5 days in Chicago & Mississippi Itinerary

5 days in Chicago & Mississippi Itinerary

Created using Inspirock United States trip planner

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— 3 nights
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— 3 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Bring the kids along to The Art Institute of Chicago and Shedd Aquarium. There's much more to do: engage your brain at Museum of Science and Industry, stroll through Millennium Park, take in panoramic vistas at 360 Chicago Observation Deck, and ponder the design of Buckingham Fountain.

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

The Route module shows you all the different ways you can get to Chicago. In July in Chicago, expect temperatures between 83°F during the day and 67°F at night. Wrap up your sightseeing on the 14th (Wed) to allow time to fly to Jackson.

Things to do in Chicago

Museums · Parks · Childrens Museums · Zoos & Aquariums
Find places to stay Jul 11 — 14:


— 1 night
Jackson, officially the City of Jackson, is the capital city and largest urban center of the U.S. state of Mississippi. On the 15th (Thu), learn more about the world around you at Mississippi Museum of Natural Science, then examine the collection at Mississippi Civil Rights Museum, then find something for the whole family at DEFY Jackson (High Heaven), and finally stroll around Winner's Circle Park.

To find photos, maps, other places to visit, and tourist information, go to the Jackson tour itinerary planner.

You can fly from Chicago to Jackson in 4 hours. Alternatively, you can drive; or take a bus. Expect a bit warmer temperatures when traveling from Chicago in July; daily highs in Jackson reach 91°F and lows reach 73°F. Cap off your sightseeing on the 15th (Thu) early enough to catch the flight back home.

Things to do in Jackson

Museums · Parks · Shopping · Theme Parks

Side Trip

Find places to stay Jul 14 — 15:

Mississippi travel guide

Casinos · Historic Sites · History Museums
The Magnolia State
Still relatively unspoiled by mass tourism, Mississippi epitomizes rich history and offers warm hospitality to those who vacation here. The Mississippi River forms most of its western border, so it's no surprise that this mighty waterway shapes the lives of people calling the "Magnolia State" their home. The river influences everything from the food they eat to the music they listen to. Perhaps the easiest way to discover Mississippi is to take a drive on the 715 km (444 mi) long national parkway, which follows a route used since pre-colonial times that's famous for its scenic beauty and attractions of historical interest. At the end of the parkway sits a town packed with nearly 600 antebellum homes.