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When the weather is frightful But Chicago is so delightful
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125 Reasons for the Season

Chicago Wintertime Activities

Figuring out what to do during the winter season in Chicago? No winter blues here! Enjoy our list of 125 activities when the weather is frightful but the city is so delightful. Book our special offer to start your exactly like nothing else Chicago adventure.

1. Write a letter to the North Pole on our Vintage Oliver Typewriter from 1910, located in the lobby. The Oliver Typewriter Company was headquartered in Chicago until 1928. (636 S Michigan Ave)

2. Go behind the crime scenes on Chicago’s Original Gangster Tour. Learn more and sign up for a tour through their official website: gangstertour.com

3. Chicago Blackhawks games are hot tickets in this town! Go to an NHL game at the United Center to see legends in action. Buy tickets here! (1901 W Madison St)

4. Take a selfie with a friend at The Bean (A.K.A. Cloud Gate) in Millennium Park. (201 E Randolph St)

5. Learn about Chicago’s architectural roots...And Other Such Stories at the 2019 Chicago Architecture Biennial. This citywide event is at various locations in Chicago, including the Chicago Cultural Center, through January 5th.

6. Follow the yellow brick road to Oz Park, located in Lincoln Park. (2021 N Burling St)

7. Ride a water taxi to Chinatown to visit the neighborhood’s extensive selection of shops, restaurants, tea houses and cultural landmarks. Taxis operate through December 15th.

8. Enjoy glunwein and a pretzel at the popular, festive and ever-growing Christkindlmarket, open November 15th through December 24th. (50 W Washington St)

9. See beautiful sites of Chicago during a glass-enclosed voyage on the Odyssey Chicago River.

10. See the world’s largest digital art installation! Projected on the Merchandise Mart building along the Chicago River, Art on the Mart takes place every Wednesday through Sunday at sunset. (278-294 W Wacker Dr)

11. Grab your friends, Miranda, Samantha, Charlotte and Carrie, for your own episode of “Skate in the City” at the Skating Ribbon in Maggie Daley Park. (337 E Randolph St)

12. Improve your aim at Bad Axe Throwing in Chicago’s West Loop or Lakeview neighborhoods. (2828 N Clark St Atrium Level, 165 N Loomis St)

13. Walk like an Egyptian at the Field Museum. The current exhibit Inside Ancient Egypt features a three-story replica of a Mastaba tomb. (1400 S Lake Shore Dr)

14. Dine next to the extravagant (and gigantic!) Christmas tree in the Walnut Room at Macy’s, open year round but displaying holiday decor during the holiday season. (111 N State St)

15. Unwind from the Windy City weather with K'alma Spa. Book an in-room wellness journey, focusing on muscle and joint health, natural immunity and stress relief. Choose from revitalizing massage experiences, face mask treatments and more.

16. City lights, tree lights, zoo animals, oh my! See the Zoo Lights at Lincoln Park Zoo, on display from November 29th through January 5th this holiday season. (2001 N Clark St)

17. Celebrate the holidays in every country at the Museum of Science and Industry’s Christmas Around The World tree exhibit from November 14th - January 5th. (5700 S Lake Shore Dr)

18. Take a stop on every guest room floor during your stay to see The Blackstone Vertical Art Gallery, featuring contemporary art inspired by the hotel’s history and design.

19. Wine and dine in an “igloo” along the Chicago River. River Domes are available to book at City Winery through mid-December. Make sure to book your reservation in advance! (11 W. Riverwalk South)

20. Frosty’s, the ultimate Christmas bar, is always filled with decorations galore. Enjoy this popular holiday pop-up bar from November 15th through the end of December. (809 W Evergreen Ave)

21. Navy Pier is opening one of the largest indoor winter playgrounds for one night only! Experience Cheer at the Pier on December 5th. Ticket purchase required! (600 E Grand Ave)

22. Sundays are for football! Catch a Chicago Bears game at the historic Soldier Field. (1410 Museum Campus Dr)

23. Explore the architecture of Frank Lloyd Wright. Chicago’s suburb of Oak Park boasts more Frank Lloyd Wright homes than anywhere else in the world. Book a tour during your Chicago stay here.

