Departing from: TPA to MDW or ORD
Flight duration: 2.5 – 3 Hours
Nonstop flights: Year-round
Airlines: Southwest, Frontier & United
From iconic architecture and renowned museums to legendary dining and a storied past, Chicago offers something for nearly every traveler. The city’s walkable neighborhoods and convenient public transit make it easy to explore, whether you’re searching for the perfect slice of deep-dish pizza, delving into its colorful mob history or discovering the roots of Chicago blues.
Where to Stay
The Sono Chicago is a boutique bed-and-breakfast in Chicago’s historic Old Town district. This cozy stay is within walking distance of a variety of shops, favorite Michelin restaurants, and an entrance to get onto the “L”, Chicago’s elevated subways. For a more luxurious stay, the Chicago Athletic Association Hotel, located across from Millennium Park, is a top choice.
Where to Eat
For Michelin-level cuisine, head to BOKA for parsnip tortelli and black sesame kasutera, or just a few feet away, enjoy a one-of-a-kind gastronomic experience at Alinea. Just be sure to secure your reservation ahead of time, as reservations are limited for this dinner and show.
For breakfast, the line out the door at Wildberry Pancakes & Cafe at Prudential Plaza speaks for itself. You can’t go wrong with the signature Berry Bliss pancakes or the savory breakfast hash. Harry Caray’s Italian Steakhouse on West Kinzie Street was once a popular mob hangout and still houses Frank Nitti’s secret vault, so it’s the perfect spot for a bite and a taste of history.
In the mood for a more diner styled breakfast or lunch? Check out Pittsfield Cafe, hidden inside the Pittsfield Building, built in 1927. Once finished, explore the Chicago Pedways, with an entrance just right across the street.
What to Do
Some of the best things to do in the Windy City are free. The Lincoln Park Conservatory is housed in a Victorian-era glass house and filled with exotic plants from around the world. Nearby, the Lincoln Park Zoo is one of the oldest zoos in North America and is home to nearly 200 species.
Tom (Ping) Memorial Park is known for its Chinese landscape design elements, while Cloud Gate—popularly known as “The Bean”—is an iconic downtown Chicago landmark. While visiting “The Bean” be sure to pass through the Lurie Garden for a peaceful moment in the city.
Architecture is a defining aspect of Chicago, and one of the best ways to learn more about the city’s unique buildings is aboard the Shoreline Sightseeing or Wendella architecture river tours, which combine history with a little comedy. Another water-based attraction is the Shedd Aquarium, which offers touch-tank experiences, summer stingray feedings and shark-feeding tours.
Don’t miss the Magnificent Mile, a shopping and culinary paradise. Here, you can enjoy a mug of butterbeer at the Harry Potter Shop Chicago or coffee and light bites at the five-level Starbucks Reserve Roastery.
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