15 days in Chicago Itinerary

15 days in Chicago Itinerary

Created using Inspirock Chicago trip itinerary builder

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Chicago
— 14 nights

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Chicago

— 14 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get some historical perspective at Frank Lloyd Wright's Robie House and Ernest Hemingway Birthplace. You'll enjoy a bit of beach vacationing at Atwater Park & Beach and North Beach Park. Get out of town with these interesting Chicago side-trips: Veteran Acres Park (in Crystal Lake), Swallow Cliff Stairs (in Palos Park) and Panhandle Pathway (in Winamac). And it doesn't end there: admire the masterpieces at The Art Institute of Chicago, pause for some serene contemplation at Basilica of the Sacred Heart, hike along Little Red Schoolhouse, and stop by The Magnificent Mile.

To find traveler tips, ratings, reviews, and other tourist information, use the Chicago trip itinerary planning app.

If you are flying in from New Zealand, the closest major aiports are Chicago Midway International Airport, Chicago O'Hare International Airport and Gary Chicago International Airport. In November, plan for daily highs up to 11°C, and evening lows to 1°C. Cap off your sightseeing on the 17th (Sun) early enough to travel back home.

Things to do in Chicago

Parks · Outdoors · Trails · Historic Sites

Side Trips