- 3-hour food and walking holiday tour of downtown Chicago
- Visit the German-style Christkindlmarket, a festive outdoor market with warming cider and holiday shops
- Stop at a local bar to taste seasonal craft brews
- Head to the historic Palmer House Hotel, where brownies were invented, to try the popular chocolate treat
- Admire the outdoor ice skating rink and magnificent architecture at Millennium Park
- Sample Chicago's famous deep dish pizza at a festive restaurant
- See Chicago's most majestic Christmas tree display at Millennium Park and the holiday windows at Macy's
- Taste the famous Chicago-style hot dog
