Plan and Book

Located on the shore of Lake Michigan, Chicago was incorporated as a city in 1837 near portage between the Great Lakes and the Mississippi River watershed. It rapidly grew in the mid 19th century by 1860 where Chicago was the youngest U.S. city to exceed a population of 100,000. Today, with a population hovering near three million, Chicago is the state’s largest and the country’s third most popular city. It’s well known for its jaw-dropping architecture, vibrant music scene, amazing food, and its iconic neighborhoods.

The main attractions you can visit start with Wrigley Field where you can enjoy a Cubs baseball game. The Park opened in 1914 and the Cubs played their first game in 1916. Wrigley Park was originally named Cubs Park but was changed after chewing gum magnate William Wrigley Jr. obtained full positions of the Cubs in 1921. Before the game starts, visit Chicago Riverwalk, where you can enjoy a great view of Chicago’s skyline. You can walk along the paths that parallel the Chicago River. The Riverwalk will also bring you to many restaurants, shops for souvenirs, or many rest stops with sweeping views of downtown. Lastly, you don’t want to miss a visit to Navy Pier on the shoreline of Lake Michigan. Navy Pier has over 50 acres of shops, restaurants, and family attractions. This Chicago landmark hosts thousands of visitors annually who come to enjoy the amusement rides, the food, and the entertainment.

After the many attractions, you’re sure to work up an appetite. Chicago is well known for its deep-dish pizza, also called Chicago-style pizza.  To get the best Chicago-styled pizza, make sure you stop by Pequod’s, Spacca Napoli, or Vito & Nick’s. Not really in the mood for pizza? Chicago barbecue uses a unique method to create mouthwatering ribs. They place meat inside a box of bricks, wrapped in stainless steel to cook for hours. The best barbecue can be found at Soul & Smoke, Smoque BBQ, and ATX Bodega.

Ready to stay out longer to enjoy music and nightlife? Steeped in Chicago’s music history, the Green Mill Cocktail Lounge, in the Uptown neighborhood, is known for hosting jazz performers as well as poetry readings. As you enjoy your cocktail, you can feel the history of Chicago as you sit in the same booth Al Capone has sat in. You can also go to the Jazz Showcase, that’s put thousands of performers on stage.  It's hosted some of the best jazz acts in Chicago and beyond. Today, you can sit where Chicago’s VIPs once sipped drinks at the front row tables and be entertained by top name international and home-grown Chicago jazz performers.

With so much to do in Chicago, make sure you fly Contour Airlines into Chicago O’Hare International. For Airport information, click here.

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