14/04/2026
Thinking about your next city break? Let me introduce you to Chicago — a bold, beautiful destination packed with culture, food, and unforgettable experiences.
Why visit Chicago?
Set on the shores of Lake Michigan, this city blends striking architecture with a relaxed, welcoming feel. It’s big enough to impress, yet easy to explore. Whether you love skyline views, world-class museums, or incredible food, Chicago delivers.
What you need to enter the USA
If you’re travelling from the UK, here’s what you’ll need:
• A valid UK passport
• An approved ESTA (apply online before travel)
• Return or onward travel details
• Travel insurance is strongly recommended
Always check the latest entry requirements before you go to stay up to date.
Top things to do in Chicago
Take in the skyline
Head up to Skydeck Chicago at Willis Tower for breathtaking views. Step onto the glass ledge if you dare.
Stroll Millennium Park
Snap a photo at Cloud Gate, better known as “The Bean”. It’s one of the city’s most iconic spots.
Explore Navy Pier
Navy Pier is perfect for a relaxed afternoon with lake views, food, and entertainment.
Discover world-class museums
Visit the Art Institute of Chicago or the Field Museum for culture and history lovers.
Eat like a local
You can’t leave without trying Chicago-style deep-dish pizza. It’s rich, filling, and completely different from anything in the UK.
Take an architecture cruise
A river cruise along the Chicago River is one of the best ways to see the city’s famous buildings and learn their stories.
When to visit
Spring and autumn offer mild weather and fewer crowds. Summer brings festivals and energy, while winter transforms the city into a snowy wonderland.
Chicago is a city that surprises you. One moment you’re admiring historic buildings, the next you’re discovering a hidden jazz bar or enjoying lakefront views.
Ready to plan your Chicago escape? Get in touch and I’ll help you create a tailor-made trip that fits you perfectly.
Haywood Escapes, an Independent Travel Consultant with Jamie Wake Travel.
Member of Protected Trust Services. All holidays are ATOL protected.