Best Itinerary for 24 Hours in Chicago
Only have one day in Chicago and are not sure how to spend it. We can help!
John and I went to Chicago a few years back to run the Hot Chocolate Race. We had an absolute blast sightseeing the day before.
And whether you’re travelling solo, having a couple’s weekend like us, or taking the kids along, Chicago offers a whirlwind of experiences that can fit into a single day.
From seeing the top attractions to wandering the Magnificent Mile, and tasting some deep-dish pizza, we were able to see quite a bit without rushing.
Ready to learn more? Let’s jump in!
One Day in Chicago Itinerary – Quick Guide
If you are in a hurry, here’s a quick list of the best places to visit in Chicago in one day:
- Magnificent Mile – A famous stretch in Chicago known for its shopping, dining, and impressive skyscrapers.
- Adler Planetarium – Offers exciting space exhibits and shows, with great views of the city skyline.
- Millenium Park & the Bean – Millennium Park features the iconic Bean sculpture, lush gardens, and outdoor concerts.
- Willis Tower – Known for its Skydeck, where you can step onto glass boxes high above the city for jaw-dropping views.
- Navy Pier – Family-friendly spot with a Ferris wheel, boat rides, shops, and eateries along the waterfront.
One Day in Chicago – Map
The map shows the stops that are suggested on this one-day itinerary. We tried to group activities close enough together so that you wouldn’t be running all over the place.
Clicking on the map above will take you to Google Maps. There, you will be able to see the destinations in better detail.
How to Spend 24 Hours in Chicago
With one day in Chicago, you can see a few of the main attractions without wearing yourself out.
However, if you do find that you have some extra time, we will include some additional activities at the end of this post that you can tack onto your itinerary.
1. Visit the “Bean” in Millennium Park
Start your day in Chicago at the iconic Bean. No… not coffee… but a huge sculpture that I’m positive you have seen when looking at photos of the Windy City.
Officially known as Cloud Gate, the Bean can be found in Millennium Park. This shiny, bean-shaped sculpture is a must-see for its fun, reflective surface.
This is also one of the most popular spots in the city to grab that photo for the ‘Gram!
It was a pretty busy day at the park during our visit, and it was November! However, we still managed to get some fun photos of the Bean.
I have to admit, if I looked at the Bean for too long in some places, I definitely got a case of vertigo! But it was definitely a cool sculpture to see!
While we were in Millennium Park, we took the time to stroll through the beautifully landscaped gardens.
There is even an amphitheatre in the park where you may be lucky enough to catch a free concert or event.
2. Splash Around in the Crown Fountain
Before you leave Millenium Park, you definitely need to check out the Crown Fountain. And trust me when I tell you, this isn’t just any fountain!
The Crown Fountain is a truly unique piece of public art that combines sculpture with an interactive water feature.
Designed by Spanish artist Jaume Plensa, the fountain consists of two 50-foot glass block towers facing each other across a shallow reflecting pool.
The towers display video images of Chicago residents’ faces.
But the fun part comes when every so often, a face will pucker its lips, and water spouts out—mimicking a spitting action.
It’s a favourite spot for kids and a great place to cool off during Chicago’s warmer months.
3. Walk the Magnificent Mile
The Magnificent Mile, also known as “The Mag Mile,” is considered Chicago’s main commercial strip.
It runs along Michigan Avenue from the Chicago River up to Oak Street.
This stretch is lined with over 400 stores, including big-name brands, luxury boutiques, and large department stores.
While I did have fun shopping in many of the stores (I bought an exclusive Chicago charm for my Pandora bracelet), the Magnificent Mile also features famous buildings to admire.
From the historic Water Tower to the 875 North Michigan Avenue skyscraper (previously the John Hancock Center), there are plenty of impressive buildings to see
Plan to spend a couple of hours here, whether you’re shopping, grabbing a bite, or just enjoying the busy city vibe.
4. Indulge Your Sweet Tooth at Stan’s Donuts
And speaking of grabbing a bite! At this point, you may be ready for a coffee and treat fix.
Our favourite place to stop along the Magnificent Mile was a little place called Stan’s Donuts. Initially, it was the pink sign and logo that caught my eye.
But when I noticed the display of colourful stand mixers on the wall, I had to go in (I’m an avid baker, so stand mixers are like bling to me)!
Oh boy! Everything looked soooo good! We couldn’t resist grabbing a coffee and a donut and having a seat in the cute shop… you know… to warm up!
The seating area isn’t very big, but we were lucky enough to find a spot.
I had a blueberry fritter, while Hubby had an old-fashioned plain donut. We both agreed – we would definitely be back!
And wouldn’t you know it, there was also a Stan’s right around the corner from our hotel! Serendipity? Most definitely!
5. Explore Navy Pier
Navy Pier is one of Chicago’s top attractions, especially for families.
Unfortunately, we didn’t spend too much time here during our visit, as the kids were not with us.
