J.P.
Hi S.-
In Woodfield Mall, there's a new place called Yu's Island. It's right next to Sears on the first level. It's new and it looks really clean. $10 may sound like a lot for each child BUT you can stay as long as you want and I THINK you can leave and walk around the mall, have lunch with your friend and the kids, etc... and come back THE SAME DAY for no additional money as long as you save your receipt. The kids can play and you and your friend can chat nearby in the play area. They serve coffee and a few other things there. Here's a description of it from Kidwinks: (you'll also find a coupon for a free cup of coffee.) http://www.kidwinks.com/FamilyFun/4/YuKidsIslandIndoorPla...
I am not sure how crowded it will get though because the mall does tend to get crowded on the weekends. (It would be nice if Yu's had a limit of kids that wasn't too high. Not sure if they do) There's also a free kid's area in the mall but I always see that play area being so crowded! (This playarea is relatively new.... they didn't have it a few years back when my twins would have enjoyed it.)
I've heard mixed reviews about Legoland as well. That's near Woodfield Mall. If you do go to Legoland, there's a place called Red Mango that has delicious frozen yogurt with many toppings to choose from. Gameworks is a very cool place but there is a limited amount of games for 2 year olds... an older kids place really.... after they outgrow Chuck E. Cheese . But... it probably would keep a 2 yr. interested because there is a lot going on!
This website can also help with planning somewhere with kids and you can narrow your search for a specific town: http://www.trekaroo.com/places/chicago-illinois/activitie...
Here's another site I use that helps me plan kid friendly activities in specific areas: http://www.oakleesguide.com/
Have fun and I hope this helps!
Oh... one more thing.... If you do decide to go to Legoland, DON'T pay without finding a coupon for buy one child's admission, get one adult admission free. (Although.... maybe your little guy would get in free since he's only 2. I am not sure.) I do know that it's approx. $20 per person but I don't know the age that they start charging for. Coupons for BOGO can be found in Lego magazines. My son gets these mailed to him free every other month from the Lego store where I filled out a card for him. Also... these coupons are on the plastic wrapper of small, cheaper kits.
