14 days in Chicago Itinerary

Eschew the tourist crowds and head to Richard H. Driehaus Museum and Grotto of Our Lady Lourdes. Explore the numerous day-trip ideas around Chicago: Matthiessen State Park (in Utica), Ottawa (Reddick Mansion and Gardens, Washington Square Park, &more) and Starved Rock State Park (in Oglesby). There's still lots to do: admire the masterpieces at The Art Institute of Chicago, explore the activities along Chicago River, don't miss a visit to Chicago Skyline, and explore the landscape on two wheels at Lakefront Trail.

For where to stay, ratings, more things to do, and tourist information, read Chicago trip planner.

In October, plan for daily highs up to 65°F, and evening lows to 49°F.