Located right on the waterfront, this 3,300-foot-long pier has a lot to offer.
There’s a giant Ferris wheel that gives you awesome views of the city and Lake Michigan, an old-fashioned carousel, and even a children’s museum.
Besides rides and games, Navy Pier is also packed with places to eat and shop.
You will find fireworks shows in the summer as well as a variety of events and festivals throughout the year.
It really is a great place to hop on some rides, enjoy a meal, or just to take a stroll along the water.
6. Test Your Courage on the Willis Tower Skydeck
Formerly known as the Sears Tower, the Willis Tower offers some of the best views in Chicago. And at 1451 feet, it is the 3rd tallest building in North America.
The Skydeck, which is the highest observation deck in the US, is definitely a must-see when visiting the Windy City.
In fact, on a clear day, you can see for approximately 50 miles and four states (Illinois, Indiana, Michigan, and Wisconsin)!
One of the Sykdeck’s highlights is The Ledge. This attraction is made up of a series of glass boxes that extend out from the side of the building.
The boxes give you the feeling of standing in the air 1,353 feet (103 stories) above the city streets.
If you have a fear of heights, The Ledge is probably not for you!
Even though I don’t have to worry about heights, it was STILL a little intimidating to take the first step out!
Of course Hubby… he just likes to JUMP right in!!
The Skydeck is quite popular, so don’t be surprised if you have to wait in line to get out on the Ledge.
However, if you are looking for that Instagram-worthy photo, you will definitely find it here!
7. Take a Stroll Through Grant Park
Grant Park, known as “Chicago’s front yard,” spans a whopping 319 acres in the heart of downtown. It’s the perfect place for a stroll and to do a little photography.
The park is famous for hosting major events like the Taste of Chicago and Lollapalooza.
In fact, the start and finish lines for our Hot Chocolate race were both located in Grant Park.
The park is also home to several key attractions. Buckingham Fountain, one of the largest fountains in the world, is a centrepiece here.
If you are visiting during the warmer months, the fountain puts on a spectacular water display every hour, with evening shows featuring lights.
And while we were in Chicago in November, the fountain was still pretty impressive in its winterized (waterless) state.
Grant Park is also home to some impressive gardens, walking paths, and sports facilities.
We enjoyed admiring the numerous sculptures and artworks scattered throughout the park.
8. Visit Adler Planetarium
On the agenda for the late afternoon, is a visit to the Adler Planetarium.
I am a space geek, so I can’t pass up on the opportunity to visit a planetarium whenever we travel.
And the Adler Planetarium did not disappoint! As the first planetarium in the US, it had loads of things to see and do.
You can watch awesome shows that take you through space, check out hands-on exhibits about how we explore the universe, and even look at stars and planets through their telescopes.
We started off our visit with a sky show in the Dome Theatre. You will need to purchase separate tickets for the shows, but I found it to be quite worth it.
After the show, we wandered around the various exhibits.
We learned everything from meteorites that had crashed into Chicago suburbs to advancements in astronomy, to stories about the first moon landing.
It was all fascinating and I loved it!
John and I found the museum to be very family-friendly with many exhibits aimed at the younger crowd.
We finished our visit to the Planetarium in their extensive gift shop. After all, we couldn’t go home without souvenir magnets and pressed pennies for the kids’ collections!
Before leaving, be sure to stroll around on the Planetarium’s grounds. There are some really awesome views of the Chicago skyline, right on their doorstep!
9. Devour a Deep Dish Pizza
The last item on our Chicago 1 day itinerary is dinner.
After all, we couldn’t leave Chicago without sampling their famous deep-dish pizza!
Not too far from Adler Planetarium and Grant Park, you will find Giordano’s Pizza.
And while I realize that this is a chain restaurant, Giordano’s Pizza is famous for its deep-dish pizza.
While we mostly went into this place based on the reviews, we also had to check it out because of its name (which is also our surname 😜).
The restaurant first opened in 1974 and has become a staple in the Chicago pizza scene.
The pizza was amazing, the atmosphere was comfortable and family-friendly, and the staff was excellent.
Expect a wait, as these pizzas take about 45 minutes to bake. But it’s worth it for a taste of authentic Chicago flavour.
It was the perfect way to end our big adventures in Chicago!
Other Things to Do in Chicago
If you have more time to spend in Chicago, we have included a few more attractions that you can add to your itinerary:
Best Tours to Take in Chicago
If you prefer to take a guided tour while visiting Chicago, there are several that may interest you.
The following are a variety of top-rated tours that are definitely worth a look:
Where to Stay in Chicago
If you are looking for somewhere to stay in Chicago, the good news is that the city has a pretty great variety of hotels to suit any budget.
So whether you’re looking for a budget-friendly option or a more upscale experience, you won’t have any trouble finding the perfect accommodations in the city.
Luxury Hotels
The Langham, Chicago
Located by the river, this hotel offers elegant rooms, a spa, and a swimming pool, making it perfect for a luxurious stay.
