Illinois Route 66 Attractions: The Ultimate Road Trip Guide from Chicago to St. Louis

Ready to explore the Illinois stretch of Route 66? In this article, Gary Crallé shares his simple five-day, 301-mile road trip plan from Chicago to St. Louis, with can’t-miss stops, charming small towns, and classic roadside attractions to watch out for.

USA TravelGary CralléFebruary 17, 2026Route 66, Illinois, Chicago, Road Trip

How to Spend 2 Days in Chicago - Your Chicago Trip Planner

Even with just 2 days in Chicago with a carefully planned Chicago itinerary, you can see a lot! Welcome to your 2 day Chicago trip planner!

USA Travel, North America TravelChristopher James MitchellOctober 4, 2023Chicago, Illinois, Chicago itinerary, Chicago trip planner, Art Institute of Chicago, two days in Chicago, 48 hours in Chicago, 2 days in Chicago, Chicago in 2 days, Chicago in two days, Bobby's Bike Hike Chicago, Chicago vacation, Chicago river cruise, Chicago's First Lady Architecture Tour, Wrigley Field, The Skydeck Chicago, The Skydeck Chicago at Willis Tower, Willis Tower Chicago, Wicker Park, Bucktown, Chicago Greeter Tour, Millennium Park, Cloud Gate, The Bean, Lou Mitchells, Revival Food Hall, Au Cheval, Angelos Wine Bar, The Purple Pig, Pequod's Pizza, Gino's East, Chicago Pizza and Oven Grinder Company, Lou Malnalti's Pizzeria, Portillo's Hot Dogs, Al's Beef, Jimmy's Red Hots, Superdawg Drive-In, Hot "G" Dog, Ricobene's, Johnnie's Beef, Kingston Mines, Chicago Magic Lounge, Sluggers Chicago, Green Mill Cocktail Lounge, Logan Arcade, CityPASS Chicago, CityPASS, JW Marriot Chicago

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