Fall is a great time to take a day trip to Chicago and you can easily experience some of the city’s best highlights in just one day. Here’s how I maximized 24 hours in the Windy City using only public transportation.
Key Takeaways
- Save $35+ on transportation: Take the L Train Blue Line from O’Hare ($5 day pass) instead of rideshares
- Book Willis Tower Skydeck in advance: This popular attraction sells out quickly during peak season
- Walking downtown covers major attractions: Cloud Gate, historic architecture, and Batman: The Dark Knight filming locations are all within walking distance
Getting to Downtown Chicago
Upon arriving at the Chicago O’Hare International Airport, you’ll want to take the L Train (Blue Line) straight from the airport to downtown Chicago. At just $5 for a day pass (versus $40+ for Uber), this is hands-down the best travel hack for budget-conscious travelers.
Before leaving the airport, stop by the information desk at the terminal to grab free maps and ask for insider tips on the best things to do for a one-day Chicago experience. This small step saved us time by helping us trace out our route for the day.
Morning (9:00 AM – 12:00 PM): Architecture & Downtown Attractions
We all know Chicago is renowned for its incredible architecture, which, honestly, I fell in love with from the minute I stepped out of the train. It’s a beautiful blend of historic buildings and greenery that makes it very unique and different from other big cities like NYC.
We visited during mid-September, and the weather was very pleasant. If, like me, you’re not a fan of cold weather, then definitely opt for spring and fall as your best times to visit Chicago, when the weather is perfect for walking tours around downtown.
Start your morning exploring downtown on foot – no rental car needed!
📍Cloud Gate (The Bean) – Millennium Park
Address: 201 E Randolph St, Chicago, IL 60602
Cost: Free
Best Time: Early morning for fewer crowds
Start your day at Cloud Gate, Chicago’s iconic “Bean” sculpture, because why not, right?! You’ll find Cloud Gate in Millennium Park, which is a great spot for spending the afternoon or taking a break from all the walking.
The Bean’s polished surface creates incredible reflections of the city skyline, quite lovely during golden hour.
We spent way more time here than planned, capturing different angles of this interesting piece of architecture. A stop here was a must for our mom-and-son trip!
Historic Buildings and Architecture Walk
I’m not even kidding when I say that Chicago’s downtown is an open-air museum of architectural history. Aside from the iconic historic buildings, you may recognize some of the sites that served as filming locations for the 2008 film Batman: The Dark Knight.
The city’s Gothic Revival and Art Deco buildings provided the perfect Gotham City backdrop.
You’ll also find yourself amazed at the beauty and details of the Rookery Building’s interior. It’s incredible!
Must-See Architecture:
- Chicago Theatre: Perfect for your Chicago photos
- Rookery Building: Frank Lloyd Wright’s stunning light court redesign, a Chicago Landmark
- Chicago Cultural Center: Free admission with gorgeous Tiffany glass domes
🍿Film Buff Bonus: Keep your eyes peeled for Batman filming locations throughout downtown! The city doubled as Gotham in several scenes, and spotting these locations adds an extra layer of excitement to your architectural adventures.
Midday (12:00 PM – 3:00 PM): Sky-High Thrills & Sweet Snacks
📍Willis Tower Skydeck & The Ledge
Address: 233 S Wacker Dr, Chicago, IL 60606
Cost: $30-50, depending on package
Important: Book Willis Tower The Ledge in advance! This popular attraction sells out quickly, especially during peak season.
The highlight of any Chicago visit has to be the Skydeck and stepping out onto The Ledge at Willis Tower. At 103 floors up, The Ledge is the glass box that extends 4.3 feet from the building and is definitely not recommended for those afraid of heights.
Although my son is not a fan of heights, he loved the experience and agrees that the panoramic views of the city and Lake Michigan are absolutely breathtaking and so worth it!
For those of you not interested in stepping on The Ledge, you can enjoy the Skydeck for a longer amount of time and walk around to enjoy the skyline view from different angles.
🎟️Pro Tip: If you purchase tickets for The Ledge, get them for late morning or early afternoon to get the best lighting for photos.
Sweet Stops: Chocolate Heaven
Of course, no day trip to Chicago is complete without indulging in some world-class chocolate.
📍Ghirardelli Ice Cream & Chocolate Shop
Address: 830 N Michigan Ave, Chicago, IL 60611
Hours: Daily 10 AM – 10 PM
What I loved the most is that this Ghirardelli shop is located inside the historic Wrigley Building, on the Magnificent Mile, and right by the DuSable Bridge. This makes it the perfect stop for a sweet break during your architectural walking tour.
📍Nutella Cafe
Address: 31 E Randolph St, Chicago, IL 60601
Hours: Monday-Thursday 8 AM – 10 PM, Friday-Saturday 8 AM – 11 PM, Sunday 9 AM – 9 PM
Pro tip from my experience: Check the hours before visiting! I had dreamed of visiting the Nutella Cafe, but arrived when they were closed. If this is also a must for you, make sure to plan ahead of time.
