How to Spend One Day in Chicago (Perfect for First-Timers)

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Are you thinking about spending 24 hours in Chicago? Great idea! Chicago is my favorite city in the US, and I simply can’t get enough of it.

As I write this, I’ve been to Chicago four times in just over a year. And to put things into perspective, I’ve never visited any other city as much as I’ve been here.

There’s so much to do and I always return home with even more of a burning desire to go back to Chicago. Now that I’ve been multiple times, I think it’s the perfect time to put together a 1-day itinerary for you as a first-timer.

While one day certainly isn’t enough to see, do, or taste everything, you should be able to cover a nice amount of ground.

Ready, friend? Let’s travel to Chicago!

THIS IS A ONE DAY IN CHICAGO ITINERARY.

HOW DO THIS ONE DAY IN CHICAGO ITINERARY WORK?

These Chicago itinerary is perfect if you’re taking your first solo trip to the city, and want to see some of the best sights & indulge in some delicious food.

Here are some things you should know before you continue reading:

• I created a FREE Google Map for this itinerary. Click here to view and use it during your trip! I don’t have a PDF version, but I’ll be more than happy to create one. Just let me know and I can get it made for you.
• There’s minimal backtracking. This is particularly helpful so you don’t waste unnecessary time zigzagging across the city.
• This itinerary is budget-friendly. If you’re visiting Chicago on a budget, I’ve got you covered! Read this post for more budget travel tips.
• This itinerary doesn’t include museums or observation decks. Chicago’s best museums — The Art Institute, Field Museum & Museum of Science and Industry — can easily take at least two hours to explore, so it’s better to save those for a longer trip (like my three-day itinerary here).
• You should be able to follow this itinerary completely on foot. There’s no more than a 40-minute walk between stops, so you don’t need to worry about spending extra time or money on Ubers or taxis.
• This itinerary is customizable. Use it as a starting point and adjust to your liking. I made sure to throw some optional stops in there if you just can’t get enough wanderlust.
• I included some trip-planning tips and details at the end of this guide. Be sure to check out this information so you’re fully prepared for your trip.

And without further ado, let’s get into this one day in Chicago itinerary. I think you’re going to love it!

ONE DAY IN CHICAGO ITINERARY

Follow this day trip itinerary for Chicago if you’re spending a full twenty-four hours in the city.

Today, you’ll walk through four areas: South Loop, The Loop, Streeterville and Gold Coast. You’ll start with breakfast near your hotel and check out Millennium Park before boarding a 90-minute architecture river cruise.

Then you’ll indulge in a Chicago-style hot dog before relaxing at one of the city’s numerous beaches and finally ending the night with a scrumptious dinner.

MORNING

FUEL UP AT A NEARBY BREAKFAST SPOT

📍 Eleven City Diner | 📍 Cafecito | 7-min / 8-min walk from hotel | Time Needed: 45 mins | Budget: $25-30 Including Tip

Today will be a moderately-paced day, so you’ll want to fuel up at a nearby breakfast spot before you start exploring.

I recommend Eleven City Diner, an old-school diner and delicatessen in South Loop that has a large menu with various items.

They serve breakfast all day, including dishes like omelettes, scramble bowls, burritos, breakfast sandwiches and more. Here’s a link to the PDF menu.

I know there’s a lot to choose from, so I recommend the 11 City French Toast and one or two sides. You get three delectable slices of French toast and some syrup to pour on top. As for sides, order the house potatoes and/or smoked bacon.

If you want something a bit more casual and laid-back, Cafecito is a Cuban coffee house and cafe. The closest location to your hotel is this one, just an eight-minute walk away.

They serve specialty salads, soups, gourmet sandwiches with all-natural ingredients, and of course, coffee.

Like Eleven City Diner (ECD), their menu is fairly big, so I recommend a pavo sandwich and an iced chai latte. These will cost around $22, which is a bit cheaper than ECD.

Know that there aren’t many tables at this location and lines can get rather long at times, but don’t let that discourage you from going!

