What to do in Chicago by night

When night falls in Chicago, things really begin to hot up. The city’s morass of twinkling lights is a spectacular backdrop to an amazing array of things to do after the sun goes down, that will keep you entertained well into the early hours. Whether you are a culture vulture, music fan or food lover, the possibilities are endless. Experience some of the city’s renowned live music venues, see a rib tickling comedy performance, sample a flavour of the city’s bourgeoning restaurant scene, catch a show, or simply enjoy a romantic lakeside walk - Chicago by night has something for everyone.

As well as being the birthplace of improvised comedy, Chicago is the city that helped launch the careers of several comedy heavyweights like John Belushi, Bill Murray, Stephen Colbert, Mike Meyers and countless others. Many of them got their break at one of Chicago’s most celebrated comedy clubs, The Second City, which has been on the go since 1959 and has two resident troupes who stage new and original comedy every day of the week. Zanies is another of Chicago’s comedy hotspots, regularly featuring some of the biggest names in stand-up.

Chicago’s vibrant theatre scene has rightfully gained a place as one of America’s most highly regarded, with many of its first rate productions, from musicals to Molière, regularly garnering critical acclaim. Its celebrated Steppenwolf Theatre, has seen the likes of John Malkovich Joan Allen and John Cusack tread its boards, while Broadway in Chicago often plays host to shows before they hit the streets of their Manhattan counterpart. One of these is the hotly anticipated “Addams Family Musical”, which gets its pre-Broadway run in Chicago at the Ford Centre for Performing Arts for two months from 13 November. Another one not to miss is the Tony-award winning Broadway hit musical “Spring Awakening”.Those in the know log on to the Hot Tix website to get half-price tickets to many of Chicago’s best selling performances.

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As well as theatre, performances of opera, symphony and dance are staged throughout the city on a nightly basis. The Chicago Symphony Orchestra, the innovative Joffrey Ballet, Hubbard Street Dance and the Lyric Opera, are just a few of the world-class companies that call Chicago home.

The perfect destination for music lovers, Chicago’s streets resonate to the rhythms of jazz, blues, salsa, gospel, rock and folk with live performances at countless different venues every day of the week. In the 20s and 30s this city was at the centre of the Jazz movement and its rich and diverse music scene is something you cannot leave without experiencing. Buddy Guy’s Legends, this year celebrating its 20th anniversary, is one of the spiritual homes of Chicago Blues and its stage has played host to scores of the world’s top artists. The sophisticated Green Dolphin Street club and its adjoining restaurant is another must for Jazz lovers, but its line-up also spans everything from R&B to Blues.

Given its cosmopolitan heritage, Chicago’s thriving dining scene is an intrinsic part of any visit and spans the entire gastronomic spectrum from the traditional to the innovative. Some of the current hottest tables in town include the stylish, French restaurant Tru, the Catalonian inspired Mercat a la Planxa and Publican, which is a slick, contemporary take on a European beer hall, offering simple yet delicious fare and a wide range of artisan beers.

Those with more traditional tastes should not miss the chance to order a classic Chicago hot dog at city institution, Weiner’s Circle – just make sure you don’t add ketchup to your dog, which is considered a sacrilege in these parts. Another of Chicago’s much-loved landmarks is the Billy Goat Tavern, which was immortalised in Saturday Night Live sketch starring John Belushi, Dan Aykroyd, Bill Murray and Loraine Newman.

A great way to sample some of Chicago’s diverse culinary highlights is to sign up for the Chicago dine-around - this novel evening out gives diners the chance to eat a course in each of three different restaurants across the city. The Culinary Concierge is another ingenious initiative, offering comprehensive gourmet-related advice for eager foodies keen to explore.

When the cocktail hour beckons, sophisticated sips come with mesmerising views of the city skyline from the 27th floor of Chicago’s new and achingly fashionable ROOF bar at the Wit Hotel. Also don’t miss a pre or post dinner aperitif at the C-View bar at the Affinia Hotel, another lounge with jaw dropping views. These, along with the new boutique Dana Hotel & Spa and eco-chic Hotel Felix, are also currently some of Chicago’s hippest places to check in for a stay. Wine buffs should make a beeline for the laid back surroundings of the Juicy Wine Company, a bar wine shop and lounge rolled into one.

Or spend a balmy night retro-American style at the Chicago Outdoor Film Festival, a free annual event that takes place every Tuesday between 14 July and 25 August in Grant Park’s Butler Field. Open-air screenings to enjoy with your popcorn include classics like “Sunset Boulevard” and “Tootsie”.

Jutting out into Lake Michigan and with al fresco dining, regular firework displays and amusements, city classic, Navy Pier, is also a perfect place to spend a summer’s evening. If you are visiting from now until 7 September, don’t miss the chance to see the gravity defying antics of the Cirque Shanghai’s newest show, “Bright Spirit”, which returns to its Pepsi Skyline Stage and is the company’s only stateside appearance this summer.

There are also plenty of distractions beyond Chicago’s centre, if you want to explore further. Pull up a chair and see if Lady Luck is smiling on you at one of the many casinos, or, do as the locals do and book tickets for the annual Ravinia festival in Ravinia Park on the outskirts of the city. This was first established 1904 and has played host to greats like Ella Fitzgerald, George Gershwin and Isaac Stern. Order a picnic and soak up the atmosphere while enjoying one of the many performances of classical music, pop, jazz and dance taking place on a regular basis throughout the summer months. For more ideas, be inspired at gochicago.com.

To experience Chicago in person, enter our “Sun and fun trip to Chicago” competition.

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