5 days in Chicago and Beyond Itinerary

5 days in Chicago and Beyond Itinerary

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Route & dates

5 days in Chicago and Beyond Itinerary

Start: Jacksonville
Drive:  17​h 45​min
— 2 nights
Drive:  17​h 45​min
End: Jacksonville


Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kick off your visit on the 2nd (Thu): learn about winemaking at St. Julian Winery-Union Pier, then identify plant and animal life at Coffee Creek Watershed Preserve, and then take in nature's colorful creations at Taltree Arboretum and Gardens. Keep things going the next day: learn about winemaking at Shady Creek Winery, take in the spiritual surroundings of Shrine of the Christ's Passion, and then admire the majestic nature at Kankakee River State Park.

For ratings, reviews, traveler tips, and tourist information, use the Chicago trip itinerary builder website .

Jacksonville to Chicago is an approximately 18-hour car ride. You can also take a bus; or take a train. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. Expect a bit cooler temperatures when traveling from Jacksonville in May; daily highs in Chicago reach 71°F and lows reach 52°F. You'll set off for home on the 4th (Sat).

Things to do in Chicago

Parks Wildlife Nature

Side Trips

Kankakee River State Park, Taltree Arboretum and Gardens, St. Julian Winery-Union Pier, Shady Creek Winery, Shrine of the Christ's Passion
Highlights from your plan
Taltree Arboretum and Gardens ©
Taltree Arboretum and Gardens
Shady Creek Winery ©
Shady Creek Winery
St. Julian Winery-Union Pier ©
St. Julian Winery-Union Pier

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