24. Find yourself instantly transported into a steamy, tropical jungle or an arid desert just by stepping foot into the Garfield Park Conservatory. The conservatory is free and open to the public daily. Donations are asked for at the door but not required for entry. (300 N Central Park Ave)

25. Located in the heart of Chicago, the National Museum of Mexican Art is a cultural treasure. Check out their 5,000-piece collection of paintings, photographs and sculptures. (1852 W 19th St)

26. Embrace Andy Warhol’s flair. Check out The Blackstone and Kehoe Designs’ Project Windows display from October 20th through January 26th.

27. The annual McDonald’s Thanksgiving Day Parade makes its way down State Street on Thanksgiving morning with iconic character balloons, spectacular marching bands, special guests and so much more! Catch the parade on State Street from Congress to Randolph.

28. At 10-stories tall and more than 750,000 square feet, the Harold Washington Library takes up a full city block and even has its own train stop. Many events take place all year long and private tours can also be organized for small groups. (400 S State St)

29. The One of a Kind Show, held two times per year at the Merchandise Mart, features handmade items from hundreds of makers. Enjoy a one-of-a-kind experience with great food and entertainment while you shop. (222 W Merchandise Mart Plaza)

30. The world’s largest Louis Comfort Tiffany Dome, composed of 30,000 stained-glass pieces, crowns the neoclassical 1897 Chicago Cultural Center. Go on the Tiffany Treasures Tour, hosted by Chicago Architecture Center, to learn more about this magnificent Installation and more.

31. Mosaic, mosaic on the floor (of our elevators), who’s the best artist at its core? The artist in you will explore all facets of the medium in a creative environment at the Chicago Mosaic Art School. Register for a class or workshop here.

32. Time to jazz it up! Enjoy Blackstone Beats, featuring live jazz performances by Columbia College students, every Saturday evening in The Blackstone’s lobby.

33. Looking to feel inspired? Go to the Andy Warhol—From A to B and Back Again exhibition at The Art Institute of Chicago from October 20th through January 26th.

34. Running with the Chicago Bulls is a stone’s throw from The Blackstone. Take a group photo in front of the iconic Michael Jordan statue before attending a Bulls game at the United Center.

35. Check out the best city skyline view along the Lakefront Trail in front of the Shedd Aquarium. Look for our unique building and our famous green rooftop!

36. What’s with the decorations? Over-the-top holiday decor has become a staple at Butch McGuire's pub. Stop by this holiday season to see their extravagant holiday decor in person. (20 W Division St)

37. The Sculpture Objects Functional Art and Design (SOFA) Fair at Navy Pier is the premier gallery-presented art fair dedicated to three-dimensional art and design. Attend an acclaimed lecture series and explore special exhibits exploring the artworks on view and surveying new trends in the art world on October 31st through November 3rd. (600 E Grand Ave in Festival Hall)

38. Take a selfie in The Blackstone’s historic 1910 Barbershop Chair. Al Capone and Richard Nixon were a few of many infamous guests that frequented the Barbershop Room. Learn more about the hotel's history here.

39. Celebrate the holiday season in Chicago. Join the City of Chicago for their annual Christmas Tree Lighting in Millennium Park on November 22nd. The tree will be up through January 6th. (201 E Randolph St)

40. From a green rooftop (The Blackstone Hotel) to green Chicago. This former meatpacking plant has gone green. The emerging business complex, known simply as The Plant, equips people and businesses with the tools to live more sustainable. Tour The Plant and more. (1400 W 46th St)

41. Take a spin on the ice during the 19th season of this Chicago winter tradition. Free skating at Millennium Park McCormick Tribune Ice Rink through March, weather permitting. (201 E Randolph St)

42. Tour Chicago’s first craft distillery: KOVAL. Learn about the differences between white and aged whiskey, the subtle intricacies of distillation, and the delicious beauty of small-batch spirits. See where each and every step of the process takes place. Tasting of numerous spirits is just one of the perks! (5121 N Ravenswood Ave)

43. We might have been built in 1910, but Chicago is still the capital of architecture. Take a tour of some of the sites Jeanne Gang, Chicago’s renowned architect, developed and discover some of the most iconic buildings and projects in the world. Take a selfie and post it using hashtag #makeyourownhistory!

