9 days in Bloomington & Kissimmee Itinerary

Bloomington is a city in and the county seat of Monroe County in the southern region of the U.S. Take a break from Bloomington with a short trip to Holiday World & Splashin' Safari in Santa Claus, about 2 hours away. Next up on the itinerary: engage your brain at WonderLab, explore the activities along Monroe Lake, hike along Pate Hollow Trail, and learn about winemaking at Oliver Winery.

For other places to visit, traveler tips, reviews, and other tourist information, go to the Bloomington trip planning tool.

Chicago to Bloomington is an approximately 4-hour car ride. You can also fly; or take a bus. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. In July in Bloomington, expect temperatures between 83°F during the day and 64°F at night. Wrap up your sightseeing on the 19th (Sun) to allow time to travel to Kissimmee.

A popular vacation destination in the central part of Florida, Kissimmee's major claim to fame remains its sunny weather and proximity to a large Disney entertainment complex.

Explore Kissimmee's surroundings by going to Saint Pete Beach (in St. Pete Beach), Legoland Florida Resort (in Winter Haven) and St. Petersburg (Morean Art Center & Outerlife Studios - Escape Room St. Pete). There's lots more to do: get a new perspective on things with Boat Tours & Water Sports, get in on the family fun at Fun Spot America, have fun at Machine Gun America, and take an unforgettable tour with a helicopter tour.

To find maps, more things to do, and tourist information, read our Kissimmee route builder website.

Traveling by flight from Bloomington to Kissimmee takes 7.5 hours. Alternatively, you can drive; or take a bus. Traveling from Bloomington in July, things will get a bit warmer in Kissimmee: highs are around 90°F and lows about 75°F. Finish your sightseeing early on the 24th (Fri) so you can travel back home.