Top 10 Hidden Gems in Chicago

Chicago, the Windy City (also known as the Second City and Chi Town), is a popular tourist destination in the Midwest. Chicago offers tourists and locals alike unique, exciting, and vibrant flavor, both culturally and culinary-wise. Here you will find some of the best of classic American architecture, history lessons, and opportunities for fun, as well as several options for education at their world-class museums, zoos, gardens, and aquariums.

This city is serious when it comes top attractions, though sometimes the best landmarks, iconic hotspots, and eateries get overlooked in the shadow of something more mainstream. Being such huge Chicago fans we feel that it isn’t right to miss these next 10 amazing hidden gems in Chicago in lieu of visiting too many others, which is why we’ve made this great list to help you out!

  1. Oak Park - Forest AvenueOak_Park_Il_Walter_Gale_House4
    • This spot often gets overlooked, hiding within the monumental shadows of the massive city skyline bordering popular Grant and Millennium Parks. Oak Park on Forest Avenue, however, is a great place to see some of the best architecture and personal city history and culture in our opinion, the village being the former home of celebrated designer Frank Lloyd Wright. Here you can see a row of his designs, his own home, and even his personal studio!
  2. Tommy Gun’s Garage - Wabash Avenue
    • You better know the password if you come to Tommy Gun’s, one of our favorite well hidden gems of the Windy City. Here you will find the longest running interactive dinner show in Chicago, a historical and entertaining display of the prohibition period of the Roaring '20s. See the spots in the eatery where Al Capone and his mafia buddies would hang out, learn about speakeasies, and learn to do the Charleston!
  3. Jackson_Park,_Osaka_GardenOsaka Japanese Garden - Jackson Park
    • The Osaka Japanese Garden is located on the south side of the city, right behind the Museum of Science and Industry. Here, within Jackson Park, you will find some of the most breathtaking and authentic Japanese Garden scenery in the state, maybe even in the country! Explore the gorgeous gardens and find your inner zen while learning about the city's personal ties to WWII history and the internment of Japanese prisoners and families.
  4. Billy Goat Tavern - Michigan Avenue
    • The Billy Goat Tavern is actually a chain of several taverns throughout the Chicago area, the original created in 1934 and located on Michigan Avenue. Here you will get the legend of the "best innkeeper in Chicago," Billy Goat Sianis, his famous guests’ dishes such as the John Belushi Cheezbuiga, and maybe even run into the working team of the Chicago Tribune or Sun Times grabbing a quick (and very delicious) lunch!
  5. Big Monster Toys - West LoopHeph14_BigDoor_web
    • Head to the West Loop for some serious inner-kid fun at the mostly unrecognized Big Monster Toys. This stop is purely just an iconic photo spot, like the Bean, only here you will surpass the crowds and get a peek through the popular monster ridden window at the inside real-life toy design firm.
  6. Maggie Daley Park - The Loop
    • Maggie Daley Park is a 20-acre public park around the Loop of Chicago that offers fun outdoor recreation options, access and views of the Lake Michigan shoreline, and a really fun ice skating ribbon that provides all the greatest views of the city skyline, all without the waits and larger crowds of skating at Millennium. There is also a playground and rock climbing wall for the adventurous!
  7. 8049086892_a99e4e17b6_bMyopic Books - Milwaukee Avenue
    • If you are a book fan of any sort you must stop at this locally loved hidden gem, Milwaukee Avenue’s Myopic Books. This bookstore is considered to be the oldest and largest in the city, very proudly boasting over 80,000 editions and a strict no-cell phone rule while in the building. Get a quick picture outside and then disconnect from the bustle of the city as you immerse yourself into the wonderful world of literature!
  8. International Museum of Surgical Science - Lake Shore Drive
    • Chicago is known for its many world-class museums, and though this one perhaps isn’t as visited as the others, it is definitely no exception to the city standards. The International Museum of Surgical Science is the place to learn all about international aspects of surgical science and history, a truly interesting lesson on international medical practices. The architecture of the museum is worth a trip as well, the 1917 historic landmark building designed after a French Chateau suited for Queen Marie Antoinette.
  9. Kuma's Corner - Belmont AvenueNachtmystium_burger_-_Kuma's_Corner,_Chicago
    • Heavy metal and delicious greasy food await you at Kuma’s Corner on Belmont Avenue, a unique eatery hidden deep in Chicago’s local culture. This head-banging bistro has been serving up fancy, delicious, and classic burgers and pub fare since 2005. Some of the most popular dishes include the Slayer, Metallica, and Pantera (with ranchero salsa, bacon, roasted poblano, and tortilla strips) burgers! Another great thing, the beer is local here, so feel free to indulge and support!
  10. Chicago Cultural Center - The Loop
  • Last but not least we have the Chicago Cultural Center, a Loop classic that we feel may always be the destination saved for last and skimmed over, but one that truly needs much time to observe and appreciate while in town. This always-free museum is interactive and supports local art, always offering the best personal glimpse at local culture and history that you can get while in Chicago!

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