Chicago: An Essential Guide

One of Chicago’s many nicknames is “City of Neighborhoods,” and the moment you leave The Loop you’ll see why. Each of the city's 77 neighborhoods is distinct from the next. In a matter of miles, you can pass by the historic mansions of The Gold Coast, sunbathe on the shores of Lake Michigan at the sandy North Avenue Beach, and then head Lincoln Park’s Lincoln Park Zoo for a free day of fun. Add the El (the train – El stands for Elevated, although parts go underground) into the mix, or hop on a sky-blue Divvy, via Chicago’s bike share program, and you can jet all across town, savouring dim sum in Chinatown, perusing the art galleries of Pilsen or heading to Wrigleyville to partake in the raucous bar action or catch a Cubs game. Along the way, check out Chicago’s remarkable food and dizzying beverage scene, from craft cocktails to home-away-from-home dive bars. 

Whether you’re here for a day or a week, this essential guide to Chicago will help you get your bearings and highlight some must-see spots on your trip to the Windy City. 


The first thing you need to know when getting around the city: embrace the grid. When you understand just how brilliantly organized the streets are, you will (hopefully) never get lost again. Chicago’s grid system starts at Madison and State Street (zero east/west zero north/south). From there, the numbers rise according to their distance from the zero mark. Every time you walk past 800 units, you’ve hit a mile. Lake Michigan is to the east. When in doubt, follow the train tracks to the nearest station, hail a cab or use your phone to bring Uber to the rescue. 

The Loop – the downtown commerce district – is composed of skyscrapers and highrises encircled by a literal “loop” of train tracks. Most Chicagoans use the Loop loosely to refer to the area bounded by the Chicago River (north and west), Lake Michigan (east) and Roosevelt Road (south). While this part of town bustles during business hours, it thins out quickly on evenings and weekends. Still, this is where you’ll mostly find tourists, who are staying in the hotels that fill and border the area, which is a hop skip and El ride away from incredible shopping, world-class museums, a rich dining scene, an array of music venues and more. 

One must-visit: Grant Park, aka the city’s front yard, which is home to a variety of festivals, art fairs, concerts (many are free), dance events, an elaborate garden, and incredible sculptures (including the famous “Bean,” or Cloud Gate, a which reflects passersby and the skyline in funhouse fashion) is well worth your time. East of Grant Park is the Museum Campus, home to the Shedd Aquarium, Field Museum and Adler Planetarium, and just beyond those cultural institutions is Lake Michigan, pride and joy of Chicagoans, which is bordered by an 18-mile path perpetually filled with pedestrians, joggers and cyclists.

Even if you’re staying downtown, visitors in the know follow the trail of residents as they head home to their respective neighborhoods to find great food, shopping, and entertainment, and get a true feel for the real Chicago.


Public transit 

The Chicago Transit Authority (www.transitchicago.com) runs an integrated network of public trains and buses within Chicago.

The short of it is, fare is $2.25 per ride for train or bus. However, it’s more complicated than that. Both buses and trains accept something called the Ventra card, which you can order online (www.ventrachicago.com) or purchase in vending machines at train stations and retailers, such as convenience stores. You have three choices with the Ventra card: a single-ride ticket, a reusable card that you load with money or an Unlimited Ride pass. The single-ride pass charges $3 per ride (that covers the $2.25 ride plus a transfer plus a fee). If you choose the reusable card there is a $5 surcharge, but it will be refunded if you register the card online (where you can connect it to your credit card for easy reloading). The Unlimited Ride Pass is available for one day ($10), three days ($20), seven days ($28) or 20 days ($100). Bus riders can use the Ventra card or pay with cash (no change is given). If you transfer to a bus or train within two hours of your first trip the fee is 25 cents. If you transfer a second time within those two hours it’s free.

Google Maps does a reliable job of choosing CTA routes for you. Follow its instructions, and if you’re unsure, ask a CTA staffer or a local – Chicagoans are generally quite friendly and helpful when asked for directions.

