What to do if You Only Have 48 Hours in Chicago

Big cities, like Chicago, can be overwhelming. But if you go into visiting them with a plan, you can hit the major sights all in a weekend! Here’s a list of the must-do-and-see things on your trip.

1.     Try Chicago-Style Deep Dish Pizza

Chicago-style deep-dish pizza is one of the major recognized pizza styles in the United States. As you can tell from the name, it’s made by piling ingredients (crust, creese, your chosen meat and/or vegetable toppings, and sauce in that order) into a deep dish to create pizza a few inches tall. It takes about 45 minutes to completely cook one of these suckers, so make sure you plan ahead for the wait.

Foodies and pizza-lovers alike need to try this unique pizza style at the source! There are multiple places that serve up these pies, and the competition for the title of best deep-dish pizza in the city is intense; you’re sure to get different answers if you ask a local which one you should try, but the most common answers are likely to include Lou Malnati’s, Giordano’s, and Pequod’s.

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2.     Take a Selfie in Millennium Park

If you don’t have a picture of your reflection in the giant stainless-steel statue in Millennium Park, officially name Cloud Gate, but affectionately called “the Bean”, did you even really go to Chicago? Just kidding. But you would be remiss if you didn’t at least walk past Millennium Park to see the famous work of art that has become synonymous with the city.

The giant sculpture was installed after winning a design competition. It was designed to reflect the Chicago skyline in its curved surfaces to give a different view of the cityscape, but it also provides for a great selfie opportunity!

3.     Check Out the Views from the Top of Willis Tower

Speaking of different views of the city, the view from above, in Willis Tower (originally Sears Tower), is spectacular. For a while Willis Tower was the world’s tallest building. It no longer holds that title, but the Skydeck on the 103rd story is still high enough to be exhilarating. Instead of simply looking out a window, you actually venture out onto “the ledge” - a glass box cantilevered out from the building so that you can look down through the floor as well as around you.

The Skydeck and ledge is open every day of the year, with hours that vary slightly based on the season and day of the week. Even so, the line is often long; we’re talking 2 to 4 hours. The wait times will be posted at the entrance, and are usually pretty accurate since Willis Tower Employees time each group’s stay on the ledge to keep the lines moving. They give 60 seconds to a party of 3 or less and 90 seconds to groups of 4 or more. It doesn’t sound like much, but it is truly plenty of time to take in the views and snap a ton of pictures.

4.     Go on a River Architecture Tour

Even if you aren’t a huge architecture buff, a River Architecture Tour should be on your list of things to do in Chicago. The Chicago River played a large part in the development of the city, so along with pointing out significant architectural features along the river front, your boat guide will tell you a lot about the history of the city. For example, the Chicago River originally flowed into Lake Michigan, but in 1900 engineers were able to reverse the direction, so that it now flows backwards!

There are 45, 60, 75, and 90-minute tour options to choose from, that depart from either Navy Pier or the Michigan Avenue Bridge. The tours will run rain or shine, so make sure to check the weather forecast and dress appropriately.

5.     Meet Sue at the Field Museum

The Field Museum of Natural History in Chicago is home to the largest, most complete, T-Rex skeleton ever discovered (named Sue), along with over 24 million other specimens and artifacts. The chance to see Sue, alone, is worth a trip to the museum, but seeing everything the museum offers typically takes a minimum of 3 to 4 hours.

The museum is open from 9am to 5pm, with last admission at 4pm, every day of the year except Christmas and Thanksgiving.

6.     Explore Navy Pier

Navy Pier is one of Chicago’s top attractions because of the variety of things to do and see on the pier. There are lots of dining options, cruises (such as the architecture cruises we’ve discussed, or Lake Michigan cruises, and dinner cruises), the Chicago Shakespeare Theater, a beer garden, the Chicago Children’s Museum, greenspace to relax on in Polk Bros Park, the Centennial Wheel that takes you up over the pier and Lake Michigan, Funhouse Maze, live music, rides, games, art exhibits, and plenty of shopping. There are events and festivals scheduled on the pier year-round, but it’s particularly known for the fireworks shows that are put on at the pier throughout the summer.

The pier is free to enter, but attractions on the pier typically cost money. Operating hours are 11am to 9pm Sundays through Thursday, and 11am to 10pm on Fridays and Saturdays in 2023.

7.     Take a Stroll Through Grant Park 

Grant Park includes Millennium Park, and the Museum Campus, so if you’ve seen the Bean or gone to the Field Museum, then you’ve actually already been in the 300+ acre park. However, if the weather is nice, I recommend taking a stroll through “Chicago’s front yard” to the Buckingham Fountain too.

If the weather is not cooperating, or you have any spare time on your trip, the park also encompasses the Art Institute of Chicago, the Shedd Aquarium, and the Adler Planetarium.

Creating the Perfect Itinerary

I’ve put all these activities into one perfect, 48-hour itinerary for you, here.

Parking is not ideal in downtown Chicago; in fact, many of the places recommended here don’t have any parking options at all. It’s usually easiest to either walk, or use Uber/Lyft to get around. If you drove to Chicago, there are trains that run from the suburbs to downtown that have plenty of parking available (for just a couple bucks per day), or there are paid underground lots relatively close to all the attractions where you can stash your car for a while. Alternatively, make sure wherever you choose to stay has parking available and use a rideshare service from there!  

To save some money when booking tours and tickets, check out the Chicago City Pass or the Chicago C3 pass. The City Pass gives a discounted rate for the Shedd Aquarium, Skydeck Chicago, and your choice of three other tickets from a list of options. This typically amounts to paying about half ($134 for adults and $104 for kids ages 3 to 11) of what you would pay if you book everything independently. The C3 is an abbreviated version of the City Pass – you pay $96 for an adult or $72 for a child (3-11 years old), and covers any three attractions you choose from the provided list.


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