October and November are of the most wonderful months to live in Chicago - not only is there beautiful scenery as the leaves change, there are plenty of special events, festivals, and holiday celebrations.
Starting in the middle of October, there are Halloween celebrations for all ages, from Lincoln Park Zoo's "Boo! At The Zoo" to adults-only Halloween parties. The Haunted River tour can be a great neutral ground - it is a bit scary, but not too much for kids (and still fun for adults!). The greater Chicagoland area is home to plenty of other haunted houses, corn mazes, pumpkin patches, and other seasonal activities as well. And you can't forget trick or treating - many neighborhoods (including Lakeshore East) offer special trick or treating outings for local families.
The Chicago Bears, Blackhawks, and Bulls seasons are also in full swing. Whether you attend a game in person or choose to watch them play at one of our city's many sports bars (all of which are full of passionate fans), you're bound to have a good time. You don't even have to be a local fan to enjoy the atmosphere, but it does help.
For the more culturally inclined, the Chicago International Film Festival, Chicago Artists Month, and Chicago Ideas Week (among many other niche events) occur during October as well. And of course, there are also plenty of special programs happening at the Field Museum, the Art Institute of Chicago, the Museum of Contemporary Art, and many of the city's smaller niche museums and cultural centers.
And it is never too early to plan ahead for Thanksgiving. With some of the city's most established and desirable restaurants serving the classic fare, along with trendier options from Chicago's more contemporary spots, there is something for everyone if you don't want to cook at home. Avid chefs are also in for a treat - the city's farmer's marketers and many grocery stores have plenty of fall produce, turkeys, and other amazing local Midwest food. You just need to plan ahead if you want reservations at a popular spot!