The CTA has eight lines (Red, Blue, Brown, Green, Orange, Purple, Pink and Yellow). The Yellow is the only line you won’t see in the Loop. If you’re spending time in the Loop, you’ll have multiple colour options for getting around.

The Metra (www.metrarail.com) is Chicago’s commuter train. It has 12 train lines that serve the six counties surrounding Chicago. Here, schedules are exact and the fare changes depending on distance travelled, ranging from $3.25 to $10.25. Unlimited ride passes are offered on weekends for $8. 


Base fare: The initial charge is $3.25, plus $1.80 for each additional mile. There is a $1 charge for the first additional rider, and 50 cents per rider after that. 

Cabs are plentiful downtown and in the neighbourhoods closest to the core of downtown. There are a number of companies operating in Chicago, including Flash Cab, Yellow Cab and Checker Cab. Taxi drivers also participate in Uber; use the app to find a ride regardless of neighbourhood.

When arriving at Chicago Midway International Airport from Billy Bishop airport, there are plenty of cabs. The Orange Line runs from the airport to downtown. Budget about a half hour or so to make the journey.

In the summer, Chicago Water Taxis (www.chicagowatertaxi.com) are a delightful option to get around Chicago. The taxis run every half hour and stop at five different spots near major attractions, such as Navy Pier, Willis Tower, Michigan Avenue and Chinatown. Fares range $4 to $6, depending on distance.


• There are more than 100 radio stations serving Chicagoland. Tune in to Newsradio 780 (AM 780) for news; KISS FM (103.5) for rock and pop; public radio station WBEZ for news and interviews (91.5 FM); WDCB Public Radio (90.9 FM) for jazz; WFMT (98.7 FM) for classical; Q101 FM for alternative; WGCI (107.5 FM) for hip-hop; and The Loop (97.9 FM) for classic rock.

• On the hotel TV: Local TV news stations include CBS 2, NBC 5, ABC 7, WGN 9 and WTTW 11. For cable news, tune into CNN or MSNBC.

• Listings for arts and culture, events, food and drink: choosechicago.com

• LGBT-focused listings: windycitymediagroup.com


Doing the tourist thing

Soak in the views: Yes, it’s touristy, but a trip up to the Willis Tower’s Skydeck is absolutely worth the time spent in the fanny-packed crowd. Willis Tower (né Sears) is the tallest observation deck in the United States and the second tallest building in the Western Hemisphere. Here, you can stand in a translucent box, called The Ledge, 103 floors above street level – that's 412 metres (1,353 feet) above the city – and have a panic attack while looking down. On a clear day, you can see as far as three other states (Indiana, Wisconsin and Michigan). The displays leading up to the views are impressive, providing a thoughtful timeline of Chicago’s history and insights into what it means to be as high as you are.

Lines can be pretty insane, particularly in the summer (1.5 million people visit here a year). It’s worthwhile to splurge on the $45 fast pass and zip right up to the top. Another consideration: the CityPass (www.citypass.com), which includes the fast pass to Skydeck as well as admission to four other Chicago attractions. The $96 pass ($79 for kids ages 3 to 11) saves more than half off the following: VIP entry to Shedd Aquarium, The Field Museum, Museum of Science and Industry or 360 Chicago, Adler Planetarium or Art Institute of Chicago. 

Take a free tour: The Chicago Greeter (www.chicagogreeter.com) program is one of the city’s coolest free offerings. Volunteers lead hour-long walking tours around Millennium Park, the Loop and the Uptown neighborhood, or, for a more in-depth tour, visitors can register at least 10 business days in advance and a tour guide will customize a free two- to four-hour walking tour that fits your interests (neighborhood, food, art, etc.).

