Nov 13 5 min read City Guide Holiday Travel
Corporate Headquarters
200 North LaSalle Street Suite 400
Chicago, IL 60601
Customer Service Hours
8 am - 5 pm CST Mon-Fri
Top 50 Chicago Attractions and Fun Things to Do
DEC 16, 2024 5 MIN READ CITY GUIDE HOLIDAY TRAVEL
Top 50 Chicago Attractions and Fun Things to Do
PreFlight is proud to call Chicago one of our homes. And what better way to celebrate The Second City than to show off the outstanding features of our great town by compiling a list of the top 50 Chicago attractions and fun things to do for tourists and locals alike. From iconic landmarks to hidden gems, this compilation encompasses the very best that Chicago has to offer, ensuring that everyone can indulge in the vibrant spirit and captivating allure of our extraordinary town.
Public Spaces Throughout Chicago
Millennium Park is one of the largest and most versatile parks in the city limits. Opening in 2004 at the cost of $475 million, Millennium Park quickly rose to prominence, now finding itself among the top ten tourist destinations in the United States. Because of its positioning on top of a parking garage and train station, it is considered the world's largest rooftop garden.
Running from the northern Indiana border past Wrigley Field, the Chicago Lakefront Trail is 18 miles of paved bike and pedestrian trails running along the beautiful shores of Lake Michigan.
Carving the downtown area into two halves, the Chicago River is an engineering feat that can now be traversed with stunning views. In 1900 the City of Chicago successfully reversed the river's flow and, over the next 100+ years, paved its banks with beautiful business facades and public areas.
Named after Illinois-born United States President Abraham Lincoln, Lincoln Park is the largest park in the city and stretches for seven miles, incorporating many features. Home to other items on this list, such as the Lincoln Park Zoo and Alinea restaurant, Lincoln Park also boasts an outdoor theatre, rowing canal, and two gorgeous ponds.
Neighboring Millennium Park within the overall confines of Grant Park, Maggie Daley Park is home to one of the most unique experiences in downtown Chicago. The center ribbon morphs into a stunning ice skaters paradise during winter months, wrapped around an expansive climbing wall. There is also a mini-golf course, the Cancer Survivors' Garden, and several other activity spaces.
Transforming an old rail yard into a mid-city oasis, the Ping Tom Memorial Park hosts activities of all kinds, including concerts, dance performances, Shakespeare in the Park, Movies in the Park, and more. The architectural inspiration comes from Chinese landscape design elements, rendering the area a distinctive escape in a city of skyscrapers.
Beaches (North Ave, 57th Street, Montrose, Ohio, Oak)
Boasting 26 miles of lakefront, Chicago has several options for rest and relaxation at the beach. More popular spots are North Avenue Beach, 57th Street Beach, Montrose Beach, Ohio Street Beach, and Oak Street Beach.
An artificial peninsula, Promontory Point cuts into Lake Michigan, sitting between the downtown area and the Illinois-Indiana border. This picturesque picnic spot has a panoramic view of the lakeshore, ideal for a warm, sunny afternoon.
This long, shotgun barrel park sits on the city's South Side and spans the length of a mile. One of the city's most prestigious institutions shares this lot of land, the University of Chicago. Mainly a green area, Midway Plaisance Park once was heavily used during the 1893 Chicago World's Fair.
On the west side of Chicago is this 200-acres park that features just about everything imaginable. At the center of it is a massive fieldhouse with everything from a ballroom to tennis courts. Humboldt Park even houses Little Cubs Park, a miniature version of the famous Wrigley Field.
Chicago Museums
One of the oldest museums globally, the Art Institute of Chicago, was founded in 1879. Located in the heart of "The Loop," the Institute is on the periphery of Grant Park and continuously changing its exhibits.
Museum of Science and Industry
Originally the Palace of Fine Arts during the 1893 World's Columbian Exhibition, the modern-day Museum of Science and Industry is home to roaming exhibits and cutting-edge, permanent installations.
Famous for displaying the largest and most complete Tyrannosaurus Rex fossil, Sue, the Field Museum is a natural history museum that welcomes 1.65 million guests every year.
A magnificent 4.5-acre greenhouse, the Garfield Park Conservatory is over 140 years old and houses plant specimens from around the world.
The most popular cultural attraction in Chicago, the Shedd Aquarium is home to over 30,000 animals. Just off the shores of Lake Michigan, the Shedd is one of the largest indoor aquariums in the world.
