CHICAGO | Looking to see the real Chicago through the eyes of a local? Well you’ve come to the right place. Chicago is known worldwide for its unique architecture and for being the start of the old US Route 66. In addition, it boasts an impressive set of museums including the Art Institute of Chicago and the Museum of Science and Industry. Chicago is set on 26 miles of lakefront on Lake Michigan the majority of which features public parks and beaches. Many think that Chicago’s nickname “The Windy City” refers to the wind generated from Chicago’s lakefront. However, local legends report that name was coined by New Yorkers, referring to a lot of hot air coming from local politicians around the time of the World’s Fair in the late 19th century, which Chicago and New York were both bidding for.
Chicago is served by two international airports which are connected to the city by train, Chicago O’Hare and Chicago Midway. O’Hare is notorious for delays and cancellations, but don’t let that tarnish you initial impression of the city. If you find yourself at O’Hare with time to spare, we highly recommend enjoying some delicious food and cocktails at celebrity chef Rick Bayless’ restaurant, Tortas Frontera.
Chicago seems a big city instead of merely a large place.
– AJ Liebling
Chicago is the third largest city in America, and a popular city for tourists, but there’s a lot to see and do off the tourist path. Unlike other major US cities, Chicago is a city where many of its residents have roots unlike what you may find in Los Angeles or New York. Many immigrate to the city from abroad, but once they settle here, they tend to stay here. There is a long standing rivalry between New York and Chicago as New Yorkers were the first to refer to Chicago as the “Second City”.
It’s 106 miles to Chicago, we’ve got a full tank of gas, half a pack of cigarettes; it’s dark and we’re wearing sun glasses. Hit it!
– Elwood Blues (The Blues Brothers), 1980
Chicago Is A City Of Neighbourhoods
After you complete the typical tourist circuit downtown (Willis Tower, Grant Park, the museums etc), make sure you explore Chicago’s neighborhoods. It’s often said that Chicago is an amalgamation of quaint neighbourhoods that form a big city. So jump on the “L” – the nickname for the subway system in Chicago (referring to the fact that many of the trains are elevated above the city) and roam.
Another option for exploring the diversity of Chicago’s neighborhoods is the newly opened “606” trail. The 606 is Chicago’s version of New York’s acclaimed High Line, which has become one of Manhattan’s biggest attractions. The 606 is named for the first three digits that make up all Chicago postal codes. When a city ordinance was passed back in the 1890s, Chicago’s railways were required to be elevated to improve civilian safety. This meant the existing railway lines on the ground were no longer in service and left miles of unused rail line tracks throughout the city.
As the surrounding neighbourhoods of Wicker Park, Bucktown, Humboldt Park and Logan Square became more residential, the community started to rediscover the former Bloomingdale train line’s potential as a solace from the city. Over a decade in the making, a consortium of civilian, civic, and governmental groups have now opened the 606 trail which has transformed the disused Bloomingdale train tracks into a nature trail and transportation corridor, with beautiful views to boot.
If you don’t feel like walking the trail, or any other part of the city for that matter, just hop on a Divvy bike. Divvy bikes are rental bikes that are conveniently located throughout all of the Chicago neighborhoods that allow you to feel like a local and explore the city by bike.
Easily accessible via L Train, the 606, or Divvy bike, one of the most striking intersections in the city is the junction of Kedzie and Logan Boulevard at Milwaukee Avenue: the center of the Logan Square neighbourhood. In recent years, Logan Square has become a destination to eat, drink, and shop. Every Sunday from May onwards you will find a sprawling outdoor Farmer’s Market by the monument at the Logan Square L stop. After the Farmer’s Market, there are loads of excellent brunch options to hit up such as Lula Cafe, Scofflaw, and Longman & Eagle (which also doubles as a boutique inn).
Another must-visit neighbourhood for foodies is the West Loop. The West Loop was once the warehouse district of Chicago and was home to Oprah’s Harpo Studios. Now the West Loop is mostly residential and is also home to “Restaurant Row”, a cluster of amazing restaurants on Randolph Street between Halsted and Ogden Avenue.
