How to Spend 24 Hours in Chicago

 “It is hopeless for the occasional visitor to try to keep up with Chicago—she outgrows his prophecies faster than he can make them. She is always a novelty; for she is never the Chicago you saw when you passed through the last time.”

Mark Twain, Author and Humorist

Please note: Thanks to vaccinations and relaxed mask and travel rules, travel has slowly begun to relaunch. However, please keep your safety and the safety of others in mind at all times. If you are comfortable with traveling, please travel responsibly and within regulation as any travel is at your own risk. 

If you do decide to travel at this time, here are our recommendations: 

• Wear a face mask. 
• Bring hand sanitizer and wash your hands thoroughly and on a regular basis. 
• Check official websites before your trip for the latest updates on policies, closures, and status of local businesses and attractions. 

ONE-DAY CHICAGO ITINERARY

Do you have a 1-day layover? Are you pressed for time but still want to experience an awesome city in all its glory? Collaborating with Hotels.com, I’ve got the ideal itinerary for you and, if you’re looking for cosmopolitan flair, look no further. Grossly underrated as a travel destination, Chicago is the perfect city to get to know in 24 hours. Is there a better city in which to spend a whirlwind day than the Windy City itself? The following itinerary is jam-packed for a reason—options are key when planning a quick trip as it allows you to pick and choose what’s suitable for you. 

Situated on Lake Michigan, Chicago is one of the largest cities in the United States and is known for its bold architecture, dining and art scenes, and nightlife. As with most major cities, Chicago’s vibe is at its most electric and vibrant in the downtown area which is where I would recommend staying in order to be closer to major attractions and restaurants. 

Visit The Bean in Millennium Park 

Ah, The Bean—chances are if you’ve seen pictures of Chicago online, you’ve seen the social media-worthy oversized metal orb that looks like a gargantuan jellybean. Officially, it’s called Cloud Gate but locals and tourists alike know it by its casual nomenclature. Its mirrored surface and distinct shape draw both architecture lovers and those looking for unique Instagrammable photos. The sculpture is housed in admission-free Millennium Park, but fair warning—the park is an entertainment and concert hub and is often crowded (especially when it’s warm). 

Visit the Art Institute of Chicago 

Located conveniently next to Millennium Park, the Art Institute of Chicago is one of the oldest and largest museums in the US and is definitely worth a visit. It frequently tops the art world’s best-of lists; aficionados will appreciate the museum’s various curated exhibits and collections.  

Get Sky High  

One of the benefits of being in a big city is actually being able to see the city. Taking advantage of downtown’s skyscrapers is a must-do and there’s no shortage of rooftops in the area, especially bars. Cerise, part of the Virgin Hotel group and one of the city’s hottest restaurants, offers not only sweeping views of downtown Chicago but elevated cocktail and food menus. The in-house DJ is nothing to sneeze at, either. 

Get Sky High, Part Two 

If you’re not fearful of heights and you’re looking for a little adrenaline-inducing adventure, try the Skydeck at Willis Tower. The glass structure is one of the country’s coolest observation decks and includes a unique feature known as The Ledge—and it is not for the faint-hearted. The Ledge is a parapet that overlooks the city and makes you feel like you’re floating and can either be exhilarating or terrifying depending on your feelings about heights. What’s even more intriguing about the Skydeck is that you can view 4 states simultaneously from its platform, so while you may not be able to say you visited the states, you can certainly say you’ve seen them. 

People-Watch Along the Chicago Riverwalk  

Sometimes a break from a packed itinerary is needed and people-watching is the perfect slowdown activity. The Riverwalk is a popular pedestrian promenade (how’s that for alliteration?) that offers the opportunity to watch both passersby and the boats floating along the Chicago River. Strategically placed restaurants, bars, and seating make this pedestrian oasis the perfect place to kick back and relax. If cruising and moving is your thing and you’re looking to see other city sights, grab a water taxi. 

Act Like a Tourist at Navy Pier 

Admittedly, Navy Pier is one of the more touristy destinations in the city, but it’s also a fun place even for residents. There’s a giant Ferris wheel, shops, and restaurants not to mention the Chicago Shakespeare Theater and the Chicago Children’s Museum. Aside from being a tourist hotspot, Navy Pier also serves as the boarding site for many of the city’s waterway boat tours. 

Explore Chicago’s Culinary Side 

Sure, you know about the city’s deep-dish pizza, neon relish-slathered hot dogs, and you may have even heard of cult classic Garrett Popcorn, but there’s so much more to the city than that. A lot more. (With that said, iconic restaurants like Giordano’s and Lou Malnati’s should not be overlooked, despite what airheaded fictional character Emily in Paris says.) Overlooking Chicago’s rightful place in the country’s culinary upper echelons is a mistake, indeed. Nosh on juicy fried yardbird from Harold’s Chicken Shack, grab some sloppy carnitas from any number of taco joints, or try a hot Italian beef sandwich. Chicago is also home to several Michelin-starred fine dining restaurants, including chef Grant Achatz’s lauded Alinea—a lofty, molecular gastronomy wish on the bucket list of most gastronomes. 

Shop on the Magnificent Mile 

If you’ve chosen to see the city on foot, your feet have likely gotten quite the workout, so why not give your wallet a bit of a stretch, too? Shopping along Chicago’s famous Magnificent Mile—the city’s premier commercial district—can be an exercise in restraint or excess, depending on your spending (or credit) limit. The area is home to upscale shops and luxury retailers as well as cool restaurants and tony hotels; it boasts more than 450 stores including several flagships and international designers. If it’s luxe you seek, there is no place in the city more fitting. 

Have you ever visited a city for just one day? How would you spend 24 hours in the Windy City? No matter how you choose to get a taste of the city, it’s sure to be one of your most exciting travel experiences.