If neither of these restaurants sound good, that’s fine! Here are some other spots in the area:

• Go to Wildberry Pancakes & Cafe for the most options. Located on the first floor of Prudential Plaza, this is one of the most popular breakfast spots in Chicago. Make sure to get there early, as this specific location does NOT take reservations. They serve specialty Benedicts, omelettes, pancakes, waffles, French toast and more. I recommend the cinnamon roll pancakes, turkey bacon and chicken sausage. It’s 4 minutes from the Chicago Cultural Center (the first optional stop on this itinerary), so you can either stop there on the way to Wildberry or pop in after breakfast.
• Go to Lou Mitchell’s, located in West Loop, if you want a more traditional diner. It’ll be a slight detour from, but if you really want to go, it’s worth it. They serve fluffy pancakes, waffles, jumbo omelettes, Benedicts and more. Price range from around $4 to $22, making Lou Mitchell’s one of the cheaper options. Please note they’re closed on Monday and Tuesday.

EXPLORE MILLENNIUM PARK

📍Google Maps | Time Needed: 40-45 minutes | Budget: FREE

Millennium Park is 24.5-acre park full of art, greenery, and fun budget-friendly activities. Here are some things worth checking out:

• Cloud Gate (The Bean): this is British artist Anish Kapoor’s first public outdoor work installed in the United States. The iconic city skyline and clouds are reflected on the sculpture, and you can walk underneath, giving it the name “Cloud Gate.”
• Crown Fountain: this fountain with two 50-foot video screens on each side was designed by Spanish artist Jaume Plensa. There are holes in the towers that eject water every few minutes.
• Lurie Garden: is a beautiful place to slow down, unwind and reflect. Here, you’ll find all kinds of plants, including grasses, shrubs and trees. Lurie Garden is free, so it’s the perfect activity for us budget travelers.
• Millennium Monument: a neoclassical colonnade that honors the 115 donors who helped fund the creation of Millennium Park. It’s a great spot to snap some photos and take in some of the park’s history.

OPTIONAL STOP: CHICAGO CULTURAL CENTER

📍Google Maps | 4-min walk Millennium Park | Time Needed: 30 minutes | Budget: FREE

This is a free landmark building featuring the world’s largest stained-glass Tiffany dome, music events, art exhibitions and more.

As the city’s first central public library, the center was designed by the Boston architectural firm Shepley, Rutan & Coolidge.

This building is nicknamed The People’s Palace because it’s a large, palace-like space for all residents and visitors to enjoy, free of charge. It was designed to prove that Chicago had become a real, structured metropolis.

I finally visited on my most recent trip to Chicago and am SO glad I went. There weren’t too many people, which made it easy to navigate through the center.

On the building’s south side (East Randolph Street), you’ll find the world’s largest stained-glass Tiffany dome.

It stretches 38 feet in diameter with around 30,000 pieces of glass. Stop in for about thirty minutes to check out the dome and the rest of the center before heading to the riverwalk for your architecture river cruise (the best activity on this itinerary)!

AFTERNOON

GO ON AN ARCHITECTURE RIVER CRUISE

📍 Meeting Point | 11-min walk from Millennium Park | Time Needed: 1.5 hours | Budget: $60 | Book on GetYourGuide

I always say this, but it’s true… the architecture river cruise is the best thing to do in Chicago.

You spend an 1.5 hours cruising on a boat while learning about all these historic buildings as you pass them. Even if you aren’t into architecture, this tour is absolutely worth your time and money.

Some people recommend taking the $20 Chinatown Water Taxi if you don’t care to learn about the architecture, but I honestly still think the river cruise is a better experience. There’s a distinct purpose and the ride lasts longer, which I enjoy.

Be sure to arrive at the meeting point about fifteen minutes before the tour starts. You’ll want to give yourself enough time to find it since there are multiple meeting points for different tour providers. And plus, if you’re close to the front of the line, you’ll have better shot at getting a good seat on the boat.

There’s a good number of tour providers for the architecture river cruise, but I recommend the First Lady tour for your first time. While the most expensive, it’s inarguably the best, most comprehensive tour you’ll find. The others simply don’t compare.

