No matter what kind of vacation vibe you want to roll with, the Windy City can cater to it.
An insider's guide to Chicago
21.07.2023 - 08:40 / roughguides.com
Hitting new records for visitor numbers in 2018 and having recently been named “Best Big City in the USA” by Conde Nast Traveler readers for the second consecutive year, there’s never been a better time to visit Chicago. Many visitors head straight to the downtown district and never leave, charmed by the Windy City’s world-famous architecture and tourist-friendly restaurants and museums. But instead of rushing across the city to frantically tick off all the tourist hotspots, consider immersing yourself in some alternative things to do in Chicago instead. The places suggested here offered by Chicago insider Jay Gentile promise a real taste of the city’s culture by getting out of the downtown and into the neighbourhoods, where the “real” Chicagoans live.
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While most visitors are content to stroll along Chicago’s scenic downtown lakefront, a more authentic alternative is the recently opened 606 urban trail that passes through some of Chicago’s coolest neighbourhoods including Bucktown and Humboldt Park. Modeled after New York City’s High Line, the 2.7-mile elevated green walkway sits atop a former railway line and offers panoramic views of the local neighborhoods. The best part? There are plenty of great bars and restaurants to stop at just off the trail, including the bustling summer patio hangout Parson’s Chicken & Fish.
The 606 urban trail in Chicago © Jay Gentile
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Chicago is a festival-lovers paradise, hosting an array of big-name summer festivals, from Lollapalooza to the Chicago Blues Festival. But during the summer months, a simple stroll though many of the city’s 77 neighbourhoods will likely result in you discovering the streets blocked off and people wandering around with drinks in their hands as the city puts on a large number of local block party-style street festivals. One of our favourites is Do Division Street Fest in the city’s lively Wicker Park neighbourhood, where you can shop for locally made artisan goods while day-drinking in the sun. Hey, it’s the Chicago way.
Chicago’s beaches are some of the most underrated urban beaches in North America, perhaps because they’re only open for about three months a year (from late May to early September). After one of our notoriously long winters, Chicagoans make the most of their summers by soaking up the sun at the city's lakeside beaches – including several that seem to jut right up against the buildings. While technically still downtown, Ohio Street Beach is a less-visited beach tucked away in a picturesque corner of the city offering unobstructed views of the downtown skyscrapers on
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