24 Hours in Chicago

If you only have a day to spare on your visit to Chicago, it can be stressful to figure out what to do and where to go. I have had friends consult me about this. I’ve also taken several people on a personal guided tour of my city. Of course, each itinerary usually differs as I tailor it based on what interests them the most. People would usually say they want to see “The Bean” and eat deep dish pizza. I had someone who has never heard of the bean before until I mentioned that we were heading there next. Imagine my reaction.

I created a general but helpful guide that can at least narrow down some of the things you might want to see in the Windy City. It is also important to note that this guide is about making the best out of your visit in terms of time, location, budget and practicality, especially if it is your first time in Chicago.


8:00 am to 12

Where to go: The Loop

Most of the things you would want to see can be found in this area. Start off your day with breakfast or brunch at Bridge House Tavern by the river, where you can park your boat at their dock if you have one. Ok, I didn’t mean to already sound sarcastic early on. Sometimes, I just can’t help myself. There are plenty of restaurants located by the Chicago River. After brunch, you can just walk to Millennium Park, where you need to go next to see the infamous bean aka the Cloud Gate as well as the Crown Fountain. If you’re into art, you can find the Art institute next door. Willis Tower is also in the vicinity where you can experience Skydeck Chicago’s spectacular views of the city, 103 floors from the ground!


12 noon to 4 pm

Where to go: Gold Coast – Magnificent Mile; 360 Chicago; Giordano’s

Chicago’s fashion district – the Gold Coast – is the place to be if you want to do some shopping. There are also tons of souvenir stores along North Michigan Ave’s Magnificent Mile. For lunch, Giordano’s is a nice place to finally have that infamous deep dish pizza you’ve been wanting to try. Note: It takes about 40 minutes for that deep dish pizza to be served, so plan accordingly. While you’re in this neighborhood, don’t forget to go up John Hancock’s observatory, now called 360 Chicago to get a beautiful 360 degree view of the city. If you prefer a quick bite, go to Portillo’s, home of the Chicago-style hotdog. I always get the decadent chocolate cake which is the best thing there.


4pm to 8pm

Where to go: Museum Campus; Navy Pier, Buckingham Fountain

One of my favorite things about Chicago is its list of museums. The Museum Campus not only offers the city’s best museums namely, the Field Museum, Shedd Aquarium and Adler Planetarium but it also offers spectacular skyline views of Chicago. This area is perfect for families but if you are flying solo and love museums in general, it is perfect for you too. I recommend to go during sunset hours because the view of the skyline at this moment is truly breathtaking. If you still have time, take a leisurely walk along the river to the Buckingham Fountain for some Instagram shots.


8pm to 12 midnight

Where to go: Back to Millennium Park, John Hancock Observatory, Rooftop bars

For dinner or a night cap, I suggest going back to Millennium Park for the rooftop bars and to see the Cloud Gate at night. The Tavern at the Park, which is located across the park has a cozy rooftop bar. The city looks entirely different after the sun goes down! My best suggestion and my favorite secret weapon of making visitors fall in love with Chicago is the Signature Lounge at the John Hancock Observatory. Nothing beats having a nice martini with a stunning view of Chicago enveloped in city lights .

Hopefully, you don’t get too drunk and wake up with a nasty hangover for your early flight the next morning. Chicago airport lines can be excruciating sometimes … I kid, I kid. That is not the case any more. At least in my experience. While at the airport, grab some of that Garrett Popcorn you see everywhere for your airplane snack. It also makes a good last minute Chicago gift.

24 hours may not be enough to see the city but it is definitely enough to make you fall in love.

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Jen is a Chicago-based traveler and a full-time Director of Development for an arts & culture organization. Originally from Connecticut, she created JetsettingJen as a place to share her travel stories and photos with friends and family. Now, it is a place for adventurers, explorers and dreamers. Its purpose is to inspire and encourage people to see the world and achieve a better work-life balance.