Cheap Fun Activities in Chicago

For deep dish I recommend Lou Malnati's Pizzeria on Rush near Division. Other free or cheap activities would be Zoo Lights at the Lincoln Park Zoo, a Segway tour or walking architectural tour, Navy Pier and Magnificent Mile shopping.

Would you be willing to travel a little outside of the city? In Oak Park (Illinois) you can visit the Frank Lloyd Wright Home and Studio tour. I'm not a huge architecture person but still really enjoyed it. They also have a cute downtown so you could have lunch and make a day of it. It's also the birthplace of Hemingway and there is a museum there. I wasn't totally impressed with this but as long as you are there might as well check it out.

If you like antiques Andersonville and Ravenswood are cute neighborhoods with lots of shops for that and good restaurants. 

I lived in Chicago for 8 years (my last apartment was close to Moody!) and my favorite deep dish is still Pequod's Pizza. Hard to beat their caramelized crust!

For some different ideas, have you thought of doing a food or drink tour?

If you like coffee, Intelligentsia Coffee offers a Roasting Tour: http://www.intelligentsiacoffee.com/product/merchandise/chicago-roasting-works-tour 

If you like brandy, Rhine Hall Distillery is a family owned distillery, all locally sourced. They offer tours and have tastings - helllloo apple brandy cocktails!

There is also Revolution Brewing Brewery which is always a fun experience to taste some local craft beers.

Have fun!

If you like Blues, definitely go to Kingston Mines.  Definitely drink some Half Acre Beer Company, too!

I haven't seen it yet but this looks like a cool place to try ice skating and is new this year.

http://www.redeyechicago.com/news/local/redeye-maggie-daley-park-ice-skating-ribbon-opening-soon-20141022,0,6103513.story

Deep dish pizza, any of the Lou Malnati's Pizzeria locations, the one on Wells Street in River North or the one Lou Malnati's Pizzeria in the South Loop on South State might be a little less busy than the one on the Gold Coast.  Giordano's is my other favorite but that is stuffed, not deep dish.

The Chicago History Museum might be a place to stop, it's up near Moody, I bought a Groupon not too long ago and they might still have a free day although most of those are limited to Illinois residents nowadays.

Check out the Christkindlmarket Chicago which is free, have a wander through the Chicago Cultural Center which is free and a beautiful building.

Zoo Lights is a good suggestion since it's free, stop by RJ Grunts for good burgers and shakes and what they claim is the original salad bar.

Yes to Pequod's Pizza! 

Also, check out what's going on at the Chicago Cultural Center. Its a great way to see some of the cultural offerings in Chicago without breaking the bank.

If you are a teacher or student - read on! There are so many museums you can see for free or very discounted. I know that the The Art Institute of Chicago, Field Museum of Natural History, and Museum of Science and Industry have free admission for teachers (and perhaps college students as well, though check first if its any state or just Illinois). If you plan ahead, you can also see the Shedd Aquarium for free if you are an Illinois teacher. And along those lines, the Chicago Symphony Orchestra, Broadway in Chicago and Lyric Opera of Chicago offer heavily discounted tickets to people holding a college student ID.

Best deep dish is Pequod's Pizza.  Avoid Gino's East, Lou Malnati's, and Giordano's.  These are all tourist traps.