk

As you walk down North Michigan Avenue, head towards the Chicago Riverwalk for amazing views, terrific restaurants, and world-famous architecture. Enjoy a leisurely walk to a restaurant of your choice ranging from Middle Eastern cuisine like Beatnik on the River to fast casual eateries like O’ Brien’s Riverwalk Cafe. After your meal, enjoy an hour-long river cruise and get a tour of downtown Chicago and its architecture without leaving the boat.

Hangout at Millennium Park

Now that you’ve eaten your fill and feel a bit rested after the cruise, why not get your exercise in by heading to Millennium Park? This park is the quintessential spot for any Chicago visit: it has The Bean, The Crown Fountain, The Lurie Garden, The Jay Pritzker Pavilion, and Maggie Daley Park. You can try rock climbing, ice skating, or rollerblading, depending on the season.

No Chicago itinerary is complete without a museum visit! You can either check out The Art Institute of Chicago right next to the Millennium Park, or head a bit further south to the Museum Campus to any of the three major museum’s in this area. Plan to spend a couple of hours here–these museums have astounding collections that deserve to be seen.

Observe Spectacular Views From A SkyDeck

For a perfect sunset activity, why not visit the Skydeck at the Willis Tower for some beautiful panoramic views of the city? Also known as the Sears Tower, this building is the tallest one in Chicago, boasting 103 floors! If you’re not afraid of heights you can even step on The Ledge, a transparent balcony platform on the side of the building.

Grab Dinner in the Fulton Market District

Head west to Fulton Market to enjoy your final meal of the day. This district is colorful, lively, and trendy–you’ll have a hard time picking which restaurant to choose! Our recommendation: Monteverde. It is woman-owned and combines Italian tradition with modern flair. What’s better than fresh pasta? 

Bar Hop in the West Loop

One of the best ways to end your 24 hrs in Chicago is by bar hopping! The city has an amazing nightlife scene with incredible places ranging from dive bars to upscale speakeasies. End the night in the West Loop by checking out Federales, City Winery, and The Tribe.

Tips and Tricks For Getting Around Chicago

If you’re looking to explore Chicago, getting around the city is a breeze, especially if you’re focusing on one particular area or neighborhood.

  • Travel by foot: The city is very walkable and a great way to get some exercise while exploring the city. Lace up your walking shoes and set out to explore the bustling streets, beautiful parks, and vibrant neighborhoods. 
  • Take a ride on the CTA: The CTA(Chicago Transit Authority) is a reliable public transportation system that will take you to the most popular destinations throughout Chicago.
  • Pedal your way on a Divvy Bike: f you’re feeling adventurous, you can also rent a Divvy bike and pedal your way through the city at your own pace. With thousands of bikes and hundreds of stations, it’s easy to explore any of Chicago’s 77 neighborhoods.

As a local, I understand how challenging it can be to recommend the best things to eat, see, and do in the city. That’s why I recommend focusing on just one or two nearby neighborhoods, planning ahead as much as possible, and taking your time to truly enjoy your experience. With this step-by-step guide, you’ll be able to enjoy the best that Chicago has to offer, inspiring you to visit again in the future.


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