One Day in Chicago, Illinois: Itinerary & Where to Go in 24 Hours

Thinking of heading to the Midwest and exploring the Great Lakes Region? Be sure to spend at least one day in Chicago, Illinois. Set on the sweeping shores of Lake Michigan, the nation’s third-largest city is bursting with awe-inspiring architecture, world-renowned museums, and a foodie scene to die for.

Even if you can only squeeze in 24 hours in the Windy City, you’ll quickly appreciate this urban-meets-natural beauty. Stroll along the lakefront and wander through beautiful urban parks. Take in awe-inspiring architecture and browse bustling markets. Dive into Chicago’s sublime culinary scene with fuel stops at a few of the many award-winning eateries around town. Pop into trendy breweries for a craft beer along the way.

Not sure where to go in Chicago in one day? Make the most of your visit with this complete 24-hour Chicago travel plan!

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Where to go in Chicago in one day: A complete itinerary

Fuel up with breakfast in the Near North Side

Kickstart your 24-hour adventure in Chicago in the hip neighborhood of Streeterville. This bustling enclave is home to the historic Navy Pier, the Museum of Contemporary Art, and a gorgeous stretch of lakefront.

A busy day of sightseeing needs a hearty breakfast, and you’ll find a fantastic choice of coffee shops and cafés in the area. Stroll down Chestnut Street, and you’ll find Tempo Café, a 40-year-old institution with all the traits of a local diner. You can tuck into eggs and bacon anytime at the 24-hour café or order to go.

Tempo Cafe

If you have a hankering for pancakes, a short walk along East Pearson will take you to Wildberry Pancakes and Café. Towering stacks of buttermilk pancakes with fresh fruit and golden syrup are the order of the day. Try the fresh hot apple cider for something different.

For classic Cuban coffee and traditional Cuban sandwiches, Cafécito is a hit. You’ll find one of their bustling cafés at the end of Chestnut Street, where you can relax with a cup of coffee or grab an espresso and sarmie to go.


Fueled up and ready to do some sightseeing? Your first point of call is to take in some spectacular views of the city, and there’s no better place to do this than at 360 CHICAGO in the John Hancock Center.

Located on North Michigan Avenue, the 100-story, 1,128-foot skyscraper overlooks the Magnificent Mile district. Head up to the 360 CHICAGO Observation Deck on the 94th floor for amazing panoramic views of the city.

360 Chicago

If you love heart-stopping adventure, then try Chicago’s highest thrill ride, TILT. Tilt outward 1,000 feet above the city below for views worth screaming for!

Calm your nerves afterward with a coffee or cocktail at the casual CloudBar.

Magnificent Mile

Next on your list is exploring the Magnificent Mile. The ‘Mag Mile’ stretches along North Michigan Avenue from Oak Street in the Near North Side to the Chicago River. Home to historic landmarks, cool restaurants, and posh boutiques, it bustles with energy.

After visiting 360 CHICAGO in the John Hancock Center, amble south towards the river. You’ll pass the historic Water Tower and Water Tower Place shopping center. Browse major department stores and international designers and boutiques along the way.

Magnificent Mile

As you reach the end of the Magnificent Mile and the Chicago River, check out the Shops at North Bridge on the right. Marvel at the exquisite neo-Gothic Tribune Tower, an architectural masterpiece that graces the city with its extraordinary beauty and rich history. It’s also home to the Chicago Tribune newspaper.

Wrigley Building

Finally, admire the terracotta Wrigley Building skyscraper, a landmark 1920s skyscraper with an elegant clock tower and another one of Chicago’s architectural masterpieces.

Chicago Riverwalk

After your stroll down North Michigan Avenue, you’ve reached another one of Chicago’s fantastic neighborhoods worth exploring. Cross the historic DuSable Bridge with its beautiful decorative work to the Chicago Riverwalk on the left bank of the Chicago River. The 1.25-mile-long path meanders along the riverbank from Lake Street to the lakefront and is lined with bars, cafés, and restaurants.

