The most relaxing things to do in Chicago

By Ian Packham
Published: July 18, 2024
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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Where to stay in Chicago

Made up of a long list of neighborhoods and districts each offering something different, deciding where to stay in Chicago can be a bit of a headache, especially if you’re a first-time visitor to the city. Whatever you’re looking for out of a leisure trip to the windy city, our pick of the best areas of Chicago to stay is sure to be a help! The Loop Enclosed by the Chicago River to one side and Grant Park to the other, the Loop is probably the best place to stay in Chicago for those new to the city since its streets include the central business district and many of the city’s top attractions, including the Willis Tower’s Skydeck observation level and the Art Institute of Chicago. It takes its name from the elevated railway which has looped around it since the Great Fire of 1871. Synonymous to most with the downtown area, it’s also one of the commercial hubs of the city. Being at the heart of the action (Route 66 starts here too), there’s no shortage of hotels either. Predominantly populated by luxury stays – the Hyatts and Radisson Blus of this world – budget travelers will likely find themselves looking at more affordable neighborhoods nearby, such as Lincoln Park. However, the Loop does it have a good quantity of backpacker hostels for those just looking for a central place to lay their head at the end of a long day of sightseeing. Streeterville Immediately north of the Loop on the shores of Lake Michigan, the Streeterville neighborhood is still close enough to downtown to be a worthwhile base and is a good pick for solo travelers and visiting couples. Known to be a very safe neighborhood in Chicago for visitors, it has some similarities to its southern counterpart. Gleaming tower blocks line the Magnificent Mile (a part of North Michigan Avenue), containing roughly 450 stores as well as the famed 875 North Michigan Avenue (John Hancock Center). Its southern extent stretches out into Lake Michigan thanks to the 50 acre Navy Pier. Its rides include Centennial Wheel, which replicates the world’s first Ferris Wheel, built in 1893 for the World’s Fair. Lincoln Park A little further out, but linked to the rest of the city by a number of metro stations and lines, Lincoln Park is one of the largest and most affluent districts in Chicago’s North Side. It is popular with young families and urban professionals, ensuring it feels fresh and ever changing. Named after the city’s largest park, which sits beside Lake Michigan for an uninterrupted seven mile run, the area is one of the best parts of Chicago for those on a budget. Attractions include the 32,000 creatures which call Lincoln Park Zoo their home, as well as Chicago History Museum, the first port of call for anyone interested in discovering how Chicago became one of the world’s leading cities. Lincoln Park also contains the northern half of Old Town, where buildings remain low to the ground – at least by Chicago standards – to create a homely feel. This is where you’ll find the Second City Theater, the previous stomping ground of everyone from Tina Fey to John Belushi. River North It may not have the lake shore, but River North does have a reputation as the coolest place to stay in Chicago. Separated from Streeterville by the Magnificent Mile, River North oozes stylishness and perhaps contradiction too – it has more galleries than anywhere outside of Manhattan, but is also known for its nightlife. For this, you should head to Hubbard Street. The banks of the Chicago River have to be the top place for a stroll in the area, whilst landmark buildings to look out for include the Wrigley Building and the monumental behemoth of a structure known as Merchandise Mart, whose exterior façade becomes the world’s largest projector screen for a few months of each year. A good range of restaurants, many with riverside terraces, means you’re unlikely to go hungry for long. West Loop That said, foodies should stake their claim to accommodation in West Loop, which – that’s right – is west of the Loop. Occasionally also known as the Near West Side, West Loop shines from a gastronomic perspective, with Greektown and Little Italy just two destinations you should be aware of thanks to the twentieth century’s influx of immigrants into this former industrial port area. Randolph Street is otherwise known as Restaurant Row for good reason, but for sumptuous food without any pretension head to the French Market tucked inside Ogilvie train station. Its 30+ independent vendors make it one of the best spots in the city for fresh ingredients as well as mouthwatering dishes from sushi to empanadas. Seating is available. Wicker Park Well-to-do Wicker Park is growing in confidence when it comes to where to stay in Chicago. Northwest of West Loop and centered around the Damen metro stop, this neighborhood has the sort of self-assurance which usually leads to great things. And Wicker Park is no exception to this rule. A charmingly informal blend of eclectically-stocked clothing stores, groundbreaking restaurants and we-just-have-to-stop-there bakeries, Wicker Park is also pretty hot when it comes to night spots, with a wealth of live music venues all vying to be the place to head. With median house prices of $550,000 it can never really be called hipster, but that’s certainly the vibe it gives off. Budgeting for trips to Chicago Finding where to stay in Chicago that’s right for you comes down to a balance of location, feel and price. The best neighborhoods in Chicago for visitors are generally those in and around the downtown area, although the closer you are to the Loop, the higher the per night cost you’re probably looking at. When it comes to attraction admission, you can make incredible savings simply by opting to travel with Go City. Our pre-pay passes take all the mystery out of budgeting for trips to Chicago whilst providing you with great savings on many of the city’s top attractions.
Ian Packham
Night time view of the Navy Pier Ferris wheel in Chicago
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Things to do in Chicago at Night Time

