22 days in Chicago, New Orleans & Orlando Itinerary

22 days in Chicago, New Orleans & Orlando Itinerary

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Route & dates

22 days in Chicago, New Orleans & Orlando Itinerary

London
Fly:  11​h 45​min
Chicago
— 7 nights
Fly:  5​h 15​min
New Orleans
— 4 nights
Fly:  5​h 15​min
Orlando
— 9 nights
Fly:  13​h
London

6
days
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll get in some beach time at Grand Mere State Park and Centennial Beach. Museum-lovers will get to explore The Art Institute of Chicago and The Field Museum. Change things up with these side-trips from Chicago: Jasper-Pulaski Fish and Wildlife Area (in Medaryville), STATELINE BLUEBERRIES (in Michigan City) and Tom's Farm Market and Greenhouse (in Huntley). There's lots more to do: wander the streets of The Magnificent Mile, look for gifts at American Girl Place, admire the landmark architecture of 360 CHICAGO, and get curious at Museum of Science and Industry, Chicago.

To see reviews, more things to do, where to stay, and other tourist information, you can read our Chicago online itinerary creator.

London, UK to Chicago is an approximately 12-hour flight. The time zone changes from Greenwich Mean Time to Central Standard Time, which is usually a -6 hour difference. Expect a daytime high around 20°C in October, and nighttime lows around 10°C. Finish your sightseeing early on the 15th (Mon) to allow enough time to travel to New Orleans.

Things to do in Chicago

Parks Museums Wildlife

Side Trips

Tom's Farm Market and Greenhouse, Frank Lloyd Wright Home and Studio, STATELINE BLUEBERRIES, Jasper-Pulaski Fish and Wildlife Area, Grand Mere State Park
Highlights from your plan
Midewin National Tallgrass Prairie ©
The Art Institute of Chicago ©
The Art Institute of Chicago
Silver Beach County Park ©
Silver Beach County Park

4
days
New Orleans

New Orleans ©
Known for its Creole cuisine, rich musical tradition, and nearby swamps and plantations, New Orleans is one of the nation's oldest cities.
Museum-lovers will appreciate The National WWII Museum and Mardi Gras World. Your cultural itinerary includes sights like Laura Plantation: Louisiana's Creole Heritage Site and French Quarter. Venture out of the city with trips to Nature & Wildlife Tours (in Slidell) and Oak Alley Plantation (in Vacherie). And it doesn't end there: appreciate the extensive heritage of Garden District, explore the different monuments and memorials at Lafayette Cemetery No.1, look for gifts at Kitchen Witch, and take in the architecture and atmosphere at St. Louis Cathedral.

To see more things to do, photos, reviews, and other tourist information, you can read our New Orleans vacation planner.

Getting from Chicago to New Orleans by flight takes about 5.5 hours. Other options: drive; or take a train. Traveling from Chicago in October, you can expect nighttime temperatures to be a bit warmer in New Orleans, with lows of 22°C. Wrap up your sightseeing by early afternoon on the 19th (Fri) to allow time for travel to Orlando.

Things to do in New Orleans

Historic Sites Neighborhoods Museums

Side Trips

Vacherie, Nature & Wildlife Tours
Highlights from your plan
French Quarter ©
French Quarter
The National WWII Museum
The National WWII Museum

9
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.
Get some cultural insight at International Drive and Enterprise Heritage Center and Museum. Eschew the tourist crowds and head to Orlando Vineland Premium Outlets and Ellie Schiller Homosassa Springs Wildlife State Park. You'll find plenty of places to visit near Orlando: Alpaca Magic USA (in Homosassa), Peterbrooke Chocolatier (in The Villages) and Oakland Nature Preserve (in Oakland). Have a day of magic on the 26th (Fri) at Disney's Animal Kingdom. There's still lots to do: stop by World of Disney, get a new perspective on things with Boat Tours & Water Sports, buy something for everyone on your list at The Mall at Millenia, and contemplate the long history of Stetson Mansion.

To find more things to do, photos, traveler tips, and more tourist information, you can read our Orlando itinerary builder.

Traveling by flight from New Orleans to Orlando takes 5.5 hours. Alternatively, you can drive; or take a bus. The time zone difference when traveling from New Orleans to Orlando is 1 hour. While traveling from New Orleans, expect somewhat warmer days and about the same nights in Orlando, ranging from highs of 34°C to lows of 23°C. Wrap up your sightseeing on the 28th (Sun) early enough to travel back home.

Things to do in Orlando

Parks Wildlife Shopping

Side Trips

Cocoa Beach, Stetson Mansion, Alpaca Magic USA, Enterprise Heritage Center and Museum, Oakland Nature Preserve
Highlights from your plan
Ponce de Leon Inlet Lighthouse & Museum ©
Beach at Daytona Beach ©
Beach at Daytona Beach
Stetson Mansion ©
Stetson Mansion

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