30 days in Chicago Itinerary

30 days in Chicago Itinerary

Created using Inspirock Chicago holiday planner

Make it your trip
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Chicago
— 29 nights

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Chicago

— 29 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your cultural itinerary includes sights like The Art Institute of Chicago and Frank Lloyd Wright's Robie House. We've included these beaches for you: Rosewood Beach and Kathy Osterman Beach. Explore Chicago's surroundings by going to Prairie Wolf Slough (in Highland Park), Three Oaks Recreation Area (in Crystal Lake) and Lake Forest (Wildlife Discovery Center & Fort Sheridan Forest Preserve). There's lots more to do: learn more about the world around you at Field Museum, enjoy breathtaking views from Skydeck Chicago - Willis Tower, look for all kinds of wild species at Jasper-Pulaski Fish and Wildlife Area, and take a stroll through The Magnificent Mile.

To find other places to visit, more things to do, reviews, and more tourist information, read our Chicago holiday planner.

If you are flying in from South Africa, the closest major aiports are Chicago Midway International Airport, Chicago O'Hare International Airport and Gary Chicago International Airport. In April, plan for daily highs up to 17°C, and evening lows to 5°C.

Things to do in Chicago

Parks · Wildlife · Outdoors · Museums

Side Trips