When it comes to planning a USA city break, some cities steal the spotlight straight away – think New York, Los Angeles, or Las Vegas. But if you’re looking for a destination with authentic charm, stunning lakefront views, incredible food, and world-class culture, Chicago deserves a prime spot on your shortlist.
Whether you’re planning a romantic couples’ escape or just fancy soaking up big-city energy with a bit of extra soul, Chicago is a place that surprises and delights. Here’s why this vibrant city should be your next Awesome Travel Experience…
🌆 A City of Stunning Architecture and Skyline Views
Few cities in the world can compete with Chicago’s iconic skyline. Set on the shores of Lake Michigan, the cityscape is both dramatic and beautiful, especially at sunrise or sunset. It’s home to some of the tallest and most influential skyscrapers in the world, including the Willis Tower (formerly Sears Tower), the John Hancock Center, and the strikingly modern Aqua Tower.
For couples, the Chicago Architecture River Cruise is a must. It’s the best way to take in the skyline while learning how Chicago shaped the modern world of architecture – all from the comfort of a boat, glass of wine in hand.
🎷 Culture, Music & Museums for Days
Chicago is famous for its deep connection to jazz and blues. For an evening out that’s full of atmosphere, head to a live music venue in the South Loop or Lincoln Park – think exposed brick bars, low lighting, incredible talent, and cocktails that don’t miss.
Culturally, Chicago punches well above its weight. The Art Institute of Chicago is one of the top art museums in the world – perfect for an afternoon of quiet wandering and inspiration. Prefer modern works? Don’t miss the Museum of Contemporary Art, or if you’re into history and science, explore the Field Museum and Adler Planetarium.
🌳 Parks, Lakes & Outdoor Living
One of Chicago’s most appealing traits is how well it blends urban excitement with green spaces and waterfront views. Millennium Park, home to the famous “Cloud Gate” (better known as The Bean), is a brilliant starting point. It’s where locals and tourists alike relax, take selfies, or enjoy outdoor concerts in summer.
For a romantic walk or bike ride, the Lakefront Trail stretches over 18 miles and offers breathtaking views of Lake Michigan. You could even rent a tandem bike, or simply stroll with an ice cream, watching sailboats drift by.
Looking for that perfect Instagram moment? Navy Pier delivers – with its waterfront promenade, rides, rooftop bars, and sweeping views.
🍕 Foodie Heaven – From Deep Dish to Fine Dining
Let’s not forget the food. Chicago is legendary for its deep-dish pizza, and it’s worth every bite. Try it from Giordano’s, Lou Malnati’s, or Pequod’s. But that’s just the start. The city is a melting pot of flavours – from hearty Italian beef sandwiches to award-winning Michelin-starred restaurants.
You’ll also find world-class brunch spots, rooftop dining experiences, and hidden speakeasies serving up creative cocktails. Whether you’re after street food or silver-service, Chicago serves it with passion and flair.
💖 Perfect for Couples
What makes Chicago so appealing for a city break is how it manages to be lively without being overwhelming. It has all the excitement and sophistication of a big American city – but with a more relaxed and welcoming vibe.
You can spend your days museum-hopping or shopping on the Magnificent Mile, then unwind with rooftop drinks or a jazz show. Or simply catch a sunset from North Avenue Beach, picnic in the park, and stroll the lit-up bridges by night. It’s a city made for making memories together.
✈️ Easy Access & Direct Flights from the UK
Chicago is well-connected from the UK, with multiple direct daily flights from London Heathrow to O’Hare International Airport. Flight time is around 8.5 hours, and thanks to the time difference, you can often arrive in the early afternoon – just in time to freshen up and head out for dinner and a show.
🎯 Let’s Make Your Trip to Chicago Awesome
At Awesome Travel Holidays, we specialise in tailor-made holidays that go beyond the ordinary. A Chicago city break can be a quick getaway or part of a longer USA adventure. Why not combine it with a train ride to the Rockies, a Great Lakes cruise, or a foodie tour through the Midwest?
Whatever your travel style, we’ll craft your Chicago trip with personal touches and insider knowledge – so you experience the very best the ‘Windy City’ has to offer.
Other travel guides in this USA series include:
🌎 Not Just Travel – Awesome Travel Experiences 🌎
