"During much of the last half of the 19th century, Chicago's politics were dominated by a growing Democratic Party organization dominated by ethnic ward-heelers. During the 1880s and 1890s, Chicago had a powerful radical tradition with large and highly organized socialist, anarchist and labor organizations. For much of the 20th century, Chicago has been among the largest and most reliable Democratic strongholds in the United States, with Chicago's Democratic vote the state of Illinois has been "solid blue" in presidential elections since 1992." -Wikipedia
For short stays, there are over one thousand people from Chicago registered for Couch Surfing.  The HI hostel in Chicago is also a good value. A bit expensive at $35 a night, but it's large, clean and they serve breakfast.
For longer stays, there are a number of intentional communities located in Chicago, like the Stone Soupe Community on the north side, included in the Intentional Communites Directory. 
Cornerstone Community Outreach, a Chicago homeless shelter, operates a number of other programs, including a free store for their clients. 
Lucy Parsons Workers Center Supports tenants in direct actions against landlords to return deposits, making repairs, resisting eviction, etc.
The Greater Chicago Food Depository operates a number of soup kitchens, food pantries, and other programs. 
Chicago can lay claim to a number of regional specialties, all of which reflect the city's ethnic and working-class roots. Included among these are the nationally renowned deep-dish pizza - although locally the Chicago thin crust is also equally popular; the Chicago-style hot dog, typically a Vienna Beef dog loaded with an array of fixings that often includes Chicago's own neon green pickle relish, yellow mustard, pickled sport peppers, tomato wedges, dill pickle spear and topped off with celery salt (ketchup on a Chicago hot dog is typically frowned upon). There are two other distinctly Chicago sandwiches that can be found at eateries throughout the area: The Italian Beef sandwich, which is thinly sliced beef slowly simmered in an au jus served on an Italian roll with sweet peppers or spicy giardiniera; and the Maxwell Street Polish, which is a kielbasa - typically from either the Vienna Beef Company or the Bobak Sausage Company - on a hot dog roll, topped with grilled onions, yellow mustard and the optional sport peppers.
Chicago's standing in the culinary world is not limited to 'street food', however. Featuring a number of celebrity chefs, including Charlie Trotter, Rick Tramonto, Jean Joho, Grant Achatz, and Rick Bayless, Chicago has in recent decades developed into one of the world's premiere restaurant cities.
The grand tour of Chicago cuisine culminates annually in Grant Park at the Taste of Chicago, a festival that runs from the final week of June through Fourth of July weekend. 'The Taste', as it is abbreviated by locals, showcases Chicago's ethnic dining diversity as well as all the locally favorite stalwarts (see above). Booths representing myriad local eateries form the centerpiece of the city's largest festival, which draws millions each summer to sample the cuisine, while enjoying free concerts and fireworks.
With the large number of restaurants in Chicago their are endless opportunities to hustle a free meal, but if you don't feel like risking attention from the Pigs take a note from our ancestors and forge. Like any other major city, Chicago love to pretty up their nicer neighborhood and parks by replacing the destroyed natural environments with carefully planned landscapes, some of which are fruit baring. Many parks come spring will be covered in Crab Apples, not the tastiest treat in the world by it self, but hell it's food. If you are luck enough to have a kitchen, then with plenty of sugar and some water you can produce your own preserves. Be sure to research what you eat at the library before chowing down. In the alley you will find a green leafy weed everywhere. This is called Lambsquarter, it has a mild milky flavor good for salads (try a spoon full of Crab Apple preserves with a little oil and vinegar for a tasty dressing on your alley way salad). You can also find community gardens around the city that provide a good variety of food ripe for the picking, most people don't think much of a person picking in a community garden, but is your are nervous just go in the hours when no one is there. The same goes for backyard gardens, sometimes all you have to do is reach over the fence and grab a tomato.
It's really meager food, but if you are in some need of meat try the butcher shops. Some of them will give you scraps and bones if you ask, just boil the bones for a few hours and you have a good stock for soup. If you scrap the bones afterwards you can have a bit of meat for the soup, not the best of quality, but something to chew on.
- Community Health - Free Health Care Clinic 
- Howard Brown Health Center, Broadway Youth Center - Free anonymous HIV testing, free confidential Syphilis testing, free condoms and lube, free services for youth 24 and under 
- Planned Parenthood - Seven health centers 
- Aid For Women - Free services for pregnant women (group is anti-abortion) 
- Pomegranate Health Collective - DIY, feminist, non-hierarchical Health Collective 
Chicago is home to the Illinois Medical District on the Near West Side. It includes Rush University Medical Center, the University of Illinois Medical Center at Chicago, and John H. Stroger, Jr. Hospital of Cook County, the largest trauma-center in the city. The University of Chicago operates the University of Chicago Medical Center.
The University of Illinois College of Medicine at UIC is the largest medical school in the United States (1300 students, including those at campuses in Peoria, Rockford and Urbana-Champaign). Chicago is also home to other nationally recognized medical schools including Rush Medical College, the Pritzker School of Medicine of the University of Chicago, and the Feinberg School of Medicine of Northwestern University. In addition, the Chicago Medical School and Loyola University Chicago's Stritch School of Medicine are located in the suburbs of North Chicago and Maywood, respectively. The Midwestern University Chicago College of Osteopathic Medicine is in Downers Grove.
ACLU, free legal aid/counseling, pro bono attorneys, etc.
Cook County Jail has the reputation for being the worst jail in the US, but people have have gotten locked up in many places say the suburban jails can be worse. Chicago police have a well deserved reputation for torture; be careful.
If you or someone you know is arrested, detained, or called in for questioning by Chicago Police, call 1-800-LAW-REP4 (1-800-529-7374)
First Defense Legal Aid ("FDLA") is an innovative program that protects civil rights by offering free 24-hour legal representation and advice to any individual taken into Chicago Police Department custody. The Program's services cover the initial and most critical stage of police detention: immediately after arrest until the time when a public defender has been assigned by the court system. Volunteers are trained to handle emergency calls by determining the nature of the call and whether a station visit is necessary to represent the individual in police custody. If a station visit is necessary, FDLA volunteers will interview the arrestee, inform the arrestee of his/her constitutional rights, provide the arrestee with bond information, and serve as a link between the arrestee and his/her family. 
- General Defense Committee IWW Defense and relief to members of the working class who are being persecuted for their activity in the class struggle.
- National Lawyers Guild Chicago
- People's Law Office
Armed Forces/Deployment Avoidance Counseling
Legal aid, resources, etc.
The Art Institute of Chicago has free admission from 5-8pm on Thursdays, and the Museum of Contemporary Art has free days on Tuesday June thru Agust. The Field Museum is free on the second Monday of each month, as well as a number of other days throughout the year. Check the website. The Museum of Science and Industry (An excellent museum) is free on select days throughout the year. Check the website.
For information about the dozens of other museums that are free or offer free days, check out these resources
The parks and neighborhoods are filled with free festivals and concerts throughout spring, summer, and early fall. The parks themselves are a good places for kicks through the summer, once the weather changes it's hard to keep Chicagoans inside.
The Chicago History Museum does a surprisingly good job of covering radical history including labor strikes, anti-war and black power riots, and Chicago's social movements. The Chicago History Museum is free on Mondays.
The Garfield Park Conservatory is free all the time and is one of the largest public greenhouses / indoor gardens in the world. It's especially nice to visit in the winter.
The National Museum of Mexican Art is free all the time. The exhibits are lively, local and international, often critical of imperialism/the state/capitalism/etc power. It's more beautiful and challenging than the stuffy Art Institute.
The local paper The Chicago Reader, both in print and online, has a section titled "Free Shit" which list daily events that, as the title suggest, don't cost a thing.
The Chicago Freecycle Network has over five thousand members. 
There is also an active Free section of the Chicago Craigslist. 
There are dozens of colleges and universities in Chicago and the Chicago metropolitan area. These schools are homes to some of the city's chapters of local radical political organizations. Dumpsters near college campuses typically have amazing finds around the time students move out for the summer. Local schools include the University of Chicago, Northwestern University, Illinois Institute of Technology, Loyola University Chicago, DePaul University, the University of Illinois at Chicago, Chicago State University, and the School of the Art Institute of Chicago.
