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One Day in Chicago Itinerary

Updated: October 9, 2023
 By Mel

Chicago, the third largest city in the USA, is a fantastic city to visit.

If you only have 24 hours in Chicago to spend, we want you to make the most of it.

Therefore we compiled a Chicago itinerary of things to do and things to bring on your next trip to the windy city.

The people here are friendly, the food is delicious, and Chicago's architecture along with its skyline is exquisite.  

Of course, we recommend you spend as much time as you can to enjoy the wonderful things that Chicago has to offer.

However, if you only have one day and really just want to experience the most famous “highlights”- here is your guide.

Check out our Chicago Visitors Guide, with budget advice, travel guides, and information about local Chicago attractions.

Tip: Save more money in Chicago with a tourist discount pass, which offers one-day attraction discounts.  Read our post to see if one is worth it for you.  

We also offer several pay-what-you-like walking tours.  

What should you bring with you for a day in the city?

  • Cash, an I.D., your phone (and/or a map)
  • A refillable water bottle
  • SmartPhone/Camera
  • Comfortable walking shoes
  • Umbrella/Layered clothing if the weather is forecasted to be rainy and/or cold

Click the map to enlarge or click here for a movable map.

Breakfast in Chicago

We recommend you start the day with some food, so you can easily accomplish this full day of Chicago fun!

There are so many delicious breakfast food places in the city.  

For breakfast downtown, one suggestion is Pittsfield Café at Washington and Wabash (map) for a hearty diner-style meal. 

They open at 7:00 a.m. every day, so you can start your day early.

Enjoy the stunningly beautiful architecture inside the Pittsfield Building while you dine.

If you have a sweet tooth and just want a quick bite, try one of Chicago’s boutique donut shops. 

Our suggestion is Stan's Donuts at Randolph and Dearborn (map) open daily from 7 am - 2 pm.

They are known for their original glazed, and we recommend the Nutella pocket, birthday cake donut, or a Stanwich! Don't forget your coffee.

Another great place for coffee is Dollop Coffee Co., which has several options in the downtown neighborhood.

Visit the Cultural Center Chicago

If you just ate at the Pittsfield, the Cultural Center is across the street at Washington and Michigan.

The Cultural Center offers free admission with traveling exhibits on different floors. 

Check out the second floor to see a 38-foot-wide stained-glass Tiffany dome - the largest in the world!

Hours: Open 10 am to 5 pm daily.

At the bottom level, there is a visitor’s center with maps galore.

If you don’t have a map or a smartphone - we recommend you pick one up here.

Tour Downtown Chicago (the Loop) & Millennium Park

Taking a walking tour is always a great idea to better get to know a city, to meet a local guide and possibly some other nice travelers, and to gain some general orientation of Chicago.  

Free Tours by Foot offers many different tours and frankly, they all show different wonderful sections of Chicago but if you only spend 24 hours in Chicago we recommend the Loop & Millennium Park tour.

The Loop Tour runs several times per week, but please check the calendar to choose your date and to reserve a spot click here.

We also offer it as a GPS-led audio tour, which you can take any time of day.

Your Chicago-loving guide will take you on a journey through the downtown Loop district of the city which begins near State and Lake.

You will see the Chicago Theatre, Marshall Fields, the Picasso, and the Sears Tower (aka Willis Tower).  

While learning the history of Chicago you will gaze up at the magnificent skyscrapers and appreciate the architectural genius that is in Chicago’s concrete landscape.

The tour ends at Millennium Park the famous sculpture “Cloud Gate” (aka “The Bean”). You can also see the Crown Fountain nearby.

Alternatively, Maggie Daley Park is also a great option, especially with kids, which offers activities like ice skating, mini golf, a climbing wall, playgrounds, and scenic strolls in its beautiful gardens.

Chicago Museums

Chicago's museums are world-renowned, and certainly a highlight for many visitors. There are several options to choose from.

For adults and teenagers, the Field Museum and Art Institute of Chicago are two of the most popular, and largest museums.

You won't be able to see everything inside in one day, but you can spend a few hours at one of them.

If you're traveling with children, the Adler Planetarium and Shedd Aquarium are wonderfully educational - and fun! - places to visit.

Also, check out the Chicago Children's Museum.

Be sure to read our post on free museums in Chicago


By now you’ve probably worked up an appetite. We recommend heading over to Al’s Beef at 548 N Wells St. (map) for a quick bite to eat. 

They have Chicago-style hotdogs, which are all beef, with mustard, tomatoes, onions, relish, pickle, hot peppers, celery salt, a poppy seed bun, and NO KETCHUP and Italian Beef Sandwiches. 

Chicago Hot Dog
Chicago-style hotdogs NEVER have ketchup!

Although we call them Italian, this sandwich is certainly not from Italy. Most Chicagoans ask for Italian Beef with mozzarella cheese, and sweet or hot peppers (which we call giardiniera).

