Exploring Chicago Neighborhoods,  museums,  music,  theatre

the perfect 3-day Chicago travel guide

Here is my guide to help you plan the perfect 3-days in Chicago with insight from a local (born & raised) & a tour guide. It is for first-time visitors to Chicago, including solo travelers, couples & families with kids. It includes an itinerary for each of your 3-days in Chicago. I’m warning you now, 3-days won’t be enough time, but it’s a good start!

day #1 – explore the Loop

I suggest starting in the Loop. The Loop is the central business district in downtown Chicago. It’s close to everything: world-class public art & architecture, the Lakefront, museums, and green space, so it’s a good place to begin. Make your way to the Cultural Center, 78 E Washington St (Michigan Ave & Washington St).

If you need a coffee and/or snack, my recommendation is to walk through the alley behind the Cultural Center (notice the mural Rushmore) and make a quick left onto Randolph St to the Intelligensia Millennium Park Coffeebar. A local, homegrown company that began in 1995 with a great mission & story. And IMHO, it has the best coffee in the city. Now that you are all fueled up and ready for an adventure, explore the inside of the Cultural Center. Head east (toward the lake) and head into the Randolph entrance.

Here is a video tour narrated by Chicago’s favorite local historian. Click here to get the latest, updated Cultural Center events & exhibits as they become available. Or hire me as your guide!

Make sure that you check out both domes, the Tiffany Dome in the Bradley Preston Hall (the city’s first library) & the G.A.R. Grand Army of Republic Memorial. There are many free exhibits on various subjects, music, art, architecture, etc., that you can peruse while walking through the building. You may even be lucky to enjoy the free weekly classical concerts at noon. They also have bathrooms. Now, it’s time to head over to Millennium Park.

A stroll through Millennium Park includes the very popular Cloud Gate (aka the Bean), Pritzker Pavilion, Lurie Gardens, and Crown Fountain. Admire the art & architecture and enjoy some good people-watching. And don’t forget the kid-focused Maggie Daley Park right next door with a few playscapes, garden spaces, a skating ribbon, a climbing wall, and mini-golf. Here’s more stuff to do with the kiddos.

Time to jump on a Divvy bike and go check out Buckingham Fountain. Click here to read my post on Buckingham Fountain. Now, ride to the museum campus for the best view in the city. Here, all in one place, are the Shedd Aquarium, the Planetarium, and the Field Museum. If you are riding a bike, please be safe and find and use the designated bike lanes. Interesting fact: Did you know that in 1995, Lake Shore Drive was relocated to create the Museum Campus? It used to run right through the Museum Campus.

Remember, most museums are open until 5 pm, and some have a day with extended hours, so you may want to put this on your list for earlier or later, depending on the day.

Looking for something to do in the evening? Come back to catch a concert/movie at the Pritzker Pavillion. Bring a chair/blanket, snacks/drinks, and relax under the stars.

day #2 – explore the Chicago river

Go on an Architectural River Cruise. There are many options to choose from: Chicago Architecture Center, Wendella, Shoreline, etc. They offer slightly different options, so you should check each company to see what best fits your style & budget. But it’s a definite must-do while in Chicago. You can schedule this any time of day, morning, noon, or night. You’ll want to keep this in mind when planning your day. Check the weather and remember it can get pretty chilly on a boat or anywhere along on the Lakefront. My favorite time to go is in the evening when the sun is setting & the city lights come on.

Check out the Riverwalk. Take a stroll down the 1.25-mile stretch on the Chicago River’s south bank to the lakefront. Go to the McCormick Bridgehouse and Chicago River Museum, grab a drink/bite, or just people-watch. While you are on the Riverwalk, don’t forget to come back at dusk to check out Art on the Mart. I cover this area on my Near Northside neighborhood tour. Click here to book!

Before heading north on the Magnificent Mile to the Historic Water Tower, it’s time to relax, have a drink, and take in the cityscape at the LondonHouse rooftop. This is one of the most spectacular views of the Chicago River. Inside tip: go off-season & off-hours when it’s not so crowded.

day #3 explore the North side

Go to Lincoln Park Zoo. And while you are here, you’ll want to check out a spectacular secret garden. From the Loop, take the #151 Sheridan bus south. After a scenic bus route along the lake & through the park, it will drop you off right in front of the zoo. Use the cta trip planner to find where to catch the bus. Interesting fact: The Lincoln Park Zoo is the nation’s oldest & free zoo and started with a pair of swans.

The Chicago History Museum is not far from the zoo. Like the name says, everything you ever wanted to know and more about Chicago history. Great for all ages. Here’s my post on the CHM.

You are close to Old Town. Go check out a comedy club at either Second City or Zanies. My favorite places to eat in Old Town are Kamehachi, a sushi pioneer, Adobo Grill for exquisito Mexican, & Twin Acres, a Chicago Institution since 1932.

Since you are already on the North side, go check out a Cubs game. Get on the Brown Line at the Sedgwick stop and head north to the Belmont stop. Switch here and take the Red Line to the Addison stop. You could also take a rideshare, but be warned traffic is crazy on game day. Want to see this area by car? Hire me as your guide!

If you would like someone to help guide & navigate you through the city, you could always hire me to tour you around. Go to Tours by City Girl to book a tour with me today!

I hope my perfect 3-day Chicago guide helped you plan your next trip to Chicago. Enjoy your stay and have a memorable trip! Click here to read a post on preparing for your next trip to Chicago.


  • mimi

    Thanks, Krysten! Chicago loves you too! Looks like everything should be open by early July. Yay! I’m thrilled we will have Summer this year. I hope you can come to visit soon!

  • simplyjolayne

    I saw the pizza picture and it made my mouth water. Great overview. I love the details on things to see and do as well as the restaurant recommendations.

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