44. Watch Michigan Avenue light up for the holidays and more at the Magnificent Mile Lights Festival. Celebrations at various locations on November 22nd and 23rd.

45. Visit the world’s only known button museum. Busy Beaver Button Museum features over 30,000 pins dating back to 1896.

46. Embrace the chill and take a selfie along the Lakefront Trail with either the lake or skyline as your background. Good luck!

47. Improv anyone? You are too funny and you want everyone to know it! Take an improv class at the one and only Second City, home of some of the most famous SNL actors.

48. Chicago is known around the world for its architecture. Visit the new Chicago Architecture Center on Wacker Drive to learn all about the city’s skyscrapers, elegant hotels and the
legendary houses of Frank Lloyd Wright. (111 E Wacker Dr)

49. Take in a show at the Joffrey Ballet. Based in Chicago, it is one of the world’s premier dance companies. The Joffrey regularly performs classical ballets, including Romeo & Juliet and The Nutcracker, and modern dance pieces. (10 E Randolph St)

50. Visit the official site of Chicago’s popular craft brewery, Goose Island Brewery. The brewery is open for tours in the West Loop or you can visit their brewhouse on Clybourn in Lincoln Park. (1800 W Fulton St, 1800 N Clybourn Ave)

51. More of the literary type? Find your words at the American Writers Museum. In the heart of downtown Chicago, the American Writers Museum celebrates all genres of writing through Interactive exhibits and programming. (180 N Michigan Ave, 2nd Floor)

52. Explore the hip neighborhood of Wicker Park, just off the blue line train stop. North Milwaukee avenue is known for its bustling nightlife and entertainment venues, with Subterranean and Davenport’s setting the bar for the city’s trendy music clubs.

53. Do you only wear pink on Wednesdays? Mean Girls is coming to Broadway in Chicago this Winter. See this cult-movie in action at the James M. Nederlander Theatre on December 25th through January 26th.

54. Ferris Bueller’s Day Off is a quintessential Chicago movie. Relive the film by visiting some of its more recognizable and iconic locations, including Grant Park, Lake Shore Drive, Italian Village, Willis Tower, Chicago Board of Trade and Wrigley Field.

55. Chicago is a living canvas — literally. Discover all the unique murals tucked in various spots around the city. The Wabash Arts Corridor, featuring large-scale murals, is right near The Blackstone on Wabash Avenue from Van Buren to Roosevelt and framed to the east by Michigan Avenue and to the west by State Street.

56. Each year in the dead of winter, Chicagoans venture out in the cold to visit popular food spots and indulge in Chicago Restaurant Week. Get your taste buds ready for this year’s
delicious celebration on January 25th through February 9th!

57. Just because it’s winter, doesn’t mean there aren’t fun ways to exercise. Learn the ropes at Brooklyn Boulders in Chicago’s West Loop neighborhood with more than 25,000 square feet of climbing surfaces available. (100 S Morgan St)

58. Paint the iconic Beaux-Arts façade of The Blackstone Hotel. Post your finished masterpiece on Instagram and tag us @theblackstonehotel.

59. Stop and smell the (holiday) flowers at the Holiday Flower Show at the Lincoln Conservatory from November 23rd to January 6th. (2391 N Stockton Dr)

60. Create a one-of-a-kind glass artwork at Ignite Glass Studios, located in Chicago’s West Loop. (401 N Armour St)

61. Go underneath the Windy City with Chicago Detours. On this signature interior architecture walking tour, you’ll step into magnificent interior spaces and the Underground Pedway. Discover a creative route that weaves through buildings, secret short-cuts, hidden architectural gems, and of course, some Chicago history. Book the tour here!

