Chicago is the first stop on my road trip, and hopefully, one of two long drives that I’ve planned (the second long drive will be the one that takes me back home in about 8 weeks.)
The drive from Toronto to Chicago is easy, albeit long. All it takes are two highways – the 401 highway in Canada, and the I-94 in the States. Maps not required, although breaks for the ~800km journey are, and a lovely detour is a stop in Ann Arbor, Michigan. The town is home to the University of Michigan, and you can’t miss the town’s athletic pride. The town, even in the summer when many students have left the city, is painted blue and yellow. The buses are blue and yellow. There are numerous blue and yellow Wolverine merchandise stores. Several windows display the blue and yellow Wolverine flag. As we walked the streets we even heard football players that were in town exchange pleasantries with their coach who was cruising around town in a golf cart. It made me crave a visit to the city during football season, imagining football madness as portrayed in Friday Night Lights.
Ann Arbor is easy to stroll around – just find State Street and turn off the main road when you see something interesting. Aside from the University of Michigan, Ann Arbor has beautiful bookstores, cafes, a drive-thru liquor store and lots of trees, hence the ‘Arbor’ – the ‘u’ was dropped many years ago.
We arrived in Chicago during rush hour and the first task for a roadtripper is to find safe overnight parking. Parking in Chicago is a pain. An expensive pain. Many hotels offer paid parking, ranging between $25 to $45 for 24hrs and I even saw parking for $24/30min. There are early bird deals, and parking outside of the city core is cheaper. It’s probably best to get in touch with someone who lives in Chicago and kindly ask them for their visitor parking permits in exchange for drinks and dinner. Thankfully, my roadtripping friend, J, knows a couple who lives here and we were able to get these 🙂
A quick note about my roadtripping friend: We met in London 8 years ago. We arrived to the UK on the same day and shared a bunk bed at the International Hostel on Great Portland Street. Three days later, after walking, eating, dancing and drinking our way through town, we moved into a studio flat in Cricklewood, London. J returned to the States 6 months later, while I stayed in London for another 6 years, but we have remained great friends. Whenever I road trip through the States, visiting J is always on the itinerary. That’s the beauty of travelling – you’re going to meet incredible people on your travels, and a few of these people are bound to become your closest friends.
Back to Chicago. The city lies on the south-eastern tip of Lake Michigan, with beautiful canals winding through the city. The tunnels are perfect for wind play, hence the nickname, I suppose, ‘The Windy City.’ I, however, think that more than windy, Chicago is a city of textures – rough, soft, angular, curvy, glossy, granular, pointed, silky, smooth. In 1871 a great fire burned over 70,000 buildings, but Chicago rebuilt quickly and many of these older structures are still standing, but now they are hugged by modern buildings. The intricate blend of old and modern architecture is a treat for those who like to walk the city with their heads high and their eyes busy. The contrast is created by buildings such as Marina City, the floors of which look like flower petals (to me anyways), the Smurfit-Stone Building which looks like it has been expertly sliced, diagonally, the enormous Civic Opera House which imposes itself on the riverfront, and the old-fashioned brick townhomes which extravagant balustrades, decorative crowns and stone statues. What Chicago homes also do very well are roof-top patios and gardens – the city has atmospheric, tree-lined avenues, but you see trees and bushes and lots of green when you look up at the buildings, too. The city is sprinkled with colourful murals, so when you come to Chicago, don’t just strut along Michigan Ave where all the big stores live – there is a lot to see if you turn here and there.
Of course, for budget travellers like me, enjoying the textured city is amazing because walks are free. Other relaxing, yet stunning walks, include the waterfront walk along the beaches and a stroll through Millennium Park – the home of the Bean and other fun sculptures.
- Free movies in the park – we happened to be in Chicago on a viewing of ‘Dirty Dancing’ and had a wonderful time. Bring a blanket, snacks and wine. It will make you feel like a local (I don’t think I spotted other travellers there, unless they too, were excellent at blending in.) If you happen to forget a bottle opener, don’t fret – people are willing to share theirs.
- Free people gazing – we sat down to take a break on one of our river walks and noticed, on a bridge, a man in a bright red dress shirt and a neon pink suit. Every time a tour boat passed under the bridge he would break into a routine, swiftly taking off his suit, spinning it around, gliding it back on, and finishing the routine with happy jazz fingers. We watched this in awe for sometime until we heard a tour guide shout into his microphone, ‘Hey Vincent!’ followed by the announcement that this was Chicago’s famous ‘Suit Man.’ We learned it was his birthday. As we continued our walk, we stopped to wish Vincent a happy birthday and were treated to puns and smiles. An eccentric fellow in a great city. Google this man – Vincent Falk – there are plenty of articles and even a documentary about him.
- Cheap fun – The ‘Second City Neighbourhood Tour’ for $15, or a comedy show in the evening for ~$22. We went to both – it’s always a perfect day if you spend the entirety of laughing. The Neighbourhood Tour takes you around Chicago’s Old Town while you learn about Second City’s history. You’ll also learn really important facts, like Chicago means ‘stinky onion.’ The tour guide will share funny stories about the Second City alumni, including Bill Murray, John Candy, Chris Farley, if you ask. In the evening we saw, ‘Afro-Futurism’ – it was hilariously witty.
- Cheap fun – Chicago is a city full of cheap and affordable eats, and this is a place where you can choose to do a tour of the world’s foods. If you’re in Wrigleyville you may try ‘Paul’s Noodles’ – they make their own noodles and the ramen is delicious. If you like Indian, we enjoyed the lunch buffet at Mughal India – it’s a no fuss kind of a place. And, of course, you’re in Chicago, so do step into any of the joints that claim to be Chicago’s first deep dish pizza and gorge on the stuff.
- Cheap fun – Happy Hour, in most pubs, starts at 4pm. Chicago has many of its own breweries, and host to plenty of other flavourful craft beers.