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7 reasons Chicago is the perfect gateway to gay-friendly Illinois – from Boystown to Route 66

7 reasons Chicago is the perfect gateway to gay-friendly Illinois – from Boystown to Route 66

Sponsored: Few cities make being hip, cool, fresh and inclusive look effortless. But Chicago is one of them.

The beautiful world class city of Illinois, which sits proudly on the blue shores of Lake Michigan, is home to 2.7 million people.

A gay cultural capital, at least 114,449 of them are LGBTQ.

Indeed, the Windy City’s reputation for being progressive is reflected by some of the famous names it’s produced.

Gay writer and queer rights campaigner Dan Savage was born here, as well as former POTUS Barack Obama.

The city is also known for its remarkable culinary scene – be sure to try the traditional deep dish pizza, like at Lou Malnati’s– and its long list of iconic attractions.

The Bean [pictured above] in Millennium Park and the 442m-tall Willis Tower, the second tallest in the States are just two of them.

Here are seven more reasons you need to visit the US’s coolest city, and the state it calls home, ASAP…

1 It’s genuinely one of the US’s gay-friendliest cities

It’s no wonder LGBTQ travelers feel so comfortable in Chicago, and more and more choose to visit over established gay capitals like San Francisco and New York City.

Chicago scored a perfect 100 in the the Human Rights Campaign Foundation’s Municipal Equality Index (MEI) last year. And in 2014, it was also voted the fifth gay-friendliest city in America in Vocativ’s Queer Index.

2 It’s home to the world’s greatest gayborhood, Boystown

Most gay ‘villages’ are really comprised of just a clutch of queer spaces in a tucked-away corner. Boystown, meanwhile, is an actual district. And its big.

The officially-recognized east Lakeview neighborhood is home to over 35 queer bars across Halsted St and Broadway. Places favoured by locals include Roscoe’s Tavern and Progress Bar. For more information, visit Boystown’s informative dedicated section on Enjoy Illinois’ official website.

3 Plus, the queer-tastic Andersonville – known to many as Girlstown…

So sizeable and spread out is Chicago’s queer community, that other pockets of the city have become popular queer areas. It’s a neighborhood that celebrates diversity and exudes small town charm.

Historic Swedish neighborhood Andersonville has a more chilled out vibe than Boystown; head here for achingly cool lesbian bars like Big Chicks and an eclectic collection of hip, independent shops and locally-owned restaurants

4 Amazing festivals all year round

The alternative music festival Lollapalooza returns to Millennium Park from 3-6 August. This year’s lineup has yet to be announced, but past headliners include Lana Del Rey and G-Eazy.

The artsy Northalsted Market Day is a big event on the Boystown calendar, and is rich in arts and craft stalls and organic food stands. It next takes place from 12-13 August. It’s largest street festival in the Midwest. Meanwhile, the Chicago Blues Festival (9-11 June) is the largest of its kind in the world.

5 The quaint town of Galena is only three hours by car

With a population of less than 3,500, the city of Galena is perfect compliment to Chicago’s buzzing energy. Head here for a dream weekend break.

Photo ops abound on Galena’s Historic Main Street, which boasts almost 100 charming 19th-century storefronts. It’s crammed full of romantic B&Bs, cute boutique shops, intimate restaurants, gorgeous wineries and cool bars such as Miss Kitty’s Grape Escape. Enjoy bed and breakfast at Jail Hill Inn and Inn at Irish Hallow, and perhaps zip lining at Long Hollow Canopy Tours.

6 It’s the starting point for Route 66

The world’s most iconic road begins in Chicago and passes through 482km of the Prairie State, such as the quaint town of Pontiac, pictured above. Illinois also includes the town of Springfield, the beloved home of President Lincoln, and his final resting place.

It ends in Santa Monica, California, with the route covering a distance of 2,400-mile, or 3,900 km.

7 There are 8 non-stop flights to Chicago per day from London

Chicago O’Hare International is one of the best-connected airports in the world, with 2,409 aircraft operations per day, according to its website.

It’s directly connected to 60 international destinations, including London. One stop flights are also available from Edinburgh, Glasgow, Birmingham, Manchester and more.

Plan your trip at

Photos of skyline and The Bean from Pixabay.