43 days in Orlando & Chicago Itinerary

43 days in Orlando & Chicago Itinerary

Created using Inspirock United States sightseeing planner

This plan was created by another user.  Make it your plan

Route & dates

43 days in Orlando & Chicago Itinerary

Start: Auckland
Fly:  22​h 15​min
1
Orlando
— 24 nights
Fly:  5​h
2
Chicago
— 17 nights
Fly:  20​h 15​min
End: Auckland

24
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.
Explore Orlando's surroundings by going to Space Shuttle Atlantis (in Merritt Island), Titusville (Valiant Air Command Warbird Museum & NASA Kennedy Space Center Visitor Complex) and Kissimmee (Osceola County Welcome Center and History Museum & Shingle Creek Regional Park). There's lots more to do: discover the magic at Walt Disney World Resort, try out the rides at Discovery Cove, find something for the whole family at Universal's Islands of Adventure, and add some entertainment to your itinerary with Happily Ever After Fireworks.

For more things to do, maps, ratings, and more tourist information, read our Orlando travel itinerary planner.

Auckland, New Zealand to Orlando is an approximately 22.5-hour flight. You can also do a combination of flight and bus. Due to the time zone difference, you'll gain 17 hours traveling from Auckland to Orlando. When traveling from Auckland in September, plan for warmer days in Orlando, with highs around 37°C, while nights are a bit warmer with lows around 27°C. Finish your sightseeing early on the 5th (Sat) so you can travel to Chicago.

Things to do in Orlando

Theme Parks Parks Museums

Side Trips

Tampa, St. Augustine, Winter Park, St. Petersburg, Merritt Island
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

17
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll find plenty of places to visit near Chicago: South Bend (University of Notre Dame, Basilica of the Sacred Heart, & more), Church Street Brewing Company (in Itasca) and Century of Progress Architectural District (in Beverly Shores). There's still lots to do: explore the world behind art at The Art Institute of Chicago, walk around Millennium Park, enjoy breathtaking views from Skydeck Chicago - Willis Tower, and take a leisurely stroll along Navy Pier.

For photos, where to stay, reviews, and more tourist information, read Chicago trip itinerary planning site .

Fly from Orlando to Chicago in 5 hours. Alternatively, you can drive; or take a bus. Due to the time zone difference, you'll gain 1 hour traveling from Orlando to Chicago. Traveling from Orlando in October, expect Chicago to be colder, temps between 21°C and 11°C. Finish up your sightseeing early on the 22nd (Tue) so you can travel back home.

Things to do in Chicago

Museums Parks Historic Sites

Side Trips

South Bend, Wheaton, Milwaukee, Oak Park, Aurora
Highlights from your plan
Basilica of the Sacred Heart ©
Basilica of the Sacred Heart
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry

Similar Plans

50 days in United States BY A USER FROM PHILIPPINES September, teens, kids, culture, relaxing, romantic, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: September, teens, kids, culture, relaxing, romantic, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 7 days in Chicago BY A USER FROM MEXICO December, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: December, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 13 days in Orlando BY A USER FROM UNITED STATES June, teens, kids, outdoors, relaxing, beaches, historic sites, shopping, wildlife, slow & easy, hidden gems PREFERENCES: June, teens, kids, outdoors, relaxing, beaches, historic sites, shopping, wildlife ATTRACTION STYLE: Hidden gems PACE: Slow & easy 33 days in United States BY A USER FROM UNITED STATES August, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: August, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 6 days in Chicago BY A USER FROM UNITED STATES August, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: August, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 7 days in Orlando BY A USER FROM UNITED STATES September, kids, culture, outdoors, relaxing, romantic, beaches, wildlife, fast-paced, hidden gems PREFERENCES: September, kids, culture, outdoors, relaxing, romantic, beaches, wildlife ATTRACTION STYLE: Hidden gems PACE: Fast-paced 4 days in Chicago BY A USER FROM UNITED STATES August, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: August, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 8 days in Chicago BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, slow & easy, popular sights PREFERENCES: September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 7 days in Miami & Orlando BY A USER FROM UNITED STATES January, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, popular & hidden gems PREFERENCES: January, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 25 days in United States BY A USER FROM UNITED KINGDOM July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 50 days in United States BY A USER FROM AUSTRALIA January, culture, outdoors, relaxing, museums, shopping, popular & hidden gems PREFERENCES: January, culture, outdoors, relaxing, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium
View more plans