Know that if it rains or is chillier than expected, you can sit inside the boat (tours still run regardless of weather). Also inside you’ll find drinks and snacks that you can buy if you’re hungry. Just try not to eat too much — you’re going to eat lunch after the cruise!

EAT LUNCH AT PORTILLO’S

📍 Google Maps | 17-min walk from the Riverwalk | Time Needed: 30 minutes | Budget: $15-20 | Order Ahead

If you didn’t know, Chicago is known for quite a few different foods including chocolate brownies, deep-dish pizza, and um, these things called Chicago-style hot dogs.

And you might be wondering, “What’s so special about them?”

Well, they’re made with all-beef hot dogs on poppyseed buns and “dragged through the garden” with yellow mustard, relish, white onion, tomatoes, a dill pickle, sport peppers and a dash of celery salt.

Now, I admit that sounds like overkill for something as simple as a hot dog. But it’s a lot more refreshing and flavorful than you’d think. Portillo’s is a popular spot to get them since they’re near downtown Chicago, which is where most tourists stay during their visit.

Along with this wild concoction, I recommend the chocolate cake shake, which is exactly what it sounds like: a slice of chocolate cake blended into a delectable milkshake. Consider ordering a side of crinkle-cut French fries to complete the meal.

OPTIONAL STOP: GARRETT’S POPCORN SHOP

📍 Google Maps | 9-min walk from Portillo’s | Time Needed: 30 minutes | Budget: $5-10 | Order Ahead

Another popular Chicago dish is the Chicago Mix, which is a mix of sweet caramel and cheddar popcorn.

The flavors go incredible together, and is the perfect snack to walk around the city with. I recommend getting some from Garrett’s, which is where this iconic mix originated.

If you don’t like the sound of sweet caramel and cheddar popcorn, there are some other options that are just as delicious:

• Cheddar cheese popcorn
• Caramel popcorn
• Buttery popcorn
• Caramel popcorn mixed with roasted almonds

This is an optional stop since you just ate, but I highly recommend making the stop. You won’t regret it — and that’s coming from someone who typically doesn’t enjoy popcorn.

RELAX AT A BEACH AND WALK THE LAKEFRONT TRAIL

📍 Google Maps | 15-min walk from Garrett’s | Time Needed: 1-2 hours | Budget: FREE

This might come by surprise, but Chicago has beaches. Multiple of them, actually! Like, with sand and everything.

Sure, they may not be the most traditional beaches, but they’re as close as you’re going to get to one in the Midwest.

Only fifteen minutes away, Oak Street Beach is closest to Garrett’s. Just behind North Avenue Beach, this is the second busiest in the city, which I personally don’t mind.

But if you prefer slightly thinner crowds, I recommend Ohio Street Beach. You’d think it’d be busier considering it’s near Navy Pier (a massive tourist area in Chicago), but it usually isn’t that bad since people gear toward the more popular beaches.

Along these beaches, you’ll see the Chicago Lakefront Trail (LFT). It stretches over eighteen miles from Ardmore Avenue in the north and 71st Street in the south.

It has an 18-mile bike trail for cyclists and 18.5-mile pedestrian trail for walkers. Consider walking the trail for thirty minutes to an hour.

If you want to bike the trail instead, rent a Divvy. These electric bikes are operated by Lyft and you can find them all around the city. I recommend getting a day pass for $19.90.

This will give you unlimited three-hour rides for 24 hours. Just make sure to hop off the bike and find another one after three hours — or else, you’ll have to pay $0.20 per minute.

Visit the Divvy website here for more information and up-to-date pricing.

EAT DINNER AT THE DEARBORN OR THE GAGE

📍 The Dearborn | 📍 The Gage | 31-min walk / 33-min walk from Oak Street Beach | Time Needed: 1 hour | Budget: $35-55 Including Tip

To end your day, you’re going to eat dinner at The Dearborn or The Gage — both of which are American restaurants in Downtown Chicago.

You’ll pass both on your way back to your hotel, so you don’t have to worry about making any unnecessary detours or backtracking at all.

