19/05/2026
Slightly embarrassing fangirl moment in the final slide - but if it helps me persuade you that you need to get to Chicago, I regret nothing! 🙀
I have visited more times than I can count. I wrote my dissertation on its architecture. I have friends who call it home - including my brilliant Chicago insider Lesley, who has been showing me round for decades. I genuinely don’t think there’s a UK travel agent who knows this city better than I do, and every single time I’ve sent someone there, it has become their favourite city in America.
Here are a few photos from over the years - since the digital age, anyway. There are plenty more on film, which I’ll save for another time! You’ll spot a Chicago hot dog in one of the pics - do you know how it differs from a New York dog? Let me know in the comments to win bragging rights…
Now I have a new reason to visit, as if I needed one. The Obama Presidential Center opens on 19th June, and it looks extraordinary. But Chicago has always been extraordinary - the city that rebuilt itself from the Great Fire of 1871 and gave the world the skyscraper. World-class food, music, architecture and culture, and a lakefront that stops you in your tracks every single time.
It’s also one of the greatest film cities on the planet; Blues Brothers, Ferris Bueller, The Dark Knight. You’ll also spot me and Lesley at Medieval Times - if you get the reference here you’re my kinda film fan! And, well... slide to the end and see a pretty famous set for yourself. 🎄
Until the end of May I have £100 off any Chicago itinerary as part of my independence launch offers. Whether it’s a standalone city break built around the Presidential Center opening, a wider US trip with Chicago as the centrepiece, or something completely bespoke - I’d love to build it with you.
If Chicago is on your radar, I’m your agent. Just drop me a message.
Check out for more inspo!