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- 1. Chicago in the winter? Yes! FEBRUARY 26, 2014 by melissabrenner tags: Boutique Hotels, chicago deals, Chicago hotels Contrary to popular belief, Chicago is a great year-round destination. Did you know that Chicago’s nickname, “The Windy City,” actually comes from their long-winded politicians, not the weather? Yes, the winter months do bring some serious chill, but with so many fun things to do and super low boutique hotel rates, it might all just be a breath of fresh air. During the day, explore one of Chicago’s great attractions: The Field Museum, Shedd Aquarium, and Adler Planetarium are all located on one campus. This means you can park or take public transportation once and visit all three venues. Each offers great exhibits, events and tours. To save money on some of Chicago’s best destinations consider purchasing a CityPASS which lets you visit the Shedd Aquarium, Skydeck Chicago, the Field Museum, John Hancock Observatory or the Museum of Science and Industry, and the Adler Planetarium or the Art institute of Chicago all for one discounted price. Chicago is a foodie’s delight. From Chicago pizza, famous hot dogs, gourmet restaurants and any ethnic food you could desire, this city has no shortage of great options. If you are a bacon lover, you must have brunch at Zed 451…you will thank us later! Chicago is a great city for theater offering everything from full-on Broadway shows to small regional productions. If comedy is more your speed, be sure to check out Second City, one of the world’s premier comedy clubs where many alltime greats got their start…this place is no joke! Here is the best part, winter months mean rock bottom hotel rates at great boutique hotels. The 4 star Allerton Hotel is a landmark located right on Michigan Ave. Stay in the heart of great shopping and restaurants for only $93 per night! For $113 per night, enjoy the stylish guest rooms at the 4.5 star Raffaello Hotel, located right off the Magnificent Mile. Need extra convincing? Check out more great Chicago boutique hotel deals.