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"Life moves pretty fast. If you don't stop and look around once in a while, you could miss it."
A line immortalised in 1886 movie Ferris Bueller's Day Off, filmed right here in Chicago 40 years ago, and more relevant in a chaotic world than ever.
I'm back to this contradiction of a city because Chicago (fun fact it's known as' 'The Windy City' due to hot air from politicians rather than the weather, which can also be windy) has my heart. This is a woefully, but also wonderfully, underestimated destination with British tourists and it's hard to understand why it gets talked about less than New York or Los Angeles.
Chicago is a city you have probably seen on screen more than you think. Those heading to New York for the movie filming spots will be surprised to find out how much of New York was actually Chicago - even the Home Alone franchise filmed in the city. (Yes. Kevin's family home is in Chicago). There are endless big and small screen links to the city from The Bear, to the Dark Knight when Chicago became Gotham City, The Fugitive, High Fidelity. The Untouchables, Ozark.. it’s a very long list and even Emily in Paris has filmed scenes in the city.
Chicago looking across Millennium Park to Lake Michigan (view from Cindy's Rooftop) | Nicola Adam | for Iconic MediaMy favourite, the iconic Ferris Bueller's Day Off filmed 40 years ago in 1986, was largely filmed in Chicago and suburb Northbrook. But there's so much more to the city than a location even if official filming notices are plastered to every lamppost or sign with impunity.
Chicago has heart, it has depth, and a fascinating history, which plays out through the smoky jazz bars, the prohibition eras iconography complete with speakeasies and the glossy skyscrapers glinting in the sun. (get a First Lady Chicago architecture tour - see below).
It is evident through the fiercely proud food, drink and dance culture and the very geography which ensures summer sizzles and winter is bitter at this city by the lake. You can walk from central Chicago to Michigan lake-side easily, giving Chicago a unique feel as you can escape from the madness any time you want and walk and gaze across the water.
The iconic film Ferris Bueller's Day Off celebrates 40 years in 2026For my return visit to Chicago I made the most of this, staying at the wonderfully historic Chicago Athletic Hotel on Michigan avenue. From my fourth floor hotel room I can see the famous landmark 'The Bean' - real name Cloud Gate - glinting across the road, while looking at park views all the way to Lake Michigan. These are moments from the start of the legendary Route 66 and a short walk into the central city. The hotel itself is constantly abuzz with life in its historic hallways which are tiled with marble, mosaic tiles and custom stained glasswork, accentuated with dark wood, which has been preserved throughout.
Chicago Athletic Hotel | Nicola Adam | Iconic MediaThe former, as the name indicated, athletic club, is atmospheric in its gothic detail playing homage to a different time where women were only allowed through the back door and only then to work. The rooms reflect its story, with furniture design inspired by athletic equipment.
Luckily there's no compulsion now to anything more physically energetic than a drink at the bar or to gaze at the astonishing view of the lake and city from the buzzing rooftop Cindy's restaurant.
If you do venture out the door you are straight into the heart of the city and it's a chance to get your step count up while deciding which cultural moment you want to be a part of. From the somewhat eccentric and interactive Yoko Ono: Music of the Mind at Museum of Contemporary Art Chicago where you can, amongst other things, hammer a nail into a wall, or travel in the lift which features the noise of a flushing toilet, to the American Writers Museum where you can read about those who have shaped US literature or perhaps start to write your own work on a proper old fashioned typewriter - the experience options are myriad.
Rosa's jazz bar, Chicago | Nicola Adam | Iconic MediaMeanwhile. the night is always young in Chicago, a city which still remembers the1920s prohibition era, and has been making up for it its lack of freedom ever since with an abundance of personality. Rose’s Lounge epitomises the spirit of the city with it’s authentic jazz vibes and we spent a fascinating evening at the Chicago Magic Lounge - which you enter via secret door in a laundrette into a dark and atmospheric club to be beguiled by magic tricks and cocktails. You don’t get more Chicago than that - Ferris Bueller would approve. Here are my top Chicago city tips:
MY CHICAGO RECOMMENDATIONS
STAY at Chicago Athletic Association Hotel Full of personality and history, this hotel is ideally located for Chicago newbies on Michigan Avenue so you can walk into the city, to the shore, to the Millenium park and 'The Bean and even to the start of Route 66. Plus, it’s a destination in itself and a mecca for history lovers.
HACK Save 48% on combined admission to five “Windy City” sights with a Chicago CityPASS® ticket. The cost $139 U.S.for adults and $109 U.S. for children 3-11. It's well worth the purchase and includes treats such as Skydeck Chicago and Shoreline Sightseeing Architecture River Tour. Purchase mobile tickets online at CityPASS.com.
BEST KEPT SECRET Chicago Magic Lounge, where you leave the ordinary behind you as you enter through the secret laundry entrance into a luxurious retro-inspired “speakeasy”. The rest is magic
TASTE Book Yes Chef Chicago: A Bear-Inspired Food Tour. This takes you to the restaurants featured on the TV phenomenon, The Bear. You travel and try the food at the actual spots where Carmy, Sydney, and Richie cook up their magic from beef sandwiches to doughnuts. My top tip is - don't eat breakfast first.
SELFIE SPOT ‘The Bean’ at Millennium Park, real name Cloud Gate, is a strangely fascinating large, highly-polished, mirrored bean-shaped sculpture by Indian-born British artist Anish Kapoor which reflects the city and is a magnet for tourists. Go early and wander through into lakefront Grant park (where the Lollapalooza festival is held) and the lake front trail.
FOOD My favourite meal of the trip was the buzzing and atmospheric Tortoise Supper Club. Expect Prime Rib, Hand-Cut Steaks & Fresh Seafood in a swanky, Jazz-Era setting, with live jazz on Fridays and Sundays. We also ate memorable German cuisine and the freshest pretzel I’ve ever had at The Berghoff, one of the city’s oldest family-owned restaurants which also brews its own craft beers.
WALK Lincoln Park; one of Chicago’s most beloved and picturesque neighbourhoods it's well worth getting a free guide or ‘greeter’ to walk you around the historic streets and tell you all the insider stories - shout out to the lovely Esther.
JAZZ Rosa’s Lounge, an authentic music joint with the vibes to match is a 40-year institution and a great place to spend an evening.
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