8 days in Chicago Itinerary

8 days in Chicago Itinerary

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1
Chicago
— 7 nights

7
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Take a break from the city and head to Starved Rock State Park and Apple Barn Orchard and Winery. Deepen your sense of the past at sights like John Deere Historic Site and Livingston County Courthouse. Venture out of the city with trips to South Bend (Grotto of Our Lady Lourdes & Basilica of the Sacred Heart), Prarie States Winery (in Genoa) and Carpenter Creek Cellars (in Remington). The adventure continues: admire the natural beauty at Weber House and Garden, enjoy the sand and surf at Silver Beach County Park, steep yourself in history at Historic Steppingstone, and tee off at Hawks View Golf Club.

To see reviews, photos, where to stay, and more tourist information, refer to the Chicago day trip tool .

If you are flying in from Canada, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. In April, daytime highs in Chicago are 17°C, while nighttime lows are 5°C. Wrap up your sightseeing on the 29th (Mon) to allow time to travel back home.

Things to do in Chicago

Outdoors Golf Wineries

Side Trips

Lake Geneva, Pontiac, South Bend, Southport Light Station Museum, Carpenter Creek Cellars
Highlights from your plan
Chicago Cultural Center ©
Chicago Cultural Center
Starved Rock State Park ©
Starved Rock State Park
John Deere Historic Site ©
John Deere Historic Site

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