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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14
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Chicago

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), Panhandle Pathway (in Winamac) and Swallow Cliff Stairs (in Palos Park). Next up on the itinerary: take a stroll through The Magnificent Mile, brush up on your military savvy at Cantigny Park, contemplate the long history of Frank Lloyd Wright Home and Studio, and get curious at Museum of Science and Industry.

For traveler tips, maps, more things to do, and other tourist information, read our Chicago holiday planning site.

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. Expect a daytime high around 11°C in November, and nighttime lows around 1°C. Finish up your sightseeing early on the 17th (Sun) so you can travel back home.

Things to do in Chicago

Parks · Outdoors · Trails · Historic Sites

Side Trips