Chicago's weather is very, very nice in the summer, not to hot, not to cold. Winter, however, is a different story. Your saliva will freeze in your mouth.
The city's waterfront allure and nightlife has attracted residents and tourists alike. Over one-third of the city population is concentrated in the lakefront neighborhoods (from Rogers Park in the north to Hyde Park in the south). The North Side has a large gay and lesbian community. Two North Side neighborhoods in particular, Lakeview and the Andersonville area of the Edgewater neighborhood, are home to many LGBT businesses and organizations. The area adjacent to the North Side intersection of Halsted and Belmont is a gay neighborhood known to Chicagoans as "Boystown." The city has many upscale dining establishments as well as many ethnic restaurant districts. These include "Greektown" on South Halsted, "Little Italy" on Taylor Street, just west of Halsted, "Chinatown" on the near South Side, "Little Seoul" on and around Lawrence Avenue, a cluster of Vietnamese restaurants on Argyle Street and South Asian (Indian/Pakistani) on Devon Avenue. Chicago's Black communities concentrated on the South and West sides have struggled for the liberation of oppressed peoples through legal and direction action methods. Predominantly Black communities include the Near West Side, East and West Garfield Park North Lawndale, Austin, Woodlawn, Kenwood, Oakland, Douglas, Englewood, Washington Park, etc. Chicago's Hispanic/Latino/Chicano communities, located along two corridors radiating out from the city center (southwest and near northwest--roughly the 4th congressional district) have also used militant tactics such as land, factory, and building occupations to help build a freer society. The Mexican and Meso-indigenous community is centered around Pilsen (Lower West Side) and Little Village (South Lawndale). Other predominantly Latino/Hispanic neighborhoods include McKinley Park, Brighton Park, Gage Park, New City, (some of) West Town, Logan Square. Humboldt Park is majority Puerto Rican.
Publications and Books
- Windy City Media Group: Windy City Times, Nightspots, Identity - LGBT publications and events listings [windycitymediagroup.com]
- Newcity Magazine - Alternative publication 
- The Chicago Public Library has 79 locations in the city, at which there are many free events. 
- The Seminary Co-op Bookstores - Member-owned and operated 
- Quimby's - Alternative, independent bookstore, with lots of zines 
- Women & Children First - Independent, feminist bookstore 
- Barbara's Bookstore - Independent bookstore, with free events 
- Chicago Comics - Independent comic store 
- New World Resource Centre - Left wing and labor bookstore and meeting place currently without a home 
- IWW Literature Department 
- Radical union bookstore and headquarters
2117 W Irving Park Rd, Chicago IL 60618 773-857-1090
- Biblioteca Popular del Barrio 
Infoshop/radical space 1921 S. Blue Island Chicago, IL
- Crossroad Fund, Fire This Time Fund -Community supported grants for social change 
- Chicago Activist Calendar 
- Center On Halsted - LGBT community center 
- Hull-House Museum - Museum with lefty events named after lefty leader 
Subways, Buses, Ferries, Shuttles, etc.
Chicago is a major transportation hub in the United States. It is an important component in global distribution, as it is the third largest inter-modal port in the world after Hong Kong and Singapore. Additionally, it is the only city in North America in which six Class I railroads meet.
Chicago is one of the largest hubs of passenger rail service in the nation. Many Amtrak long distance services originate from Union Station. Such services provide connections to New York, Seattle, New Orleans, San Francisco, Los Angeles and Washington, D.C. Amtrak also provides a number of short-haul services throughout Illinois and toward nearby Milwaukee.
Nine interstate highways run through Chicago and its suburbs. Segments that link to the city center are named after influential politicians, with four of them named after former US Presidents. Traffic reports tend to use the names rather than interstate numbers.
The Regional Transportation Authority (RTA) coordinates the operation of the three service boards: CTA, Metra, and Pace. The Chicago Transit Authority (CTA) handles public transportation in Chicago and a few adjacent suburbs. The CTA operates an extensive network of buses and a rapid transit system known locally as the "L" (for "elevated"), with several lines, including service to Midway and O'Hare airports. Pace provides bus and paratransit service in over 200 surrounding suburbs with some extensions into the city. Bicycles are permitted on all CTA and Metra trains during non-rush hours and on all buses 24 hours. Metra operates commuter rail service in Chicago and its suburbs. The Metra Electric Line shares the railway with the South Shore Line's NICTD Northern Indiana Commuter Rail Service, providing commuter service between South Bend and Chicago.
