Travel Tips

Off the Brochure Travel Guide: Chicago, Illinois

Locations in this article:  Chicago, IL

Chicago downtownWe may advocate traveling in the off season (lower prices, lesser crowds), but odds are you held back on visiting Chicago in the winter. Yes, weather can be a factor. After all, a common Chicago joke is that the city enjoys only two seasons a year: winter, and construction. Indeed, statistics show that Chicago tourism is hopping in the summer: 32 percent of leisure travelers visit the city in the summer months, as compared to 24 percent in the winter (and only 17 percent in the fall–as it turns out, winter discounts and programming do draw a decent, albeit chilly, crowd).

Now that summer is here, the thawed-out city is bursting with outdoor festivals and concerts and Wrigley Field is officially open for business. From celebrated architecture to deep-dish pizzas to soulful blues, the city is known for a lot of things … so we’ve uncovered some of the lesser-known variations of what makes Chicago a hot summer destination.


The city is designed in an easy-to-navigate grid and boasts one of the best public transportation systems in the country. But if you’re not ready to manage Chicago on your own, try getting your bearings with a city tour. Skip the cheesy bus tours that whiz you by the Sears Tower, and opt for an experience that really gets you out and about.

Chicago Frank Lloyd WrightAfter the 1871 Great Chicago fire, the “Second City” was rebuilt as one of the great centers of modern architecture. Get an in-depth crash course: a walking tour with the Chicago Architecture Foundation. The Frank Lloyd Wright and his Contemporaries tour takes you through the historic Oak Park district, where you’ll find homes and buildings designed by the celebrated turn-of-the century architects.

A weekly “Tiffany Tour” visits art glass and mosaic installations that were designed by the Tiffany Glass and Decorating company. Or pay a visit the city’s past luminaries on a two-hour walk through the old Rosehill Cemetery. $5-$15. 312-922-3432,

Travelers on a super-tight budget can take advantage of the city’s free Greeter Tours. These two- to four-hour tours are led by local volunteers (who are often far more enthusiastic about showing off their city than a tour guide on payroll). You’ll feel like a native in no time as you traverse the city on foot and via public transportation… best of all, you get a free visitor’s pass to the bus or the ‘L’ train. To register for a tour, visit


John Belushi & Gilda RadnerSince the 1960s, the Windy City has been the breeding ground for some of our most iconic comedians — The Second City theater is perhaps the most famous of the bunch, bringing us legends like Bill Murray, John Belushi, Gilda Radner, John Candy, and Stephen Colbert, to name just a few.

While the venue itself may be “on the brochure,” what you may not know is that Second City offers free sets every night. This is the chance to see future Saturday Night Live stars honing their craft… without putting a dent in your wallet. Free sets take place after the main show, Monday through Thursday around 10 p.m., Saturday around 1 a.m. and Sunday around 9 p.m. 1616 N. Wells St., 312-664-4032,

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Improv Olympic is considered to be the (often cheaper) alternative to Second City. The venue, which you’ll find on the way to Wrigley Field, boasts its own impressive roster of alumni, including Chris Farley, Tina Fey and Vince Vaughn. There are nearly 30 shows to choose from throughout the week, with prices ranging from free (check out “The Improv Match Game” on Saturday nights) to $14. 3541 N. Clark St., 773-880-0199,

Chicago Sears TowerYou can’t talk about Chicago without singing the blues. While the Mississippi Delta is considered to be the official birthplace of the blues, Chicago nurtured the sounds and the culture, eventually eclipsing all other cities to become the “blues capital of the world.”

Hundreds of thousands flock to the Chicago Blues Festival in early June, and you can always catch a show at mainstays like The House of Blues or Buddy Guy’s Legends. But there are also dozens of smaller, out-of-the way blues club to explore. Rosa’s Lounge is something of a local secret, tucked into a residential part of town. The intimate venue gives the stage to traditional performers and modern-day legends. The club is owned by Italian blues enthusiast Tony Mangiullo, who named the place after his mother who joined him in the U.S. to help him out — in fact, you can still often find Mama Rosa behind the scenes tending bar. $10-$15. 3420 W. Armitage Ave., 773-342-0452,

Chicago JazzGangster culture is an integral part of the city’s history, but if you’d rather skip the Al Capone tour, you can go straight to the source at Green Mill. Once co-owned by a Capone henchman, this old-school jazz club served as the headquarters for Chicago gangsters during Prohibition, complete with bullet holes in the walls. These days, the smoky lounge can get packed, especially on the weekends, but is worth a visit for the music and the cheap martinis. 4802 N. Broadway St., 773-878-5552,

Cheap Eats

The city isn’t exactly known for its light and healthy cuisine, and even the most weigh-conscious travelers can’t resist a bite of deep-dish pizza or Eli’s famous cheesecake. If you’re temped by pheasant sausage with black truffle butter and a side of duck fat fries, stop by Hot Doug’s. The self-proclaimed “Sausage Superstore and Encased Meat Emporium” is also the site of the city’s first foie gras felony–Hot Doug’s was busted last February when Health Department inspectors found 30 pounds of foie gras and related products after the city passed a ban on the delicacy. Owner Doug Sohn has been riding the wave of publicity ever since (but took the illegal substance off his shelves). 3324 N. California Ave., Avondale, 773-279-9550,

Polish flag - Chicago’s Polish heritageChicago is considered to be second only to Warsaw in terms of the number of Polish residents. Translation? This is where you’ll find some of the most authentic Polish cuisine in the country.

Located in Wicker Park, just down the street from the Polish Museum of America, is Podhalanka — a true-blue hole-in-the wall eatery. What the simple restaurant lacks in ambiance is more than made up for by its fried potato pancakes and homemade applesauce. Boiled pierogies, borscht and other traditional Polish comfort food are all served at rock bottom prices, which you can order at the counter or at the communal tables (where it’s perfectly okay to sit with strangers). 549 W Division St., 773-486-6655

Outdoor Happenings

Chicago Grant ParkYou may have heard of Grant Park, the largest park in the city, but you may not know about all that goes on inside. Located between Michigan Avenue and Lake Michigan, the 300-acre park is home to a host of activities that flourish in the summertime (not to mention the well-known Art Institute, the Field Museum of Natural History, and the Shedd Aquarium). Here, the Chicago Outdoor Film Festival screens classic films every Tuesday evening between July 17 and August 28. The lineup this summer includes old favorites like “Young Frankenstein,” “Double Indemnity” and “Butch Cassidy and the Sundance Kid.” Admission is free, and bikers can get free bike valet parking. 312-744-3315,

This summer, the Garfield Park Conservatory (one of the world’s largest conservatories, aka “landscape art under glass”) is the site of Niki in the Park, part of the city’s “Art of Play” series. This family-friendly exhibition showcases the works of sculptor Niki de Saint Phalle, where kids can even climb and crawl through more than 30 enormous, whimsical works. Encrusted with mosaics, glass and semi-precious materials, the sculptures represent mythical creatures, animals and sports heroes. The exhibition runs through October 31. $5 donation. 300 N. Central Park Ave., 312-746-5100,

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By Sarika Chawla for