Chicago, Second City? Not by our count pal
Chicago is world-class in so many categories; cutting-edge architecture, stand-up comedy, art, Instagram-worthy dining, and a massive brewing scene make the Windy City one of the US’s buzziest destinations.
“Chicago is the great American City,” Norman Mailer once said, and he’s bigger than us so who are we to argue?
Edgy, progressive, dynamic and impressive there are few skylines as confident as Chicago’s. Since the Great Chicago Fire swept through in 1871 (destroying huge parts of the city), the spectacular urban sprawl has become nothing short of an architectural melting pot. Attracting the World’s big-hitting architects and urbanists from Mies van der Rohe to Frank Lloyd Wright to modern day masters like Jeanne Gang.
It is the birthplace of the skyscraper and the best way to see these downtown architectural wonders is from the water. Both the Chicago Riverwalk and Lake Michigan offer unparalleled vantage points for taking in the city’s world-famous buildings. A great way to see these concrete marvels is by hopping aboard the ‘First Lady’ on a Chicago Architecture Foundation Center River Cruise – it is a must-see experience. The tours are conducted by local volunteers full of insightful anecdotes and a real enthusiasm for the Chicago skyline and its history.
CHICAGO RIVERWALK
The bustling waterfront has redefined the downtown core integrating a scenic pedestrian walk with its historic neo-classical skyscrapers. The Riverwalk is the ‘lungs of the city’ and is all about recreational experiences, whether walking, cycling or kayaking.
If that all sounds a bit energetic the Riverwalk is also the backdrop to Art on theMART; the largest video-projection art installation in the world. Taking up approximately 2.5 acres of theMART’s river-facing facade, The Merchandise Mart is the world’s largest commercial building and design center. Since its 2018 launch, the project has provided a public platform for large-scale moving image work by renowned local and international multi-disciplinary artists such as Nick Cave and Barbara Kruger. (See curated video art Wednesdays through Sundays, from March through December, 7:15 – 9:15pm).
But Chicago isn’t just a city of skyscrapers and rivers, it is also a city of neighbourhoods. Made up of more than 200 that are collectively referred to as ‘Chicagoland’ it’s an international city with a local feel and a plethora of hip locale hang-outs to explore.
In three days we couldn’t get to all of them, but some of the ones we did get to include:
ANDERSONVILLE
On Chicago’s Northside, Andersonville is known for its Swedish roots, historic architecture and bustling urban Main Street. Scandinavian history and culture are kept alive and well through The Swedish American Museum, which houses artefacts dating back to the mass immigration of Swedes to Chicago 200 years ago, as well as a series of rotating exhibitions of contemporary Swedish artists’ work.
The area is also recognised as the “shop local capital of Chicago,” supporting the largest network of local and independent businesses in the area as well as home to one of Chicago’s largest LGBTQ+ populations.
WICKER PARK / BUCKTOWN
Wicker Park and neighbouring Bucktown are hipster havens known for their art, community, nightlife, and food scenes. Each neighbourhood has a unique architectural style, but both are brimming with street art, bars, and restaurants.
You can easily spend an afternoon checking out the eclectic independent stores scattered throughout and Milwaukee Avenue is home to an array of funky vintage shops with vinyl lovers able to spend hours browsing the racks of Reckless records.
A great way to see these areas is on the 606, a repurposed walkable rail line that gives you an elevated view. You’ll find public parks, art installations, and plenty of joggers along the 2.7-mile stretch.
THE BEAN: MILLENNIUM PARK
It seems that no trip to Chicago can happen without taking a selfie next to Anish Kapoor’s giant sculpture ‘Cloud Gate’. Affectionately known as ‘The Bean’ the public artwork has become synonymous with the Chicago experience.
Inspired by liquid mercury, it is one of the world’s largest permanent outdoor art installations. Its stainless-steel surface reflects the activity and lights of the park and surrounding city skyline, inviting visitors to touch and interact with its mirror-like surface and see their image reflected from a variety of perspectives. If insta selfies are your thing then this is the spot for that quintessential shot. ‘The Bean’ is an icon of the city and a wonderful piece of outdoor art that members of the public continually engage.
LURIE GARDEN, MILLENNIUM PARK
An urban oasis for city dwellers and wildlife alike, Lurie Gardens is a perfect model of urban responsible horticulture, providing a healthy habitat for a wide variety of plants, animals and insects. Built over the top of an underground parking garage, the Gardens reclaim three acres of land in the downtown area to offer a quiet respite for people and urban wildlife.
