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One Day in Chicago Itinerary

Book A Guided Walking Tour

Chicago 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 list of things to do and things to bring on your next trip to Chicago. The people here are friendly, the food is delicious, and the architecture is exquisite.  

Of course, we recommend you spend as much time as you can to enjoy the wonderful things that Chicago has to offer, but 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
  • Camera! (or phone with a camera)
  • Some healthy snacks to chop on like an apple or carrots. (You will be eating indulgently in Chicago so your body might need a break)
  • COMFORTABLE walking shoes. (Don’t worry- Chicago won’t judge your sneakers.)
  • Layers- Chicago’s weather can be tricky. Check out the weather before your day hear and be prepared.

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

Chicago in 24 hours 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 6:00 am Monday-Saturday (closed on Sundays), so you can start your day early!

Plus, they are hidden inside of an architectural gem, the Pittsfield Building

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

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

Their donuts are AMAZING and fresh.  So fresh that at this location when they are out of donuts- they close up for the day, so make sure you come early.

Try the pistachio lemon donut, the good old buttermilk, and the maple bacon donut.

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 giant, beautiful glass Tiffany dome chicago cultural center dome

Most days it is open by 9 am (Sundays and Holidays 10 am). 

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 a folding map up here.

Be sure to read our post on free museums in Chicago.

Tour Downtown Chicago (the Loop) & Millennium Park

Chicago Bean YonzonTaking 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 ay.

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 Field’s, the Picasso, and the Sears Tower (aka Willis Tower).  

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

The tour ends at Millennium Park the famous sculpture “Cloudgate” (aka “The Bean”).


By now you’ve probably worked up an appetite. We recommend heading over to Al’s Beef at 234 Wabash Ave. (map) for a quick bite to eat. 

Chicago Hot DogThey 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. 

Although we call them Italian, this sandwich is certainly not from Italy. Most Chicagoans ask for the Italian Beef with mozzarella cheese, sweet or hot peppers (aka 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 essential but messy, and 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). Chicago in a day springmagmile yonzon

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.

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            
Chicago Style Deep Dish Cheese Pizza FotoliaDinner? 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 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 and Chestnut. Chicago Hancock Tower view

We do recommend you visit the Observation Deck, it's worth the ticket price and you can take great photos and enjoy the view.

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 96th 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 but 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 an Improv Theatre. 
Lincoln Park Blues
There are options for both that are only a few train stops away or just go ahead and treat yourself to a cab since you are only here for a day.  

For improv, one option is to head to the 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.  

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


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 12th, 2021
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