62. If walls could talk! The Chicago History Museum shares Chicago’s stories, serving as a hub of scholarship and learning, inspiration and civic engagement. Spend a day here and make personal connections to the Windy City’s history. (1601 N Clark St)

63. Celebrate the holiday season at Gallagher Way, located outside the iconic Wrigley Field. Skate with Clark the Cub and more! (3635 N Clark St)

64. Chicago is the home of the blues. Take in some tunes while you’re here and visit Buddy Guy’s Legends, located a block away from The Blackstone. (700 S Wabash Ave)

65. Rejuvenate the senses at Aire Ancient Baths. Located in a restored factory from 1902, get ready to pamper yourself while relaxing your body and mind. (800 W Superior St)

66. Shop until you drop at Chicago’s State Street in the loop. Take in the holiday lights and decorations along the way.

67. Browse locally made foodie gifts and products at The Night Market Before Christmas by Sauced on December 10th at City Hall, featuring a large collection of Chicago chefs, artists and artisans. (838 W Kinizie St)

68. Take in 24 miles of twinkling lights from the sky on the Chicago Helicopter Experience. Book your experience in advance! (2420 South Halsted St.)

69. Bask in the magical world of Macy’s Holiday Windows on State Street, transformed every year for the holiday season from November 1st through January 5th. Discover more holiday traditions at Macy's here.

70. Make it a date night - not with romance, but with an order of bacon-wrapped dates from Mercat a la Planxa! (638 S Michigan Ave)

71. For the renegade in you - made for museum lovers and skeptics alike, the Un-highlights Tour of The Art Institute of Chicago will show you a side of the museum you’ve never seen before! (111 S Michigan Ave)

72. Channel the Color of Money by playing pool on The Blackstone’s Pool Table of Legends, Gifted by actor Paul Newman and located on the hotel’s concourse level.

73. Chicago is known for its deep dish pizza. But what restaurant reigns supreme? You be the judge! Try Giordano’s, Lou Malnati’s and Pequod’s Pizza. Let us know your favorite!

74. Explore Chicago’s Swedish roots by taking a trip to the Swedish American Museum and a trip to Lost Larson Bakery in Andersonville.

75. Perfect your winter waltz by taking a lesson with Fred Astaire Dance Studios. Schedule a dance lesson at their West Loop location! (1239 W Lake St)

76. Hitch*Cocktails at Annoyance Theatre & Bar begins with an audience suggestion of an unusual fear. Then, sit at the edge of your seat as the nefarious and well-dressed improvisers create a full-length improvised thriller in the style of Alfred Hitchcock. (851 W Belmont Ave)

77. Find your inspiration! Sketch a picture of The Blackstone’s lobby.

78. You’ve been ghosted. Do you celebrate Halloween year round? Check out The Original Chicago Hauntings Tour to experience first hand chills in one of the most haunted cities in America. (Tour starts in the Congress Hotel Lobby at 520 S Michigan Ave)

79. Indulge in Chicago’s world-class dining scene by trying one, or all, of the city’s 25 Michelin-starred restaurants.

80. Take me to church. Holy Name Cathedral is the seat of the Archdiocese of Chicago, one of the largest Roman catholic dioceses in the United States. (730 N Wabash Ave)

81. From the hip to the esoteric, leave a KOVAL Distillery cocktail class with a new set of techniques and knowledge to enhance your cocktail prowess. Whether an uncertain beginner or scholar of the craft, the KOVAL team will get you on your way to a better drink. (5121 N Ravenswood Ave)

82. Nature calls you. Escape the cold and experience the sights, sounds and smells of nature at the Peggy Notebaert Nature Museum. (2430 N Cannon Dr

