15 days in Chicago, Nashville & Mississippi Itinerary

15 days in Chicago, Nashville & Mississippi Itinerary

Created using Inspirock United States trip itinerary builder

Plan created by another user. Make it yours
1
Chicago
— 3 nights
2
Nashville
— 5 nights
3
Tupelo
— 1 night
4
Vicksburg
— 1 night
5
Natchez
— 2 nights
6
Biloxi
— 1 night

S M T W T F S
31
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3
nights
Chicago

Chicago ©

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Basilica of the Sacred Heart and Grotto of Our Lady Lourdes will appeal to history buffs. Eschew the tourist crowds and head to Baha'i House of Worship and Fox in a Box Chicago. You'll find plenty of places to visit near Chicago: Indiana Dunes State Park (in Chesterton) and Lake Geneva (Mountain Top at Grand Geneva Resort & Geneva Lake). There's much more to do: tour the pleasant surroundings at Garfield Park Conservatory, wander the streets of Lincoln Park, get to know the fascinating history of Chicago Riverwalk, and contemplate in the serene atmosphere at Holy Name Cathedral.

To find reviews, ratings, more things to do, and tourist information, go to the Chicago trip maker site.

Bologna, Italy to Chicago is an approximately 14-hour flight. The time zone changes from Central European Standard Time to Central Standard Time, which is usually a -7 hour difference. Expect a bit cooler temperatures when traveling from Bologna in February; daily highs in Chicago reach 2°C and lows reach -7°C. Finish your sightseeing early on the 8th (Mon) so you can travel to Nashville.

Things to do in Chicago

Parks · Historic Sites · Nature · Outdoors

Side Trips

Highlights from your plan
Basilica of the Sacred Heart ©
Basilica of the Sacred Heart
Baha'i House of Worship ©
Baha'i House of Worship
Grotto of Our Lady Lourdes ©
Grotto of Our Lady Lourdes

5
nights
Nashville

Nashville ©

Music City U.S.A.

Known as the capital of country music, the thriving city of Nashville combines old-world southern charm with a progressive urban flair.
Get a sense of the local culture at McGavock Confederate Cemetery and Tennessee State Museum. Popular historic sites such as Bicentennial Capitol Mall State Park and Lotz House Museum are in your itinerary. Get out of town with these interesting Nashville side-trips: Kingston Springs (Narrows of the Harpeth & Adventureworks) and Franklin (Carnton & Carter House). And it doesn't end there: admire the masterpieces at Frist Art Museum, examine the collection at Madame Tussauds Nashville, appreciate the extensive heritage of Natchez Trace Parkway, and ponder the world of politics at Tennessee State Capitol.

For maps, photos, traveler tips, and more tourist information, read our Nashville day trip site.

You can fly from Chicago to Nashville in 4.5 hours. Other options are to drive; or take a bus. Prepare for somewhat warmer weather when traveling from Chicago in February: high temperatures in Nashville hover around 13°C and lows are around 1°C. Finish your sightseeing early on the 13th (Sat) to allow enough time to travel to Tupelo.

Things to do in Nashville

Museums · Historic Sites · Parks · Tours

Side Trips

Highlights from your plan
Lotz House Museum ©
Lotz House Museum
Carnton ©
Carnton
Carter House ©
Carter House

1
night
Tupelo

Tupelo ©
Tupelo is the county seat and the largest city of Lee County, Mississippi. Kick off your visit on the 14th (Sun): cruise along Natchez Trace Pkwy and then steep yourself in history at Elvis Presley Birthplace & Museum.

Find out how to plan Tupelo trip without stress by asking Inspirock to help create an itinerary.

Fly from Nashville to Tupelo in 3 hours. Alternatively, you can drive; or take a bus. February in Tupelo sees daily highs of 16°C and lows of 2°C at night. Finish your sightseeing early on the 14th (Sun) so you can drive to Vicksburg.

Things to do in Tupelo

Scenic Drive · Outdoors · Historic Sites · Museums
Highlights from your plan
Natchez Trace Pkwy ©
Natchez Trace Pkwy
Elvis Presley Birthplace & Museum ©
Elvis Presley Birthplace & Museum

1
night
Vicksburg

Vicksburg ©
Vicksburg is the only city and county seat of Warren County, Mississippi, United States. On the 15th (Mon), take an in-depth tour of U.S.S. Cairo Museum, stroll the grounds of Vicksburg National Cemetery, and then ponder the world of politics at Old Courthouse.

For other places to visit, traveler tips, photos, and other tourist information, read our Vicksburg driving holiday planning app.

Traveling by car from Tupelo to Vicksburg takes 5 hours. Alternatively, you can fly; or do a combination of bus, train, and taxi. Plan for a bit warmer temperatures traveling from Tupelo in February, with highs in Vicksburg at 20°C and lows at 6°C. Finish your sightseeing early on the 15th (Mon) so you can drive to Natchez.

Things to do in Vicksburg

Historic Sites · Museums
Highlights from your plan
Vicksburg National Cemetery ©
Vicksburg National Cemetery
U.S.S. Cairo Museum ©
U.S.S. Cairo Museum
Old Courthouse ©
Old Courthouse

2
nights
Natchez

Natchez ©
Natchez is the county seat and only city of Adams County, Mississippi, United States. Start off your visit on the 16th (Tue): pause for some serene contemplation at St. Mary Basilica, then don't miss a visit to Longwood, then steep yourself in history at Rosalie Mansion, and finally steep yourself in history at Stanton Hall. On the 17th (Wed), you'll have a packed day of sightseeing: explore the wealth of natural beauty at Melrose.

To see reviews, more things to do, traveler tips, and other tourist information, read our Natchez travel itinerary planner.

You can drive from Vicksburg to Natchez in 1.5 hours. In February, plan for daily highs up to 20°C, and evening lows to 7°C. Wrap up your sightseeing on the 17th (Wed) early enough to drive to Biloxi.

Things to do in Natchez

Historic Sites · Parks · Nature · Museums
Highlights from your plan
Longwood ©
Longwood
Melrose ©
Melrose
Rosalie Mansion ©
Rosalie Mansion

1
night
Biloxi

Biloxi ©

Playground of the South

A busy city on the Gulf Coast, Biloxi is one of the nation's oldest communities, first settled by Europeans in 1699.
Start off your visit on the 18th (Thu): steep yourself in history at Beauvoir, then take a leisurely stroll along Biloxi Lighthouse Pier, then look for all kinds of wild species at Gulf Islands National Seashore, and finally try your luck at Beau Rivage Casino.

To find maps, reviews, more things to do, and tourist information, you can read our Biloxi tour website.

Traveling by car from Natchez to Biloxi takes 4.5 hours. Alternatively, you can do a combination of car, train, and bus; or do a combination of car and bus. Traveling from Natchez in February, expect somewhat warmer with lows of 11°C in Biloxi. Wrap up your sightseeing on the 18th (Thu) early enough to travel back home.

Things to do in Biloxi

Parks · Wildlife · Casinos · Fun & Games

Side Trip

Highlights from your plan
Gulf Islands National Seashore ©
Gulf Islands National Seashore
Beauvoir ©
Beauvoir
Beau Rivage Casino ©
Beau Rivage Casino

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