14 days in Chicago Itinerary

14 days in Chicago Itinerary

Created using Inspirock Chicago trip planner

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Chicago
— 13 nights

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Chicago

— 13 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll discover tucked-away gems like Chicago Riverwalk and Silver Beach County Park. Get outdoors at Starved Rock State Park and Jasper-Pulaski Fish and Wildlife Area. Get out of town with these interesting Chicago side-trips: Baker Lake Park (in Peru), Weber House and Garden (in Streator) and Saint Joseph (St. Joseph Lighthouses & Lions Park Beach). And it doesn't end there: trek along Geneva Lake Shore Path, take in the architecture and atmosphere at Basilica of the Sacred Heart, look for all kinds of wild species at Sarett Nature Center, and get to know the fascinating history of Riverwalk Lot.

To find where to stay, other places to visit, and other tourist information, read our Chicago trip itinerary website.

In June, daily temperatures in Chicago can reach 81°F, while at night they dip to 63°F. Finish your sightseeing early on the 23rd (Sat) so you can travel back home.

Things to do in Chicago

Parks · Outdoors · Wildlife · Beaches

Side Trips

Find places to stay Jun 10 — 23: