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DTour Part 8: How to spend 3 days in Chicago


           After the humid warmth of Texas it was a brutal awakening to find myself in freezing cold temperatures and icy winds in Chicago, in Illinois. I quickly made the switch from denim shorts and sun dresses to boots and multiple layers of knitwear and was able to brave the outdoors. So many of the best things to see and do in Chicago are in fact outdoors so I would carefully pick the month of your trip if I were you!

           I was staying at another DoubleTree by Hilton hotel, the Wit, in a perfect location on State St and Lake St. It’s perfectly close to the riverwalk, State St is one of Downtown’s most thriving and active areas and it’s only a short walk away from Millennium Park and the landmarked Michegan Avenue Streetwall. It also has the no.1 roof bar in the whole of Chicago on the 27th floor, called Roof, which is a nightclub on the weekends. I’ll admit to not knowing a huge amount about Chicago before arriving, so I set about working out what the city is known for and what I shouldn’t miss during my three-night stay in the metropolis.

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           On my first day in a new city, walking around aimlessly is my favourite way to familiarise myself with the area. As I’m not focussing on getting anywhere in particular, I open my eyes up to my surroundings and simply follow whatever catches my eye. My meanderings took me all through Downtown, through parts of Grant Park and even to the lakeside from where I took photos of the impressive skyline. Going on local recommendations I then headed to Pizano’s on Madison St, a typical American sports bar-restaurant showing ice hockey & American football on screens, to try the infamous Chicago deep-dish pizza. Sitting at the bar rather than a table, I ordered a small pizza and barely managed half of it, I was completely stuffed. It was very rich but I think I’ll stick to the thin crust pizzas from Italy that I know and love.

           On Day 2 I had a more structured plan. The Art Institute of Chicago has a phenomenal number of famous paintings and works of art from every era, every country and every movement. You really need a couple of days to explore it thoroughly and appreciate the entire collection but the museum has cottoned on to the fact that most people won’t have enough time to see it all, and they’ve created an excellent app that guides you around the museum based on what collection you’re interested in, how much time you have available, what the occasion is (Rainy day? First date? Family visit?) and even by theme. Their 1-hour tour is particularly good as it guides you through all parts of the museum and you can stop along the way to linger in any section that particularly strikes you.

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           As you emerge from the Art Institute you will see the Chicago Architecture Foundation opposite you. Architecture is what Chicago is famous for, and some even claim that it’s the home of the skyscraper. I couldn’t leave the city without learning about some of the buildings that make it such a striking city, and a walking tour of the historic Downtown seemed the perfect way to do so. I opted for the tour of the North Loop called ‘Treasures of Culture and Commerce’ and a group of 6 of us set off into the bracing but sunny day outside to learn. CAF tours are given by volunteer docents who have had hundreds of hours of training, and as they’re volunteers rather than paid staff, they all give these tours out of a deep passion for the architecture of their city. Our guide Marcia was absolutely lovely and really knows her stuff. This 2-hour tour focussed on the area along Michegan Avenue and State St, so we learnt about the Art Institute, the Streetwall, Millennium Park, the fire of 1871 that largely destroyed the wooden-built city and made way for the newer skyscrapers, the commercial and industrial boom that Chicago enjoyed as a transportation hub thanks to its railroads and waterways. We even explored inside some buildings, such as the former Public Library, the Marshall Field building and the gorgeous Palmer Hotel, all of which I would heartily recommend. The two hours were up in the blink of an eyelid and I headed into Millennium Park to see the infamous “Bean” (its real name is Cloud Gate), the Pritzker Pavillion and some of the outdoor artwork and sculpture on display. The park was in fact completed four years after the millennium, but it has created a focal point in that area of Downtown that the locals seem to love.

