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If you qualify for unemployment, until your yearly allotment is out you can get up to around $600 a week in benefits. However there are some things you need to know:
You can do the whole application process online, though; the form is long and annoying but it's at least convenient.
Illinois Job Link is operated by the Illinois government and companies and organizations post job listings there. If you're applying for unemployment you're forced to sign up for it, in fact. The listings can be kind of hit-or-miss as far as relevancy, but there's a lot of them. The site also has a bunch of articles on putting together resumes, preparing for interviews, and so on.
A really useful thing is their email newsletter, which in addition to sending you listings of questionable relevance, also sends you information about occasional job fairs. Some are industry-specific (e.g. hospitality) or more general, and they usually have a lot of employers present. You'll need to sign up (free, usually through eventbrite) and print a stack of copies of your resume (if you don't have a printer, check your local library).
Re-entry Employment Service Program - if you're formerly incarcerated or just exiting incarceration, these resources are available to you that have information on how to handle the job application and interview process with a criminal record, where to find legal aid, how to pursue expungement, etc. Note that you are able to visit an IDES office in-person for more hands-on help.
HireVets.gov - Official government website that notes employers with a commitment to hiring veterans. At present writing, in Chicago, the companies that meet the employment standard are ACCIONA Energy, America Works of Illinois, Invenergy, Richard Group LLC, and Semper Fi Doorman.
Job Openings for Disabled Veterans - what it says on the tin. Job openings are posted by companies directly, so they've committed to an interest in hiring disabled veterans.
NationalAble - Provides in-person job fairs, free online and in-person workshops/training, and additional help for veterans among other things. Targeted towards "vulnerable populations" which means you, probably.
Employment & Employer Services - Provides job placement help and career help events (impressively dense event calendar). Sign up for a Workforce Program Orientation to take advantage of job placement assistance.
DisabilityWorks - Has some resources related to finding disability services, employment-related help, and calculation of how a job might impact your existing disability benefits.
Chinese American Service League Culinary Training - 12-week culinary training program targeted at Chinese-American residents. Program has a fee, but may be waived for low-income applicants. Has vocational English language support for Chinese speakers.
Instituto de Progreso Latino - Serving Chicago's latinx community, and offers development programs toward healthcare, manufacturing, and retail. Also helps with job referral and placement, digital literacy, general literacy, childcare, financial planning, and tutoring. ESL-friendly; programas disponsible en español.
Boys and Girls' Club of Chicago - Provides career assistance services for young adults ages 16-24, including resume workshops, training, dropout prevention, and financial aid.
There are a lot of organizations that offer free training programs, many of which also provide certificates and job placement help. This kind of depends on what kind of work you want to do—most of the opportunities are in hospitality and service industries.
Silver Fork - Free culinary workforce training program, seven weeks long, provides a lot of assistance in job placement. Operated by the Center on Halsted and open to members of the LGBTQ community and allies. Check page for next cohort start date.
Hospitality Job Training Program - Affiliated with the Greater Chicago Food Depository. Paid 4-week training program providing certifications, career counseling, job placement, and a completion bonus.
A Just Harvest Apprenticeship - Urban agriculture, community kitchen and community engagement positions; note that apprenticeships slots are limited and do require an interview, but the apprenticeship period is 1-2 years long which is good stability.
UCAN Workforce Development - Provides career help (in some cases training, it seems like?) and job placement assistance; additionally has a special summer program for youth ages 16-24.
Project:Vision Chicago - Workforce development for the Chinatown community; two programs, one of which serves older youth (18-24) and the other of which is a 20-week program for adults of all ages working towards careers in education and childcare.
Hire360 - Workforce development for hands-on trade careers (largely construction) that helps match people with apprenticeship programs; provides tools, boots, and other job expenses free of charge.
Chicago Federation of Labor Workforce & Community Initiative - Provides career counseling and job search assistance for trades, potential grants up to $8000 for skills training, workshops, and matching with apprenticeships. Also has on-site access to computers, printers, internet access and phones if you need those for your job search.
UIC Entreprenurial Support Program - If you're working on starting your own business of some kind, UIC provides counseling and potential grants.
The Chicago Public Library - Has a bunch of resources free to anyone with a library card (which is also free, get one if you don't have one); you get free access to LinkedIn Learning and other digital learning tools, including ones oriented toward resume workshopping and citizenship applications.