Museum of Contemporary Art, Chicago
Located in the Streeterville neighborhood on the Near Northside, MCA can boast some notable debut exhibits. From the famous, Mexican painter Frida Kahlo's first U.S. exhibit to the American artist and sculptor, Jeff Koons.
Nestled in a corner, jutting into the rocky shore of Lake Michigan, the Adler Planetarium has undergone renovations in recent years to update the 90-year-old structure. When it opened in 1930, it became the first Planetarium in the United States. It now has National Historic Landmark status and is a must-see museum in Chicago.
The Windy City's long and rich history is housed in the Chicago History Museum, including the infamous Great Chicago Fire. Also, among the exhibits, the museum pays homage to President Abraham Lincoln, the city's icon placement in the country's heartland, and Chicagoans' unique culinary taste.
Containing artifacts from excavations performed in Egypt, Israel, Syria, Turkey, Iraq, and Iran, the Oriental Institute is one of the leading collectors of ancient civilization artifacts in the U.S. The Institute is also a hub for continued research, attempting to trace modern Western civilization back to the Middle East.
DuSable Museum of African American History
Dedicated to the study and conservation of African American history, the DuSable Museum of African American History has remained entrenched on the city's south side for over 60 years. Named after Chicago's first non-indigenous settler, Jean Baptiste Point du Sable, the museum now shares a name with the Lake Shore Drive – which was recently renamed after DuSable.
Chicago Landmarks
One of the most unique fountains you'll encounter anywhere in the world, Chicago's famous Crown Fountain is a fusion of technology, art, and nature. Two towering structures feature LED screens displaying images, with water flowing from various points onto a reflective black granite pool.
Affectionately referred to as "The Bean" by Chicagoans, Cloud Gate was revealed to the public at the same time as Crown Fountain – the opening of Millennium Park in 2004. Created by artist Anish Kapoor, Cloud Gate has a polished reflective surface absent of seams, making it a perfect picture for tourists and locals needing a Chicago-themed selfie or two.
One of the most iconic sites in Chicago, Navy Pier welcomes more than two million visitors a year. Initially conceived for function over form, Navy Pier has converted into a local attraction thanks to its large Ferris wheel, which punctuates the pier's presence on the lakefront.
Another fountain makes the list, this time a more traditional fountain. Traditional, but anything but average. Buckingham Fountain is one of the largest fountains in the world. Situated in the middle of Grant Park, the attraction is approaching 100 years old as one of Chicago's most iconic sites.
Technically, it is called the Willis Tower, but ask any Chicagoan, and they'll answer without hesitation – it's the Sears Tower. The building claimed the title of the tallest building in the world from 1974 to 1998. It is now the 23rd tallest building and is a staple of the Chicago skyline.
Predating the Willis Tower, the John Hancock was the second tallest building in the world upon completion in 1968, behind only the Empire State Building. It now sits at #5 in the Chicago lineup of cloud scrapers, but its 360-degree observation deck keeps visitors flocking to the architectural marvel.
Predating most of the attractions on this list, Wrigley Field is synonymous with both Chicago and baseball. The second-oldest park in baseball behind only Fenway Park in Boston, Wrigley Field hosted its first Cubs game in 1916 and remains the home to the MLB franchise. The ivy-covered brick walls are consistently ranked one of the most unique features in a professional sports arena in the world.
For over 50 years, local artists have used the walls of a viaduct and the surrounding area on the city's west side as a canvas for boundless colorful works of art. Now a collection of over 250 pieces of art, the Hubbard Street Murals are a beautiful example of aesthetic reclaiming urbanized expansion.
Technically outside the city limits, the Bahá'í Temple is a sight to behold from ground-level or overhead, sitting a short distance away from the shores of Lake Michigan in Wilmette, Illinois. Open to the public and those of any religious denomination, the Bahá'í Temple is the oldest House of Worship remaining in the world.
Paying homage to a famous former resident, Lyman Frank Baum, author of The Wonderful Wizard of Oz, this park contains each of the main protagonists within its 13-acre plot of land.
Top Chicago Activities
Running parallel with the shores of Lake Michigan, the Lincoln Park Zoo is the fourth oldest zoo in North America. Since its opening in 1868, the zoo has continued adding exotic animals and exhibits to its collection. Each winter, it hosts an annual light show, which is a spectacle if you're prepared to bundle up in the cold.
The Magnificent Mile, or Mag Mile, is a stretch of road lined with upscale retail and jewelry stores, restaurants, residential and commercial buildings, and hotels running from the river to the city's northeast side. If you're looking to shop, this is the spot.