Afternoon (3:00 PM – 6:00 PM): Lakefront Views & Architecture Photography
📍DuSable Bridge & Chicago Riverwalk
Location: Chicago River between Michigan Ave and Lower Wacker Dr.
Cost: Free
One of my favorite parts of our day was exploring the Chicago Riverwalk and DuSable Bridge. The riverwalk offers incredible perspectives of the city’s layered architecture, and I spent considerable time here capturing photos of the stunning skyline.
Also, I personally think the DuSable Bridge provides an excellent vantage point for taking pictures of Chicago’s distinctive architectural blend.
The Riverwalk stretches along the Chicago River and gives you that quintessential Chicago experience – surrounded by towering skyscrapers with the river cutting through the urban canyon.
This is an epic spot for all those visiting Chicago, and it’s certainly a must for those visiting for the first time.
What I Missed (But You Shouldn’t!)
During my research before the trip, locals consistently recommended the Chicago Architecture Boat Tour and I really wanted to go on it, but unfortunately, I knew I wouldn’t have the time and didn’t book the tour.
While I enjoyed the riverwalk views from street level, this 90-minute cruise along the Chicago River provides unique perspectives of the city’s famous skyline that you simply can’t get from the bridges and walkways.
Chicago Architecture 90-minute Boat Tour
Duration: 90 minutes
Cost: Typically around $35-50
Best Time: Afternoon for optimal lighting
🎟️ Book tickets for Chicago Boat Tour
Evening (6:00 PM – 9:00 PM): Pizza & Night Views
📍Giordano’s Deep Dish Pizza
Multiple Locations
Cost: $15-25 per person
C’mon, now! You know you can’t visit Chicago without trying authentic deep-dish pizza! And for that, Giordano’s was on my bucket list.
For years, I had wanted to go here and it did not disappoint.
If you’re adding this popular pizza place in Chicago to your dinner plans, just remember that deep dish takes 30-45 minutes to prepare, plus Giordano’s is popular amongst locals and visitors alike, so plan accordingly!
📍Magnificent Mile Evening Stroll
Location: Michigan Avenue from Oak Street to the Chicago River
Cost: Free (window shopping!)
We ended our perfect day in Chicago with an evening stroll down the famous Magnificent Mile. The historic buildings and architectural gems are beautifully illuminated at night, creating a completely different atmosphere from the daytime views.
You’ll most likely fall in love with the modern skyscrapers and historic architecture along Michigan Avenue, which perfectly showcases Chicago’s urban evolution.
Walking from the DuSable Bridge area up toward Oak Street, you’ll pass incredible shopping, restaurants, and some of the city’s most photographed buildings.
Transportation & Practical Tips
Getting Around:
- CTA Regional Day Pass: Starting at $10, depending on zones (includes buses and L trains). Get more info on Chicago CTA Day Pass.
- Walking: Downtown Chicago is very walkable and most attractions are within walking distance
- No rental car needed: I found Chicago’s public transportation and walkability the best way to explore the downtown area without the hassle of parking and rental or rideshare expenses.
Money-Saving Tips:
- Buy the Chicago CityPASS for multiple attractions
- Many architectural sites are free to view from the outside, which makes for great photography
- Pack snacks and water for your walking tour
Best Times to Visit:
- Fall is a great time to visit Chicago: Perfect weather, fewer crowds, beautiful foliage
- Early morning: Best for photos at Cloud Gate
- Early afternoon: Best for photos at The Ledge
Final Thoughts
One day in Chicago barely scratches the surface of what this incredible city offers, but with thoughtful planning (and no rental car needed!), you can experience some of downtown’s most iconic highlights.
The combination of world-class architecture, delicious food, and stunning lakefront views makes Chicago the perfect destination for a weekend getaway.
From stepping out onto The Ledge at Willis Tower to discovering Batman filming locations during your architectural walking tour, Chicago delivers unforgettable experiences in just 24 hours. And yes, fall is a great time to visit Chicago, but honestly, this city shines in every season.
🏙️Planning a longer stay? I offer personalized travel planning services! Book a free consultation and let’s create the perfect Chicago getaway!
Have you visited Chicago? What was your favorite architectural discovery? Let me know in the comments below!
Hey, I’m Yanitza 👋 Adventure Travel & U.S. Destination Specialist, travel writer, and hidden-gem hunter with over 8 years of experience helping travelers explore deeper and travel slower. I specialize in crafting authentic, stress-free adventures from small towns to scenic hikes and scuba dives. I’m a firm believer that the best stories happen when you venture beyond tourist hotspots. When I’m not planning getaways or writing travel guides, I’ll probably be home rewatching The Vampire Diaries like it’s my job and daydreaming about future adventures in Spain.