A favourite of ours is the Girl and the Goat. It has been a city favourite since it was opened by Bravo’s Top Chef Winner, Stephanie Izard, in 2010. If you are in a big group, try to get the chef’s table to maximize your enjoyment of a constantly changing menu of small plates, rotating an array of seasonal ingredients. Also worth checking out in the area are La Sirena Clandestina, and the amazing Au Cheval. Au Cheval offers an array of enticing upscale diner style dishes, including one of the best burgers in America, and gets very busy – our advice is to go for a late lunch during the week, when you’ll be able to avoid the queues and walk straight inside.
From the West Loop, head south for a taste of the Greek Isles on Halsted Street. Greektown, as its known, features heaps of energetic taverns and copious amounts of flaming sagnanki.
Moving closer to the lake is Old Town, which is a wonderful neighbourhood near Lake Michigan’s beautiful lake front. There is a great a stretch of bars, restaurants, shops, and nightclubs clustered on Wells Ave popular with thirty-somethings. For one weekend in June the area bustles with a street festival focused on art aptly named the Old Town Art Fair. Old Town is home a Chicago institution, the Second City comedy theatre. Second City alumni include many famous comedians such as Joan Rivers, John Belushi, Bill Murray, Steve Carrell and Tina Fey to name a few. Second City has nightly performances so don’t miss an opportunity to check out literal laugh-out-loud comedy in a Chicago institution and make sure to stop at one of the local restaurants before or after a show, a personal favourite is Twin Anchors
Heading west on North Avenue from Old Town you will find Bucktown/Wicker Park. This area is the creative hub of Chicago. Bucktown and “Wicker” as it’s commonly known, have no shortage of independent shops, craft cocktails, and nightlife. The Violet Hour is a clandestine cocktail bar that is guaranteed to impress a date. They don’t take reservations but it’s worth the wait for this discrete craft cocktail spot. Piece Pizza is a not-to-miss brewery and pizzeria; if New Haven style pizza and award winning brews aren’t enough, they always have the games on and feature live band Karaoke on Saturdays from 11pm. If it’s a drink of the non-alcoholic kind you’re after, grab a tasty hot chocolate from Mindy’s Hot Chocolate.
Wrigleyville is a pocket of the Lakeview neighbourhood, in the shadow of the iconic Wrigley Field, home of the Chicago Cubs. Wrigley Field, or the “Friendly Confines” as it is commonly known, is over 100 years old and the second oldest ballpark in the National League which features the distinctive ivy on the outfield walls. Outside the stadium you can still find a neighboring rooftop apartments selling seats that allow one to enjoy the game from a distance. More recently, Wrigley Field has been a popular venue for big name music acts and occasionally hosts other sporting events.
The Wrigleyville area attracts a load of single young professionals, so you’re guaranteed a fun night out. There are a cluster of bars on Clark Street that are always heaving after every Chicago Cubs baseball game. Another option for a night out is the thriving Southport Corridor,” which is another cluster of bars, restaurants, and shops just a few short blocks south of Wrigley Field. If jet lag is still looming and you need a caffeine fix, head to Julius Meinl, an Austrian coffee roaster. If it’s food in the area that you’re after, check out Mexican hot spot Tuco & Blondie.
Another pocket of the Lakeview neighbourhood is Boystown, Chicago’s energetic gay neighbourhood on Halsted Street. In 1997, then Chicago Mayor Daley proclaimed Boystown the first official gay neighbourhood in America. Chicago has a long history of embracing the LGBT community. In fact, Chicago’s Henry Gerber formed the first ever LGBT civil rights organisation back in 1924. The parade has rapidly grown over the past few years, and now draws crowds in excess of one million people. Boystown is home to many gay friendly haunts including the Kit Kat Club and Sidetrack that are packed every Sunday year round, not just on parade day.
I am going to St. Petersburg, Florida, tomorrow. Let the worthy citizens of Chicago get their liquor the best they can. I’m sick of the job – it’s a thankless one and full of grief. I’ve been spending the best years of my life as a public benefactor.
– Al Capone, 1927
When You Can, BYOB
As it can be difficult to get a liquor license in Chicago, many restaurants have found a way for patrons to still enjoy libations during their dinner by opening as BYOB (bring your own bottle). BYOB restaurants in Chicago run the spectrum from cheap Indian restaurants along Devon Avenue to gourmet spots like Schwa in Wicker Park. Some places do charge a nominal corkage fee for BYOB, which may technically be illegal but don’t forget, it’s Chicago, where dirty politics rule.
