Chicago Travel Agent Specialist

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Ashton Marshall, Travel Agent in Orlando, FL

Ashton Marshall

Orlando, FL Travel Agent

Ashton Marshall

Orlando, FL · 6 Years of Experience

Davisville Travel, an independent agent with Travel Leaders Davis, CA
About
My Places

Areas of expertise

Destinations:

Chicago, Downers Grove, Oakbrook, Naperville, Springfield

Interests:

Arts & Culture, Historical Sites, Museums, Theatre & Music, Business Travel

About Me

Centered in the heart of the Midwest among the 48 continental states, you’ll find Illinois — the 21st state, founded in 1818. As the sixth most populous U.S. state and home to over 21 million Americans, Illinois’ history is deeply rooted in agriculture, architecture, and the music shaped by American migration. It’s the birthplace of Walt Disney, home to the first McDonald’s, and boasts more nuclear power plants than any other state. Yet, about 76% of Illinois’ land is dedicated to farming, with roughly 71,000 (95%) of those farms being family-owned. The state ranks among the nation’s top producers of corn, soybeans, and even Christmas trees.

And then there’s Chicago "The Windy City"— the city where I was born and will always call home. In my book, Chicago is the incomparable gem of Illinois and, honestly, the best city in the world! Yes, you can never go wrong bringing a light jacket for an evening out Downtown.

Chicago is one of those U.S. cities that feels larger than life. Founded by a Haitian man, Jean Baptiste Point du Sable, in the late 1700s, it’s easy to forget that Chicago is just one city within Illinois. Before the pandemic, Chicago welcomed more than 60 million tourists annually, and even today, it attracts over 50 million visitors each year — both domestic and international. Tourism contributes billions to the local economy, drawing travelers for business, leisure, food, and world-class entertainment.

If you’re looking to spend some of your own tourist dollars, downtown Chicago is the perfect place to start. Along Michigan Avenue’s Magnificent Mile and State Street, you’ll find hundreds of retailers ranging from luxury brands to local boutiques. The Magnificent Mile stretches 13 blocks and is home to more than 450 stores, the 100-story John Hancock Center (don’t miss the 360 CHICAGO observation deck), upscale hotels, renowned dining, and museums.

The greater metro area, known as Chicagoland, includes surrounding towns that, while technically outside city limits, play an essential role in the region’s identity and culture. To dive into Illinois’ rich history, visit the Abraham Lincoln Presidential Library and Museum in Springfield, the state capital. There, you’ll learn how waves of migration — including Polish, Italian, Chinese, Mexican, and Southern Black American communities — helped shape the diverse culture reflected in Chicago’s food, music, and architecture today.

In Northern Illinois, travelers can venture through the historically industrial city of Rockford or head to the Illinois Railway Museum in Union — the largest railway museum in North America. Thrill seekers can make their way to Six Flags Great America and Hurricane Harbor in Lake County, just south of Milwaukee. The park covers 273 acres of rides and attractions, including classics like the Raging Bull and American Eagle wooden roller coaster, plus ocean-sized waves at the Surf Lagoon — all in the heart of the Midwest.

If you plan to explore the Chicagoland area, be prepared for some traffic — Illinois ranks seventh in the U.S. for the longest average commute times. Still, it’s worth every minute once you arrive.

Every summer, Chicago comes alive with world-famous events like Lollapalooza in Grant Park and, in 2025, the NASCAR Cup Series race returned to that same iconic downtown park. If a love for fashion brings you to the city, Chicago Fashion Week in early fall is the perfect time to stroll the streets and explore downtown attractions like The Bean (officially Cloud Gate) in Millennium Park or Navy Pier, which stretches gracefully along the Lake Shore Drive coastline. Explore its 50 acres of restaurants, event venues, and arcade games, and catch the summer fireworks from the Centennial Wheel, offering another stunning 360° view of Lake Michigan and the Chicago skyline.

One thing to remember: the pizza most commonly eaten by locals in Chicago is actually “tavern style.” It’s thin-crust, square-cut, and loaded with authentic Italian flavor — but of course, the famous deep-dish pizza is also a must-try, especially for cheese lovers. And don’t leave the city without a bag of Garrett Popcorn — their legendary Chicago Mix (a blend of cheddar cheese and caramel) is irresistible. With seven locations in downtown Chicago alone and more than 50 worldwide, it’s an easy and delicious souvenir.

Whether you’re visiting for business, sports, or studies — home to over 100 post-secondary institutions — or cheering on the Bulls or Blackhawks, Illinois has something for everyone. So pack your bags and come experience your next unforgettable travel moments in the Land of Lincoln — and, of course, in the City of Big Shoulders.

My Places

When it comes to travel planning, real-world experience makes a huge difference. Check out the map below to see all the places I have personally visited or booked for my clients. I know these destinations well and can give you reliable guidance.
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