There's nothing more painful for a thrifty Chicagoan than watching naive tourists shell out big bucks for overpriced entertainment when there's so much good, free fun happening around the city. To join Chicago's savvy thriftsters, check local media for free events; you'll find some of the most extensive listings in the Chicago Reader, Time Out Chicago, Metromix Chicago, Centerstage Chicago, Gapers Block, Chicagoist and New City. Chicago's official tourism site, www.explorechicago.org, also has listings of free events and tours.
Here are just a few of my favourite ways to show visitors a good, cheap time:
1. Music
If you're visiting between mid-May and early October, look for free outdoor concerts and weekend music festivals. The Chicago Gospel Music festival in early June usually kicks off the big summer downtown festivals, which wind through the musical genres, from top acts in blues and country to jazz and Celtic music. The city also hosts free indoor concerts year-round, many of them at the Chicago Cultural Center. And plenty of bars and nightclubs charge nothing for performances to accompany your drinks: try the late-late night drop-in jazz sessions at the historic Green Mill in uptown, or Lee's Unleaded Blues, a classic blues club that also hosts R&B and reggae.
2. Dancing
Now in its 14th year, Chicago SummerDance provides free, one-hour dance lessons followed by free concerts and dancing in a different style each night: swing, country line dancing, cajun, salsa and dances from around the world. Most sessions are in the Spirit of Music Garden, 601 South Michigan Avenue, from mid-June through mid-August. Weather permitting, SummerDance events run every Thursday through Saturday from 6-9:30pm and every Sunday from 4-7pm. The Chicago Cultural Center also hosts free dance performances throughout the year.
3. Theatre
Don't expect to see Broadway-style blockbusters at downtown venues such as Cadillac Palace for free. But most of Chicago's small-to-medium-sized theatres use volunteer ushers who show up a little early to hand out programs and then get to see plays for free. A nonprofit group called the Saints organises a lot of this, and charges a $65 (£41) annual membership fee. But many theatres welcome individual volunteers, too, so if you don't want to cough up a membership fee for a short visit, contact the theatres to try to arrange ushering opportunities on your own. Make sure to ask about dress code: many require black pants or skirts and white shirts.
4. Comedy
In 1967, the Second City brought the world The Second City, a comedy sketch troupe that has since spawned branches in Toronto and Los Angeles. Many Second City alumni – including John Belushi, Gilda Radner, Mike Myers, Stephen Colbert and Tina Fey – have gone on to star in Saturday Night Live, movies and TV sitcoms. You can see the latest incarnation perform during free improv sets following the last regular performances every night except Friday. Alumni, both famous and obscure, occasionally stop by to join in.
5. Spoken word
Chicagoans are great talkers, and we have the free poetry readings, monologues and storytelling events to prove it. For up-to-date listings of free readings, check ChicagoPoetry.com, the Bookslut Reading Series or the Guild Literary Complex. If you visit in February or March, you may be just in time for Columbia College Chicago's annual Story Week festival, which includes storytelling events at the college as well as local libraries, bars and cafes. The Chicago Humanities festival hosts spoken-word events throughout the year, including book readings and performances.
6. Tours
You could pay big bucks for someone to show you around downtown Chicago – or you can take advantage of several free options. The Chicago Greeter Program of the city's tourism office pairs visitors with friendly local volunteers eager to show off their favorite neighborhoods during free walking and public-transit tours. If you'd rather go it alone, you can download self-guided tours, including articles and interactive maps, from the Commission on Chicago Landmarks. Tours are organised by theme, such as architecture, historical periods, ethnicity, music, art and neighborhoods. The tourism office also offers free audio tours for your MP3 player, along with interactive maps; tours so far include Millennium Park, Chicago for Kids, and a Chicago Blues tour hosted by local legend Buddy Guy.
7. Museums
Most of Chicago's major museums used to offer one day of free admission each week. Those free days have become a moving target, with many clustered together during the tourist low seasons of January and February. Corporate donors sponsor free admission slots at a handful of venues: for example, the retail chain Target provides free entry to the Art Institute of Chicago on Thursday from 5-8pm and the Chicago Children's Museum the first Sunday of every month; Kraft does the same for the latter on Thursdays from 5-8pm. If you have friends or family in Chicago, they are eligible for a limited number of free museum passes from the Chicago Public Library.
8. City in a garden
The long-reigning mayor, Richard M Daley, has poured a lot of money into developing Chicago's downtown parks into horticultural specimens to rival those of Europe. But don't limit your visit to those crowded-yet-lovely lakefront jewels. Venture south to historic Jackson Park, which includes tranquil lagoons and Osaka Garden, a holdover from the 1893 world's fair. In Lincoln Park, on the north side lakefront, you'll find the always-free Lincoln Park Zoo and the sometimes-free Peggy Notebaert Nature Museum, both of which are surrounded by bird sanctuaries, restored prairie habitats and formal gardens. When the weather turns cold, Lincoln Park Conservatory offers a free, tropical escape. So does the larger Garfield Park Conservatory on the city's west side.
9. Sand and ice
"The lakefront by right belongs to the people," decreed the city planner Daniel Burnham in his 1909 Plan of Chicago. "Not a foot of its shores should be appropriated by individuals to the exclusion of the people." With precious few exceptions, the city has maintained that philosophy ever since, with a string of lovely parks and free beaches that stretch along the city's eastern shore from south to north. Your visit to Chicago won't be complete without some quality time staring at our little stretch of majestic Lake Michigan. In winter, the Chicago Park District operates ice rinks at various parks, including Millennium Park downtown. Skating is free, though skate rental will set you back $5 or $6 (£3-£4).
10. Food
It's hard to be anything but one of the chubbiest cities in the US with so much great food around. A lot of this food comes in the form of free samples at gourmet grocery stores such as Fox & Obel and Whole Foods Market. And if you're planning to visit a bar, you may as well get some free appetisers, barbecue or even buffets to accompany your libations. (Remember to tip your bartenders and servers!) A few of my favourite freebies include early-evening happy hours at Boston Blackie's near the river in Chicago's West Loop financial district, free food and cultural events at the travel-themed Map Room in Bucktown, and a free Sunday dinner (with $2.50 vodka lemonades) at Big Chicks, a straight-friendly gay bar in uptown.