3 Day Itinerary | Chicago, Illinois
Situated on the majestic Lake Michigan and visited by over fifty million people a year, Chicago towers like a shining cosmopolitan beacon smack dab in the heart of the Midwest. As you approach the city by plane or car, the skyline looms tall with steel giants such as the John Hancock Center, the Tribune Tower, and the famous Willis Tower (which used to be called the Sears Tower).
Chicago is home to United Airlines and even Boeing has headquarters here. It rivals New York City as a financial hub, and O’Hare Airport is the busiest airport in the world.  And who can forget the Chicago Cubs? Wrigley Field is an iconic landmark, and worth checking out, even if you can’t catch a game. With all of this and more, we can pack your trip with crazy architectural features and amazing food.
Getting Around
Known as the Windy City, Chicago has a world-class public transportation system, and to take advantage of this, buy a CTA (Chicago Transit Authority) metro pass. Ventura is the company that handles ticketing for CTA. You can buy passes all over the city at a Ventura kiosk or retailer. These days, every major city has an app you can download to keep track of rail and bus line schedules, and Chicago is no different. You really don’t need a car if you plan to stay in the city.  And in a pinch, there is always Uber. Or better yet, use your feet!
Saving Money
Chicago is similar to any big city, in that the prices for just about anything can be exorbitant. Stretch your dollar further by always carrying snacks and water with you. And for a really good meal, you need to try the world-famous Chicago pizza! These tasty meal-pies are a good alternative to an expensive meal, and there are tons of pizzerias to choose from. (Keep reading for my pizza recommendations!)
Pro Tip:
Get the Chicago CityPASS: This is a book of tickets you can purchase online as a mobile app, and will get you priority entry to the following attractions:
- Skydeck Chicago
- Shedd Aquarium
- Field Museum
- Adler Planetarium
- Art Institute of Chicago
- Museum of Science and Industry
- 360 Chicago Observation Deck
With the CityPass, you get priority entry (i.e. skip the lines!) and thus more time to enjoy the attraction itself. By purchasing the CityPass you will save about 50% over buying each admission ticket separately.
Day 1
Head straight to Millennium Park and check out Cloud Gate, also known as ‘The Bean.’ This is the huge silver, mirrored structure you’ve seen in all the pictures, and is incredible to see up close and personal.
360 Chicago. This is a great thing to do at the Hancock Building, morning or evening. Either way, it’s spectacular. While similar to Skydeck Chicago (mentioned later), you get a much different view, with views of Lake Michigan being more prominent here.
Check out Navy Pier. Here you will find the Centennial Wheel & Rides, the Chicago Children’s Museum, and even an Architecture River Cruise. Other activities include an IMAX theater, Crystal Garden, and a whole slew of outdoor activities such as bike rentals and viewing street art. Stop by Giordano’s Pizza for some of the best deep dish in the city.
Then head south to the Chicago Riverwalk. Take in the city’s stunning architecture on this walk. The best time of day to do this is around sunset or ‘golden hour’. And the sun goes down, the city lights up and is truly spectacular.
Pro Tip:
Wear comfortable shoes on this trip! You will be doing a LOT of walking!
Day 2
The Art Institute of Chicago. As the city’s oldest and largest museum, it is also the city’s most popular, and you will no doubt spend several hours here taking it all in. Seemingly countless paintings and sculptures line every nook and cranny, from the ancient all the way to today’s contemporary. Be sure to check out the current main exhibition, which rotates continuously.
If space exploration is your thing, you must go to the Adler Planetarium. Located on the shores of Lake Michigan, it’s not far of a walk from the Art Institute. Find out the history of our space activities, as well as what the future holds for us among the stars.
Then head a short way’s over to the Field Museum, one of the largest natural history museums in the world. Allow at least 2-3 hours for this.
Are you a fan of comedy? Then catch a show at Second City in the evening. This is where Amy Poehler and Tina Fey got their start, among other famous notables! Check their website for current shows, they aren’t’ expensive!
Pro Tip:
I did mention pizza, and my top five picks for great Chicago deep dish are: Gino’s East, Spacca Napoli Pizza, Lou Malnati’s, Giordano’s, and Chicago Pizza and Oven Grinder Company. I can’t pick a favorite here, they’re all good!
Day 3
Start your last morning by getting a birds’ eye view of the city and head to Skydeck Chicago. Located high on the 103rd floor of the Willis Tower, the tallest building the city (and at one time, the world!) It’s a breathtaking way to spend an hour of your morning.
Shedd Aquarium. There are eight main exhibits to explore and so many interesting sea creatures to enjoy. The aquarium prides itself on its conservation efforts; you will come away with a new appreciation for the sea.
If you can squeeze in a bit of shopping, head further up Michigan Avenue to Magnificent Mile. Alternatively, a great tour I highly recommend is the Chicago Crime & Mob tour.
Pro Tip:
If shopping is not your thing, take advantage of your CityPass and visit more museums, such as the Museum of Science and Industry.
On your last evening, enjoy some great music at any one of Chicago’s many jazz clubs (Andy’s Jazz Club is a good one!), or take in a theater show.
Chicago is a big-city culture combined with friendly, Midwestern hospitality. Come see why the Windy City is such a popular spot. Have you been to Chicago? How would you spend 3 days in Chicago?
