36 days in Chicago Itinerary

36 days in Chicago Itinerary

Created using Inspirock Chicago trip planner

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1
Chicago
— 35 nights

35
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Millennium Park and Basilica of the Sacred Heart will appeal to history buffs. Satisfy your inner culture vulture at The Magnificent Mile and Ernest Hemingway Birthplace. Explore Chicago's surroundings by going to Lemon Creek Winery (in Berrien Springs), Saint Joseph (Silver Beach County Park, Whirlpool Compass Fountain, & more) and The Promenade Bolingbrook (in Bolingbrook). There's lots more to do: relax in the rural setting at Bengtson's Pumpkin Farm, tour the pleasant surroundings at Lincoln Park Zoo, kick back and relax at North Beach Park, and trek along Cowles Bog.

To find maps, other places to visit, traveler tips, and other tourist information, refer to the Chicago road trip planner .

If you are flying in from Colombia, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. In November, daytime highs in Chicago are 11°C, while nighttime lows are 1°C. Cap off your sightseeing on the 10th (Mon) early enough to travel back home.

Things to do in Chicago

Parks Outdoors Beaches

Side Trips

Oak Park, Saint Joseph, South Bend, Lake Geneva, Grosse Point Lighthouse
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park

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