Chicago is one of the best cities to visit in the U.S. And we’re not just saying that because we are from the area. Located on Lake Michigan in the northeast corner of Illinois, the Windy City boasts an incredible skyline, world-class museums, architectural wonders and delicious food. Obviously, you can’t see all that Chicago has to offer in a single day. But if you are traveling through the Midwest and only have time to spend just one day in Chicago, it’s still worth a visit! Below, we share an itinerary for a fun-filled day in the Second City.
A MORNING IN CHICAGO
While Chicago is made up of diverse neighborhoods that each have their own charm and attractions, we will focus on the main downtown area (or “The Loop”) since we’re only spending one day in the city.
Breakfast:
Start your morning with some delicious breakfast. Our favorites include Wildberry Pancakes and Cafe and Yolk. Both of these restaurants have your classic breakfast staples as well as some more creative options. Either way, you won’t be disappointed. For something more historic, check out Lou Mitchell’s. This diner is listed in the National Register of Historic Places and serves as a tasty stop on the start of Route 66. From donut holes to Milk Duds, you know you’re in for a memorable breakfast experience at this classic diner.
Morning Attractions:
After breakfast, head over to Millennium Park to get a photo in front of the iconic Cloud Gate, or as it’s more commonly known, “The Bean”. The park can get quite busy, so we recommend going there earlier in the day to beat the crowds. The only time we recommend coming later in the day is if there is a free concert going on in the Jay Pritzker Music Pavilion.
Nearby is Maggie Daley Park, a must-stop if you have kids. There are many great activities here, including a fantastic playground, a climbing wall, mini golf, and our personal favorite: the skating ribbon. In the winter, it’s a great place to ice skate. The ribbon provides a much more fun course than going around in circles on a traditional rink. With turns and ups and downs, it’s a blast for both beginner and experienced skaters. During the warmer months, you can roller blade or ride scooters on the ribbon instead. There are rentals available, but be prepared to wait in line. If you bring your own, the ribbon is free to use, so you can strap on your gear and go!
Grant Park: Wrap up a morning in the parks with a stop at Buckingham Fountain in Grant Park. When the water is on, it is quite a spectacular sight, making it another popular photo spot! Grant Park is also the site for many major festivals like Lollapalooza and Taste of Chicago.
AN AFTERNOON IN CHICAGO
Lunch:
For lunch, dive into some foods that made Chicago famous.
First is the Chicago hot dog (our personal favorite style). These are made by placing a beef frankfurter in a poppyseed bun, then topping it with mustard, chopped onions, relish, a pickle spear, sliced tomatoes, sport peppers (for some heat) and a dash of celery salt. The most important thing to remember: putting ketchup on your hot dog is unacceptable! Hey, we don’t make the rules.
Another staple of Chicago food is the Italian Beef sandwich. This roll is stuffed with thinly sliced seasoned roast beef, dipped into the meat juices and then topped with hot or sweet peppers. It’s going to be messy, so grab a handful of napkins and dig in!
There are plenty of hot dog and Italian beef places throughout Chicago. Unfortunately, some local favorites have closed due to COVID-19. If you want to try both in a single restaurant, head over to a Portillo’s. This chain serves up not only hot dogs and Italian beef sandwiches, but burgers, salads and pasta as well. And don’t forget their infamous Chocolate Cake Shake for a decadent dessert.
You can’t really go wrong at any Chicago hot dog stand or Italian Beef joint. So come hungry!
Afternoon Attractions:
Plan your afternoon based on your interests. It’s impossible to see and do everything, so pick and choose what will be the most fun and interesting for you and your family!
First option: Chicago is home to several world-class museums. Which should you visit near the Loop area?
- The Field Museum: a natural history museum for people interested in animals, plants and our planet. Home to the famous Sue T-Rex skeleton!
- The Adler Planetarium: a great attraction for future astronauts who want to learn more about the wonders of our universe.
- The Art Institute: a must-stop for art enthusiasts. As one of the oldest art museums in the U.S., it boasts an impressive collection of exhibits.
