Chicago: The Bean, The Beef, & Beautiful Boat Scenes

The last time I set foot in Chicago, it was 2008 and I was sleeping on the sitting room floor of my friends who were doing a J1 there. Charming in a student-budget sort of way, but this time I was more than ready to swap that for something a little more sophisticated.

Thanks to Choose Chicago, we headed over for a trip themed around icons of the screen and legendary soundtracks. And the city definitely delivered. Our base was The Chicago Athletic Association Hotel, a luxury boutique spot that began life as an 1893 private men’s club and now blends modern chic with old-world charm.

Think Gryffindor Common Room vibes in the lobby, only with better drinks. From my window, I had stunning views of The Bean and Millennium Park, and late October was the perfect time to do some exploring.

We kept night one relaxed with dinner at The Dearborn Tavern, made even better when we learned it was owned by Irish sisters Amy and Clodagh Lawless. Impeccable service and excellent food set the tone for the days ahead.

Day two began with the First Lady’s Chicago Architecture River Cruise Tour – a jaw-dropping glide through the city’s iconic skyline and the stories behind it. After a wander around the American Writers Museum, we spent the evening at the Chicago Magic Lounge.

Entering through a fake launderette, we found ourselves in a world of sleight-of-hand and comedy, discovering Chicago’s unexpectedly rich magic tradition along the way.

Our CityPASS came in handy throughout the trip, giving us access to extra sights. I headed to The Art Institute of Chicago (as seen in Ferris Bueller’s Day Off) to admire its standout pieces, then took in sweeping city views at 360 Chicago on the 94th floor of the John Hancock Building.

A major highlight was Yes Chef Chicago: A Bear-Inspired Food Tour. Fans of The Bear will appreciate the thrill of stepping into some of the show’s real-life references, mainly from Sydney’s whistle stop tour of Chicago food hotspots in season 2, episode 3.

Things kick off where you’d expect though – the Italian beef shop that inspired Mr Beef, the chaotic centre of season one. 

Dinner another night was at Tortoise Supper Club. Low light, velvet booths and hand-cut steak, it felt like a very authentic Chicago experience.

A jazz trio played throughout the meal, which was a lovely touch. Afterwards we swapped jazz for blues as we pushed on to Rosa’s Lounge to see the Carlos Johnson Band.

This one fills up quickly so if you’re heading along, don’t leave it too late! Get in early and nab yourself a good view.

Our Chicago Greeter tour of Lincoln Park with local guide Esther Honson was another standout.

Esther was hilarious, and wonderfully in-the-know, guiding us through picturesque streets and very wealthy neighbourhoods where the Halloween decorations were gloriously over the top.

For a trip themed around screen icons, Chicago itself turned out to be the star. Sign us up for a sequel!

For more information on Chicago, visit www.choosechicago.com