Four Seasons Hotel Chicago
Set near the Magnificent Mile, this hotel features plush rooms with stunning city views and includes an indoor pool and a spa.
Moderate Hotels
Hampton Inn Chicago Downtown
The Hampton Inn Chicago Downtown is conveniently located in the heart of the city, offering comfortable rooms and modern amenities. Guests can enjoy easy access to major attractions like the Magnificent Mile and Millennium Park.
The Drake
A historic hotel known for its traditional style and prime location near Lake Michigan, offering quality accommodations and excellent dining options.
Budget Hotels
Best Western Grant Park Hotel
Right across from Grant Park, this hotel provides affordable comfort with easy access to major attractions and public transportation.
John and I stayed at this hotel and were pretty happy with our stay.
It’s right across the street from Grant Park, close to the bus stop, and within walking distance to plenty of great restaurants.
Chicago Getaway Hostel
Located in Lincoln Park, this hostel is ideal for travellers looking to save money while enjoying a social atmosphere. It offers both private and dorm-style rooms.
How to Get to Chicago
Getting to Chicago is really easy, thanks to its accessible location and awesome transportation options.
Here are the main ways to reach the city:
Air
- O’Hare International Airport (ORD): One of the busiest airports in the world, O’Hare has flights to and from cities all over the globe. It’s about 17 miles northwest of downtown Chicago.
- Midway International Airport (MDW): Located about 10 miles southwest of downtown, Midway primarily serves domestic flights and some international connections.
Since we were not renting a car, we took the train from O’Hare to downtown Chicago. It was pretty simple and took about an hour.
Train
- Amtrak: Chicago’s Union Station is a major hub for Amtrak trains, with routes connecting to cities across the USA, including New York, Washington D.C., and San Francisco.
Car
- Chicago is well-connected by highways and can be easily reached by car from anywhere in the continental United States. Major highways include I-90, I-94, and I-290.
Bus
- Major bus companies like Greyhound, Megabus, and others operate routes to Chicago from various cities across North America. The main bus terminal is downtown near the Amtrak station.
Getting Around Chicago
Getting around Chicago is easy with its well-developed public transit system and other options.
Here are the best ways to navigate the city:
CTA ‘L’ Trains and Buses
- The Chicago Transit Authority (CTA) operates the ‘L’ (elevated and subway) train system and buses that cover the entire city and some suburbs.
- The trains are a great way to get to major attractions quickly, especially with lines like the Red and Blue Lines running 24 hours.
Bicycles
- Chicago’s bike-share program, Divvy, offers thousands of bikes at hundreds of stations across the city.
- It’s perfect for short rides or leisurely exploring neighbourhoods.
On Foot
- Many of Chicago’s attractions are concentrated in areas that are pleasant and safe to walk, like the Loop, Magnificent Mile, and along the lakefront.
Taxis and Rideshares
- Taxis are readily available, and rideshare services like Uber and Lyft operate extensively throughout Chicago.
- They offer convenient but more costly rides compared to public transportation.
Water Taxi
- For a scenic route, consider taking a water taxi along the Chicago River or Lake Michigan during the warmer months.
- This is not only practical but also offers a unique view of the city’s architecture.
Driving
- If you prefer to drive, Chicago has an extensive network of roads and expressways.
- However, be prepared for heavy traffic during rush hours.
- Parking costs are also quite high in downtown areas.
Best Time to Visit Chicago
The best time to visit Chicago largely depends on what you’re looking for in your trip. Here’s a seasonal guide to help you decide:
Spring (March to May)
Summer (June to August)
Autumn (September to November)
Winter (December to February)
Chicago 1 Day Itinerary – FAQs
One day in Chicago isn’t enough to see everything, but you can still visit some top attractions. It’s perfect for getting a taste of what the city offers.
Absolutely! Chicago is worth visiting for its stunning architecture, world-class museums, vibrant food scene, and beautiful lakeside parks. There’s something for everyone, making it a great destination.
Yes, Chicago is very walkable, especially in areas like the Loop, Magnificent Mile, and along the lakefront. These areas have lots of attractions close to each other, making it easy to explore on foot.
Yes, downtown Chicago is generally safe, especially in popular tourist areas and during daytime hours.
Deciding between Chicago and New York City depends on what you like. Chicago has great architecture, a laid-back vibe, and is famous for its deep-dish pizza. New York City is always bustling, known for landmarks like Times Square and Broadway shows. Both cities offer a lot of culture and fun things to do.
Final Thoughts on Our 24 Hours in Chicago Itinerary
And that was how John and I spent one day in Chicago! Hopefully, you have enjoyed our travel tips for this truly fantastic city.
With so many fun things to do, sites to see, and experiences to have, you will definitely find something that everyone in your family will enjoy.
And while spending 1 day in Chicago was a lot of fun, we would totally recommend staying longer if at all possible.
We definitely wouldn’t say no to another return visit… and this time WITH the kids!
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