One Day in Chicago Itinerary – Top things to do in Chicago, US

Author: Ray_LAC, Photo source: Flickr
Author: Ray_LAC, Photo source: Flickr

Chicago is one of the most vibrant cities in the world – combining an eclectic mix of sports, architecture, music, food and art. Located on the shores of Lake Michigan, the towering skyscrapers stand proudly over the beaches of Lake Shore Drive and the outdoor spaces of Millennium Park. Whether you want to enjoy a hot dog in the outfield at a Cubs game or visit the world renowned Art Institute of Chicago, this city provides unlimited activities for even the most discerning traveler. You could never see all of Chicago in a single day but this itinerary will take you to the top destinations.


Guest post by Deborah Janowski


What’s the best time to visit Chicago?

Chicago is known as the “windy city” and winter means it can be very, very cold, so the best time to visit Chicago is during the summer when the weather is a beautiful eighty degrees and sunny – and the outdoor parks and streets are alive with activity.


What’s good to know about Chicago?

Chicago is very compact so the majority of sights are located in the downtown area which makes it easy to see a lot in a short period. North of Wacker Drive is where you can find most of the stores and restaurants of Michigan Avenue and south of Wacker Drive is Millennium Park, The Art Institute of Chicago and Soldier Field.

Millenium Park in Chicago
Millenium Park, Author: Vincent Desjardins, Photo source: Flickr


One Day in Chicago Itinerary:

Top things to do in Chicago, US


Millennium Park, Art Institute of Chicago

Begin your morning by walking Millennium park. This park is home to the Buckingham Fountain, the Cloud Gate sculpture (often referred to as The Bean), large outdoor modern sculptures and gardens. After touring the park, The Art Institute of Chicago is located at the southern end. The museum houses some of the most famous works of art in the world including Grant Wood’s American Gothic and Edward Hopper’s Nighthawks. After perusing the art, The Gage across the street is a local favorite for lunch complete with Scottish Eggs and Poutine Fries.

Chicago Cloud Gate
Cloud Gate, Author: Bosc d’Anjou, Photo source: Flickr


Wrigley Field

If you like sports, you may want to try to head a bit north to visit historic Wrigley Field and catch a Cubs game on a beautiful afternoon. The stadium is home to a number of Chicago staples including craft sausages, hot dogs and buffalo chicken fries. And Chicago fans are typically very welcoming and happy to talk with visitors about their love of the city and their home teams.


Architectural Boat Tour

Or, if you don’t particularly like baseball or there is not a game in town the day you are visiting, you can take one of the many architectural boat tours in the harbor of Lake Michigan to learn about the history and sights of the Chicago skyline from the water while enjoying the cool Summer breeze.

Chicago Architectural Boat Tour
Architectural Boat Tour, Author: Kimberly Vardeman, Photo source: Flickr


Hancock Tower, Michigan Avenue

Many visitors will visit the Skydeck where you can purchase tickets to stand in a glass outcropping to see the entire Chicago area from the top of the Sears Tower. However, locals prefer to visit the Hancock Tower and the Signature Lounge on the 96th floor. As the sun begins to set, you can enjoy a glass of wine while enjoying a 180 degree view from your own table. Before or after visiting the tower, there is also time to stroll along the famed Michigan Avenue which is always crowded with visitors from around the world and a large number of boutiques and stores.

Signature Lounge Hanckok Tower Chicago
Signature Lounge View, Author: Adam James, Photo source: Flickr



Like any major city, there are simply too many places to eat in Chicago to pick just one. If you want to enjoy a Chicago pizza, you can stop at any of the pizza locations in the Michigan Avenue area. We won’t recommend one over the other (Lou Malnati’s, Pizzeria Uno, Bartoli’s, etc.) as that would simply lead to an argument with most Chicagoans over which is the best.

If you want something unique, you can enjoy dinner at the RL restaurant right around the corner from the Hancock Tower. The RL Restaurant is attached to Ralph Lauren’s signature store and specializes in burgers and corned beef.

If you want something more lively, you can head over to Gibson’s on Rush Street by cab and either sit around the piano singing songs with the locals or head upstairs for a steak dinner.


Blues Music

After dinner, no trip would be complete without enjoying live Chicago blues music. This can entail a trip south to Buddy Guy’s Legends by Millennium Park. Or north to Kingston Mines in Lincoln Park. But whichever way you travel, cabs are plentiful and rides are short.


Some extra tips for visiting Chicago?

We recommend against using a rental car. Parking in Chicago is difficult and taxis are everywhere and very convenient, so it is quite easy to walk and catch a quick ride anywhere in the city.

Traffic to and from the airports in Chicago can be very congested so plan your trips accordingly.


Guest post by Deborah Janowski


In case you have more than just One Day in Chicago check out Tripadvisor for detailed list of all the sights and activities in Chicago.


Find the Best Hotel Deals in Chicago


Pin for later!

Chicago Illinois One day itineraryChicago Illinois Top things to do


If you have any other prepositions for this One Day in Chicago Itinerary feel free to share it in the comments below!









Relaxed Nomad Logo
Deborah Janowski
Travel Blogger at

Deborah runs the travel website, RelaxedNomad, which specializes in sharing itineraries, notes and travel plans for entire areas of the country and road trips. One of her goals is to make traveling easier for families while finding truly unique activities in unusual places.

Related posts:

One comment

Leave a Reply

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