- The Shedd Aquarium: our personal favorite of the Chicago museums. 5 million gallons of water hold a beautiful variety of aquatic life.
- The Museum of Science and Industry: this famous science museum is located on the south side of Chicago and can be easily reached using public transportation from the Loop.
- Lincoln Park Zoo: this free zoo is located north of the Loop. So while it is not walking distance from downtown, it may be of interest to families with animal-loving kids.
We also highly recommend an architectural boat tour. Not only do you get a relaxing ride down the river, but learn some fun facts about Chicago’s landmarks along the way! Other boat tours include a more fast paced Seadog tours and kayak tours.
And speaking of architecture, if you want a thrilling look from the top of the city, you’ll want to check out the Skydeck in the Willis Tower (or the Sears Tower as many locals still call it!) Journey up to the 103rd and step out onto a glass balcony that extends 4 feet over the edge. It’s an adrenaline-filled way to get amazing views of Chicago and on a good day, you can see up to four states!
If you are into shopping, look no further than Michigan Ave. The “Magnificent Mile” is known for its upscale stores, fancy dining and luxury hotels. During the holiday season, you will be treated to beautiful lights and decorations.
Another area to go shopping is Navy Pier, although it’s much more than that. There are many attractions here, including the Chicago Shakespeare Theater, the Chicago Children’s Museum and most notably, the massive Centennial Wheel. While it’s a bit overpriced, this Ferris Wheel is another great way to get aerial views of the city. The entertainment schedule may also influence your decision to visit Navy Pier. We’ve enjoyed watching shows such as the acrobatics of Cirque Shanghai and nighttime firework displays here.
Like we said, there’s a lot to do in Chicago. And while you can’t fit everything we mentioned above in one day, you definitely have plenty of options to create an afternoon tailored to your interests.
AN EVENING IN CHICAGO
Dinner:
Once your afternoon wraps up, there’s only one right answer for dinner: Chicago deep dish pizza. Baked in a pan, the higher crust offers more room for pizza goodness. Chicago-style pizza is assembled with the cheese first, then toppings, followed by the sauce on top. Deep dish pizza takes longer to bake, so we recommend either calling ahead to place an order if allowed, or take a look at the menu beforehand so you know what to order as soon as you get a table. Some locations may also take your order while you’re waiting to be seated.
Our personal favorite is Giordano’s and their amazing super cheesy deep dish pizza. But some of the other pizza places we also recommend are Lou Malnati’s Pizzeria, Pizano’s Pizza & Pasta, Pizzeria Uno, Gino’s East and Nancy’s Pizzeria. Of course, there are even more options throughout the Chicago neighborhoods, but these are some of the most popular options in or near the downtown area. Again, you can’t go wrong with any of these!
Note: if you are big foodies, another great afternoon activity option is to take a Chicago food tour.
Evening Attractions:
If you enjoy Broadway, there are multiple theaters that are part of the Broadway in Chicago program. Many popular musicals like Hamilton and Wicked, just to name a few, have come through the Windy City. While it’s not always easy to get tickets (and they can get pretty pricey), this is a great way to end an amazing day in Chicago.
Especially during the summer, there are plenty of free concerts and events going on in areas like Millennium Park and Grant Park. So depending on when you visit, you may have some other entertainment options to close out your day.
If you’re looking for a place to get some drinks to wrap up your night, there are plenty of choices. We recommend Miller’s Pub, a Chicago institution since 1935. There is a great selection of craft brews, plus wines and spirits, as well as a delicious food menu (if for some reason you’re not full from the deep dish pizza!)
PLAN YOUR DAY IN CHICAGO
You can spend several days in Chicago and still not see everything. But sometimes, travel plans only allow for one day in a destination. And our Chicago guide is meant to help you put together a single incredible day in the Second City. From museums to unique architecture to mouthwatering cuisine, there is something for every family in Chicago.
Do you have any questions about visiting Chicago? Let us know in the comments below. Thanks for reading and be sure to check out our other Trips and Tips!
We need to go back just for the food! WOW!
Definitely! There’s so many good options, even beyond the “Chicago-style” foods!