11 days in Chicago & Fort Myers Itinerary

11 days in Chicago & Fort Myers Itinerary

Created using Inspirock United States visit planner

Make it your trip
1
Chicago
— 4 nights
Fly
2
Fort Myers
— 5 nights
Fly

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Chicago

— 4 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, nightlife, and parks. Your trip includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, stroll around Millennium Park, take in the waterfront at Navy Pier, and admire the striking features of Skydeck Chicago - Willis Tower.

To see traveler tips, photos, ratings, and more tourist information, you can read our Chicago trip builder.

Use the Route module to find travel options from your starting location to Chicago. In November, plan for daily highs up to 50°F, and evening lows to 35°F. Cap off your sightseeing on the 24th (Tue) early enough to catch the flight to Fort Myers.

Things to do in Chicago

Museums · Childrens Museums · Parks · Zoos & Aquariums

Side Trip

Find places to stay Nov 20 — 24:

Fort Myers

— 5 nights
Get out of town with these interesting Fort Myers side-trips: Fort Myers Beach (in Fort Myers Beach), Sarasota (Sarasota National Cemetery, Mote Marine Laboratory & Aquarium, &more) and Siesta Beach (in Siesta Key).

To see where to stay, ratings, traveler tips, and other tourist information, go to the Fort Myers online journey planner.

Getting from Chicago to Fort Myers by flight takes about 4.5 hours. Other options: drive; or do a combination of bus and subway. The time zone difference when traveling from Chicago to Fort Myers is 1 hour. Prepare for much warmer weather when traveling from Chicago in November: high temperatures in Fort Myers hover around 82°F and lows are around 63°F. Wrap up your sightseeing on the 30th (Mon) to allow time to fly back home.

Things to do in Fort Myers

Parks · Outdoors · Museums · Beaches

Side Trips

Find places to stay Nov 24 — 30: