16 days in Chicago Itinerary

16 days in Chicago Itinerary

Created using Inspirock Chicago sightseeing planner

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Route & dates

16 days in Chicago Itinerary

Start: Casablanca
Fly:  33​h 30​min
— 13 nights
Fly:  21​h
End: Casablanca


Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your day-by-day itinerary now includes Millennium Park as well as Rockit Bar & Grill. The Magnificent Mile and The Field Museum are good opportunities to explore the local culture. The Art Institute of Chicago and Swedish American Museum will appeal to museum buffs. Explore the numerous day-trip ideas around Chicago: Centennial Beach (in Naperville), Kernel's Gourmet Popcorn & More (in Geneva) and Prarie States Winery (in Genoa). And it doesn't end there: relax in the rural setting at Bengtson's Pumpkin Farm, trek along Little Red Schoolhouse, enjoy the sand and surf at Silver Beach County Park, and stroll through North Beach Park.

To find photos, traveler tips, reviews, and tourist information, read our Chicago trip itinerary builder app .

Casablanca, Morocco to Chicago is an approximately 21-hour flight. The time zone changes from Western European Time (WET) to Central Standard Time (CST), which is usually a -6 hour difference. Expect colder temperatures when traveling from Casablanca in November; daily highs in Chicago reach 11°C and lows reach 1°C. Finish your sightseeing early on the 30th (Fri) to allow enough time to travel back home.

Things to do in Chicago

Parks Outdoors Beaches

Side Trips

Racine, Prairie States Winery, Little Red Schoolhouse, Pirate's Cove Children's Theme Park, Bengtson's Pumpkin Fest
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum