The Insider’s Guide to Visiting Chicago

21 May

Chicago, the largest city in the Midwestern US, sits on the shores of Lake Michigan in the northeast corner of Illinois. Nicknamed the Windy City, it’s the birthplace of the modern skyscraper, the home of not one, but two Major League Baseball teams (the Cubs and the White Sox), and a city with signature styles of pizza, hot dogs, and blues music that bear its name.

Unlike its flashier counterparts of New York and LA, Chicago feels more like a big small town than a major city. Downtown, glass and steel buildings reach for the sky as the el train clatters around “the Loop” and water taxis ply the river. Shoppers form a moving mass up and down Michigan Avenue, the city’s many museums showcase treasures of art and science, and downtown’s massive green spaces teem with people picnicking in summer or ice-skating in winter. But just a few blocks away, the city’s vibrant neighborhoods have an entirely different feel, with cozy corner bars, tree-lined streets, and quiet parks and gardens.

Where to Stay

Michigan Avenue

Michigan Avenue. Photo credit: Spiterman via Flickr.

Most of the big tourist attractions are downtown, so it’s usually your best bet to make that your home base as well. Downtown is divided into the Loop (the downtown core surrounded by the elevated train tracks), the Magnificent Mile (Michigan Avenue north of the Chicago River up to North Avenue), and the South Loop.

Hotels on Michigan Avenue are generally a great choice for tourists. They’re close to everything and offer easy access to public transit. The Loop is another great option, but tends to be quieter after business hours, as does the South Loop. Unless your flight times require it, it’s best not to stay at either of the airports (O’Hare or Midway) as your commute time will be at least 40 minutes. If you’d rather stay in a quieter neighborhood but still be close to public transit lines, there are a few smaller hotels and B&Bs in Bucktown, Lakeview, and Lincoln Park. They’re only about 20 minutes from downtown on the el train and they can often be cheaper in price.

Really, so long as your hotel is within the city limits and close to an el station, you’ll be able to get just about anywhere in the city in 20-30 minutes. The main el trains a tourist would need to take would be the red line, which runs north and south and also provides access to both baseball stadiums; the blue line, which heads northwest from the city to O’Hare Airport; and the orange line, which runs southwest to Midway Airport. Other transit options include the Metra (a train that runs from the city to the suburbs), an extensive bus network, and plentiful taxis.

What to Do

Grant Park and Downtown Chicago

Grant Park and Downtown Chicago

The biggest attractions in Chicago are: the Willis Tower (formerly called the Sears Tower), with its glass-bottomed ledges on the observation deck; the Hancock Building, another skyscraper with great observation deck views; the Lake Michigan beachfront; Grant Park and its smaller sub-park, Millennium Park; Lincoln Park and its free zoo, just north of downtown; luxury shops on Michigan Avenue; the kitschy carnival atmosphere of Navy Pier, home to the giant Ferris Wheel; and the city’s fantastic collection of museums: the Art Institute, Shedd Aquarium, Field Museum, Museum of Science and Industry, and Adler Planetarium (if you plan to visit multiple museums, look into the cost savings of a Chicago City Pass).

You could try to see and do it all, but that’s a difficult feat if you’re not staying a week or more. Instead, pick and choose based on your interests, budget, and time of year (winters in Chicago are notoriously bitter cold, and summers can be hot and sticky). If you do want to see and do a lot in a short amount of time, a Hop-On, Hop-Off tour of Chicago is a good choice.

Sue the T-Rex

Sue the T-Rex

If you’re a museum lover, don’t miss the Art Institute; you may also want to see “Sue” the T-Rex skeleton at the Field Museum, or descend into a mine shaft at the Museum of Science and Industry. If you’re visiting with kids, the Shedd Aquarium can’t be beat, and you shouldn’t miss a visit to Grant Park; in addition to live music and free events in the summer and free ice-skating in the winter, it’s also home to “the Bean” a shiny sculpted blob that reflects the city’s skyline and distorts the faces of those who stand before it, making it a great photo op.

