1. Gibson's-- if you love steaks and big portions, come eat here. They have all the vegetable sides one could ask for and an amazing house salad. Also if you are a dessert person and don't care about calories, be sure to order a "slice" of cake for dessert. $
2. RPM--What an unbelievable restaurant. The ambience is chic and modern. My friends and I ate here for my birthday party and we got a high table for 8 near the bar. The staff was friendly and helpful and the food was american-italian. You cannot go wrong. Just make sure you dress appropriately because the crowd in there is fancy. And make reservations ahead of time too! Also they have a gluten-free menu with gluten-free pastas. Personally, I got salmon with a pistachio pesto sauce and a side of brussel sprouts (of course). It was absolutely fabulous. I just love a whole foods meal like this. $$
3. Zed 451-- a delicious brazilian steakhouse, this restaurant is even suitable for vegetarians. It has an amazing bar of side dishes from raw salads to yummy cooked vegetable dishes, each with a name tag so you know the ingredients (and can steal the recipes). While you grab your vegetables, waiters come by with different cuts of meat from lamb to beef and even fish. Just be sure to put your green card to red before you get too full! $
2. Take a stroll down Michigan Ave and window shop.
3. Check out Ghirardelli's for dessert.
4. Hang out by the lake for a day and people watch.
5. Bike, walk, or run on the lake.
6. Visit one of the museums on a rainy day. The art museum is very cool.
7. Walk or segway through millennium park!
8. Go see a show, whether comedian or acrobatic. We saw a cirque de soleil show at the Chicago theatre and it was fabulous.