15 days in Tampa & Chicago Itinerary

15 days in Tampa & Chicago Itinerary

Created using Inspirock United States planner

Make it your trip
1
Tampa
— 8 nights
Fly
2
Chicago
— 6 nights
Fly

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Tampa

— 8 nights

Big Guava

Tampa ranks among the country's most livable cities, attracting newcomers with its growing economy and status as a major port on the Gulf of Mexico.
You'll explore and learn at Museum of Fine Arts and Chihuly Collection. Popular historic sites such as Marie Selby Botanical Gardens and Sacred Heart Catholic Church are in your itinerary. Get out of town with these interesting Tampa side-trips: St. Pete Beach (Saint Pete Beach & Pass-a-Grille), Treasure Island Beach (in Treasure Island) and St. Petersburg (Craftsman House Gallery & Jon Hair Monumental Sculpture). Spend the 6th (Fri) exploring nature at De Soto National Memorial. There's lots more to do: snap pictures at Sunshine Skyway Bridge, meet the residents at Big Cat Rescue, try your luck at Seminole Hard Rock Casino Tampa, and get to know the fascinating history of Beach Walk.

For photos, more things to do, ratings, and other tourist information, you can read our Tampa driving holiday planner.

The Route module shows you all the different ways you can get to Tampa. November in Tampa sees daily highs of 80°F and lows of 62°F at night. Wrap up your sightseeing on the 12th (Thu) to allow time to travel to Chicago.

Things to do in Tampa

Parks · Outdoors · Museums · Historic Sites

Side Trips

Chicago

— 6 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Deepen your sense of the past at sights like Chicago Riverwalk and Grotto of Our Lady Lourdes. Discover out-of-the-way places like Field Museum and Holy Name Cathedral. Explore Chicago's surroundings by going to South Bend (University of Notre Dame, Basilica of the Sacred Heart, &more). Next up on the itinerary: wander the streets of The Loop, indulge in some culinary diversions at a local gastronomic tour, grab your bike and head to Lakefront Trail, and admire the masterpieces at Richard H. Driehaus Museum.

To see ratings, maps, where to stay, and more tourist information, you can read our Chicago trip maker.

You can fly from Tampa to Chicago in 5.5 hours. Alternatively, you can drive; or do a combination of bus and subway. You'll gain 1 hour traveling from Tampa to Chicago due to the time zone difference. Plan for cooler temperatures traveling from Tampa in November, with highs in Chicago at 50°F and lows at 35°F. Cap off your sightseeing on the 18th (Wed) early enough to travel back home.

Things to do in Chicago

Historic Sites · Museums · Tours · Parks

Side Trip