IYKYK: Chicago will keep you coming back for more

Mar 2, 2023

Over 25 miles of beautiful Lake Michigan shoreline. The lively Chicago Riverwalk. Iconic landmarks like the sky-high Willis Tower and the century-old Wrigley Field ballpark. Seemingly endless food options from simple classics like a Chicago-style hot dog to Michelin-starred restaurants with celebrity chefs.   

Top it all off with some Midwest charm, and it's no wonder why Chicago has been voted the Best Big City in the US by the Condé Nast Traveler’s Readers’ Choice Awards for a sixth year in a row.

While locals will tell you there’s nothing like summer in Chicago, you’ll find events and celebrations to experience all throughout the year—like the annual St. Patrick’s Day tradition of dyeing the Chicago River green in March, the Chicago Air and Water show on the lakefront in August and the cozy Christmas markets every December. 

Cloud Gate ("The Bean")

For those who have never been, well-known spots like Cloud Gate, also known as “The Bean,” and Navy Pier are worthy of a visit. But with 77 unique neighborhoods to explore, one trip to this evolving city just isn’t enough. So, whether you’re a first-timer or return visitor, we’ve compiled a quick guide to help you plan your next Chicago getaway.   

Windy City sights 

First Time 

There’s a few key stops every first-time visitor to Chicago should plan for. “The Bean” sculpture in Millennium Park and the Skydeck on Willis Tower’s 103rd floor are perfect photo opps to commemorate your trip.

Skydeck Chicago

The bustling Magnificent Mile (also known as “The Mag Mile”) is lined with hotels, restaurants and shops galore, with unique offerings including a five-story Starbucks Reserve Roastery; American Girl Place Chicago, a kid-friendly favorite; and the historic Drake Hotel, which offers afternoon tea service in their elegant Palm Court.  

Take in blue views of Lake Michigan as far as the eye can see by heading to Navy Pier for a ride on the Centennial Wheel or a drink at Offshore, named the world’s largest rooftop bar by Guinness World Records. 

Return Visit 

For some of the city’s most unique museums in a scenic setting, head to Hyde Park the second time around.  The neighborhood was once the site of the World's Columbian Exposition (aka the World’s Fair) in 1893. One of the last remaining buildings from the fair now houses the Museum of Science and Industry. Here you'll find interactive exhibits like their "Whispering Gallery" and a captured U-505 submarine from World War II on display. Nearby is also the DuSable Black History Museum and Education Center, the oldest independent African American museum in the country. 

DuSable Black History Museum and Education Center
Located in the Lincoln Park neighborhood, the Lincoln Park Zoo is open year-round and offers free admission. Admire exhibits like the recently renovated, state-of-the-art lion habitat and check out annual events like ZooLights in the holiday season.

Take a trip around the world with the city's dining scene 

First Time 

Ask any Chicago resident, and they’ll have a strong opinion on where you should eat—and especially where to go for pizza. You’ll end up in one of two groups: deep dish vs. tavern style. With a flaky crust, lots of cheese and a layer of sauce piled on top—Chicago deep dish pizza is worth sampling at least once. Pizzeria Uno is located downtown and considered by some to be the original deep dish. Lou Malnati’s Pizzeria and Giordano’s are also ubiquitous options located throughout the city.  

Lou Malnati's

While deep dish may be the most famous Chicago pizza, some locals would argue authentic Chicago pizza is tavern-style. The thin, crispy pie cut into squares pairs great with a cold beer and can be found at pubs around the city.

Next up, the Chicago-style hot dog. A poppy seed bun with an all-beef hot dog, topped with yellow mustard, relish that’s greener than the Chicago River on St. Paddy's Day, diced onions, tomato wedges, a pickle spear, sport peppers, celery salt andthis is very importantabsolutely no ketchup.  Find these at local hot dog shops throughout the city, or for a sure bet, head to a Portillo’s.

Lastly, don't leave town without heading to Al's Italian Beef for an Italian beef sandwich. Thinly sliced beef on sturdy French bread, topped with your choice of gravy and giardiniera, this Chicago original is worth the number of napkins you need while eating it. 

Return Visit 

On your second visit, make time to dive into Chicago’s international dining scene to discover an array of cuisines from around the world.

Triple Crown Restaurant in Chinatown

Find Polish fare like pierogi and kolaczki at Staropolska in Avondale; head to Papa's Cache Sabroso in Humboldt Park for a jibarito, a Puerto Rican-inspired sandwich created in Chicago that's made with fried plantains instead of bread; fill up on dumplings at Qing Xiang Yuan Dumplings in Chinatown; try Momotaro’s take on modern Japanese cuisine in West Loop, a former industrial area turned dining destination; enjoy Ethiopian cuisine at Demera in Uptown; and savor a slice of tres leches cake from Kristoffer’s Cafe and Bakery, a treasure of the Pilsen neighborhood.

