16 days in Chicago, Austin & Orlando Itinerary

16 days in Chicago, Austin & Orlando Itinerary

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Route & dates

16 days in Chicago, Austin & Orlando Itinerary

London
Fly:  11​h 45​min
Chicago
— 5 nights
Fly:  4​h 45​min
Austin
— 4 nights
Fly:  5​h 15​min
Orlando
— 5 nights
Fly:  13​h
London

5
days
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, historic sites, nightlife, zoos & aquariums, and childrens museums. Your plan includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, appreciate the extensive heritage of Millennium Park, take in panoramic vistas at Skydeck Chicago - Willis Tower, and explore and take pictures at Wrigley Field.

To see maps, where to stay, more things to do, and tourist information, read our Chicago route planner

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. Due to the time zone difference, you'll gain 6 hours traveling from London to Chicago. Expect somewhat warmer temperatures when traveling from London in September; daily highs in Chicago reach 29°C and lows reach 18°C. Wrap up your sightseeing by early afternoon on the 17th (Mon) to allow enough time to travel to Austin.

Things to do in Chicago

Museums Parks Zoos & Aquariums
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Wrigley Field ©
Wrigley Field
Museum of Science and Industry, Chicago ©

3
days
Austin

Austin ©
Despite its laid-back college vibe, Austin is an influential center for politics, technology, film, and music.
Change things up with these side-trips from Austin: San Antonio (The Alamo & The San Antonio River Walk). There's much more to do: ponder the world of politics at Texas State Capitol, trek along Barton Creek Greenbelt, tour the pleasant surroundings at Lady Bird Lake Hike-and-Bike Trail, and contemplate the long history of The Driskill Bar.

For where to stay, traveler tips, other places to visit, and more tourist information, go to the Austin travel itinerary planner

Getting from Chicago to Austin by flight takes about 5 hours. Other options: drive; or take a bus. Expect a bit warmer temperatures when traveling from Chicago in September; daily highs in Austin reach 40°C and lows reach 25°C. Wrap up your sightseeing by early afternoon on the 21st (Fri) to allow enough time to travel to Orlando.

Things to do in Austin

Parks Outdoors Trails

Side Trip

San Antonio
Highlights from your plan
The San Antonio River Walk ©
The San Antonio River Walk
The Alamo
The Alamo
Texas State Capitol ©
Texas State Capitol

5
days
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.
Pack the 22nd (Sat) with family-friendly diversions at Walt Disney World Resort. Pack the 24th (Mon) with family-friendly diversions at Universal Orlando Resort. There's lots more to do: get in on the family fun at Universal's Islands of Adventure, make an unforgettable trip to Magic Kingdom Park, try out the rides at SeaWorld Orlando, and take in a show at Happily Ever After Fireworks.

For reviews, where to stay, and tourist information, go to the Orlando travel route planner

You can fly from Austin to Orlando in 5.5 hours. Other options are to do a combination of flight and train; or drive. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Expect little chillier weather when traveling from Austin in September: highs in Orlando hover around 37°C, while lows dip to 27°C. Cap off your sightseeing on the 26th (Wed) early enough to travel back home.

Things to do in Orlando

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

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