83. See Marc Chagalls’ Four Seasons in the heart of downtown Chicago at Chase Tower Plaza, a colorful mosaic piece celebrating the arrival of spring, summer, winter and fall. (10 S Dearborn St)

84. Brunch anyone? Get your Sunday started right with gospel music guaranteed to raise your spirits and indulgent soulful food at the House of Blues Gospel Brunch. (329 N Dearborn St)

85. Make it a night to remember by taking in the stunning views of the city from up above at 360Chicago. Then, dine in the Signature Room at the 95th for more Chicago sights with an Extravagant meal included. Cheers! (875 N Michigan Ave, 94th and 95th floors)

86. Everybody in. Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field tours. (1060 W Addison St)

87. Visit Trunk Club’s flagship clubhouse in Chicago. Get styled for your Windy City activities! (325 W Ohio Street)

88. Tour Through A Lens with professional photographer and city expert, Teresa Peek. Discover popular photo op spots for your cherished travel memories. Book your tour in advance!

89. A holiday in paradise. Escape the cold and head to a tropical getaway at Three Dots and a Dash. Known for their extravagant and shareable tiki drinks! (435 N Clark St)

90. Lake forest native, musician and singer/songwriter Andrew Bird performs at the breathtaking Fourth Presbyterian Church every winter. Join in on the tradition and see this amazing performance by a local Chicago artist. (126 E Chestnut St)

91. Like going out but also like video games? Head to Emporium for the ultimate arcade bar experience, located in Wicker Park, Logan Square and Fulton Market.

92. Take a fashion-forward photo on our gold couch in the English Room. Post it on Instagram and tag us @theblackstonehotel.

93. Experience the Shedd Aquarium like a marine mammal trainer. Enter the behind-the-scenes world where the Shedd team cares for the penguins, dolphins, sea otters and more. (1200 S Lake Shore Dr)

94. Catch a comedy show at one of the oldest continually operating clubs in the country. Zanies still embraces its old-school style but offers an impressive list of famous comedians. (1548 N Wells St)

95. Every day and night at Lips Chicago is a party! Join in the fun at Chicago’s #1 drag show experience for brunch or dinner. (2229 S Michigan Ave)

96. Grab a drink and watch a jazz show at the Green Mill, another local haunt for Al Capone and other notorious guests. (4802 N Broadway St)

97. Experience the power of sound at the Smart Museum of Art. The Chicago Sound Show is an outdoor sound art exhibition presenting site-specific works by nine Chicago artists that explore thresholds, passageways and common spaces across the University of Chicago’s Campus. (5550 S Greenwood Ave)

98. Stay at the hotel of presidents and eat at the diner of presidents. Grab a bite to eat at Manny’s Deli, a popular spot for former presidents Barack Obama and Bill Clinton. (1141 S Jefferson St)

99. The unofficial Chicago welcome: a shot of Malort. If you’re looking to get initiated by the locals, taking a shot of this bitter staple in the city’s local dive bars is a must. We dare you! Check out Eater Chicago's list of best dive bars.

100. Love the smell of a good book? Visit Wicker Park’s award-winning tri-level book store, Myopic Books, with over 80,000 books to choose from. (1564 N Milwaukee Ave)

101. Agora, designed by polish artist Magdalena Abakanowicz, is an installation of 106 headless and armless iron sculptures at the south end of grant park. Take a picture of this unique display of gigantic leg sculptures with Chicago’s skyline in the background. (1135 S Michigan Ave)

102. Learn the Lost Language of Buildings in Chicago. Read and decipher ornament on buildings on a unique architectural tour with tour guide, author and comedian Margaret Hicks.

