The Midwest has a reputation for having ‘fly-over’ states; in the sense that people only ever literally fly over them, rather than explore the areas. This reputation is unfounded because there are numerous incredible places to visit, including Chicago.
Chicago proudly sits as a beacon of culture and entertainment in America’s Midwest. This city is famous not only for its dazzling architecture and spectacular skyline, lakefront and river views but also its taste in jazz, blues and the arts. This is the perfect city for groups if you want a metropolis that is bursting with personality.
A Deep-Dish Pizza Extravaganza
Chicago is one of the best cities to go to if you’re a foodie with a taste for international cuisine, and a thriving hub for traditional American cuisine. Chicago excels as super-sized indulgent with feasts that are made with love. You’ll be spoiled for choice with restaurants to try one of these famous deep dish pizzas, so browsing local guides is the best way to pick your preference.
If you’ve already had your fill of stuffed pizzas, then visiting a restaurant such as the Eleven City Diner will give you the full flavor of Chicago’s local cuisine. Reuben sandwiches and bagels piled high with smoked salmon can all be found at this South Loop diner, which will give you a full-flavor experience.
For foodies who wish to discover more exciting, innovative flavors, why not opt for a jet charter flight from Stratos Jets Charters to ensure you arrive in style?

Chicago
Architecture Highlights
Chicago has some of the most dazzling modern and historic architectural structures in America. You can take an architecture tour of Chicago via boat, which showcases some of the city’s most iconic sites along the way. Chicago’s First Lady is one of the most popular architectural boat tours for groups visiting the city and makes for the perfect day on the river, rain or shine. If you take a stroll through Millennium Park, be sure to visit the Cloud Gate sculpture, which is now almost synonymous with the city itself.
Willis Tower Skydeck
The Willis Tower is one of the tallest skyscrapers in the world, and integral to Chicago’s history as a city. In fact, it is the tallest building in the Western Hemisphere. Those who can’t handle their heights are advised to keep away with this one, as the Willis Tower Skydeck offers a unique experience that might cause many to feel weak at the knees. This mind-bending way of challenging your fear of heights allows you to step out on a glass platform and see the city beneath you at 1,353 feet. On top of the thrilling focal-point of this skyscraper, there are also historical exhibits that detail Chicago’s history with architecture.
This is a short list to begin your Chicago planning, with a variety of activities during all four seasons, the city offers first-time visitors a diverse and culturally-thriving city experience. Whether your group is traveling for music, food or architecture, you’re bound to discover something unique here.