A mighty metropolis renowned for its world-class museums, fine restaurants and frankly epic city skyline, the Windy City is, if anything, even more thrilling at night. There’s an absolute abundance of attractions and activities worth staying up late for, from galleries and ghost tours to deep dish pizza and old-school jazz joints. Hop aboard for our whistle stop guide to some of the best things you can do in Chicago at night time. Skyline Views Chicago’s sensational skyline is the envy of cities across the States. Take a leisurely evening stroll along Lake Shore Drive or the Chicago Riverwalk and you’ll soon find out why. We’re talking soaring skyscrapers that include the awesome Willis Tower (for many years the tallest building on the planet, fact fans) and the iconic neo-gothic Tribune Tower. Incredible enough to look at during the day, these architectural titans really come into their own by night, lighting up to produce one of the world’s most recognizable cityscapes. See them from the water on a night cruise of Lake Michigan, when widescreen views of the illuminated city reflect beautifully in the glassy waters that lap the shoreline. Head in the Clouds You’ve checked it out from ground level, now take in birds’ eye views from atop some of the Western world’s loftiest skyscrapers. You need nerves of steel to ascend to Skydeck Chicago atop the Willis Tower. At 1,353 feet and 103 floors up, it’s only the highest observation deck in the United States. No wonder then that you can see four states from up here, as well as Chicago landmarks including Navy Pier, Lake Michigan and the Magnificent Mile. Daredevils/masochists can even step out onto The Ledge to see the lights of the Windy City twinkling far beneath their feet. A little closer to terra firma at a mere 1,030 feet up, 360 Chicago adds the option to experience TILT, a sky-high thrill ride in which willing victims participants climb onto a moving glass platform which then – yup, you guessed it – tilts riders forward to a perilous angle over the city. Very much not for the faint of heart.  Bean There, Done That For a unique perspective on the iconic Chicago skyline, hit up The Bean on the AT&T Plaza at Millennium Park. This huge stainless steel sculpture by British artist Anish Kapoor – officially named Cloud Gate, but more commonly known as The Bean due to its shape – has quickly become a Windy City icon. Visit at night, when the bright lights of the Michigan Avenue skyscrapers reflect on its gleaming surface, creating hallucinatory magic-mirror cityscapes that bend, twist and morph as you walk around and underneath it. Check listings for al fresco evening concerts elsewhere in Millennium Park during summer. Take a Tour There are dozens of ways to get under the skin of night time Chicago without, you know, the tedium and inconvenience of poring over a guidebook for hours. Take to the skies on a twilight helicopter tour over Lake Michigan and that famous city skyline; hear all about the Windy City’s ghosts and gangsters on a spooky walking tour; or – perhaps best of all – join a foodie tour that gives you the chance to tuck into unmissable local delicacies such as Chicago-style hot dogs, Italian beef sandwiches, and deep dish pizza. Yum. Museum Lates Chicago has a frankly superb selection of museums and galleries, many of which have regular late opening hours, allowing you to ogle Old Masters, contemporary masterpieces and ancient artifacts in relative peace and quiet. Hit up the Art Institute of Chicago on Thursday evenings, when you can check out significant pieces from Hopper, van Gogh, Picasso, Matisse, O’Keeffe and more until 8PM. Other Windy City institutions including the Chicago History Museum and Museum of Science & Industry run ‘happy hour’ events that run as late as 10PM, and the Adler Planetarium’s late Wednesday openings provide a stellar option for whiling away chilly winter evenings. Animal Magic Museums and galleries a little too stuffy for you? Fear not! Take an evening walk on Chicago’s wild side at the Lincoln Park Zoo where, on balmy summer evenings, the park stays open late for adult-only events that include the likes of wine festivals and craft beer tasting. There’s nothing quite like the roar of a nearby African lion or cackle of a laughing kookaburra to get the party started. Meanwhile over at the Shedd Aquarium, night time events for adults include animal encounters, cocktail evenings and salsa classes, though not necessarily all at the same time. Navy Pier A tad nippy in winter, but a vibrant waterfront treasure on summer nights, Navy Pier is where it’s at for old-school seaside-style vibes. That’s largely thanks to the fab Ferris wheel that dominates the shoreline here, but after-dark firework displays, buzzy rooftop bars, live music, fab fast food joints and delectable dessert stores all add to the fiesta atmosphere. Grab an original rainbow ice cream (that’s orange sherbet, pistachio, Palmer House, chocolate and strawberry stacked high on a cone) and tuck in as the sun sets over the water. All That Jazz Hipster joints abound in downtown Chicago, and the Green Mill Cocktail Lounge, with its distinctive lime green neon sign, should be at the top of every bucket list. This century-old Chicago institution was once a favorite of Al Capone and his band of bootleggers, who used tunnels underneath the bar to smuggle booze during Prohibition. So grab a seat in Capone’s old booth, order up a Manhattan, and enjoy some of the finest jazz acts in town, just like Big Al used to do. Blues fans are also well-served in Chicago, thanks to the likes of Kingston Mines, Buddy Guy’s Legends and the House of Blues, while scuzz-rockers can get their fix at hipper-than-thou dive bars including Pilsen’s beloved Skylark and the Rainbo Club in Wicker Park. Save on attractions in Chicago Save on admission to Chicago attractions with Go City. Check out @GoCity on Instagram for the latest top tips and attraction info.
Stuart Bak
Stuart Bak

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