Love it or hate it, Chicago is known for its deep-dish pizza. Some argue it's a pie; some claim it's perfection. Whether you take a walking tour or shell out for the VIP treatment, this tour will spur conversations about which pizza is the best.
The list of alums that once called The Second City home is a who's who of comedy greats. From John Belushi and Dan Aykroyd to Tina Fey and Amy Poehler, the stages at The Second City have paved the way for many beloved comedians. Spend some time viewing the alumni list, and you'll want to visit immediately to see what the next generation of talent looks like.
Featuring an iconic marquee and a long history of famous acts, The Chicago Theatre is one of the most recognizable venues in the city. Take in a stage play, magic show, comedy act, or music performance inside the hallowed hall.
River Kayaking
One of the best ways to take in the marvelous skyline in Chicago is to kayak on the Chicago River. Tours are available, including an architectural tour that will ramp up your knowledge of the windy city.
Sporting Event (Cubs, White Sox, Bears, Bulls, Blackhawks, Sky, Red Stars, Fire)
There's no shortage of sporting events within the city limits on any given day. The Cubs, White Sox, Bears, Bulls, Blackhawks, Sky, Red Stars, and Fire are just the most recognizable teams in a town steeped in rich sports history.
Concerts (Thalia Hall, The Vic, Park West, The Salt Shed, The Metro, PBottom Lounge, Aragon, House of Blues, Riviera)
Similarly, Chicago is also a regular stop for musicians on tour or local bands ready to play a show. With so many options, you can't go wrong with picking out a concert or two while in town.
Architecture Tour
We've already mentioned the kayaking architecture tour, but others will take you through the city landscape via trolley, boat, or foot.
Explore a network of tunnels and bridges that make up Chicago, experience the urban design of Chicago and its thriving stores.
Best Places for Food and Drinks in Chicago
Consistently ranked as the top cheeseburger in Chicago by locals and critics, Au Cheval will redefine the boundaries of culinary craftsmanship for the restaurant-staple-burger.
One of only 13 restaurants in the United States with three Michelin stars (the highest possible honor), Alinea is the only Chicago resident on the list. Pushing the limits of food science, gastronomy, and flavor, Alinea provides a consistent wow factor every night.
Deep Dish Pizza
Too difficult to choose just one of the staples in Chicago, deep-dish pizza, we're paying tribute to all of the restaurants who placed the city on the map and created a unique pizza (some would argue it's a pie). Lou Malnati's, Giordano's, Unos, Gino's East, and Pequod's are just some of the favorites among locals, with plenty of smaller pizzerias ready to shine given a chance.
An excellent opportunity to experience creative Japanese food and drinks for a reasonable price, Kumiko is a hot spot in Chicago's West Loop. If you're feeling extra fancy and adventurous, they even have a rare Wagyu beef sando on the menu.
Two restaurants that reside under the same management and in the same building, this location couldn't house two more drastically different experiences. Smyth is an upscale fine dining experience, while The Loyalist can challenge Au Cheval for the best burger on the block.
Manny's Cafeteria & Delicatessen
There's nothing fancy about Manny's, but it's a local favorite for a reason – it's always good. If you're craving deli food, this is your spot.
A green door signified a speakeasy was present during Prohibition, and one of the oldest remaining green doors in Chicago gives this iconic bar its name. Head downstairs and don't walk past the bookshelf is our advice.
While the sushi course may be light and refreshing, the omakase experience at Mako will also have your wallet a little light and in need of refreshing by the end of the night. However, this is a unique and memorable experience for sushi-lovers, with the restaurant just three years old and already world-renowned.
Looking for a great place to sample a wide array of beers in one place? Revolution Brewing has you covered. IPAs, porters, pilsners, Belgian-style ales… you name it, they have it. Plus, they have some great food in their BrewPub and Kitchen.
Enough with the fine dining. How about a biker bar and restaurant? Twisted Spoke is west of the Chicago River and serves excellent bar food and drinks in a relaxed setting. Perfect for a midsummer night in the Windy City.
Whether you are taking in the top 50 Chicago attractions as a tourist or local, reserving your parking space in advance means you have one less thing to worry about when it is time to fly. PreFlight can get you the off-site airport parking spot you need to make your trip that much easier with open-air, covered, and even valet parking.
Reserve Parking Today!
Choose Your Location
Atlanta
Boston
Chicago
Houston
Phoenix PreFlight Locations
AtlantaBostonChicagoHoustonPhoenix