Illinois

Illinois travel itineraries from Trips With Dipp focus on Chicago city breaks and easy Midwest add‑ons. In this Illinois category, you’ll find plans for exploring Chicago’s neighborhoods, museums, and lakefront, plus short trips to nearby towns, state parks, or Route 66 spots.

Guides include walkable sightseeing loops, food suggestions, viewpoints, and ideas for traveling with kids. Whether Illinois is your main destination or part of a larger U.S. itinerary, use these guides as a starting point for planning city and nearby nature time.