The most relaxing things to do in Chicago

A woman enjoys the green spaces of Chicago

Relaxing may not be the first word that comes to mind when thinking about the windy city. But if you’re asking ‘how can I relax in Chicago’ don’t dismay. Follow our lead and you’ll soon realize there’s a real wealth of relaxing things to do in Chicago.

Know where to look and the rush hour traffic and crowds of the Magnificent Mile will become a distant memory. So what are you waiting for? Let’s check out the best ways to go zen in the home of Al Capone and the World’s Fair.

Picnic in the parks

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The obvious place to head for a bit of tranquility in any city is its parks. Since the 1830s the official motto of Chicago has been the Latin phrase urbs in horto, or ‘the city within a garden’. Tot them up and the city’s public parks come close to topping 600 in number, equivalent to almost 9% of its area.

North of downtown, Chicago Botanic Garden was only opened in 1972, although you’d never guess from its landscape of lakes, prairie and woodland. Covering 385 acres, it is made up of 25 display gardens within these habitats, bringing the world of horticulture to this part of the city. Aside from providing an attractive place to relax, it also plays an important role in helping preserve rare and disappearing species.

Constructed 50 years earlier by the architect it’s named after, the intention of Alfred Caldwell Lily Pool was always to provide Chicagoans with a space to think. Sharing the same naturalistic appearance as the Botanic Garden, the almost Japanese scene of woodland and trickling water is situated in Lincoln Park, alongside the Conservatory glass house – a perfect alternative should a rain shower sweep over.

Explore your artistic side

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Especially calm during office hours, the Museum of Contemporary Art provides exactly the right ambience for taking your time over its permanent collection of 2500 artworks, substantially supplemented by loans from other galleries.

Puzzle over Jeff Koons’ stainless steel Rabbit, Andy Warhol’s screen prints of Jackie Kennedy, and Magritte’s The Wonders of Nature before heading out into the sculpture garden or tucking into something tasty in the restaurant designed by award-winning artist Chris Ofili.

If you’ve ever lost a few hours in the comfort of a good book, you’ll understand the serenity the written word can impart. Where better to head then when looking for relaxing things to do in Chicago than the American Writers Museum? From Nobel prize winner Ernest Hemingway to poets and playwrights, it celebrates storytelling in all its forms.

With creativity sparking off every nerve ending, you may well want to roll up your sleeves with an art workshop. Lillstreet Art Center has been at the heart of the community since 1975 and is just one of a number of galleries hosting regular sessions incorporating metalwork and jewelry making, screen printing and ceramics.

Take to the water

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Edged by Lake Michigan, one of the Great Lakes, and cleaved in part by the various branches of the Chicago River, taking to the water is another way in which to enjoy the city without setting your heart pulsing with anything but fascination.

Step aboard a Shoreline Architecture River Cruise for a jaunt along all three channels of the river. The south branch soon reveals one of the city’s most famous structures – the Willis Tower – tallest building in the world for a generation. The main branch is lined by further architectural points of note, whilst the north branch helps reveal how the city has changed over its 200 year history. Should you wish, it’s also possible to explore the river not by boat but by kayak.

However, to really absorb the Chicago skyline you’re going to need a little more distance, such as that offered by Skyline Lake Tours. Aside from the city views, these 40 minute tours give ticket holders a potted account of the growth of the city as you take in Navy Pier, Harbor Lighthouse and Museum Campus from onboard.

Enjoy a gentle stroll

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Taking in a portion of the river’s south branch is Chinatown, where there are plenty more lazy things to do in Chicago. Centered on Cermak Road and Wentworth Avenue, it has an expansive range of independent stores, teahouses and dim sum restaurants very different to the offerings on the Magnificent Mile.

Check out the Chinese American Museum of Chicago for a little more on the background of how it developed, or satisfy yourself with the replica of Beijing’s 15thCentury Nine Dragon Wall.

Other spots in the city to take a leisurely walk include the 606 (or Bloomingdale) rail trail, following the westward path of an old railroad track. Replaced with the largest greenway project of its kind in the US, it runs for 2.7 miles, meaning even if you follow it to its western trailhead you still won’t be too far from the center of the city.

Turn in the opposite direction and you’ll soon reach Lakeshore Trail, following the water’s edge of Lake Michigan for more than 18 miles, giving ample opportunity whether you’re after a walk to the nearest coffee shop or a daylong hike along the whole path. For shorter ambles, Navy Pier makes for a great target. Packed with old style rides and Centennial Wheel and extending for over 3000 feet, it’s one of Chicago’s most popular attractions.

Relaxed in body, mind and wallet

With a little effort it’s possible to find a wide array of relaxing things to do in Chicago, from spending time in the city’s multitude of gardens to hitting the heights of Centennial Wheel. Another way to stay relaxed when on vacation is by traveling with Go City. Set yourself up with one of our pre-pay passes and you’ll know you've got huge discounts on entry to many of Chicago’s most popular attractions and things to do!

