22 days in Chicago, Siesta Key & Orlando Itinerary

22 days in Chicago, Siesta Key & Orlando Itinerary

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Route & dates

22 days in Chicago, Siesta Key & Orlando Itinerary

Start: London
Fly:  11​h 45​min
1
Chicago
— 5 nights
Fly:  5​h 45​min
2
Siesta Key
— 8 nights
Drive:  2​h 30​min
3
Orlando
— 7 nights
Fly:  13​h
End: London

5
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll visit kid-friendly attractions like Wrigley Field and Museum of Science and Industry, Chicago. There's lots more to do: explore the world behind art at The Art Institute of Chicago, ponder the design of Buckingham Fountain, wander the streets of The Magnificent Mile, and take in panoramic vistas at Skydeck Chicago - Willis Tower.

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

London, UK to Chicago is an approximately 12-hour flight. You can also do a combination of train and flight; or do a combination of flight and bus. The time zone difference moving from Greenwich Mean Time (GMT) to Central Standard Time (CST) is minus 6 hours. Prepare for somewhat warmer weather when traveling from London in July: high temperatures in Chicago hover around 34°C and lows are around 23°C. On the 25th (Wed), wrap the sightseeing up by early afternoon so you can travel to Siesta Key.

Things to do in Chicago

Museums Childrens Museums Parks
Highlights from your plan
Museum of Science and Industry ©
Museum of Science and Industry
Shedd Aquarium ©
Shedd Aquarium
Lincoln Park Zoo ©
Lincoln Park Zoo

8
nights
Siesta Key

Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
Kids will appreciate attractions like Siesta Beach and Saint Pete Beach. You'll find plenty of places to visit near Siesta Key: Dunedin (Honeymoon Island State Park & Caladesi Island State Park), Floating Water Park (in St. Pete Beach) and Madeira Beach (Parasailing & Paragliding, John's Pass Village and Boardwalk, & more). And it doesn't end there: enjoy the sand and surf at Crescent Beach, tour the pleasant surroundings at Stump Pass Beach State Park, and look for gifts at Cw Fudge Factory LLC.

To find photos, ratings, other places to visit, and other tourist information, refer to the Siesta Key online itinerary builder .

Traveling by combination of flight and bus from Chicago to Siesta Key takes 6 hours. Alternatively, you can do a combination of flight and bus; or drive. The time zone difference when traveling from Chicago to Siesta Key is 1 hour. Traveling from Chicago in July, expect somewhat warmer with lows of 28°C in Siesta Key. Finish your sightseeing early on the 2nd (Thu) so you can drive to Orlando.

Things to do in Siesta Key

Outdoors Beaches Parks

Side Trips

Madeira Beach, Venice, St. Pete Beach, Dunedin, Cw Fudge Factory LLC
Highlights from your plan
Parasailing & Paragliding
Siesta Beach ©
Siesta Beach
Saint Pete Beach ©
Saint Pete Beach

7
nights
Orlando

Orlando ©
For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Kids will enjoy Walt Disney World Resort and Universal Orlando Resort. Pack the 3rd (Fri) with family-friendly diversions at Universal's Islands of Adventure. Have a day of magic on the 8th (Wed) at Disney's Animal Kingdom. There's still lots to do: find something for the whole family at SeaWorld Orlando, have fun at E.T. Adventure, cool off at Discovery Cove, and stop by The LEGO Store.

To find more things to do, where to stay, maps, and more tourist information, use the Orlando trip builder website .

Traveling by car from Siesta Key to Orlando takes 2.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. Expect a daytime high around 39°C in August, and nighttime lows around 28°C. Wrap up your sightseeing on the 9th (Thu) early enough to travel back home.

Things to do in Orlando

Theme Parks Parks Wildlife
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Universal Orlando Resort ©
Universal Orlando Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure

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