Chicago Riverwalk

You must have worked up an appetite by now, and the Chicago Riverwalk is the perfect place to have lunch. A short walk west towards the lake will bring you to the Northman Beer & Cider Garden on the Riverwalk. You can tuck into casual European fare and house-brewed ciders in a laid-back atmosphere.

If you head eastwards from the DuSable Bridge, you’ll find the Chicago Brewhouse Riverwalk and the Riverwalk Wine Garden by City Winery. Relax over lunch and a glass of wine or craft beer and watch the river traffic passing by.

For something swankier, try the London House Rooftop Baron on East Wacker Drive. Based on the 22nd floor of the London House hotel, this gorgeous restaurant boasts stunning views of the city skyline. Order orange chicken bao buns and an LH Old Fashioned. It’s also a sleek spot to head back to for a romantic dinner or evening cocktails.

Chicago Architecture Center

Whether you’re a design nut or not, visiting the Chicago Architecture Center is a must. Home to the most diverse collections of skyscrapers in the world, Chicago is famous for its spectacular architecture. The Chicago Architecture Center will give you an in-a-nutshell overview of the history of Chicago’s groundbreaking architecture.

Illinois Center

Located at One Illinois Center on E. Wacker Drive in the Chicago Loop, the CAC is based in an appropriately awe-inspiring building. Designed by one of the pioneers of modern architecture, Ludwig Mies van der Rohe, the building is an outstanding example of the International Style of architecture van der Rohe was famous for. Inside, head to the Skyscraper Gallery and marvel at the display of towering scale models of the world’s tallest structures.

When you’re done, take a guided cruise on the river and learn the history behind over 50 buildings lining the Chicago River. Join the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady and soak up some amazing views of the city skyline.

Millennium Park

The next stop is Millennium Park to see some of Chicago’s most iconic tourist attractions. A short walk from the Chicago Architecture Center down North Michigan Avenue will take you to the park, where you’ll find a lively vibe and plenty of action.

Established in 2004 by former Mayor Richard M. Daley, Millennium Park is nestled within Downtown Chicago’s Grant Park. This spectacular green space is home to the famous Cloud Gate statue, also known as The Bean. The polished stainless-steel sculpture by British artist Anish Kapoor stands 30 feet tall and reflects the city skyline and spaces beyond.

Millennium Park

Other not-to-be-missed attractions in Millennium Park include the Crown Fountain, a massive, interactive video sculpture with a granite reflecting pool. The Lurie Garden is a lush oasis in the heart of the park featuring flowering blooms, verdant shrubs, and a myriad of bird and insect life.

Kids will love Maggie Daley Park, a fantasyland fashioned in the spirit of Alice in Wonderland and Charlie and the Chocolate Factory. Tube slides, suspension bridges, and a pirate ship beg to be explored, while a 40-foot climbing wall and 18-hole mini golf course offer a challenge for older kids. The winding Skating Ribbon is perfect for rollerblading in the summer and ice-skating in the winter.

Maggie Daley Park

Feeling peckish? Just across the street from the north end of Millennium Park is Giordano’s, a local chain renowned for serving the best Chicago-style deep-dish pizza.

Another fantastic spot to eat near the park is Cindy’s Rooftop bar & eatery. Located on the 13th floor of the Chicago Athletic Association Hotel, this stylish café serves fresh seafood in a gorgeous setting.

Book a table at The Gage for dinner. One of Chicago’s most popular restaurants, this is the go-to spot for excellent food and superb views over Millennium Park.

Art Institute of Chicago

Just south of Millennium Park is the Art Institute of Chicago. One of the oldest and largest museums in the world, it’s home to an extraordinary permanent collection of art that spans centuries.

The Art Institute of Chicago

If you know your art, you will delight in some of the works that call the Art Insitute of Chicago home. At the famed art museum, you’ll see famous pieces like Grant Wood’s American Gothic, Georges Seurat’s A Sunday on La Grande Jatte, and Salvador Dali’s Buckingham Fountain.

Keeping with Chicago’s reputation for having some of the best architecture in the world, the museum recently added the internationally acclaimed 264,000- square-foot Modern Wing designed by acclaimed architect Renzo Piano.

SkyDeck Chicago

Time to head back towards the river for some incredible views. Head east along West Adams Street towards the river. Look out for the Rookery Building on your left. One of the most historically significant buildings in Chicago, the Rookery is a Historic Landmark and architectural masterpiece.

Turn right into Lower Wacker Drive, and you’ll spot the lofty Willis Tower, formerly known as the Sears Tower and the tallest building in Chicago. Make your way to SkyDeck Chicago on the 103rd floor and take in some breathtaking panoramic views of the city. You can see up to 60 miles on a clear day!

View from SkyDeck

For a heart-stopping experience, step out on The Ledge, a glass floor balcony that projects out from the side of the skyscraper offering unfettered views from 1,353 feet above the city center.

Fulton Market

Next in line is Fulton Market. Hop in a cab or catch a bus from Downtown Chicago to West Fulton Market Street in the Near West Side of Chicago. Once an industrial warehouse district, the area has regentrified into a lively, vibrant entertainment zone packed with cool cafés, trendy boutiques, and swanky restaurants.

Fulton Market

Wander around the vast Timeout Market Chicago, a 50-000-foot foodie heaven packed with chef-driven stalls serving globally inspired eats.

Let Top Chef Season 4 winner and celebrity chef Stephanie Izard feed you at one of her restaurants in the district. Girl & The Goat offers an imaginative take on classic Californian fare, while Duck Duck Goat is renowned for its exceptional Chinese cuisine. The wonton soup with blueberry broth and goat belly lo mein is to die for!

For exceptional Italian street food served in a jostling, Mediterranean atmosphere, Bar Siena on Chicago’s West Loop ‘Restaurant Row’ is where it’s at.

If you have a hankering for tacos and tortillas, then pop into Cruz Blanca Brewery. This Mexican craft brewery meets wood-fired taqueria in the heart of the West Loop neighborhood and serves mod-Mex lagers, tropical sours, and tlayudas.

Restaurant Row in Fulton Market

When it comes to classic Chicago deep-dish pizza, there’s only one name in the business, and that’s Lou Malnati. The oldest family name in Chicago pizza has 76 stores around the country, and this is the place to be for mouthwatering deep-dish pizza and other Italian delights.

More Chicago itinerary ideas

Lincoln Park

Set in one of Chicago’s most affluent neighborhoods on the North Side of the city, the eponymously named Lincoln Park is a nature lover’s dream. From lushly manicured gardens and hiking trails to a conservatory, several museums, and one of the country’s oldest free zoos, you’ll need a day just to explore the park alone!

Lincoln Park

In the park, you’ll find the Lincoln Park Conservatory, the Peggy Notebaert Nature Museum, and the Chicago History Museum. Hike the Lakefront Trail, have some fun in the sun at North Avenue Beach, stroll along the Nature Boardwalk, or watch a show at the Theater on the Lake.

The neighborhood around Lincoln Park has beautiful boutiques tucked into historic row homes and some of the best restaurants in the country.

Old Town

Another charming neighborhood to discover is Old Town Chicago. Located in Near North Side, the historic district is home to beautifully preserved Victorian-era buildings, charming eateries, and old-school pubs.

Old Town

Take a stroll along the tree-lined streets and browse the quaint stores and quirky boutiques. Admire the lovely old buildings, including St. Michael’s Church, one of the few structures that survived the Great Chicago Fire in 1871.

Pop into one of the artisanal coffee shops for a caffeine fix and catch a show at the revered Second City comedy club.

Navy Pier

Another one of Chicago’s top attractions that needs more than a few hours to explore. Navy Pier is a 3,300-foot-long pier in Streeterville, and the surrounding park is packed with family-friendly fun. From art exhibits, live music, lake cruises, and theater shows, this lakefront treasure is a hive of activity.

Navy Pier

Named to honor World War I veterans, Navy Pier Park is home to a 150-foot-high Ferris Wheel offering breathtaking lake views, an IMAX theater, and a wealth of restaurants and bars.

Lush palms and flowering plants in the Crystal Gardens are housed in a six‐story glass atrium. The Chicago Children’s Museum features 13 interactive and hands-on exhibits for kids of all ages.

Museum Campus

Museum Campus houses three of Chicago’s top museums dedicated to natural sciences in one place. Spend a day wandering through the world of natural history and world cultures at the Field Museum. Dive into the underwater world of the ocean with a visit to the Shedd Aquarium, and head into space to learn about far-off galaxies at the Adler Planetarium.

Museum Campus

The Field Museum is one of the world’s largest natural history museums. It has inspired curiosity about life on earth for over a century with a collection of over 24 million objects.

The Shedd Aquarium is home to over 1,500 species of marine and land creatures, including fish, birds, amphibians, snakes, and insects. The famous underwater world also has a 4-D theater with immersive seats and interactive elements.

Chicago’s Adler Planetarium offers unforgettable immersive sky shows in three huge theaters. Extensive space science exhibitions display a collection of antique scientific instruments and print materials.

Wrigley Field

Go Cubs! If you’re a baseball fan, visiting Wrigley Field is a must! It’s the oldest National League ballpark in the country and has been home to the Chicago Cubs baseball team since 1916.

Wrigley Field

Built in 1914, the ballpark hosted five World Series games between 1929 and 1945. The stadium is such an institution that the neighborhood surrounding the park is fondly known as ‘Wrigleyville!”

If you aren’t lucky enough to get tickets to a game, you can explore Wrigley Field on a guided tour. Venture into the press box and the visitor’s clubhouse, check out the Cubs’ clubhouse and their dugout and feel what it’s like to be in the bleachers.

Where to stay with 24 hours in Chicago

If you’re crunched for time, the best places to stay in Chicago are The Loop and River North. These central areas are home to many of the city’s top-rated hotels and accommodations. You’ll also find a variety of lodgings in other neighborhoods ringing the city center, including Streeterville, Lincoln Park, Wicker Park, and West Loop.

Hotel Blake, an Ascend Hotel Collection Member

Hotel Blake, an Ascend Hotel Collection Member

Spike your Chicago trip with a dash of history and luxury at the Hotel Blake. Located in The Loop, this beautiful boutique hotel features modern rooms with cool vintage newspaper wallpaper that pays tribute to the history of the building.

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

If you’re looking for stylish digs in the heart of the city, lay down your head at the chic Staypineapple. Before embarking on your Chicago sightseeing tour, fill up the signature pineapple coffee mugs in-room for a quick morning java boost. Splurge on the Millennium Park King Suite to wake up to spectacular views of Lake Michigan and the sun reflecting off The Bean.

The Langham Chicago

The Langham Chicago

Pamper yourself with a stay at The Langham, one of the very best luxury hotels in Chicago. Every room in this 5-star hotel faces either Lake Michigan or the Chicago River, delivering beautiful views through floor-to-ceiling windows. Unwind from a day of walking at the on-site Chuan Spa or sip on cocktails at Travelle Kitchen + Bar.

When to visit Chicago

The best time to visit Chicago is in late spring, from April to May, and in early fall, from September to October. In these shoulder season months, visitors will enjoy an excellent combination of warm weather, a wide array of festivals, and smaller crowds.

North Avenue Beach

While temperatures are pleasantly hot in the summer, the tourist crowds, too, are at their highest. Hotel prices swell as availability gets squished.

The Windy City is famed around the United States for its bitter cold winters. If you can hack it, though, winter is the cheapest time to travel to Chicago. Be sure to bundle up!


Ryan O'Rourke is a seasoned traveler and the founder & editor of Treksplorer, a fiercely independent guide to mid-range luxury travel for busy people. With over 20 years of extensive travel experience, Ryan has journeyed through over 50 countries, uncovering hidden gems and sharing firsthand, unsponsored insights on what to see & do and where to eat, drink & stay. Backed by his travel experience and in-depth research, Ryan’s travel advice and writing has been featured in publications like the Huffington Post and Matador Network. You can connect with Ryan on Twitter/X at @rtorourke.

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