Traditionally overshadowed by coastal powerhouses New York City and Los Angeles, Chicago is on the rise, with a record 55 million visitors in 2017 – and new direct flights from the UK with Norwegian and Wow making the US’s third-largest city more accessible. While visitors tend to congregate around the downtown and lakefront areas to admire the city’s world-renowned architecture, there’s a thriving music and bar scene that shouldn’t be missed.

Al’s Italian Beef



Photograph: Alamy

When it comes to eating in Chicago, there are three essential food groups: pizza, hotdogs and Italian beef. Pizza and hotdogs are well-known to most visitors, but the less-famous Italian beef sandwich is perhaps the quintessential Chicago creation. Thin slices of seasoned roast beef are served on a long Italian or French roll topped with peppers and drenched in jus, the sandwich started as a cheap way of feeding a large Italian wedding party in the early 1900s and was brought here by immigrants in the 1930s. Operating since 1938, Al’s stand in the Little Italy/University Village neighbourhood helped popularise the classic Chicago sandwich. While Al’s is now a chain, the original on Taylor Street remains a must-visit. It’s cash only and there are no seats, so grab one to go and pack extra napkins.

• 1079 W Taylor Street, alsbeef.com

Maria’s Packaged Goods



One of the more unusual things about Chicago is its “slashies” (liquor store/bar combos), where you can drink at the bar and walk home with a six-pack of beer or bottle of whiskey under your arm. While most slashies are of the dive bar variety, Maria’s Packaged Goods in the Bridgeport neighbourhood is a slightly more clean-cut version that is popular with the community’s artists, musicians, and beer nerds. As well as offering more than 500 varieties of brew and a Korean/Polish street food project called Kimski, it hosts some of the best DJ nights in the city. The bar’s co-owner is a leading force behind popular, up-and-coming local brewery Marz Community Brewing, experimental art gallery/cultural centre Co-Prosperity Sphere, and broadcaster Lumpen Radio.

• 960 W 31st Street, community-bar.com

Humboldt Park

The Boathouse and Music Court in Humboldt Park. Photograph: Alamy

Many of Chicago’s largest parks are connected through a system of historic leafy boulevards often overlooked by visitors, who often favour the lakefront. On the West Side, Humboldt Park is a massive green space to lie out on a blanket on the grass, stroll among peaceful lagoons or dine at the waterfront Boathouse cafe. A good way to explore the park is to take a short walk to it from the 606 urban hiking trail, a 2.7-mile elevated pathway on an abandoned railway line that connects several neighbourhoods. There are also many good bars and restaurants within a short walk of the trail, including Parson’s Chicken & Fish (which unfurls a bustling outdoor patio in summer) and cool neighbourhood bars such as Best Intentions and Scofflaw.

• chicagoparkdistrict.com

Reckless Records

Photograph: Alamy

Established in London’s Soho in 1984, Reckless Records also has three locations in Chicago, the most famous of which is in the Wicker Park neighbourhood, home of several music venues and other record stores. Here, a wide variety of cool tunes will soundtrack hours of crate digging in a recently expanded space a few blocks from its original Chicago home. It is also something of a gathering place for the city’s music community, hosting everything from in-store performances by local bands to drop-in visits from larger acts such as Franz Ferdinand and Jack White.

• 1379 N Milwaukee Avenue, reckless.com

Longman & Eagle

Photograph: Clayton Hauck

Most of the city’s more popular (and expensive) hotels are downtown, so good deals and more interesting places to stay can be found in the neighbourhoods. Longman & Eagle has six boutique rooms above the restaurant of the same name in the Logan Square neighbourhood. They are artfully designed and have both modern and retro touches, such as vintage cassette tape consoles with accompanying mixtapes. The hip space also makes an excellent base for exploring the many bars and restaurants that have helped turn Logan Square into Chicago’s premier party district in recent years. The downstairs restaurant stocks 400 types of whiskey.

• Doubles from $95 room-only, 2657 N Kedzie, longmanandeagle.com

Montrose Beach

Photograph: Alamy

Chicago’s lakefront beaches come alive in summer. The city’s buildings almost touch the sand at places like Oak Street Beach but venture further north and discover Montrose Beach, the city’s largest, in the Uptown neighbourhood. After a game of beach volleyball at the expansive public space – it also includes sand dunes and birding trails – go to the always happening bar The Dock at Montrose Beach, where live bands perform most nights in summer. Grab a vodka lemonade and a plate of fish tacos and watch the sunset for a true taste of Chicago summer.

