After our recent visit, we can see why Chicago has been named The Best Big City in the U.S. by Condé Nast for an impressive eighth consecutive year. Here’s a curated list of things we love and must-see attractions to make the most of your time in this vibrant city!
Getting there
Chicago O’Hare International Airport is the most connected airport in the United States, making it a great location for a pre or post stay.
For international flights – British Airways, American Airlines and United fly directly to Chicago O’Hare from London Heathrow. You can also fly direct from Edinburgh and Shannon with United. From the UK the flight is around 8-9 hours. Another great option is Aer Lingus via Dublin, which is one of the only airports outside of North America that offers a US Preclearance facility. The benefit of this is that arrivals are treated as a domestic flight allowing them to avoid immigration queues.
Once you arrive at O’Hare, you can take a taxi, a rideshare option like Uber or Lyft, or the CTA Blue Line train to downtown Chicago. The train takes around 45 minutes and is a cost-effective option.
Iconic foods
Chicago is renowned for its iconic food scene, with several must-try dishes that define the city’s culinary culture. One of the most famous is deep-dish pizza, invented in 1943 by Ike Sewell at Pizzeria Uno. This pie-like creation can be sampled at top spots like Lou Malnati’s, Giordano’s, and Pequod’s Pizza.
Another staple is the Chicago-Style Hot Dog, famously served without ketchup—asking for it is almost a sin! Instead, these hot dogs are loaded with mustard, onions, relish, tomatoes, pickles, and peppers. Popular places to grab one include Portillo’s, Superdawg, and The Wiener’s Circle.
For a sweet and savoury snack, try Chicago-style popcorn, a unique mix of cheese and caramel, often called the “Chicago mix.” The best places to sample this local treat are Moore Poppin and Garrett Popcorn Shops.
And for those who enjoy a tipple, there’s Malört—an infamous, intensely bitter liquor made from wormwood. You can find it in many bars around the city and we even have a bottle in our office, as the team have yet to muster the courage to try it!
Architecture
Chicago is home to some of the most iconic architecture in the world, including the Willis Tower (originally the Sears Tower), which held the title of the world’s tallest building for an impressive 24 years, from 1974 to 1998. While it now ranks as the 8th tallest building globally and 3rd in the Western Hemisphere, its place in architectural history is undeniable. Another standout is the St. Regis Chicago, the tallest structure in the world designed by a woman—an architectural triumph in its own right.
A fantastic way to explore Chicago’s architectural marvels is by taking an architecture cruise tour. First Lady Cruises, TripAdvisor’s top-rated boat tour, offers the best vantage point for viewing the city’s stunning skyline from the river. The 90-minute tour is led by expert guides who share fascinating insights into the history and design of the buildings.
Parks & Outdoor spaces
Millennium Park is an essential stop for anyone visiting Chicago. Situated in the heart of downtown, it’s home to the iconic Cloud Gate sculpture, fondly known as “The Bean.” One of the largest sculptures of its kind, its polished surface beautifully reflects both visitors and the city’s skyline, making it a perfect spot for photos.
The park also features the Jay Pritzker Pavilion and its expansive Great Lawn, which boasts a state-of-the-art sound system designed to recreate the acoustics of an indoor concert hall. During the summer, you can enjoy free live music while relaxing on the lawn with a picnic, creating the perfect outdoor experience.
Other highlights of Millennium Park include the playful Crown Fountain, the tranquil Lurie Garden, Maggie Daley Park, and an ice rink. Whether you’re looking for art, music, or green space, Millennium Park has something for everyone.
Sports
Chicago is renowned as one of the premier sports cities in the United States, drawing fans from near and far. No matter the time of year you visit, there’s always a thrilling sporting event to catch, whether you opt for tickets to experience the action live or settle into a lively sports bar to soak up the atmosphere there is something for everyone.
One must-visit location for sports enthusiasts is the historic Wrigley Field, the second-oldest ballpark in the country, steeped in rich history and tradition. You can go on a behind-the-scenes tour on both game-days and non-game days.
Seasonal Sports Overview
- Baseball (Cubs & White Sox): April to October
- Basketball (Bulls & Sky): November to June
- Football (Bears): September to January
- Hockey (Blackhawks & Wolves): October to May
- Soccer (Fire & Red Stars): March to September
Daredevils
Chicago’s observation decks—Skydeck and 360 Chicago—are located in two of the city’s most iconic skyscrapers and offer breathtaking views along with thrilling experiences. However, if you’re afraid of heights, these might not be for you!