Ian Packham
Go City Travel Expert

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Rainbow crosswalk in Boystown, Chicago
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Things to do in Chicago for Pride Day

The Chicago Pride Parade is one of the most highly attended festivals of its kind on the planet, pulling in something like a million revelers every year. No surprise really, given Chicago is one of the most LGBTQ-friendly cities in the States, its Northalsted neighborhood (aka Boystown) a vibrant community hub that was the first in the country to be officially recognized as a gay village. The city’s colorful month-long June Pride party is, as you might expect, a fairly flamboyant affair, taking in karaoke nights, drag brunches, art shows, skate parties, marching bands, club nights and much more. Raise your rainbow flag and read on for our guide to some of the best things to do in Chicago during Pride month. Spend the Day in Boystown There’s no better way to familiarize yourself with Chicago’s LGBTQ+ history and culture than with a visit to the Legacy Walk in Boystown. Take a stroll along the North Halsted Street Corridor between Belmont Avenue and Grace Street, where this unique open-air museum takes the form of 35-or-so steel ‘rainbow pylons’. Each standing 25 feet tall, the pylons act as monuments to those legends who helped shape the LGBTQ+ movement in Chicago and beyond, with bronze plaques commemorating individuals including James Baldwin, Josephine Baker, Harvey Milk, Oscar Wilde, Jose Sarria and Freddie Mercury, plus pivotal events like the 1969 Stonewall Riots. Afterwards, make time to check out some of the neighborhood’s other beloved LGBTQ+ hotspots, including the Center on Halsted, a community hub that’s home to the Hoover-Leppen Theater and Billie Jean King Recreation Hall among other facilities. Head up to the roof for tip-top neighborhood views that become yet more colorful during Pride month, thanks to the increased proliferation of rainbow flags and bunting that decorate the streets below. Hungry? You’re in luck. Boystown also happens to be home to some of the best brunch spots in town. Hit up local institution Drew’s on Halsted for eggs every which way accompanied by breakfast martinis and live DJs. Or mosey on over to the smart, literary Wilde Bar & Restaurant, named after guess who? Of course, the LGBTQ+ nightlife in this lively enclave is just about as good as it gets, running the gamut from karaoke parties to dive bars, drag nights and hedonistic all-night dance parties. Try Sidetrack, The Closet, Roscoe's, Hydrate and the Kit Kat Lounge for some of the very best. LGBTQ+ Art & Culture There’s plenty more going across Chicago through the month of June. Check press listings for comedy, cabaret and drag performances hosted by the likes of Boystown stalwarts the Newport Theater, Dorothy and the Whiskey Girl Tavern.  Many of the city’s largest cultural institutions also run LGBTQ-themed programs and exhibitions during Pride month. For example, the Field Museum, one of the biggest and best natural history museums in the world, hosts an annual drag pageant as well as events around the role of sex and gender in the natural world.  Meanwhile, the American Writers Museum runs readings, workshops and tours spotlighting the work of LGBTQ+ authors whose writings are exhibited here, including the likes of James Baldwin, Maurice Sendak and Susan Sontag. There are events for kids at Chicago Public Library branches including Logan Square and South Shore, with drag and rainbow story times to keep the little ‘uns entertained, and an annual party down at Navy Pier, which is usually held the day before the Pride march. It’s an all-day event that features live music, marching bands, DJs and more, and is conveniently close to all those seaside fairground rides for a spot of old-school fun and relaxation between bouts of dancing! General admission to a number of these attractions (plus many more tours and activities around Chicago) are included with a Go Chicago pass. You could save up to 50% on entry to the likes of Navy Pier, the Field Museum, the Shedd Aquarium, 360 Chicago and more. Note that additional tickets may be required for entry to some Pride-themed events. Find out more about the Go Chicago pass and get yours here. The Pride Parade and Festival As the climax of Chicago’s Pride month approaches, all attention turns towards Chicago Pride Fest and the annual parade. The Parade takes place on the last Sunday of June with Pride Fest traditionally falling on the Friday and Saturday of the same weekend (or sometimes the weekend before). Pride Fest gets the party started in earnest with two days of live performances across three stages, everything from international pop stars to the very best of Chicago’s DJ and drag scenes. Add to that 150+ food and beverage vendors and you have all the ingredients you require for a top shindig. The festival takes place on Halsted Street, from Addison to Grace St, and is free to enter, though there’s a suggested $15 donation to help pay performers and festival workers, as well as supporting local community programs. Big-name stars to grace the stages here include M People’s Heather Small, Natasha Bedingfeld, Chaka Khan, and the Chicago Gay Men’s Chorus. Find out more about this year’s Pride Fest, including the entertainment line-up, here. The main event takes place on the last Sunday of the month, and draws the biggest crowds of the month. The Chicago Pride Parade sets off from around Sheridan and Broadway at 11AM, painting a rainbow across Northalsted as it weaves its way along and around Halsted to Lincoln Park – a distance of over six kilometers. Nab your spot to watch as dozens of flamboyant floats, revelers in outlandish costumes and live performers cruise past, complete with marching bands, stilt walkers, drag kings and queens, and more. The area surrounding Belmont and Addison stations tends to get the most busy, so arrive early if you want a decent view, or bodyswerve it altogether if claustrophobic crowds ain’t your thang. Rest assured there are plenty less densely packed locations: you’ll find for example that you have a little more breathing space towards the start of the route, and on its east side. Find about more about this year’s Chicago Pride Parade here. Save on Chicago’s Most Popular Attractions Don’t miss the opportunity to check out some of Chicago’s top tours, activities and attractions while you’re in town. You could save up to 50% with a Go Chicago pass. Find out more and choose yours here.
Stuart Bak
Stuart Bak

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