We ask for it to be “dipped”, which means the cook will take your entire sandwich and dunk it into seasoned meat juice. 

It is messy, but so delicious.

Water Tower

Let’s leave the Chicago Loop and head north to see one of Chicago’s oldest buildings to survive the Great Fire of 1871.

It's the Water Tower and Pumping Station – a real Chicago gem at Michigan and Chicago Streets.

The Water Tower now hosts a series of rotating free exhibits and the Pumping Station is now the Looking Glass Theatre.

It’s free to visit and open daily from 10 am - 6:30 pm (except Holidays).

Magnificent Mile

If you are a shopper, the Mag Mile is like the American Champ-Elysees on Michigan Ave. (For real: that was Daniel Burnham’s intention as the city planner in the late 1800s).

It is an entire mile of shopping and historic hotels.

You’ll find Coach, Gucci, Burberry, Apple, H&M, and even a Nordstrom’s Rack, among others.

Along the road are some architectural highlights, including the Tribune Tower, the Wrigley Building, NBC Studios, and Trump Tower.

Eat the Chicago Deep Dish Pizza Dinner?

You can’t come to Chicago without trying the famous Chicago-style deep-dish pizza.  

Our favorites are Pizzeria Uno’s at Wabash and Ohio (map) and Gino’s East at Michigan and Superior (map). 

According to the Chicago Tribune newspaper, Uno’s is the original deep-dish pizza.

Their pizzas are great, and the restaurant feels like a friendly underground lounge.

Gino’s East also has a lot of character. Their crust deviates from the Chicago original by using cornmeal as the base. Very tasty.

(Bring a permanent marker since you are encouraged to “leave your mark” on the walls.)  

Visit the Hancock Building, 360 Chicago, and the Signature Lounge

Now is the time to see one of the best views of the city.

If you want to get a bird’s eye perspective of Chicago, head to the Hancock Building, 4th tallest building in Chicago at Michigan Avenue and Chestnut.

We do recommend you visit the Chicago Observation Deck, 360 Chicago.

It's worth the ticket price and you can take great photos and enjoy the view from the 94th floor.

From 360 Chicago Skydeck, you can see Lake Michigan with its cruises and lakefront trails, Navy Pier with the Centennial Wheel, Chicago River with its river cruises, The Museum Campus, Wrigley Field stadium (home of the Chicago Cubs), Lincoln Park Zoo and other architectural marvels of Chicago.

You can also experience TILT which is a glass enclosure that tilts outward, offering stunning views of the city from a unique angle.

If you want to save yourself the admission fee though and instead spend the money on a cocktail or two instead, ride the elevator up to the 95th floor to the Signature Lounge (you’ll have to show your I.D. here for age proof). 

The Signature Lounge is a great place for cocktails and/or dessert.

The food is wonderful and the view is unbeatable. Sip your cocktail while looking at the Sears Tower (aka the Willis Tower). 

Even though the line to get into the bar can be long (especially on weekends) the wait is worth it.

Also, attention ladies: use the ladies’ bathroom to enjoy the splendid views from the top. Sorry pals, no view for you in the bathrooms!

By now, it is either nighttime or the lights are lining the streets or perhaps the sun is about to set, so enjoy your drinks.

Enjoy Chicago Improv OR Blues

For the last event of the night, head to a blues club, or venture down to a comedy club to see some improv.

There are options for both that are only a few train stops away. A taxi or rideshare service can also take you directly there for a fee.

For improv, we recommend Second City at Wells and North Ave (map) to see a late-night show.

Second City is famous for training some of the best comedians like Tina Fey, Mike Myers, and the Belushi Brothers.

The closest Blues club would be Buddy Guys Legends at Wabash and Balbo, which is a great local spot.  

Either choice is a perfect end to a Chicago visit, especially because Chicago is known for the blues and improv.

Safe travels!


Is Chicago walkable?

Yes, Chicago is generally walkable, especially in its downtown area.

The city has a well-maintained grid system, sidewalks, and pedestrian-friendly areas.

However, the size of Chicago means that some attractions may require public transportation or other means of getting around for convenience.

What is the cheapest/fastest way to get around Chicago?

The cheapest way to get around Chicago is typically by using the public transit system, including buses and the 'L' train.

The fastest way for short distances is often walking, while ridesharing services like Uber and Lyft can be convenient for longer or less accessible routes.

Biking is also an economical and efficient option for getting around certain areas of the city.

About The Author


Mel loves to be a tourist in her own city. With a background in performing arts, tourism, and photography, giving tours and being a story-teller comes naturally to her. She loves traveling, food, and theatre. Mel splits her time between Chicago and Los Angeles (#theatrelife) and leads tours and manages both cities!
Updated: October 9th, 2023
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