KINGSTON MINES
No visit to Chicago would be complete without hitting at least one Blues club, and Kingston Mines is the largest and oldest. Its twin stages have been graced by scores of musical greats and are packed with the finest nonstop blues seven nights a week. With its motto: “Hear Blues – Drink Booze – Talk Loud – You’re Among Friends!” you know you’re in for a good time.
WILLIS TOWER
What you talkin’ bout willis? Previously known as Sears Tower, this whopping 110-story skyscraper was the tallest building in the World for almost 25 years. It’s now the second-tallest building in the US (after New York’s One World Trade) and more than 1 million people visit the observation deck each year. The highlight for most visitors is the Ledge; extending 4.3 feet beyond the building’s exterior, this platform is made entirely of glass and is a great place to get a photograph for the ‘gram’. The line can be pretty big though, so get there early in the morning to beat the rush.
willistower.com
LOU MALNATI’S
There’s pizza and then there’s Lou Malnati’s Pizza which takes it to a whole new dimension. The original Chicago-style deep dish pizza recipe was first created in the 1950s and is immense. Chicago-style deep-dish pizza is the heartiest of the pizza varieties and is typically eaten with a knife and fork. If you’re looking for great pizza in Chicago, you don’t have to look very hard. Just skip the starters and get to the Deep Dish main event. Try The Lou Deep Dish Pizza (with extra sausage).
loumalnatis.com
BANG BANG PIE & BISCUITS
Bang Bang Pie has been serving comfort food to the Logan Square neighbourhood for ten years and has gained a local reputation for its delicious food and warm hospitality.
Even during the pandemic, it often had a line stretching around the block. It’s a cool little cafe with a chalkboard menu, counter service that seats 15-20 people inside, and includes a large patio out the back. It’s part coffee house, part bakery, and wholly a place that you’ll want to eat in.
Try the Key Lime pies – comfort food doesn’t come much better than this. Over-ordering food is practically unavoidable, so clear your schedule for the rest of the day.
bangbangpie.com
MIDDLEBROW BUNGALOW
Just across the road from Bang Bang Pie sits Middlebrow Bungalow. A lovely looking bakery, it’s light, bright and serves up fresh-baked bread and pizza, but that’s not what we went for (we’d just left Bang Bang Pie after all) most importantly for us, it’s a great brewery too pouring a wide-ranging selection (including Saisons, sours, and Belgian style beers). The ‘insta’ friendly space features refurbished furniture, plants in birdcages, and communal drinking and dining on picnic tables topped with tea lights. A pleasant spot to spend an afternoon, going into the evening.
middlebrowbeer.com
CAFE TOLA
Espressos and their beloved empanadas – little pockets of fried goodness and hands down, the best snack food you will ever taste are the order of the day at this hole-in-the-wall takeaway joint. The Lakeview venue bursts with colourful Mexican pizzazz adorned with bright artwork. Try the spicy pork empanadas.
cafetola.com
AL’S BEEF
Italian beef sandwich is perfect from this hole-in-the-wall style cafe. You can get it hot (with giardiniera peppers) or sweet (with sweet peppers); dry (no gravy), wet (extra gravy on top), or dipped (the whole sandwich takes a bath).
It’s not hard to see why Al’s is a long-term favourite among Chicagoans and a mandatory port of call for many a visiting celebrity and tourist alike. No matter how you order it, you’ll be getting a taste of one of Chicago’s most famous creations — the Italian beef sandwich. The delicious (and messy) creation consists of a crusty Italian roll piled high with thinly sliced and seasoned roast beef, plus your choice of peppers and au jus sauce (or gravy, as some places call it).
alsbeef.com
SLEEP
CANOPY BY HILTON CHICAGO CENTRAL LOOP
Located directly across the street from Willis Tower, in the epicentre of Chicago’s financial district, famous attractions such as The Art Institute of Chicago, Millennium Park, and Chicago Riverwalk are all within walking distance.
The hotel is surrounded by restaurants, shopping, and theatres and the public transport links are great, with Quincy Metro Station just steps away. hilton.com
Second City? Not by our count pal. Chicago isn’t just Frank Sinatra’s kind of town, it’s ours too. For further information visit Choose Chicago.
