A Guide and Itinerary for First Time Visitors to Chicago

A Guide and Itinerary for First Time Visitors to Chicago
21 Apr 2023

Sharing is caring!

Image by David Mark from Pixabay

Are you planning your first visit to Chicago? The city has so much to offer, from top-notch museums and the famous Magnificent Mile to breathtaking architecture. But deciding where to start can be overwhelming.

This guide has got you covered no matter what your interests! Whether you’re a food lover, a history enthusiast, or simply seeking a good time, we’ve got you covered because this guide is recommended by a local.

Image by Tobias Brunner from Pixabay

The Chicago Riverwalk

The Riverwalk offers a delightful opportunity to explore the city skyline from a distinct perspective. Whether it’s enjoying a lovely picnic, taking in the mesmerizing cityscape, or sipping on a refreshing beverage at one of the numerous cafes situated along the pathway, it’s a nice way to plan time outdoors with family or friends.

At the east end, rest in the Adirondack chairs and relax with the river’s panoramic views. As you venture to the west end and reach Lake Michigan, absorb the harbor’s picturesque scenery or visit Navy Pier.

Image by Francine Sreca from Pixabay

Millennium Park

One must not miss visiting this iconic park in Chicago, home to the renowned “Bean” sculpture, or Cloud Gate. The best part? Entry is completely free! It’s an ideal location to enjoy a lovely picnic, people-watch, or take in a free open-air concert at the Jay Pritzker Pavilion.

Chicago is famous for its pizza and free summer music festivals like Summer Dance, Blues Fest, and Jazz Fest. These are fun outdoor events that bring all communities together.

You can also enjoy fantastic live music performances from renowned musicians for free at the annual Taste of Chicago. You can also visit the public park, Maggie Daley Park, which is also free, located near Millennium Park.

You can partake in a plethora of outdoor activities such as scaling a climbing wall, playing mini-golf, or ice-skating during the winter season. Visiting Millennium Park is an excellent way to appreciate the great outdoors, immerse yourself in the local culture, and have a delightful time.

Only a block away from Millennium Park, are renowned masterpieces at the Art Institute of Chicago. They are curated from around the world, providing an opportunity to admire art from various eras and countries.

Image by Morris Sneor from Pixabay

Navy Pier

Navy Pier, located in Chicago’s desirable Streeterville neighborhood, is the perfect place to spend a fun-filled afternoon. With free entry, you can explore the pier’s many entertainment options, including mini golf and free exhibits.

But the real highlight is the Centennial Wheel, which offers breathtaking views of the iconic Chicago skyline. And don’t miss the Wave Wall on the south side of the pier, where you can relax and enjoy a free firework display every Wednesday night.

Navy Pier truly has something for everyone and is a must-visit destination when in Chicago.

Image by Paola Sanchez from Pixabay

The Chicago Cultural Center

The Chicago Cultural Center is an exceptionally stunning building that showcases cultural events, exhibitions, and performances. It’s an incredible place to discover Chicago’s history and the best part, it is entirely free. The center is home to several fascinating features such as the world’s largest Tiffany glass dome and an old map of Chicago after the Great Fire of 1871. Additionally, a little-known fact is that the embossed ‘Y’ symbolizes the branches of the Chicago River, which is also showcased on the famous Chicago Theater marquee (175 N State St) and has been woven into the city’s architecture on public buildings and bridges.

Image by David Mark from Pixabay

Chicago Itinerary Day 1


No trip to Chicago is complete without a visit to the iconic Buckingham Fountain. Take a stroll along the picturesque lakefront and marvel at the fountain’s impressive size and beauty.

Next, enjoy a 20-minute stroll through downtown Chicago, past the Financial District to the awe-inspiring Willis Tower, formerly known as the Sears Tower. From the Skydeck on the 103rd floor, you’ll see jaw-dropping views of the city.


Looking for pizza? We highly recommend the thin crust at Pizano’s (61 E Madison) which is less than a five-minute walk from the museum.


After a satisfying lunch, take a stroll north on Michigan Avenue down the picturesque Magnificent Mile, a shopping district that’s home to some of the finest boutiques and department stores in the city. Take in the stunning architecture and soak up the bustling atmosphere.

Stop at the World’s Largest Starbucks to see the plethora of coffee and experience six floors of java nirvana. Make sure to stop by the historic Water Tower, a beautiful structure that miraculously survived the devastating Great Chicago Fire of 1871 (located near Chicago Ave). Inside, you can enjoy a free art exhibit.


As the sun starts to dip below the horizon, head back to the Riverwalk for a cruise along the Chicago River and Lake Michigan. Take in the views and snap some Instagram-worthy shots.

End your night on a hilarious note by catching a show at the Second City Comedy Club (230 W North Ave). This venue has launched the careers of countless famous comedians like Chris Farley, Amy Poehler, Gilda Radner, and Tim Meadows.

Image by David Mark from Pixabay

Chicago Itinerary Day 2


Day two promises to be just as exciting as the first! Start your day off with a bang by visiting the incredible Millennium Park, where you’ll be greeted by the iconic “Cloud Gate” sculpture, affectionately known as “The Bean”. Take some photos of the sky and skyscrapers reflecting on the bean. During summer, you should walk through Laurie Gardens and bask in the beauty of the landscaped grounds. During the winter, rent some ice skates and skate your way through Maggie Daley Park on the ribbon-themed ice rink.

Next, head over to the world-renowned Art Institute of Chicago. For more curious adventures, you’ll love exploring the Museum of Illusions (25 E Washington) or the Museum of Ice Cream (435 N Michigan), and it’s a great alternative for kids.


How about a taste of old Chicago? Stop at Lou Mitchell’s (565 W Jackson Blvd) for lunch. Lou’s is one of the oldest restaurants in the city and has some of the best diner food.


Next, make your way to Navy Pier for outdoor fun on the Centennial Wheel or a ride on Seadog. You can also enjoy a beer garden and free entertainment.


As the evening sets in, consider catching a baseball game at Wrigley Field, home of the beloved Chicago Cubs (if it’s baseball season, of course).

Alternatively, head to the historic Chicago Theatre, a venue that has hosted countless iconic performers over the years. You can’t leave Chicago without having some deep-dish pizza — Lou Malnati’s and Giordano’s are highly rated (they have several locations).

There are many things to see and do in Chicago. But if you’re short on time, you should tour Chicago by bus.

Tanya Taylor

Tanya Taylor is a freelance writer and content creator who has lived in Chicago for over 40 years. When she’s not writing, you can usually find her managing IT projects at a global financial services company and discovering new places to visit for vacation. She loves coffee and creating itineraries that are scenic, inspiring, and a bit spontaneous. You can find more of her travel content at Travels & Treasures.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.