If you’ve never visited the great city of Chicago, then you are missing out on one of the most magnificent cities in North America. The so-called “Windy City” is well loved for its iconic architecture, the diverse culture of its various neighborhoods, its vibrant nightlife, and for its bustling music and art scene. As we are quickly approaching what is considered to be shoulder season in the region, it may just be the perfect time to look for last-minute flights to Chicago and take advantage of the better deals you are likely to find. From a vibrant culinary scene, to a rich history that lurks behind every building, here is our guide to vacationing in Chicago.
Last-Minute Flights to Chicago
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The first step to planning your Chicago adventure is finding a good flight deal. Now, it may be tempting to take advantage of the lower winter flight prices, but this will not make for the best visiting experience. Chicago winters are notoriously brutal, and not for anyone who isn’t used to freezing temperatures. It is better to take advantage of prices in late September through October, when the real chill has not set in. You will still want to pack plenty of warm clothes, but with enough layers you will still be able to enjoy the city without having to shell out as much cash. This means you won’t be able to enjoy the beaches on Lake Michigan, but there is still plenty more for you to see!
Architectural Marvels
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After the Great Chicago Fire of 1871 that destroyed over 17,000 structures, the city was a veritable blank slate for architects from around the world to make their mark on. The result is a skyline that reaches back more than a century with ambitious skyscrapers and stunning structures running along the shores of Lake Michigan. See iconic buildings like the Willis Tower, formerly called the Sears Tower and once the tallest building in the world, where you can head to the Skydeck on top of the building to get a panoramic view of the city. To get a glimpse of what the city was like in the 19th century, check out the Gothic Revival-style water tower that is one of the last standing structures from before the fire. Check with local tour companies to take an architecture tour if you want to learn more.
Landmarks and Monuments
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The history and culture of Chicago permeate from the city’s most iconic landmarks, and many of these places have the added benefit of being completely free to visit. Any trip to the city should include a visit to Millennium Park, which is home to an enormous silver art piece called Cloud Gate(nicknamed “The Bean”, for obvious reasons), which reflects the skyline in different ways depending on where you are looking. Buckingham Fountain in Grant Park is one of the largest fountains in the world, Navy Pier is a 3,000 foot pier that acts as a hub for family-friendly activities and attractions, and Wrigley Field is one of the oldest ballparks in Major League Baseball. If you are a real history buff, you’ll want to check with local tour companies to get a guided tour of all the most significant spots.
Culinary Exploration
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Much of Chicago’s culinary influence has reached well past its streets and across the globe, with staples like their deep dish pizza and iconic hot dogs being well known. For deep dish pizza, stop by Milly’s Pizza in the Pan for one of the highest rated restaurants in the city. For an authentic Chicago-style hotdog, straight off of a street cart is the way to do it. A proper dog will be an all-beef frankfurter on a poppy seed bun, covered in yellow mustard, sweet pickle relish, chopped white onion, tomato slices, a whole pickle spear, pickled sport peppers, and finished with celery salt. Go even deeper by visiting places like Little Italy, Chinatown, and Greektown to experience what the different communities of Chicago bring to the culinary scene.
World Famous Museums
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Chicago is home to more world-famous museums than you are likely to be able to visit in a single trip. There’s the Art Institute of Chicago located in Grant Park, which is one of the oldest and largest art museums in the country and houses over 300,000 works of art. The Field Museum of Natural History houses 40 million artifacts and specimens, ranging from Egyptian history to dinosaur fossils. The Shedd Aquarium is one of the most visited aquariums in the Western hemisphere and is home to many exotic species from otters and sea lions to beluga whales. Whether you are a history buff, a nature lover, or a burgeoning scientist, anyone with a curious mind will never get bored of Chicago’s museums!
