A Long Weekend in Chicago

25 Jan 2019

Flight Centre’s Alexandra Cronin gives us a whistle-stop tour of the Windy City, taking in food, architecture and lakeside living…

The Chicago skyline (image: Alexandra Gregg)

Friday

Check into a historic landmark: I love the Beaux-Arts grandeur of the Palmer House Hilton. The longest-operating hotel in the US, it’s been welcoming dignitaries since 1875. For a taste of 21st-century Chicago, head to The Hoxton (opening spring 2019). It’s set on a former meatpacking site in trendy West Loop, where ‘Restaurant Row’ offers plenty of dining options.

Me (middle) doing TILT! (image: Sarah Barnett)

Saturday

Big Bus Tours are a great way to get your bearings and discover the city’s vibrant history, from its days as a small trading post to hosting the World’s Fair in 1893, via a huge fire in 1871. To go it alone, hop on the ‘L’ train – an above-street section loops around Downtown. Take in the landmarks, then grab a deep-dish pizza at Pizano’s. If it’s sunny, get up high. At the 360 Chicago observation deck, a moving glass platform – known as TILT – tips you forward, leaving you gazing face-down at the streets 300m below!

Be sure to try the pancakes at the Pittsfield Café (image: Alexandra Gregg)

Sunday

Start your day with fluffy pancakes in the Pittsfield Building (Chicago’s tallest tower when built in 1927), then head to Millennium Park to see city and sky reflected in Cloud Gate, aka ‘the Bean’. Stroll to the Art Institute of Chicago for masterpieces such as Grant Wood’s American Gothic, or visit the Chicago Architecture Center and uncover the city’s reputation as a hotbed of architectural innovation. For decadence at dinner time, eat at Alinea, which boasts three of the city’s 27 Michelin stars.

Centennial Wheel at Navy Pier (image: Alexandra Gregg)

Monday

Spend the day exploring the 102-year-old Navy Pier. Jutting out into Lake Michigan, it’s home to a theatre, Ferris wheel, grand ballroom, funhouse maze and plethora of restaurants. If you’ve got any dollars left, splurge in the high-end stores on the Magnificent Mile or, en route to the airport, stop off at the Fashion Outlets of Chicago.

Segwaying at Lake Michigan with  Absolutely Chicago Segway (image: Alexandra Gregg)

If there's time...

Say hello to Sue (the largest, best-preserved T. rex ever found) at the Field Museum; take a Segway tour along the waterfront; or catch a jazz show at Al Capone’s favourite Prohibition-era speakeasy, the Green Mill.


Discover the Windy City and the Deep South on our Chicago to New Orleans Journey – make an appointment with a Travel Expert to find out more about our Chicago Holidays.


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Alexandra Cronin (Gregg)

Once a roving local news reporter and now a travel-obsessed writer/sub, I'm head-over-heels for nature, wildlife and the ocean. When I'm not getting up close to animals and sea creatures, I'm seeking out the sets of my favourite TV shows around the world. Follow me @wonderg1rl89.