Chicago
The Windy City That’ll Blow You Away (Literally & Figuratively)
Deep-Dish, Dazzling Skylines & Jazz Hands at the Ready
Say hello to Chicago – a city so cool it wears architecture like a designer suit and still has room for a slice of deep-dish pizza in its pocket. Perched on the edge of Lake Michigan, this cultural powerhouse is all about bold flavours, big personalities, and beautiful contradictions. It's where blues meets skyscrapers, gangsters meet museums, and you meet your new favourite city.

Whether you’re cruising the lakefront, snapping skyline selfies, or debating whether ketchup belongs on a hot dog (spoiler: it doesn’t), Chicago is packed with moments that surprise and delight. It’s artsy, edgy, warm-hearted, and just the right amount of quirky – like your mate who wears mismatched socks but can still rock a tuxedo.
The Perfect Pit Stop: A Chicago Stopover
Chicago’s O'Hare International Airport (ORD) is a major hub for both United Airlines and American Airlines, making it a fantastic and convenient stopover destination for travelers flying with these carriers from the UK. With direct flights available from London Heathrow and Edinburgh (Chicago is a Hub for American and United), you can easily turn a connecting flight into a mini-vacation and get a taste of the Windy City's incredible culture and energy.
The airlines’ extensive networks from ORD provide seamless onward connections to hundreds of destinations across North America, allowing you to break up a long journey with a vibrant and memorable stay. Instead of a quick, rushed layover, you can extend your time in Chicago, explore its world-class museums, iconic architecture, and delicious food scene, and then continue your journey feeling refreshed and inspired.
Latest Hotel Offers
Where the City Meets the Sea: Lake Michigan
For a city known for its towering skyscrapers and bustling urban landscape, Chicago offers a stunning and refreshing surprise: the vast, beautiful expanse of Lake Michigan. This freshwater "sea" is more than just a backdrop; it's an integral part of the Chicago experience, providing a playground for locals and visitors alike. From the moment you arrive, you'll be drawn to the lakefront, a vibrant area filled with parks, beaches, and a famous trail that stretches for miles. The sheer size of the lake makes you feel as though you've been transported to a coastal town, with sandy beaches and a sparkling horizon that disappears into the distance. Whether you want to sunbathe, play volleyball, or simply take in the magnificent views, Lake Michigan offers a perfect escape from the city's fast-paced energy without ever having to leave it.
The best way to experience Lake Michigan is to dive into the countless activities it offers. You can rent a bike and cycle along the 18-mile Lakefront Trail, a scenic path that connects many of the city's major attractions, including Lincoln Park, Grant Park, and the Museum Campus. For a different perspective, hop on a boat tour from Navy Pier, where you can choose from exhilarating speedboat rides, romantic dinner cruises, or insightful architectural tours that offer a unique view of the iconic skyline from the water. In the summer, you can even kayak or paddleboard on the serene waters. The lakefront is also home to major cultural institutions like the Shedd Aquarium and the Field Museum, making it a hub of both recreation and culture. A trip to Chicago simply isn't complete without spending time by this breathtaking body of water.
Top Tips for First-Time Visitors
(01)
Chicago O’Hare is one of the busiest airports in the world and, conveniently, well connected to the UK with direct flights from London, Manchester and Edinburgh. Flight time is about 8–9 hours, and once you land, the CTA Blue Line gets you downtown in about 45 minutes – so you can go from passport control to pizza in no time.
Taking the Chi-Town Route – Getting There from the UK
(02)
As with any trip to the USA, UK travellers need to apply for an ESTA online before flying. It’s quick, costs around $40, and is valid for two years. No ESTA, no entry – and trust us, being turned away at the gate isn’t the sort of drama you want on your holiday.
Visa Stuff – Do It Before You Jet
(03)
Bring your dollars – and bring a few small bills for tipping bellhops, bartenders, and that one street performer dressed as a giant bean. (Don’t ask, just enjoy.) Credit and debit cards are widely accepted, but having cash is handy for taxis and markets. And yes, prices are listed without tax – a fun game of guess-the-total awaits!
Dollar Bills, Y’all
(04)
They speak English here – but with a Midwestern twang and a lot of enthusiasm. Expect friendly small talk, a few “you betchas”, and perhaps a deep and meaningful chat about the Chicago Bears. Locals are happy to help, especially if you show some love for the city. Just don’t mention New York pizza. Ever.
Language & Local Lingo
4 Unmissable Things to Do in Chicago
Take a Selfie with ‘The Bean’ – Because, of Course
Officially called Cloud Gate, this giant shiny bean is the city’s most Instagrammed landmark. Located in Millennium Park, it reflects the skyline, the sky, and approximately 400 tourists trying to find the perfect angle. It’s shiny, weird, and utterly wonderful.
Cruise the Chicago River – Architecture with a Side of ‘Wow’
Hop aboard an architecture river cruise and be dazzled as you float past soaring towers, historic gems, and fun facts galore. It’s the best way to appreciate the city’s skyline without needing a crane or a very tall ladder.
Experience Skydeck Chicago – Step Into the Void
At the top of Willis Tower (yes, that building), you can step out onto The Ledge – a glass box suspended 1,353 feet above the city. Terrifying? Maybe. Incredible? Absolutely. Bonus: your stomach will drop before your phone signal does.
Catch a Show at The Second City – Where the Laughs Are Born
Chicago’s legendary comedy club is the training ground for countless SNL stars and comedy legends. It’s funny, sharp, and often improvised – so no two shows are the same. And who knows – you might just see the next big name before they hit Hollywood.
Reviews
Survival Guide: 3 Tips for a Windy City Win
Dress for Four Seasons – Sometimes in One Day
Chicago weather is like a toddler with a wardrobe – it changes its mind a lot. Bring layers, prepare for wind (it didn’t get that nickname for nothing), and if you’re visiting in winter… well, bless your brave soul. Just bring thermals.
Learn the Grid – It’s a Lifesaver
Chicago’s streets are a neat and logical grid, so once you get the hang of it, it’s easy to navigate. Streets are numbered, and the city is split into north, south, east, and west. If you get lost, just look for the Willis Tower, grab a hot dog, and recalibrate.
Try the Local Eats – Even If It’s Weird
Deep-dish pizza, Chicago-style hot dogs (with everything on them except ketchup), Italian beef sandwiches – this is not a city for the faint of heart or the low-carb. Come hungry, leave happy. Then nap.
Final Thoughts: Why You Need Chicago on Your Travel Radar
Where Big City Swagger Meets Midwestern Heart
Chicago is a city that surprises you – not just with its skyscrapers and skyline, but with its warmth, creativity, and energy. It’s equal parts grit and grace, a place where jazz clubs rub shoulders with world-class museums, and every meal feels like a minor miracle. Whether you’re catching a game at Wrigley Field or staring down your first deep-dish slice, this is one city that won’t just show you a good time – it’ll make you fall in love. So book with Flying Business Holidays, and let Chicago blow you away. Literally.