Now let’s talk pizza: Chicago-style pizza is a must-try. Know before you go that “belly bomber” is an understatement for this dish, and that beneath the tomato sauce that tops the pie there is plenty of hidden cheese and, if you’re eating like a real Chicagoan, generous amounts of sausage. Some favourites for Chicago-style pie are Lou Malnati’s, Pizano’s and Gino’s East.

Book an architecture cruise: Every visitor should sign up for a Chicago Architecture Foundation River Cruise. On this 90-minute tour you’ll learn all about Chicago’s history and architecture (we’re home of the modern skyscraper, after all), take in its incredible skyline views and learn fun facts about at least 50 buildings.

When getting around, we have a lot of nicknames. First, LSD isn’t what you think – it’s the acronym for the beloved Lake Shore Drive, which follows the shores of Lake Michigan while giving way to stunning skyline views. “The Bean” refers to the whimsical kidney-bean-like Millennium Park sculpture designed by Anish Kapoor, technically named Cloud Gate. And the highway system, well, even some of locals have yet to learn the significance of various and sundry nicknames for all or parts of the freeways: The Stevenson (part of I-55), Eisenhower or “Ike” (I-290), Dan Ryan (parts of I-90 and I-94), The Edens (part of I-94), Kennedy Expressway (I-90) the Bishop Ford Freeway (part of I-94), and the list goes on. Listen into rush hour traffic reports and prepare for your head to spin!

Head to the beach: Another Chicago nickname is The Third Coast, in reverence of our Great Lake, Lake Michigan. Try taking the lake path whether you’re walking, jogging or cycling en route to one of our sandy beaches or picnicking on miles of parkland that surround the area. The water’s usually too cold for much swimming.

Ride the rails: A $2.25 ticket on the El is a great way to get a feel for Chicago. Hop on the Brown Line, which is above ground and allows some of the best views, and head to the city’s north side. Hop off in Lincoln Park (Armitage stop) for shopping, Wrigleyville (Addison stop) for a Cubs’ game or Lincoln Square (Western stop) for a walk around Chicago’s own little Bavaria.

Take a spin through Lincoln Park Zoo: Open 365 days a year and doesn't charge an entry fee, the zoo is smack-dab in the middle of Lincoln Park. Spend a couple of hours checking out the giraffes and orangutans and then head to the beach or picnic in the park.

Visit a street fest: Summer and street fests go hand-in-hand in Chicago. Every neighbourhood has them and they’re a great way to explore Chicago, its many cultures and foods. We have festivals dedicated to ribs, burgers, tacos and oysters; Puerto Rican culture, German culture, low-rider culture, and the list goes on.


Where to go if there’s something you need, and quickly

The Magnificent Mile is the nickname for the shopping district on Michigan Avenue, where you’ll find multiple malls, along with free-standing shops, and just about every fashion line known in America (along with plenty of restaurants, an Apple store and more). This is prime tourist territory and most of the shops are chains, but if you’re having a fashion emergency or an electronics meltdown, you’ll be able to solve it here. For more high end-shopping head to Oak Street, which is filled with boutiques and luxury shops. For more personal needs, Walgreens and CVS drugstores are plentiful downtown.

Beer, wine and liquor

Generally speaking, alcoholic products for home consumption are purchased at grocery stores, drug stores and liquor stores, which you’ll have no problem finding downtown and in any neighbourhood. 

Chicago’s drinking age is 21. Standard bars can stay open until 2 a.m. on Saturday and 3 a.m. on Sunday (but many close earlier, particularly during the week). Some bars have “late hour” liquor licenses and can stay open until 4 a.m. Monday through Saturday and 5 a.m. Sunday. Liquor establishments can open at 7 a.m. Monday through Saturday and 11 a.m. Sunday. Restaurants can begin serving booze at 10 a.m. on Sunday.

Because liquor licenses are so expensive, many restaurants in Chicago have a bring your own (BYO) booze policy. Call before you go so you know if you should stock up beforehand.


Published Saturday, August 1st 2015

Header image credit: Getty Images



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