The windy city is a cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh your head off at the Second City Theater, the professional launch pad of many famous comedians.
Restaurants in Chicago
5.0 based on 545 reviews
The Magic Parlour starring Dennis Watkins is an intimate evening of classic magic and mind-reading performance with this 3rd generation magician presented weekly by The House Theatre of Chicago in the historic Palmer House Hilton Hotel.
The Magic Parlour with Dennis Watkins was a wonderfully magical evening. Our party ranged from 22-75 and everyone had a fantastic time. The up close and intimate setting is what really sets this show apart from others. Dennis is a fabulous magician and entertainer!
5.0 based on 463 reviews
My husband and I walked around this pavilion while visiting Millennium Park. Designed by Frank Gehry, who also designed the Weismann Art Museum in Minneapolis and the Walt Disney Concert Hall in Los Angeles, this concert venue seats 11,000 people (4,000 fixed and 7,000 lawn). It opened July 16, 2004. It is very large and airy, which would be good for summer concerts as it can get really hot in Chicago in the summer.
5.0 based on 146 reviews
Imagine sitting on a rooftop, in the heart of downtown Chicago, with your favorite drink in hand, listening to live music, enjoying delicious food and awesome company, all while watching the most impossible magic. Each month we handpick 4 of the best magicians around to showcase their unique approaches to magic, in a fun and lively party setting...it's one event NOT to miss!!
We visited The Magic Penthouse a while ago and loved every minute of the mind blowing experience. We then hired Sin to work at a fundraiser that we hosted and he was incredible working in the crowd and speaking in front of 350+ people. Go highly recommend!
5.0 based on 407 reviews
Caught Hamilton at the CIBC Theater in the city. Great cast and musical score. Found out it was playing there and couldn't pass it up. Concierge at the hotel located our tickets on the main floor orchestra section for $105 each. Well worth it.
5.0 based on 116 reviews
"The best thing to ever happen to the theater" Slate Magazine "A live action Drunk History" TimeOut Magazine "Zany, rowdy and debaucherous" New York Times. One actor has 5 shots of whiskey and then attempts to perform in a Shakespeare play. There is a hidden library at 182 N Wabash Ave with over 10,000 books. Running Time: 90 minutes. Food & drink available. 21+ only. Photo ID required.
Shakespeare and Chicago Improv, I’m in heaven. Shout out to a hard working and talented cast. They have No fear. Small and intimate space. No bad seats. Easy to get to Loop location. Drinking highly encouraged.
5.0 based on 18 reviews
World class mentalist Jonathan Pritchard performs his live cutting-edge online streaming show “Game of Imagination.” He combines improv with skillful mental manipulations and you’ll witness demonstrations of mind power that you simply won’t believe. Pritchard has performed on 3 continents for Fortune 500 companies like BP, State Farm, United Airlines, and beyond.
Extremely entertaining and engaging, very astonishing with a jaw-dropping finale! Jonathan is a true master in his field.
4.5 based on 134 reviews
Now in its ninth straight year! Experience true stories of Chicago's paranormal past -- including ghosts, curses, and ESP -- brought to life through audience-involving demonstrations of the magical and the psychic. This interactive and creepily funny one-man show is hosted by Neil Tobin, Necromancer every Friday night in one of the city's most haunted locations, Castle nightclub. Educational and unforgettable fun! Group rates and private seatings are available.
4.5 based on 4 reviews
COMEDIANS YOU SHOULD KNOW (CYSK) is a stand-up comedy showcase featuring some of the best comedians in the country. Starting in Chicago in 2008, CYSK quickly gained praise from fans and comedians alike for its unwavering commitment to presenting only the funniest Chicago comedians and visiting guests from both the alt and mainstream comedy scenes. Tickets cheaper if bought online!
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