15 days in Chicago Itinerary

15 days in Chicago Itinerary

Created using Inspirock Chicago tour itinerary planner

This plan was created by another user.  Make it your plan

Route & dates

View / edit route

— 14 nights


Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Cantigny Park and Chicago Riverwalk will appeal to history buffs. Get outdoors at Lakefront Trail and Silver Beach County Park. Venture out of the city with trips to Baha'i House of Worship (in Wilmette), South Bend (Basilica of the Sacred Heart, Grotto of Our Lady Lourdes, & more) and Jasper-Pulaski Fish and Wildlife Area (in Medaryville). Next up on the itinerary: shop like a local with Chicago Cultural Center, hike along Geneva Lake Shore Path, take a stroll through The Magnificent Mile, and admire the masterpieces at The Art Institute of Chicago.

To see reviews, maps, and tourist information, use the Chicago trip planner .

In December, daytime highs in Chicago are 38°F, while nighttime lows are 26°F. Wrap up your sightseeing on the 3rd (Fri) to allow time to travel back home.

Things to do in Chicago

Parks Outdoors Trails

Side Trips

South Bend, Utica, Pontiac, Geneva Lake Shore Path, Swallow Cliff Stairs
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Cantigny Park ©
Cantigny Park