103. Indulge at one of Chicago’s iconic diners. Eleven City Diner is an ideal spot to grab Jewish deli standards and classic american fare with a milkshake (or two)! (1112 S Wabash Ave)

104. Take a selfie with our gold dog statue in the lobby. His name is Stone!

105. Splurge on a legendary dinner at the world-famous Alinea. Embark on one of the most unique and exciting foodie experiences in the world. Reservations are required. (1723 N Halsted St)

106. For the Love Stars. Come to the Exelon Observatory on The 606 Trail for a celestial viewing with resident astronomer, Joe Guzman, on November 8th and December 13th. (1801 N Ridgeway Ave)

107. A shuffleboard bar? Most might not get the hype but the Royal Palms has become one of Chicago’s most popular bars. Play a game of shuffleboard with a tropical cocktail in hand. (1750 N Milwaukee Ave)

108. One of Chicago’s best kept secrets: the city is filled with speakeasy bars. Some are easy to spot while others do require a password. Visit the Blind Barber, accessed through a discreet door in a barbershop in the West Loop, or the Violet Hour, hidden behind an ever-changing mural in Wicker Park. (948 W Fulton Market, 1520 N Damen Ave)

109. Take a ride on the “L”. We recommend the brown line to get a view of the steel jungle while on your CTA journey.

110. Skydiving in Chicago? It’s possible…indoors. Test your skills at iFly Chicago in Lincoln Park. (800 W Scott St)

111. Sunday show tunes? Sign us up! Sidetrack in Boystown hosts this fun event every Sunday, year round. (3349 N Halsted St)

112. Go to a concert at one of Chicago’s historic music venues from the Metro to the Chicago Theatre. Rock on! (3730 N Clark St, 175 N State St)

113. Catch a flick at the 90-year old movie palace in Lakeview: Music Box Theatre. (3733 N Southport Ave)

114. Dark tourism is a unique trend in the travel industry. See the graves of many famous Chicagoans such as Palmer, Marshall Field, McCormick, Pullman, Wacker and more at the Graceland Cemetery. (4001 N Clark St)

115. Stroll through our ever-rotating contemporary art collection in the Art Hall, curated by Elephant Room Gallery. Each piece is by a local Chicago artist and available for sale!

116. Go sledding in the Windy City. Sled down a 33-foot vertical drop at the Soldier Field Sled Hill, perfect for winter weather thrill seekers. We recommend calling (312) 235-7000 press 6 for operator to make sure it is open, weather depending. (1410 S Museum Campus Dr)

117. See the Secret Mermaid at Oakwood Beach, a sculptural piece that was sneakily carved out of public stone then permanently preserved. We recommend a clear, sunny day to find it! (4100 S Lake Shore Dr)

118. Find Chicago Flamingos by local artist Katarzyna Krol displayed in The Blackstone and then see the iconic Calder’s Flamingo in person at Federal Plaza. (50 W Adams St)

119. A well-hidden museum, the McCormick Bridgehouse & Chicago River Museum is hard to catch on your walk along the Chicago Riverwalk. Beginning at river level and spiraling five-stories up, the museum celebrates the intricate bridge system along the Chicago River. (99 Chicago Riverwalk)

120. Grab a cocktail next to the perch in Mercat a la Planxa - overlooking The Blackstone’s lobby. Post a photo of your cocktail on Instagram and tag @theblackstonehotel and
@mercatchicago. (638 S Michigan Ave)

121. Go on a treasure hunt at the monthly Randolph Street Market in the West Loop, filled with antique finds, local goods, artwork and more. (1341 W Randolph St)

122. Located in the suburbs but accessible via public transit, visit the Bahá’í House of Worship in Wilmette. It is one of ten dedicated temples of the Bahá’í faith and the oldest surviving Bahá’í house of worship in the world. (100 Linden Ave, Wilmette, IL)

123. Visit our partner gallery on Wabash Avenue. Elephant Room Gallery features local Chicago artists and is available to visit by appointment. (704 S Wabash Ave)

124. Discover the universe and beyond at the Adler Planetarium. (1300 S Lake Shore Dr)

125. Eat your way through Italy’s prized (and delicious) cuisine at Eataly Chicago, a pizza and pasta haven. (43 E Ohio St)

First Header Image: Ravenstel Photographic Courtesy of Choose Chicago