If you are itching to get out and explore a bigger city, put Chicago at the top of your list. It is the third largest city in the United States, behind New York and Los Angeles, meaning it is not as busy and easier to manage. But as a major metropolitan area, it still has all of the culture you’d expect from a big city.
However, the number one reason you should go is, because it is so much fun!
Getting there
Chicago is only an eight hour drive from Knoxville. Tyson McGee has daily nonstop flights to Chicago O’Hare on American and United airlines. There are also direct flights from Tyson McGee to Chicago Midway on Allegiant Mondays and Fridays.
Getting around
Chicago has a great public transportation system that makes it very easy to get around. Their “L,” an above ground train, is a real “W,” plus they have an extensive system of buses and underground trains. The advantages in using public transport include not having to worry about parking and really getting to see the city. You might even get mistaken for a local. If you choose to drive around, there are parking garages where you can pay hourly or daily. Taxis, Uber, and other ride share companies are available if you choose that route. 
What to do
You will not be bored in Chicago. Museum lovers of all ages will love visiting the completed T-Rex skeleton “Sue” at The Field Museum. The Shedd Aquarium will delight everyone with their beluga and dolphin shows. You can also escape to the stars at the Adler Planetarium. The Lincoln Park Zoo is fantastic (and free!) and home to a variety of animals in beautiful and well maintained enclosures. Spend a day at Navy Pier where you can eat, drink, and play the day away. The Chicago Children’s museum is also located nearby. The tasty pop-up museum, Museum of Ice Cream, has a location in the Windy City.
Additionally, the master of American architecture, Frank Lloyd Wright, made his home in Chicago, and you can take walking tours to see many of the beautiful homes he designed in Oak Park. Avid Frank Lloyd Wright fans can visit his home in Oak Park, the Unitarian Church he designed in Oak Park and his famous Robie House is south of Chicago in the Hyde Park neighborhood. As the birthplace of the sky scraper, there are a lot of historic ultra tall buildings and architectural tours in Chicago, including the Rookery and the Willis Tower.
In particular, I recommend taking a trip to the top of the Willis Tower to get stunning panoramic views of the city. For your more daring family members, you can venture out onto the Ledge on the top floor of the Willis Tower where only 1.5″ of glass separate you from 103 stories down. Millennium Park is where you can take your picture with the iconic Cloud Gate or more lovingly known as “The Bean. From there, you must venture to Maggie Daly Playground. During the warmer months you can take a river cruise and see the city from an entirely different view.
What to eat
There will be no complaints from your kids with the Chicago food scene. What kid doesn’t love pizza and hot dogs? Lou Malnati’s, Giodornos, and Gino’s East all have various locations around the city that will fulfill your deep dish pizza dreams. Portillo’s and Barnelli’s, Devil Dawgs, Superdawg Drive-In, and The Wieners Circle all offer top-notch Chicago style hot dogs. Your kids will love stopping at the Ghirardelli Ice Cream and Chocolate shop, Amorino, or at the Bakery Box dessert atm for a delicious dessert to end the day.
When to go
Any time of the year! The warmer months are definitely the best time to go. However, Chicago will be a fun spring or fall break destination with fewer crowds. Plan on bringing a few extra layers for the colder days. Christmas in Chicago is beautiful. The city is decorated, and there are the German Christkindlemarket and Christmas trees in the parks. Pack your warm coats, hats, and gloves, and drink some hot chocolate throughout the day. If you need some suggestions of what to pack, you can check out this article here for how to dress for success in the winter time.