The Willis Tower is the city’s most famous skyscraper, but many visitors prefer to head to the Hancock instead, as rather than paying to go up to the observation floor, they can opt to have a cocktail with a view in the 96th floor lounge. For more on the architecture of Chicago, don’t skip the Architecture River Cruise, on which you’ll learn all about the city’s history and how its skyline was created, building by building, after the Great Fire devastated it in 1871. I’ve actually taken this tour more than four times and I learned something new each time.

And don’t forget to get out of the downtown core for a while. Head north to Lakeview or Lincoln Park, or west to Bucktown or Logan Square for boutique shopping and great nightlife. Try some Indian food on Devon Street or travel slightly south to Pilsen for the best Mexican food in the city, or opt for German fare in Lincoln Square or authentic dim sum in lively Chinatown.

In the summer, rent a bike and head up the Lakefront Path to explore the miles of sandy shoreline that border the city, search out a street festival or farmer’s market, or head to the free Lincoln Park Zoo.

Explore Chicago’s neighborhoods by bike or take a food tour of Chinatown

Eating and Drinking

Chicago style pizza

Chicago style pizza

Chicago has one of the best, and most eclectic, progressive dining scenes in the country. From the once-in-a-lifetime experience at Grant Achatz’s Next (which operates on a ticketing system and changes its concept and menu every three months) to the molecular-gastronomy  dining of Moto to the farm-to-table gastro-pub cuisine of Longman and Eagle or pig-centric menu at Publican to any one of the city’s famed steakhouses, there’s no shortage of options.

One way to find the right spot for tastes and budget is to search on (where you can filter by area, cuisine, or budget) or check out some of these excellent options.

If you have a passion for creative cuisine (and the cash to spend on it), Next, Moto, Alinea, L2O, Bonsoiree and Schwa are among the city’s best. But expect to spend anywhere from $150–$400 per person for a multi-course tasting menu with wine.

If you prefer local, seasonal ingredients used to prepare simple but delicious meals, Publican, Longman and Eagle, and Top Chef winner Stephanie Izard’s Girl and the Goat will definitely fit the bill. If you need something family-friendly or good for a group, but don’t want to sacrifice quality, Italian small plates at Quartino, burgers at DMK, or tapas at Café BaBaReeba are sure to please.

For romance on a budget, Argentine steakhouse Tango Sur or French bistro Mon Ami Gabi both offer fantastic food at a lower price point with candlelit atmosphere. Tango Sur is also one of the city’s BYOB restaurants; at select establishments, patrons can bring in their own beer or wine and pay only a small corkage fee ($1-$3), which is a great money-saver. Other BYOB options with excellent food include HB (New American), Toro (sushi), Mixteco (upscale Mexican), and Andalous (Moroccan).

The city’s drinking scene is equally exciting, with everything from casual brewpubs to swanky clubs, dive bars to rooftop lounges, and just about everything in between. For a great beer selection and pleasant backyard beer garden, check out Sheffield’s by Wrigley Field or get your craft beer fix at the Long Room or Quenchers. For the best cocktails look for the secret door at speakeasy-style Violet Hour or check out the whimsical creations at Aviary; for perfectly paired wine flights, head to the Purple Pig or Bin Wine Cafe, and for whiskey and rock music, check out the dark and divey Delilah’s.

Insider Tips

Chicago beach

Chicago beach. Photo credit: KR1212 via Flickr.

The best free things to do are to spend a day at the beach or in the park, or to check out a free concert or street festival. You can find out what’s happening by picking up a ‘Red Eye’ paper at any el stop. The Art Institute is also free every Thursday from 5pm – 8pm.

If you only have one day in the city, start with your choice of museum and then walk through Grant Park, stopping to grab a Chicago-style hot dog lunch. Then book a ride on the Architecture River Cruise. Afterwards, walk up Michigan Avenue to the Hancock Building, where you can have a drink in the 96th floor lounge before dinner at one of the city’s best restaurants.

The best thing to eat in Chicago is not…in my opinion…the city’s famous deep-dish pizza. Instead it’s the vast array of international foods available. Within a few blocks you can sample cuisines ranging from Indian, Greek, Chinese, Thai, Italian, French, Spanish, Moroccan, Polish, Mexican, and Ethiopian, to Turkish, German, Argentine, Cuban, Jamaican, Irish, Korean, and more.

The Insider’s Guide to Visiting Chicago


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