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Things to Do In Chicago without spending a fortune

ChiTownKnows

It is called GroupOn (Group + Coupon) groupon.thepoint.com and it offers a new local “thing to do” in Chicago everyday for a heavy discount with limited availability. If the daily deal sells out, or "tips," then everyone who signed up for the deal gets the discount. If not, no one gets the deal.
Typical deals include, but are not limited to the following:
•    Places to eat & drink (restaurants, bars)
•    Something to see (concerts, sporting events, tours)
•    Something to do (wine tasting, cooking class, dancing lessons)
•    Somewhere to stay (hotels, bed & breakfasts, ski resorts)
•    Something to buy (wine, gadgets, groceries)
•    Something to join (professional networks, gym memberships)
•    Services (pet trainers, dry cleaners, cleaning services)
•    Pampering (manicures, messages, haircuts)

See also

Living in Chicago: the expat guideNew in ChicagoMeeting people in a new cityWinter soon what to wear??Seeking advise
Marie86

Check out this website chicagofree.info, lots of free stuff to do in CHicago !

Organic

Or you can check out the event calendar at this [moderated: no commercial websites].
Plus, you can't go wrong with Millennium Park and watching sunset from the top of the Hancock having a drink (which costs less than half of visiting any observatory).