The windy city has a rich musical heritage spanning from jazz to blues and the birth of house. In recent years, it's spawned some of rap's elite with Chance The Rapper and a certain Mr West once calling it home. With so much culture hiding in Chicago's streets, it's helpful to know where to head.
Whatever you do, don’t spend your time exclusively around River North – catch The El and head into the neighbourhoods to experience Chicago the local way. Here’s the NME guide to the bars, music and food of the city (with a few not-lame tourist things to do as well.)
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Best Bars in Chicago
Late-night dive bar with indoor waterfall and 90s jukebox. It’s open until 4. Here’s where your night can go very wrong or very right.
The best Tiki Bar in the city. The attention to detail with the décor is second to none as is their range of frighteningly drinkable cocktails. Our favourite was this one (see below) which came with an actual banana dolphin in it. May all our bananas look like dolphins from hereon in.
Cutesy late-night bar/club done up like a beauty parlour. Be there for some of their regular 90s parties on a Saturday night.
Late-night dive, known locally as the Jeffrey Dahmer bar due to the fact notorious serial killer Jeffrey Dahmer used to sit in the corner every night, nursing a beer. Weirdly it was also a favourite spot of John Wayne Gacy AKA the Killer Clown in the 70s. Odd, considering owner Ken is a lovely fella.
Big ol’ arcade bar with craft beer and pinball, Pac-man and a really good retro paper boy game which involves you literally doing a paper round. There are also some more complex video games if your gaming skills aren’t as challenged as this writer’s.
Sizeable rock bar with pool tables, skiiball, a pretty savage deer-hunting video game and cool murals on the walls.
Nick’s Beer Garden
Dive bar with an outdoor smoking area. No garden to speak of.
Chicago Music Venues
Chicago’s oldest-running blues club has hosted the likes of Magic Slim and Carl Weathersby and showcases the city’s vibrant blues heritage. It’s also open until 4am, which makes it a fun last stop of an evening. The vibe is super-relaxed. Turn up, grab a table (booking is advised) watch some blues and eat Southern fare from the hole in the wall rib shack.
Winter’s Jazz Club
A much more formal affair, this is for serious jazz heads. There are two sets an hour: 7:30 and 10pm. Go for cocktails and quiet appreciation of the music. We saw a poppin’ Stevie Wonder tribute band when we were in town!
Legendary 80s music venue whose first bookings included REM and Nirvana. This year, during Lollapalooza week, The National played a warm-up gig at the venue. The space is huge and Smart Bar downstairs is a great little rock club.
Ok, so this one is very much a baseball stadium, home to the Chicago Cubs, but if there are any shows on during your stay, it’s well worth a visit. We saw Foo Fighters on their ‘Concrete and Gold‘ stadium tour during our visit and Pearl Jam graced the stage a month later. Fun fact: Dave Grohl saw his first ever gig across the road from the stadium, at the Cubby Bear, aged 14.
Green Mill Cocktail Lounge
A once favourite haunt of Al Capone, Green Mill still hosts live jazz and serves epic cocktails in a velvet-lined setting.
Best Chicago Restaurants
For the best deep dish in Chicago… allegedly. Kanye and Kim have been spotted here and Kim’s bestie even sent her 20 boxes of the stuff to mark the birth of baby number three, Chicago West. Be warned: there’s a reason they call it a pizza pie. Even if you’ve been known to smash an extra-large Dominos in one sitting, you are not prepared for the heavy nature of a deep dish. This writer managed two slices.
Honey Butter Chicken
All the classic Chicago dishes aren’t going to do wonders for your waistline. Here’s another: fried chicken served with a side of honey butter. It’s delicious, though.
Ramen and margaritas. Need we say more?
In search for that perfect Chicago dog? You might just find it at Portillo’s. Remember: don’t ask for ketchup, it’s not the Chicago way
Chicago tourist stuff it’s worth doing
Tilt! at 360 Chicago.
94 floors up the John Hancock Center is 360 Chicago, which – you guessed it – gives you a bloody lovely view of the city, there’s a twist. For an extra eight bucks you can experience Tilt!, a pane of glass which literally tilts forward so you’re hanging 45 degrees out of the window. It’s sickening. It makes you shake from head to toe. We did a lot of swearing. But being tilted out a skyscraper definitely isn’t something you get to do every day.
Chicago Architectural River Cruise
Supposedly one of the top five tourist attractions in the world, the river tour of Chicago’s best buildings is a great afternoon. Plus, you get to go on a boat! And who doesn’t love being on a boat.
A nice day time stroll around the park and it’s worth a selfie in the side of Anish Kapoor’s shiny bean.
Where to stay?
We stayed at the Virgin Hotel Chicago – the first hotel in Richard Branson’s armoury, which seems odd, seeing as he’s done almost everything else. Ask the Lady In Red for city recommendations and reservations during your stay, drink signature cocktails at the rooftop bar for great views of downtown. You are nestled in the shadow of Trump Tower, but luckily the beds are comfy enough to alleviate any nightmares.