Tango Sur in Lakeview if often named one of the best BYOBs in the city. It’s an Argentinean steakhouse that delivers exactly what you want, and happy patrons leave the restaurant having spent approximately $20 per person for an outstanding meal. Another favourite is Coast Sushi, which has locations in both the South Loop and Bucktown. For a taste of Chicago style BBQ, hit up Smoque on Irving Park Road – fantastic brisket, ribs, pulled pork and more.
You shouldn’t put ketchup on your hot dog.
– President Barack Obama, 2011
Pizza And Hot Dogs, The Chicago Way
What is Chicago-style deep dish pizza you ask? Well, it’s something so good I once bought two pizzas back with me on the plane to London in a fold-up freezer bag so I could spread gospel according to Chicago style. Many people try to compare New York vs Chicago style pizzas. To me, it’s an apple vs orange comparison as the crust, toppings, and convenience are completely different. Chicago style deep dish pizza features a super thick crust and a massive amount of tomato sauce, cheese, and desired toppings. It can take about 45 minutes to bake and it’s definitely not the kind of slice you can fold up and eat on the go. To be honest, it’s more of a pie than a pizza, but there’s no doubting that it’s a delicious indulgence. Giordano’s and Lou Malnati’s are the two most well-known Chicago style pizza places with a slew of locations scattered around the city and suburbs. Luckily for you, we’ve written up a list of our favourite deep dish pizza spots in town so you know exactly where to go.
Now that you’re sorted for deep dish, let’s talk hot dogs. The definition of a Chicago-style dog is an all-beef frankfurter with yellow mustard, onions, sweet pickle relish, tomatoes, peppers, and celery salt. In Chicago, putting ketchup on a hot dog is an offense. Don’t even bother asking. Portillo’s dominates the Chicago-style hot dog market, with many locations around the city and suburbs. If you’re not in the mood for a dog, Portillo’s has a massive menu offering including another Chicago speciality, the Italian beef sandwich. Another option is the Wiener Circle. It’s located in Lincoln Park and is as famous for its hot dogs as the verbal abuse that the employees throw at late night revellers. Proceed with caution before ordering the chocolate shake!
Some people want it to happen, some wish it would happen, others make it happen.
– Michael Jordan
Chicago, A True American Sports Town
Some may say that Chicago is the best sports town in America. The proof may be in the recent celebration of the Chicago Blackhawks victory in the 2015 Stanley Cup playoffs of the National Hockey League (NHL), their third championship victory in three years. The beloved Blackhawks defeated the Tampa Bay Lightning four games to two in the Stanley Cup Finals. Crowds estimated at 2 million people gathered to toast the hometown hockey heroes with a massive pep rally and parade around the city. And of course, you only need to look at how Chicago celebrated the historic Cubs World Series win in 2016.
Whatever your take, it’s clear that no matter what time of year you visit, Chicagoans will be fanatical about the Bears, Bulls, Blackhawks, White Sox or Cubs. Expect to see a lot of bad fashion as a result, but don’t be too quick to judge. Chicago fans live and die by their teams. Chicago proudly holds onto the Chicago Bulls glorious years in the 1990s under its own king, Michael Jordan. As mentioned above, it’s hard to beat a summer night at Wrigley Field.
Anywhere in the world you hear a Chicago bluesman play, it’s a Chicago sound born and bred.
– Ralph Metcalfe
Sweet Home Chicago, The Music Scene
Before it was home to house music (pun intended), Chicago was known for its distinct form of blues and jazz. The Chicago blues was born from a wave a migration of workers from the South to the industrial centres of the North, like Chicago. Buddy Guy’s Legends in the South Loop is named for the man himself. Buddy Guy still makes a cameo every now and again. The Green Mill on North Broadway is a long standing jazz institution. It’s also famous for its mob connections. America’s most famous mobster, Al Capone, even had a favourite booth there. There are no advance tickets at the Green Mill, but there is a cover charge at the door. The Kingston Mines in Lincoln Park features live music seven nights per week. They are open until 4am during the week; 5am on a Saturday if you are need a place to kill off jet lag. Another great option any night of the week is Blue Chicago. At the far end of the dive bar spectrum, check out Carol’s Pub in Ravenswood. It has a random, fun crowd, plays live country music until 4am Honky tonk and cheap domestic beer. Why not?