At Skydeck, situated 1,353 feet up in the Willis Tower, you can step out onto The Ledge—a series of glass boxes that extend 4.3 feet from the building, allowing you to look straight down at the streets below. It’s sure to make your legs wobble! On a clear day, you’ll be treated to panoramic views of the city and can even see across four states: Illinois, Indiana, Michigan, and Wisconsin.
Over at 360 Chicago, located 1,030 feet above ground in the John Hancock Center, you’ll find the exhilarating TILT. This interactive feature allows visitors to stand against a glass-enclosed platform that tilts outward at a 30-degree angle, creating the sensation of leaning over the edge of the building. It’s a thrilling way to experience Chicago’s skyline from a whole new, downward-facing perspective.
Two scenic waterfronts
Chicago’s two waterfronts—Lake Michigan and the Chicago River—offer plenty to explore. Lake Michigan boasts 24 free beaches and the 18-mile (29km) Lakefront Trail for cycling and walking with stunning views. You can also visit Navy Pier for attractions and boat tours.
Along the Chicago River, the Riverwalk is perfect for a scenic stroll with restaurants and cafés. Don’t miss Art on theMART, the world’s largest permanent digital art installation, projecting vibrant visuals onto the Merchandise Mart building. Both waterfronts offer a mix of relaxation and activity, making them must-see spots in the city.
Route 66
The starting point of Route 66, famously referred to as the Main Street of America, is located in the Loop, just a stone’s throw from Grant Park’s iconic Buckingham Fountain. You can spot the historic Route 66 sign on Adams Street, which marks the beginning of the legendary Mother Road.
Museums
Chicago is home to over 55 world-class museums, each offering unique experiences. The Art Institute of Chicago houses the largest collection of Impressionist art outside Paris, making it a treasure trove for art enthusiasts. The Adler Planetarium, the first planetarium in the Western Hemisphere, offers a captivating journey through space. Meanwhile, the Field Museum, one of the top natural history museums in the world, features Maximo the Titanosaur, the largest dinosaur ever discovered, alongside countless other fascinating exhibits.
Big bus tour
The hop-on, hop-off Big Bus is your gateway to shopping, iconic landmarks, and the vibrant performing arts scene of Chicago. With 11 conveniently located stops, the bus takes you close to the city’s top attractions. Operating from 10 am to 6:38 pm, you can explore at your own pace.
The route includes must-see destinations such as the Chicago Riverwalk, Willis Tower, Millennium Park, The Art Institute of Chicago, Grant Park, Adler Planetarium, Museum Campus, Navy Pier, Water Tower, Magnificent Mile, 360 Chicago, and the Hard Rock Cafe.
Make sure to stop off at the Magnificent Mile, Chicago’s premier shopping district along Michigan Avenue, where you’ll find high-end stores, historic buildings, luxurious hotels, and the world’s largest Starbucks, which spans five floors.
With over 200 theatres and 250 live music venues, Chicago is a cultural hub. Whether you fancy catching a Broadway show, enjoying a laugh at The Second City, or experiencing live blues at Buddy Guy’s Legends, the Big Bus Tour will bring you close to these vibrant hotspots.
Festivals
Chicago hosts a vibrant array of festivals and events throughout the year, celebrating everything from music and food to art and culture. Top 5 you shouldn’t miss:
St. Patrick’s Day (Mid-March): Experience one of the world’s most famous traditions, featuring a lively parade downtown and the iconic green dyeing of the Chicago River—truly a bucket list event!
Chicago Blues Festival (June): Celebrate the city’s rich blues heritage with performances from both renowned and emerging artists across various venues, showcasing the heart and soul of Chicago’s music scene.
Chicago Gourmet (September): Indulge in a high-end food festival that offers exquisite tastings, live cooking demonstrations, and exciting competitions with the country’s best chefs, perfect for food lovers.
Lollapalooza (August): This iconic music festival takes over Grant Park, featuring an eclectic lineup of local talent alongside top acts from around the globe, making for an unforgettable musical experience.
Haunted Halsted Halloween Parade (October): Hundreds of witches, goblins, and zombies march through Chicago’s Boystown neighbourhood, known for its vibrant LGBTQ+ community. A panel of drag queens judges the best costumes, adding a unique flair to this spooky celebration.