You can also experience some of the fine dining scene here in Chicago at one of the 23 restaurants that were awarded with Michelin star honors last year, including Alinea in Lincoln Park, which received three Michelin stars. 

Be "in the loop" with Chicago shows and sports

First Time 

Whether it's for the love of the game or for the love of the hot dog (or both), check out one of Chicago’s legendary sports teams. Home to professional football, hockey, two basketball and two baseball teams, there’s bound to be a game any time of the year. But if you can't make it on game day, Soldier Field, Wrigley Field and Guaranteed Rate Field offer behind-the-scenes stadium tours. 

Chicago Theatre District

If “da Bears” or "da Bulls" don’t pique your interest, perhaps Chicago’s thriving theater scene will. Rotating Broadway shows like “Hamilton” and “Tina - The Tina Turner Musical” are regularly featured at some of the historic theaters in the Loop neighborhood’s Chicago Theatre District. Some shows have even premiered in the city before hitting Broadway. Plan ahead for your visit with the show lineup on Broadway in Chicago.

Return Visit 

Have a laugh at The Second City comedy theater. Opened in 1959, this landmark has seen legendary comedians like Dan Aykroyd, Chris Farley and Tina Fey pass through its doors early in their careers. Live shows featuring improv and sketch comedy are available every night. Once you've caught an improv show, there's plenty more entertainment options to keep you busy, like Zanies Chicago right down the street from Second City to see stand-up, or live music at one of the historic and intimate venues in neighborhoods around town.

Millennium Park Summer Music Series

While the city is known for hosting Lollapalooza music festival, there’s also a packed lineup of music festivals all summer long with options like the Chicago Blues Festival, the Chicago Jazz Festival and the Millennium Park Summer Music Series.  

Enjoy the Great (Lakes) views along Chicago’s waterfronts 

First Time 

The picturesque Chicago River runs through downtown. Lining the water is the Chicago Riverwalk, which features over a mile of pedestrian-friendly walkways perfect for strolling on a sunny day. There's also plenty of restaurants and bars with waterfront patios available to stop in for a drink or a bite to eat.  

Chicago Architecture Foundation Center River Cruise aboard Chicago's First Lady

One of the best ways we like to enjoy the river is with an architecture boat tour. The cruise offered by the Chicago Architecture Center is a favorite among locals and visitors, thanks to trained docent volunteers who share interesting stories and facts about how Chicago came to have such an impressive skyline.

Return Visit 

Set right up against Lake Michigan, a trip to one of Chicago’s sandy beaches is a must when visiting the city in summer. Just steps from The Mag Mile downtown, Oak Street Beach is a great nearby option for quick access. Further north is Foster Beach, which has nearby parking and is family-friendly. And if you happen to be visiting with your pup, Montrose Beach has a dedicated fenced-off section where dogs can feel the sand between their paws and take a dip in the lake off leash.  

Urban Kayaks

By now, perhaps you’ve already seen the Chicago River by boat—but how about by kayak? Urban Kayaks offers rentals for you to go on your own, or tours where you can paddle with a group.  

A destination for art and history buffs

First Time 

Spend an afternoon getting lost inside the Art Institute of Chicago, famously featured as part of the day's itinerary in the 1986 film "Ferris Bueller's Day Off". The museum displays works by renowned artists like Claude Monet, Georgia O'Keeffe and Pablo Picasso, along with one of the largest collections of Impressionist art outside the Louvre.

Shedd Aquarium

Fun for the whole family, the Adler Planetarium, Field Museum and Shedd Aquarium are situated next to each other along the lakefront on Chicago's Museum Campus. Go on "A Walk Through Space and Time" at the planetarium, learn about natural history and see impressive displays in the Field’s “Hall of Dinosaurs" then head over to the Shedd to see sea otters, dolphins and turtles.

Return Visit

A deeper dive into Chicago’s art and history scene will take you into some of the city’s historic neighborhoods and cultural havens. The National Museum of Mexican Art in Pilsen features an expansive collection of Mexican art (one of the largest in the country), ranging from textiles, to paintings, to photography and film.  

National Museum of Mexican Art

Sign up for a tour of the Frederick C. Robie House, located on the University of Chicago's campus in Hyde Park. Designed by American architect Frank Lloyd Wright and named a UNESCO World Heritage Site, the house was recently restored to its original appearance.  

Take a step back in time with a trip to the Pullman National Historical Park. This historic district, built in 1880 as one of the United States' first planned industrial communities, is filled with unique architecture and fascinating stories.

The Chicago History Museum offers a deep dive into the city’s past. Learn about the Great Chicago Fire in 1871, see dioramas of what Chicago once looked like and find out what the Chicago flag represents.  

Ready to go? Start planning your Chicago getaway, whether you're visiting for the first time or returning to explore the city's hidden gems

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