• 4400 N Lake Shore Drive, chicagoparkdistrict.com

Empty Bottle

Photograph: Jay Gentile

This 400-capacity dive bar in the Ukrainian Village neighbourhood has little on the exterior to indicate its importance to the Chicago music scene, other than an old-fashioned beer sign and the words “Music Friendly Dancing” on its awning. Yet the rock history within its walls is unmistakable: it hosted bands from Arcade Fire to the White Stripes long before they became household names. It’s the kind of place where you can shoot pool with members of Interpol before seeing up-and-coming indie talent on a small stage surrounded by cool people and stiff drinks. Head next door to the BYO Bite Cafe for food or stop by sister venue Thalia Hall in the Pilsen neighbourhood, to see rock bands in a palatial 1800s building, which also houses Michelin-starred restaurant Dusek’s and lively downstairs bar Punch House.

• 1035 N Western Avenue, emptybottle.com

The Hideout



Photograph: Getty Images

In an out-of-the-way industrial part of town inside a late 1800s-era house, this beloved local institution has a small front bar and a back room performance space that hosts live bands, comedy acts, poetry open mics and late-night dance parties. With twinkling lights and a homey vibe, it’s also just a damn fine bar to drink any night of the year with a friendly crowd. Stop by in September for the annual Hideout Block Party to get a true sense of what this scene is all about.

• 1354 W Wabansia, hideoutchicago.com

Reggie’s



Minneapolis rock act Blue Felix perform live at Reggie’s in Chicago. Photograph: Alamy

This iconic punk venue in the South Loop area is where punk and metal acts play ear-piercing sets as you sip craft beers paired with American pub food favourites such as burgers and chicken sandwiches. The popular hangout also boats one of the finest roof decks in the city: its 99-person‚ Reggie’s Trainwreck Rooftop Deck with TVs, games and picnic tables. The venue also holds events from art shows to crawfish boils, not to mention trips to local sports matches on its Halloween-style party buses. It also offers recording services for bands during live shows and if you’ve had too much to drink, not to worry – it has rooms at Reggie’s Hotel.

• 2105 S State St, reggieslive.com

Old Town Ale House



Bruce Elliott, owner of Old Town Ale House with his painting of Sarah Palin. Photograph: Chicago Tribune/MCT via Getty Images

When in Chicago, it is customary to close down a 4am bar (or go until 5am on Saturdays.) The best place to do this is the glorious dive bar Old Town Ale House in the Old Town area, across the street from world-famous improv comedy venue Second City. As a long-running incubator of comedic talent that has launched the careers of a celebrities from Bill Murray to Stephen Colbert, Second City also sends plenty of thirsty off-duty comics through the doors of Old Town Ale House, where they commiserate with a diverse cross-section of revellers from tourists and young professionals to artists and grizzled old-timers. Check out the wall art that features nude portraits of US politicians, painted by the bar’s longtime owner Bruce Elliott in his basement art studio.

• 219 W North Avenue, theoldtownalehouse.com

Way to go



Flights

Norwegian Air flies direct from Gatwick to Chicago from around £265 return. Wow flies via Reykjavik from Edinburgh, Gatwick and Stansted from around £260 return. United, American and British Airways also fly direct to Chicago.

Best time to go

Summer is festival season including the Chicago Blues Festival (the world’s largest free blues festival) in June and Taste of Chicago in July. Spring brings a massive parade in March for St Patrick’s Day and a neighbourhood costumed shopping cart race called the Chiditarod, while the Chicago Marathon takes place in October often with some of the city’s most pleasant weather (daytime highs of 17C). The average daytime high temperature in July – the hottest month – is 28C, and in January, 0C.

Exchange rate and prices

£1 = $1.42.

Average price of a beer in a neighbourhood pub: $5.

Jay Gentile is publisher of Chicago INNERVIEW Magazine, digital marketing specialist with Consequence of Sound and a regular contributor to the Chicago edition of Thrillist



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