First opening its doors in 2016, The Dearborn (an upscale American tavern) was created by Irish sisters Amy and Clodagh.

They serve Midwest fried chicken, salads, tavern pizzas, burgers, chicken sandwiches and more. Here’s a PDF menu. I recommend the buffalo chicken sandwich with French fries.

On it you’ll find blue cheese-boursin spread, buttermilk-battered chicken thigh, dill pickle, housemade buffalo sauce and rainbow slaw.

The Gage is a gastropub located just five minutes from Millennium Park. They serve items like salads, fish and chips, curry, roasted chicken, burgers and more.

I recommend the cheeseburger royale and French fries. The burger has a steakhouse patty, American cheese, griddled onions, Russian dressing, pickles, mustard — all on a sesame bun.

Whichever option you choose, PLEASE make reservations. These are some of the hottest restaurants in the area, and they get booked fast.

FREQUENTLY ASKED QUESTIONS: ONE DAY IN CHICAGO

IS ONE DAY IN CHICAGO ENOUGH?

Yes — for a nice introduction to the city, one day is enough. As shown in these itineraries, you can indulge in some of the best food, attractions, and sights.

But eventually, I’m sure you’ll want to plan a longer trip to Chicago. Check out my full 3-day itinerary when you’re ready!

IS CHICAGO SAFE FOR SOLO TRAVELERS?

Yes, Chicago is safe for solo travelers. I know Chicago appears in the headlines for different safety concerns, but as long as you take the proper precautions like in any other major city, you should be fine. Especially if you stay in the areas that I mention in this guide.

Read my solo travel safety tips guide here if you’re still hesitant or have more questions.

WHAT SHOULD I PACK FOR ONE DAY IN CHICAGO?

Be sure to bring comfortable walking shoes and a portable charger.

Check out my solo travel packing list here for more essentials.

HOW MUCH SHOULD I BUDGET FOR ONE DAY IN CHICAGO?

I’ve included a detailed budget breakdown below.

Please understand your budget will heavily depend on a number of factors including, when you’re visiting, where you’re staying, how you plan to get around the city, and what you’ll be doing during your trip.

Here’s a budget breakdown (based on one full day in Chicago in mid-September) to give you an idea of what you’ll spend on a solo Chicago trip:

• Flights: $205-300
  • $300 round-trip between LAX and ORD via Delta, United or American
  • $245 round-trip between JFK and ORD via JetBlue, American or Delta
  • $205 round-trip between FLL and ORD via JetBlue or United
• Activities: $60
  • Architecture River Cruise: $60 (book on GetYourGuide)
• Accommodation: $230 for a one-night weekend stay at Hilton Chicago in September
• Transportation: $7.50
  • CTA: $7.50 to get to & from the airport
• Food: $80-115
• TOTAL BUDGET: $580-710

BUDGET TIP: make sure you’re flexible with airports and dates when looking for flights. You could easily save $50+ by doing this.

If you’re trying to save money, read my guide here where I share over forty tips for traveling on a budget. These don’t revolve around Chicago specifically, but they can definitely help you save some coins.

FINAL THOUGHTS: ONE DAY IN CHICAGO

In this post, I shared what you should do if you have one day in Chicago, which is my favorite city to visit.

One day may not be enough to experience everything Chicago has to offer, but I believe this itinerary gives you a nice introduction to the city.

Let me know in the comments if you’ve visited Chicago before and have some insight on these itineraries, or if you’re currently planning a trip and need more help.

You can email me at demarcus@thesolosolstice.com or DM me on Instagram if you feel more comfortable doing so.

Happy travels to Chicago, friend!

ABOUT DEMARCUS

DeMarcus is a Midwest-based travel content creator and the founder of the solo travel blog, The Solo Solstice. He began his solo travel journey in December 2025 and since has been creating practical, in-depth travel guides for a like-minded community of first-time solo adventurers.

Visit the About Page to learn more about DeMarcus, and visit the Ethical & Responsible Tourism Page to learn more about his efforts to promote responsible tourism.