22 days in Chicago, New Orleans & Florida Itinerary

22 days in Chicago, New Orleans & Florida Itinerary

Created using Inspirock United States trip itinerary maker

Plan created by another user.Make it yours

Route & dates

1
Chicago
— 2 nights
2
New Orleans
— 3 nights
3
Pensacola
— 1 night
4
Orlando
— 1 night
5
Madeira Beach
— 1 night
6
Marco Island
— 1 night
7
Key West
— 3 nights
8
Big Pine Key
— 1 night
9
Islamorada
— 2 nights
10
Key Largo
— 2 nights
11
Miami
— 2 nights

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Satisfy your inner culture vulture at The Art Institute of Chicago and The Magnificent Mile. There's much more to do: get curious at Museum of Science and Industry, catch a live event at Wrigley Field, observe the fascinating underwater world at Shedd Aquarium, and don't miss a visit to Cloud Gate.

To find photos, more things to do, and other tourist information, refer to the Chicago day trip planning website.

Dublin, Ireland to Chicago is an approximately 11-hour flight. Due to the time zone difference, you'll gain 6 hours traveling from Dublin to Chicago. Expect somewhat warmer temperatures when traveling from Dublin in August; daily highs in Chicago reach °C and lows reach °C. Wrap up your sightseeing on the 3rd (Sat) early enough to travel to New Orleans.

Things to do in Chicago

Museums Parks Childrens Museums
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum
Museum of Science and Industry ©
Museum of Science and Industry

3
nights
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.
Do some cultural sightseeing at The National WWII Museum and Jackson Square. There's lots more to do: admire the landmark architecture of St. Louis Cathedral, examine the collection at Cabildo, learn about wildlife with up-close encounters at Audubon Zoo, and test your problem-solving skills at Escape My Room New Orleans.

To see reviews, more things to do, where to stay, and tourist information, go to the New Orleans holiday planner.

You can fly from Chicago to New Orleans in 5 hours. Alternatively, you can drive; or take a train. Traveling from Chicago in August, plan for somewhat warmer nights in New Orleans, with lows around °C. Wrap up your sightseeing on the 6th (Tue) early enough to drive to Pensacola.

Things to do in New Orleans

Museums Historic Sites Parks
Highlights from your plan
The National WWII Museum ©
The National WWII Museum
Garden District ©
Garden District
French Quarter ©
French Quarter

1
night
Pensacola

Pensacola ©
Surrounded on three sides by water, Pensacola offers access to white-sand beaches and emerald-green ocean unspoiled by large resorts.
Kick off your visit on the 7th (Wed): brush up on your military savvy at National Naval Aviation Museum, thensee where the action happens at Blue Wahoos Ballpark, and then enjoy the sand and surf at Gulf Islands National Seashore.

To see more things to do, other places to visit, where to stay, and other tourist information, go to the Pensacola online trip planner.

You can drive from New Orleans to Pensacola in 3.5 hours. Other options are to take a bus; or fly. Traveling from New Orleans in August, expect nights in Pensacola to be slightly colder, around °C, while days are a bit warmer, around °C. Wrap up your sightseeing on the 7th (Wed) to allow time to travel to Orlando.

Things to do in Pensacola

Museums Beaches Parks

Side Trip

Gulf Islands National Seashore
Highlights from your plan
National Naval Aviation Museum ©
National Naval Aviation Museum
Gulf Islands National Seashore ©
Gulf Islands National Seashore
Blue Wahoos Ballpark ©
Blue Wahoos Ballpark

1
night
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.
Start off your visit on the 8th (Thu): kick back and relax at Discovery Cove. Get ready for a full day of sightseeing on the 9th (Fri): make an unforgettable trip to Walt Disney World Resort.

To see traveler tips, more things to do, other places to visit, and tourist information, read Orlando route planning site.

Traveling by flight from Pensacola to Orlando takes 5 hours. Alternatively, you can drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Pensacola to Orlando. Expect a daytime high around °C in August, and nighttime lows around °C. Finish your sightseeing early on the 9th (Fri) to allow enough time to drive to Madeira Beach.

Things to do in Orlando

Theme Parks Beaches Parks
Highlights from your plan
Discovery Cove ©
Discovery Cove
Walt Disney World Resort ©
Walt Disney World Resort

1
night
Madeira Beach

Connected to the mainland by a causeway, Madeira Beach sits perched along the Gulf of Mexico.
Start off your visit on the 10th (Sat): enjoy the sand and surf at Treasure Island Beach, get up close to creatures of the deep with a dolphin and whale watching tour, thenkick back and relax at Saint Pete Beach, and finally fly like a bird with a parasailing or paragliding tour.

To find maps, ratings, other places to visit, and more tourist information, go to the Madeira Beach online sightseeing planner.

Getting from Orlando to Madeira Beach by car takes about 2.5 hours. Other options: take a bus; or do a combination of train and bus. In August, daytime highs in Madeira Beach are °C, while nighttime lows are °C. Wrap up your sightseeing on the 10th (Sat) early enough to drive to Marco Island.

Things to do in Madeira Beach

Outdoors Beaches Parks

Side Trips

Saint Pete Beach, Treasure Island Beach, Dolphin & Whale Watching
Highlights from your plan
Parasailing & Paragliding
Saint Pete Beach ©
Saint Pete Beach
Dolphin & Whale Watching

1
night
Marco Island

Marco Island is a city in Collier County, Florida, United States, located on an island by the same name in the Gulf of Mexico off the coast of Southwest Florida. Kick off your visit on the 11th (Sun): fly like a bird with a parasailing or paragliding tour, thenget interesting insight from Tours, and then get interesting insight from Tours.

To see reviews and other tourist information, you can read our Marco Island online tour planner.

Getting from Madeira Beach to Marco Island by car takes about 3.5 hours. Other options: do a combination of bus and taxi; or do a combination of bus and taxi. In August, daily temperatures in Marco Island can reach °C, while at night they dip to °C. Finish up your sightseeing early on the 11th (Sun) so you can catch the ferry to Key West.

Things to do in Marco Island

Outdoors Tours Adventure
Highlights from your plan
Dolphin & Whale Watching
Waterskiing & Jetskiing
Parasailing & Paragliding

3
nights
Key West

Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Satisfy your inner culture vulture at The Ernest Hemingway Home and Museum and Fort Zachary Taylor. Step out of the city life by going to Parasailing & Paragliding and Dry Tortugas National Park. There's lots more to do: get up close to creatures of the deep with a dolphin and whale watching tour, glide peacefully along the water with some of the best stand-up paddleboarding in the area, get some thrills out on the water with a waterskiing or jet-skiing adventure, and identify plant and animal life at Key West Butterfly & Nature Conservatory.

Use Inspirock's suggestions to plan your Key West trip and find the best activities and attractions for your vacation.

Ride a ferry from Marco Island to Key West in 3.5 hours. Alternatively, you can drive. In August, daily temperatures in Key West can reach °C, while at night they dip to °C. Cap off your sightseeing on the 14th (Wed) early enough to go by car to Big Pine Key.

Things to do in Key West

Outdoors Parks Tours
Highlights from your plan
Parasailing & Paragliding
Dry Tortugas National Park ©
Dry Tortugas National Park
Key West Butterfly & Nature Conservatory ©
Key West Butterfly & Nature Conservatory

1
night
Big Pine Key

Big Pine Key ©
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. Start off your visit on the 15th (Thu): identify plant and animal life at National Key Deer Refuge and then enjoy the sand and surf at Bahia Honda State Park.

To see reviews, maps, traveler tips, and other tourist information, use the Big Pine Key day trip tool.

Traveling by car from Key West to Big Pine Key takes an hour. Alternatively, you can take a bus. In August in Big Pine Key, expect temperatures between °C during the day and °C at night. Wrap up your sightseeing on the 15th (Thu) early enough to drive to Islamorada.

Things to do in Big Pine Key

Parks Beaches Outdoors
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge

2
nights
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
On the 16th (Fri), get a new perspective on things with Boat Tours & Water Sports, thenget interesting insight from Tours, and then glide through the air with a parasailing or paragliding tour. On the 17th (Sat), you'll have a packed day of sightseeing: identify plant and animal life at Dolphin Research Center, view the masterpieces at Michelle Nicole Lowe Art Gallery, and then get interesting insight from Tours.

To find reviews, traveler tips, maps, and other tourist information, read Islamorada trip itinerary builder tool.

Getting from Big Pine Key to Islamorada by car takes about 1.5 hours. Other options: take a bus. Expect a daytime high around °C in August, and nighttime lows around °C. Finish your sightseeing early on the 17th (Sat) to allow enough time to drive to Key Largo.

Things to do in Islamorada

Outdoors Tours Wildlife

Side Trip

Dolphin Research Center
Highlights from your plan
Fishing Charters & Tours
Scuba & Snorkeling
Dolphin Research Center ©
Dolphin Research Center

2
nights
Key Largo

The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
Kick off your visit on the 18th (Sun): see the vivid underwater world at Spiegel Grove, identify plant and animal life at Molasses Reef, and then admire the majestic nature at John Pennekamp Coral Reef State Park. Here are some ideas for day two: zoom along the surf with a waterskiing or jet-skiing adventure, identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, and then get a new perspective on things with Boat Tours & Water Sports.

To find maps, where to stay, ratings, and other tourist information, read Key Largo holiday builder tool.

Key Largo is just a stone's throw from Islamorada. In August in Key Largo, expect temperatures between °C during the day and °C at night. Finish up your sightseeing early on the 19th (Mon) so you can go by car to Miami.

Things to do in Key Largo

Wildlife Parks Outdoors
Highlights from your plan
Scuba & Snorkeling
Florida Keys Wild Bird Rehabilitation Center ©
Spiegel Grove ©
Spiegel Grove

2
nights
Miami

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Kick off your visit on the 20th (Tue): contemplate the waterfront views at Slough Slog, thenappreciate the extensive heritage of Lincoln Road, thenenjoy the sand and surf at South Beach, and finally appreciate the extensive heritage of Art Deco Historic District. Get ready for a full day of sightseeing on the next day: examine the collection at Vizcaya Museum and Gardens, thenget outside with JP Outfitters Inc., and then admire the majestic nature at Oleta River State Park.

For other places to visit, maps, ratings, and more tourist information, read our Miami holiday planner.

You can drive from Key Largo to Miami in 1.5 hours. Alternatively, you can take a bus. In August, plan for daily highs up to °C, and evening lows to °C. Wrap up your sightseeing on the 21st (Wed) to allow time to travel back home.

Things to do in Miami

Parks Nature Outdoors

Side Trips

Miami Beach, JP Outfitters Inc., Oleta River State Park, Slough Slog
Highlights from your plan
South Beach ©
South Beach
Slough Slog ©
Slough Slog
Lincoln Road ©
Lincoln Road

Similar Plans

23 days in United States BY A USER FROM SOUTH AFRICA September, culture, outdoors, relaxing, historic sites, museums, shopping, popular & hidden gems Preferences: September, culture, outdoors, relaxing, historic sites, museums, shopping Attraction style: Popular & hidden gems Pace: Medium 25 days in United States BY A USER FROM SOUTH AFRICA September, culture, relaxing, historic sites, shopping, popular & hidden gems Preferences: September, culture, relaxing, historic sites, shopping Attraction style: Popular & hidden gems Pace: Medium 24 days in United States BY A USER FROM UNITED STATES March, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, popular & hidden gems Preferences: March, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Medium 38 days in Florida BY A USER FROM UNITED STATES June, kids, romantic, beaches, historic sites, museums, shopping, popular sights Preferences: June, kids, romantic, beaches, historic sites, museums, shopping Attraction style: Popular sights Pace: Medium 60 days in United States BY A USER FROM DENMARK April, teens, kids, relaxing, beaches, shopping, wildlife, popular sights Preferences: April, teens, kids, relaxing, beaches, shopping, wildlife Attraction style: Popular sights Pace: Medium 24 days in United States BY A USER FROM UNITED STATES July, outdoors, beaches, historic sites, wildlife, popular & hidden gems Preferences: July, outdoors, beaches, historic sites, wildlife Attraction style: Popular & hidden gems Pace: Medium 35 days in Chicago BY A USER FROM INDIA March, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights Preferences: March, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 60 days in United States BY A USER FROM AUSTRALIA November, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: November, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 60 days in United States BY A USER FROM DENMARK April, teens, kids, outdoors, relaxing, beaches, historic sites, wildlife, popular & hidden gems Preferences: April, teens, kids, outdoors, relaxing, beaches, historic sites, wildlife Attraction style: Popular & hidden gems Pace: Medium 60 days in United States BY A USER FROM CANADA December, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights Preferences: December, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 9 days in Tulsa, Pensacola & New Orleans BY A USER FROM UNITED STATES July, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, hidden gems Preferences: July, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Hidden gems Pace: Medium
See more plans