Preparing for your initial 72 hours in Chicago and seeking the ideal itinerary for your trip? When exploring a new destination, it’s often wise to kick start your adventure with some classic tourist experiences before delving into the local gems. While venturing off the beaten path can be rewarding, the logistics of fitting them into a tight schedule can be challenging. If I were visiting Chicago for three days, for the first time, this is the perfect 72 hour itinerary for the trip:

Day 01

It’s day one, you’ve just arrived in Chicago, Illinois, and everything is new. If you’re flying into O’Hare International Airport, Chicago Midway International Airport or even coming in from Chicago Union Station, I always recommend stopping by a Garrets Popcorn and picking up a cheesy caramel snack.

First Impressions of Chicago – First Day in Chicago

Garret’s Popcorn

Garrett popcorn is always conveniently placed near tourist locations and I don’t mind it. Every time I go to the airport I try to pick up some popcorn because it’s one of my favorite snacks ever. The Illinois State Snack is actually popcorn so coming into a major city in this state is super fitting to have it as a snack.

📍 Garrett’s Popcorn, 26 W Randolph St, Chicago, Illinois. 60601

Take the train into the city

In most cases you will be taking the train into the city to get to your hotel. Your journey from the airport to your hotel is dependent on whether you’re stopping earlier at a residential area or further away and closer to the loop. Taking public transportation is way cheaper than reserving a taxi, but if we have a lot of bags I understand why you would prefer your own private car.

Go on a Chicago Free Walking Tour

There are paid tours available all over Chicago, but one of my favorite gems is taking advantage of the free walking tours around the city. When you’re on one of the free walking tours are able to stop and take as many photos as you want without the pressure of a host trying to make a strict timeline.

Pictures in front of the Bean & The Chicago Theater

If you’re already in the Loop area, it makes sense to take photos in front of those iconic tourist locations. Within walking distance of each other are the Bean and the Chicago Theatre and photos in front of both of those places are always beautiful. I don’t think we need to spend that much time here, but checking off this photo from your Chicago Bucket List may be something that you want to do.

📍 The Bean (Cloud Gate), Millennium Park, 201 E Randolph St, Chicago, Illinois. 60601

📍 The Chicago Theatre, 175 N State St, Chicago, Illinois. 60601

Eat a Chicago-style Deep Dish Pizza

After a full day of walking, heading over and grabbing a Chicago-style Deep Dish Pizza is the next thing your body is going to want to do. Tomorrow is a full food tour planned which is going to include a more local style of pizza so it’s best to get your tourist fix now while you have the stomach space.

Day 02

If you’re a foodie, Chicago is the place for you! There are a ton of delicious food options here and of course, we have a staple list of food items you might try when you first visit. Unlike the Chicago-style Deep Dish Pizza, all of these other food options are a lot more popular amongst local Chicagoans and tourists alike. Here are some Chicago foods you must try:

Chicago Food Tour

Chicago-style hot dogs

Chicago style hot dogs are delicious. A Vienna beef hotdog, on a poppyseed bun, topped with mustard, relish, tomatoes, and onions creates such a delicious combination of flavors – this isn’t just a simple overpriced hot dog. You can find this staple anywhere around the city where you see that Vienna hot dogs sign, which is most places really.

Jibarito

One of my personal favorites on this list is the Jibarito. With a delicious piece of steak, lettuce and cheese squished between two fried plantains and topped with garlic, this sandwich is a filling meal. You can order it with a side of rice and beans, but the staple is the sandwich. Depending on where you’re going some places may be a little bit stingy with the meats, but I recently filmed a place that serves big Jibarito sandwiches that are totally shareable.

Chicago Italian Beef Sandwich

Another popular option on this list is the Chicago Italian Beef Sandwich. An Italian Beef is thinly sliced seasoned Roast Beef on a French Roll; depending on your preference you can have the sandwich dry or get it redipped into the beef juice. This beefy sandwich was created to fill stomachs with the least amount of food and all of the flavors in the meats and the bread are definitely a great way to fill yourself up for a great price.

Thin Crust Pizza

Although Chicago-style Deep Dish Pizza is super popular among the tourist route, most locals enjoy a Chicago-style thin crust pizza when they are ordering for themselves. Unlike other pizzas that can be folded, thin crust pizza is cooked to a crisp and can barely hold the weight of the cheese up let alone be folded; the slices are also cut into squares unlike all of the other triangle cut options.

Day 03

Your last day in Chicago may be bitter-sweet; although you had two days of adventures so far, knowing that you’re leaving the city without exploring it all just gives you another reason to come back. On this last day, I always recommend doing some more relaxing activities because you probably have a long travel day ahead. Depending on where you’re located every area has a few free things to do and here are a few free activities around Chicago, Illinois:

Your Last Day in Chicago

Take a Chicago Street Art Tour

Chicago is full of art. No matter what your personal style is everyone comes to Chicago and naturally becomes a fan of architecture and art because it is everywhere. One of my favorite activities even as a local is walking around with my camera and taking photos in front of colorful spaces.

Admire some of Chicago’s Oldest Fountains and Beautiful Parks

Keeping on theme with admiring the architecture around the city, Chicago has some of the most gorgeous fountains and parks that I have ever seen. It seems like if you spend too much time looking up you’re going to miss some of the beautiful fountains nestled in gardens at the bottom of these tall glass buildings.

Visit a Museum like the DuSable Museum of African American History.

Chicago has a lot of museums; with popular titles like the Art Institute of Chicago, the Field Museum, the Chicago History Museum and even the Museum of Science and Industry Chicago, it’s always worth visiting at least one museum while you are here. One are my favorite free admission museums is the DuSable Museum of African American History near Washington Park; founded by a husband and wife team on the ground floor of their home this museum now has at least 100,000 visitors annually and you should come see it too.

📍 DuSable Museum of African American History, 740 E 56th Pl, Chicago, Illinois. 60637

Now Let’s Plan Your Next Trip Back to Chicago

There is always something to do in Chicago, Illinois and there is no way that you can see the whole city in a matter of three days. Although some people abhor the tourist routes, the tourist path in Chicago is definitely fun and delicious. The next time you come to Chicago I recommend visiting more of the residential areas so you can see the different parts of the city that Chicagoans experience every day. Depending on how popular this for 72 hour itinerary is, I may make another post about spending a week in Chicago for those of you staying here for a longer time. Of course remember to check out my other posts that include all of my adventures in Chicago if you have some extra time and need inspiration.