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           I then dashed back to the Wit Hotel to meet Jenn Winter, the Europe DTourist who just returned from her DTour a few weeks ago (I recommend you check out her blog ‘A Lady Away‘ to see what she got up to!), and the Asia DTourist MJ Tam who’ll be departing on her DTour in March 2014 (keep an eye on her website ‘Chicagonista‘) and who also happens to live in Chicago! They have both looked after me so well while I’ve been hanging out in their hometown, and have shown me parts of the city that no normal tourist would know about… We began with a private boat trip along the river with the Chicago Electric Boat Company that departs just under Marina City. You can rent out these very environmentally-friendly boats to skipper yourself, without any kind of qualification, and I can imagine myself doing that every single day in summer – it’s such a brilliant idea! Jenn’s brother-in-law took us out on the water, allowing us to enjoy some bubbly and swap stories about our DTours, about our travels around the world and about the very city we were in, Chicago. Jenn, MJ and I make up one half of the pack of six DTourists who were fortunate enough to win this incredible opportunity to travel the world with DoubleTree by Hilton, the other three being fellow Brit Jen Lowthrop, and the other two Americans Megan Claire and Loren Klein. The best view of Chicago really is from the river and it’s a perfect way to see the light fade and the city’s lights come alive for the night. We continued nattering for the rest of the night, first at dinner in Rockit just north of Chicago River & then Jenn and I headed to a Blues bar in Lincoln called Kingston Mines for some great live music.

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           By Day 3 I was in need of a lie-in (I had been on the road for over 3.5 weeks by the way!) and minimal walking. Jenn came to my rescue and suggested lunch in Museum Campus, just south of Downtown, where you’ll find the Adler Planetarium, the Shedd Aquarium and the Field Museum. That area by the Soldier Field Stadium has a fantastic view of the waterfront and the Chicago skyline, and we then drove up Lake Shore Drive past Downtown, over the river mouth, through Lincoln Park and then into the Old Town, so I could get a feel for the different neighbourhoods that comprise the enormous city. As a local guide I couldn’t fault Jenn – she explained everything from the city’s various nicknames to the local celebrities, from the best party beaches in summer to the city’s relations with the surrounding states and all the different characteristics of the various states. She dropped me off back in Downtown and I quickly managed to fit in two other not-to-be-missed activities before we regrouped that evening for dinner (ahem, that should read ‘full-on feast’) with MJ in Chinatown. The first of these two was a river boat architecture cruise by the Chicago Art Foundation. It cost about $39, lasted 90 minutes and was a great way to marry up everything I’d learnt from the walking tour and my lovely friends Jenn and MJ on my boat trip the night before. A guide explains the origins of each building you pass while you sit up-top on deck. Bring layers.

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           After that I finally made it up the Willis Tower (the locals still call it the Sears Tower), the tallest building in the western hemisphere at a mind-blowing  1,729 ft. London does of course have some skyscrapers in the financial and business districts (I went up the Shard a few weeks ago, you can read about it here) but by and large it’s much flatter than your average modern city, so I am still stunned by the sheer height and size of the skyscrapers around me in Chicago. An ear-popping and lightening-fast lift teleports you to the 103rd floor where you have a 360º view and the Skydeck. The Skydeck is a glass box stuck out on one side of the skyscraper, with a glass floor, walls & ceiling, and it is incredible to step out above the entire city! Granted, you have no risk whatsoever of falling out but it’s still pretty thrilling and it makes for a good “I can hover” photo. Try to arrive 30 minutes before sunset to see the light change and I enjoyed picking out which buildings I recognised from my two architecture tours. There’s a fantastic view of Lake Michegan too.

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           It was certainly a busy few days in the windy city but it really surprised me how much I liked it. It’ll be interesting to see how it compares to New York City… But before I skip ahead to New York I need to tell you about my trip to Niagara Falls – which was also my debut trip to Canada!


[I am travelling around North America as a DTourist on behalf of DoubleTree by Hilton. You can find out more about how I won this incredible opportunity here]


  1. Yay, so glad you had fun and it was great showing you around my city! I had such a wonderful time meeting you and hearing all about your adventures!

    One edit… Soldier Field is the big stadium on museum campus where the Chicago Bears play and Wrigley is further north, where the Cubs play.


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