Chicago offers a wide array of bicycle transportation facilities, such as miles of on-street bike lanes, 10,000 bike racks, and a state-of-the-art central bicycle commuter station in Millennium Park. The city has a 100-mile (160 km) on-street bicycle lane network that is maintained by the Chicago Department of Transportation Bike Program and the Chicagoland Bicycle Federation . In addition, trails dedicated to bikes only are built throughout the city.
Chicago is served by Midway International Airport on the south side and O'Hare International Airport, one of the world's busiest airports, on the far northwest side. Gary/Chicago International Airport, located in nearby Gary, Indiana, serves as the third Chicago area airport, although it currently lacks scheduled passenger service. Chicago Rockford International Airport, formerly Greater Rockford Airport, serves as a regional base for United Parcel Service cargo flights, some passenger flights, and occasionally as a reliever to O'Hare, usually in times of bad weather.
A good way to get around in the city is to look around the El train stations for discarded fare cards. Some of the cards will still contain a transfer or two. You can insert the card into any of the machines at the station to put money on the card to cover the transfer cost (you just need twenty-five cents on the card for a transfer onto a train or bus). If you are pulling a hustle around the stations you can sometimes sell the transfers for the full cost of a trip, people feel better about hand outs if they feel they haven't really lost anything.
The orange reduced fare cards can sometimes be reloaded at the lower rate (intended for youth and those with disability), but other times reloads don't work or CTA staff check ID. Senors and the disabled ride free.
It's often not too hard to jump turnstiles or open the bike/wheelchair gate from the outside. It might be a good idea to do this only when a train is immediately coming so that you can outrun pigs that might give chase (although enforcement doesn't appear to be a CPD priority).
If you're going to the suburbs, you can ride the METRA free on the weekends by getting a weekend pass from someone coming off the incoming train. Weekend passes are widely available and can easily be requested from friendly riders or found in the trash or ground (especially on Sundays).
Free Clothing and Furniture
Free shit in Chicago is pretty easy to come by, and even more so free furniture. Every spring when the people succumb to the Spring Cleaning desire to throw out all of their stuff and replace it with new shit you can roam the alley ways of Chicago, and find endless amounts of free furniture. This is not just the cat pee sofa that Uncle Joe is throwing out, but perfectly good items that people have decided to replace with brand new perfectly good items. Just rent or borrow you buddies car and in one evening you can fill your pad with every scratch of furniture that you need. If you can't get hold of wheels just narrow your search to your neighborhood, and you and a friend can hoof that designer sofa back to your place. It is a good idea to keep a eye on the weather because the people tossing out the goods could give a fuck what happens to the stuff once it leave their house, many a spring shower has ruined countless sofas, rug, and bookcase. Remember that the rich neighborhoods waste more and waste better stuff, so for the best goods stick to the alley ways of Lincoln Park or any rich hood.
If you don't feel like hunting for your furniture try freecycle. Freecycle is a web based community that circulates everything from furniture and electronics to boxes of old wrapping paper. You can sign on to freecycle through its yahoo group, and you will get several daily notices of stuff offered or post want ads for things your looking for. It is a good idea to select the option to have the notices sent in bundles, otherwise you will have a hundred post to sort through a day.
See Assorted Freebies Section, provide details for this city, including other topics. Whatever fits and is useful.
Go to the Survive section and provide any city-specific details, including new topics.
- AREA chicago: Art/Research/Education/Activism - Organization network, events, newsletter 
- Food Not Bombs Chicago - 
- Chicago Copwatch - 
- Four Star Anarchist Organization 
- Students for a Democratic Society - Five Chicago chapters 
- International Socialist Organization - Six Chicago branches 
- The Platypus Affiliated Society - Marxist Left 
- Generations for Peace - South-suburban Chicago residences for peace and justice