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Chicago to Dallas 7-Day Road Trip Itinerary
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Chicago to Dallas 7-Day Road Trip Itinerary
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Day 1: Exploring Chicago
Chicago, USA
8:00 AM
Breakfast at Lou Mitchell's
Start your day with a hearty breakfast at Lou Mitchell's, a classic diner known for its delicious pancakes and friendly service.
$, 1 hour
10:00 AM
Visit Millennium Park
Explore the iconic Millennium Park and take a selfie at the famous Cloud Gate sculpture, also known as 'The Bean'.
Free, 2 hours
1:00 PM
Lunch at Portillo's
Indulge in Chicago's famous deep-dish pizza at Portillo's for a satisfying lunch.
$$, 1.5 hours
3:00 PM
Art Institute of Chicago
Visit the Art Institute of Chicago to admire a world-class collection of art, including works by Picasso and Grant Wood.
$, 2 hours
6:00 PM
Dinner at Girl & the Goat
Enjoy a memorable dinner at Girl & the Goat, a popular restaurant known for its innovative dishes and vibrant atmosphere.
$$$, 2 hours
Find Hotels in Chicago
Day 2: St. Louis Stopover
St. Louis, USA
9:00 AM
Breakfast at Rooster
Start your day with a delicious breakfast at Rooster, known for its crepes and farm-fresh ingredients.
$$, 1 hour
11:00 AM
Gateway Arch National Park
Visit the Gateway Arch National Park and take a tram ride to the top for panoramic views of the city.
$, 2 hours
1:00 PM
Lunch at Pappy's Smokehouse
Savour some delicious St. Louis-style BBQ at Pappy's Smokehouse for a true taste of the city.
$$, 1.5 hours
3:00 PM
Explore Forest Park
Spend the afternoon exploring Forest Park, home to the St. Louis Zoo, Art Museum, and beautiful gardens.
Free, 2 hours
6:00 PM
Dinner at The Hill
Enjoy a traditional Italian dinner in The Hill neighborhood, known for its authentic cuisine and cozy atmosphere.
$$$, 2 hours
Find Hotels in St. Louis
Day 3: Memphis Music Experience
Memphis, USA
8:00 AM
Breakfast at Brother Juniper's
Start your day with a hearty breakfast at Brother Juniper's, a local favourite known for its delicious omelettes and friendly service.
$$, 1 hour
10:00 AM
Graceland
Visit the iconic Graceland, the former home of Elvis Presley, and explore the museum dedicated to the King of Rock 'n' Roll.
$$$, 2 hours
1:00 PM
Lunch at Central BBQ
Indulge in some mouthwatering BBQ at Central BBQ for a taste of authentic Memphis flavours.
$$, 1.5 hours
3:00 PM
Sun Studio
Explore Sun Studio, the birthplace of rock 'n' roll, and learn about its legendary recording history.
$$, 1.5 hours
6:00 PM
Dinner at Blues City Cafe
Enjoy a soulful dinner at Blues City Cafe, a popular spot for live blues music and classic Southern dishes.
$$, 2 hours
Find Hotels in Memphis
Day 4: Vibrant New Orleans
New Orleans, USA
9:00 AM
Breakfast at Cafe Du Monde
Savour beignets and cafe au lait at Cafe Du Monde, a New Orleans institution famous for its delicious treats.
$, 1 hour
11:00 AM
French Quarter Exploration
Stroll through the historic French Quarter, soak in the vibrant atmosphere, and admire the architecture of the iconic buildings.
Free, 2 hours
1:00 PM
Lunch at Commander's Palace
Indulge in a luxurious lunch at Commander's Palace, a renowned restaurant serving up classic Creole dishes.
$$$, 1.5 hours
3:00 PM
Visit Jackson Square
Explore Jackson Square, a historic park surrounded by artists, street performers, and the iconic St. Louis Cathedral.
Free, 1.5 hours
6:00 PM
Dinner at Galatoire's
Experience a traditional New Orleans dining experience at Galatoire's, where you can enjoy Creole cuisine in an elegant setting.
$$$, 2 hours
Find Hotels in New Orleans
Day 5: Houston Highlights
Houston, USA
8:00 AM
Breakfast at The Breakfast Klub
Start your day with a delicious breakfast at The Breakfast Klub, known for its southern comfort food and famous wings.
$$, 1 hour
10:00 AM
Space Center Houston
Explore the Space Center Houston to learn about NASA's space missions and see fascinating exhibits and artifacts.
$$, 3 hours
1:00 PM
Lunch at Pappadeaux Seafood Kitchen
Enjoy a seafood feast at Pappadeaux Seafood Kitchen, known for its fresh and flavourful dishes.
$$, 1.5 hours
3:00 PM
Museum District
Explore Houston's Museum District, home to a variety of museums, galleries, and cultural institutions.
$, 2 hours
6:00 PM
Dinner at Killen's Steakhouse
Indulge in a mouthwatering steak dinner at Killen's Steakhouse, a top-rated restaurant known for its prime cuts and elegant ambiance.
$$$, 2 hours
Find Hotels in Houston
Day 6: Dallas Delights
Dallas, USA
9:00 AM
Breakfast at Ellen's Southern Kitchen
Start your day with a delightful Southern breakfast at Ellen's, known for its comfort food and warm hospitality.
$$, 1 hour
11:00 AM
Dallas Arboretum and Botanical Garden
Explore the beautiful Dallas Arboretum and Botanical Garden, featuring stunning floral displays and scenic landscapes.
$, 2 hours
1:00 PM
Lunch at Pecan Lodge
Enjoy some mouthwatering BBQ at Pecan Lodge, a popular spot known for its delicious smoked meats and tasty sides.
$$, 1.5 hours
3:00 PM
Visit The Sixth Floor Museum
Explore The Sixth Floor Museum at Dealey Plaza, dedicated to the life and legacy of President John F. Kennedy.
$, 2 hours
6:00 PM
Dinner at Uchi Dallas
Indulge in a culinary experience at Uchi Dallas, a contemporary Japanese restaurant known for its creative dishes and elegant ambiance.
$$$, 2 hours
Find Hotels in Dallas
Day 7: Relaxing in Dallas
Dallas, USA
9:00 AM
Brunch at Bread Winners Cafe
Enjoy a leisurely brunch at Bread Winners Cafe, known for its delicious brunch options and relaxed atmosphere.
$$, 1.5 hours
11:00 AM
Dallas Museum of Art
Spend the morning exploring the Dallas Museum of Art, home to a diverse collection of art from around the world.
$, 2 hours
1:30 PM
Shopping at The Galleria
Shop till you drop at The Galleria, a premier shopping destination in Dallas with a wide range of stores and boutiques.
$$$, 3 hours
5:30 PM
Dinner at Five Sixty by Wolfgang Puck
Enjoy a sophisticated dinner at Five Sixty by Wolfgang Puck, a revolving restaurant with stunning views of the city skyline.
$$$, 2 hours
Find Hotels in Dallas
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More About Chicago to Dallas
Trip Packing List: United States multi-city tour (30 Aug 2026 — early Nov 2026)
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Trip Packing List: Multi-city U.S. Winter (December) — Coastal & Inland — Urban & Outdoors
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Full Guide to Michelin Star Cities: 2025 Updated List
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Global Michelin Cities & US Travel Tiers from New York
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Itinerary created by
Plantrip Team
February 13, 2024
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