In a Nutshell: Chicago, Illinois
This Chicago in a Nutshell is the final post in ‘The Big Loop’ series, which chronicles our summer road trip from Ontario out to the West Coast of Canada and back via the northern US states.
Chicago in a Nutshell
The Windy City, Porkopolis, The Second City. Chicago has had many nicknames but over the few days we’re there the name that springs to mind is ‘Green City’. Thanks to the early 20th century visionary architect Daniel Burnham, Chicago boasts large areas of green space with over 35km of Michigan lakeshore set aside as public space. Chicago is well known for jazz, theatre and food but with parkland, outdoor music venues, cycle paths and river walks there’s no wonder it also comes alive with outdoor activities in the summer. This ‘Chicago in a Nutshell’ outlines just a few of our tips from our three days in the city.“Life moves pretty fast. If you don’t stop and look around once in a while, you could miss it.”– Ferris Bueller
Chicago in a Nutshell: Outdoor Highlights
Architecture Tour
Even if you’re not an architecture junkie, a 90-minute boat-based architecture tour is well worth it to get a feel for the city. After a large part of downtown Chicago was destroyed by a huge fire in 1871, the massive project to rebuild the city was the beginning of what would make Chicago a hub of innovative architecture. As the boat glides along, the guide uses the amazing array of buildings from the 19th, 20th and 21st century that line the river to tell the history of the city.
There are several cruises to choose from but the First Lady Architecture Cruise is the only one with guides trained by the Chicago Architecture Centre. There’s not really a bad seat on the boat but possibly the best ones are on the top at the front right side. The guide tends to talk about the buildings on the right as you cruise and if you sit at the front you don’t get other tourists heads in your photos. 
Stroll the Riverwalk
Burnham’s 1909 Plan of Chicago continues to shape the urban design, including as recently as the development of the Riverwalk public space. The Chicago River has had a rough trot ever since the 19th century. Originally used to shunt sewage first into Lake Michigan and then back the other way into the Mississippi, then as a shipping channel and dumping ground for industrial waste for many years, it was only in 1999 that the city decided to clean it up. Today the Riverwalk, completed in just 2016, is a hive of activity with people walking the shoreline, kayaking and boating on the water or sitting back at one of the many cafés and bars.
Millenium Park
‘Chicago’s front yard’ is a huge parkland area and at one end sits Millenium Park which is home to a huge band shell designed by Frank Gehry that hosts all kinds of free events, two 40m video water fountains with faces of Chicago locals spouting water onto delighted children underneath, oversized stainless steel walkways and the iconic Cloud Gate statue (the Bean) by Anish Kapoor.
Tuesdays on the Terrace
If you’re looking for some free jazz on a summer evening this is a good option. Take a walk through the Museum of Contemporary Art and then sit back on the lawn and listen to the free live jazz from Chicago and music from around the world. There’s a bar with snacks or you can bring a picnic.Cycle the Lakeshore
Burnham was so determined to see a city of public spaces that he used his own money to litigate against anyone who tried to develop on the Lakeshore. Much of that land is still public today and you can walk, run or cycle for miles along the lakeshore.
Chicago in a Nutshell: Indoor Highlights
At over 150 years, old, the Chicago Institute of Art is one of the largest art galleries in the US and a magnificent way to spend a few hours, or a few days. It also hosted one of the many famous scenes from Ferris Bueller. 
A Sunday on La Grande Jatte -1884 by Georges Seurat pointillism, the idea that dots of pure color mix together when you view them from afar.
“.. The more he looks at it, there’s nothing there. He fears that the more you look at him, the less you see.”Beware that the museum is much larger than it seems. On our visit we spent over an hour in the modern art section before realising there was an underground hall that leads to the main part of the museum: a realisation that was both exhilarating and exhausting. We left in defeat but vowed to return.– John Hughes, commenting on Cameron staring at the painting in the movie
The Home of Improv
Ever since 1959, improv shows have been running at the institution of comedy, Second City. It’s famous for launching the careers of countless comedic actors including Bill Murray, Tina Fey and Mike Myers to name a few. There’s shows every night and twice a week they run a 90-minute show called The Best of Second City with an audience of about 200. There are other comedy rooms in the area too.
Chicago Architecture Centre
You get a free ticket with your river tour and it’s well worth taking a look. There are cool displays about the history of the city and some future urban design ideas. When we were there they had a fascinating display all about the use of wood for building high-rise buildings of the future.
Chicago in a Nutshell: Food and Drink
West Loop and Fulton Market
The West Loop, the old meat-packing district of the city, has been transformed into a hip area of restaurants, shops and galleries. There are several key streets including Randolf Street and Greektown, as well as Fulton Market, where warehouses that have been transformed into restaurants line the street.
J9 Wine Bar in swanky Lincoln Park is in a 100-year-old building that used to be an auto shop.
Chicago in a Nutshell: Where to Stay
We chose to stay at the Swissotel, right in the heart of downtown. It was surprisingly inexpensive for such a big city, and about the same price as most of the Airbnb’s that we looked at. The room was great (huge!) and its location was second to none. We had a car with us, but instead of using the (pricey) hotel parking, we found a cheaper long term spot a few blocks away using spothero. Easy peasy.
Chicago in a Nutshell: Getting Around
- City Bikes are easy using Divvy. Chicago has one of the highest rates of cycle commuting in the US and has a great cycle path network. So even off the lakeshore cyclepath it’s easy to get around by bike. There are over 30km of biking trails along the lakeshore and the city bike lanes are well marked.
- Chicago Greeters offer local guided walking tours of different neighbourhoods of the city. Unlike ‘free tours’ in other cities this a volunteer service with a no tip policy.
Chicago in a Nutshell: When to Go
Summer and Fall are beautiful but also the busiest times for tourists. Chicago is notorious for flight delays in winter and it’s not called the windy city for nothing. The frigid wind that comes off Lake Michigan and straight down the city streets makes for a very different experience to a warm summer day.
Chicago in a Nutshell: Before you Go
Look up music festivals, theatre or comedy shows to find a date to visit. Lollapalooza is in a huge park right in the middle of the city.
Plan your fun and food using Eater Chicago and Choose Chicago