Things to do in Gold Coast, Chicago

By Dom Bewley
Published: July 18, 2024
things to do in gold coast chicago

So, you've chosen your vacation destination. The Windy City. Chi-Town. The real-life Metropolis, minus the superheroes. Chicago is a fantastic getaway destination, full of great food, fun nights out, and plenty of top-level entertainment. But it's a big old town, with multiple districts and areas that crisscross throughout its gargantuan layout. With so many to choose from, which one is right for you? Well, don't let choice paralysis get the better of you! We've done all the research necessary, so you don't have to. Give Gold Coast a go. It's as simple as that. With a wealth of entertainment on offer, it's the perfect vacation spot. Here are our picks for the best things to do in Gold Coast, Chicago!

Including:

  • Oak Street Beach
  • Playboy Mansion
  • Broadway Playhouse
  • Washington Square Park
  • Drake Hotel Bar
  • and more!
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Hit the Beach

Why not ease into your trip with a spot of lounging? After all, you've got the rest of your vacation to go see the sights. Lucky for you, the Gold Coast lives up to its namesake. Head there, and you'll find Oak Street Beach. Of course, you'll find heaps of golden sand, clean sea, and (hopefully) glistening sun - that's what the beach is all about, after all. However, Oak Street Beach is also perfectly placed to visit at any time during the day, as it's just a stone's throw from the city itself. Take a dip in the ocean, go grab an ice cream for the kids - or yourself, who are you kidding - and then check out the nearby patio bar for a cool, refreshing drink. Easily one of the best things to do in the Gold Coast when you visit Chicago.

Feel like a Playboy

Yes, really. Though you probably know the Playboy Mansion as the once celebrity-laded party mansion near Beverly Hills, it wasn't always there. In fact, the original Playboy Mansion was bought right here on the Gold Coast back in the '50s. The rather less impressive original is well over 100 years old at this point, and has changed hands multiple times. First, Hefner donated it to the School of the Art Institute of Chicago when he moved into his legendary LA pad. Then, the institute sold it to a redevelopment firm, and it's now been converted into condos in a rather typical fashion. However, if you want to see a piece of 20th-century American history in the flesh, you owe it to yourself to go and bask in the extravagant opulence of the original Playboy Mansion. Just don't plan on buying one of the condos, unless you've got a few mill to spare.

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Broadway, baby!

If the weather takes a turn, or you just want a couple of hours out of the sun, why not retreat to the bright lights and comfort of broadway? Yes, even in Chicago, you can get a taste of the New York performance mile thanks to Broadway Playhouse! A stone's throw from the coast, you'll find a host of great plays and musicals being shown throughout the year, from all-time classics to the new shows on the block. You might even stumble upon a one-man show, or local play before it gathers steam.

Walk in the Park

Are you a fan of the color green? Do you like walking? Is the prospect of breathing in fresh air, mingling with trees, shrubs, and grass appealing to you? Answer us these questions three, and we'll give you a place you want to be. At. A park, of course! Gold Coast has you covered in flowers and grass, thanks to Washington Square Park. Go there for the giant 19th-century fountain, stay for the delightful green spaces, picnic opportunities, or simply for a stroll. So, what are you waiting for?

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Get Risky

When you're in Gold Coast, why not grab a drink at a Hollywood monument? Sort of, at least. Featured in the '80s Tom Cruise classic Risky Business, the Drake Hotel is one of Chicago's most recognizable landmarks! But we're not talking about the room service here. We're talking about the Hotel's bar, called the Coq d'Or. This lavish hotel lounge has been warming customers' cockles since the dark Prohibition days. Head inside and find a wealth of drinks, a menu to die for, and enough comfort you'll feel like a marshmallow. A pampered marshmallow.

Best Pizza in town

Wow, all that doing things, seeing things, and experiences must have made you hungry. Well, Chicago is famous for one thing in the food department, and that's deep dish. The Chicagoan take on the Italian classic is known worldwide for its deliciousness, thanks to its unusual sauce-over-cheese twist. So why not go get some and see if it lives up to its reputation? Lou Malnati's, right in Gold Coast, is arguably the best in town. The name is a staple of the Chicago style, having helped pioneer it in the early 20th century. So go grab a slice of delight and take your tastebuds to pizzatown. Or something.

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Go Shopping

Let's end this list on a shopping, surely many of our readers' favorite pastimes. Thankfully, Gold Coast is full of shops of all shapes and sizes, so no matter what item you seek, you're sure to find it there.

However, for those of you with expensive tastes, you'll be looking for The Magnificent Mile. Head there, and you'll find a shopper's paradise. Over 400 stores line the 'Mile', including the likes of Chanel, Louis Vitton, and Tiffany. So, if you're looking for some dear deals and have the cash to splash, you'll be right at home. On top of all that shopping, you'll also find a slew of gourmet restaurants, snug cafes, and much more. So, if that all sounds like heaven to you, go on down and see what's cracking!

And that's our list of the best things to do in Gold Coast, Chicago! If you want to know about the other areas of Chicago, check out our thoughts here. Heading to Chicago at the tail end of winter? The beaches might be a no-go, but there's plenty more to do and see!

Dom Bewley
Go City Travel Expert

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Things to do in Ravenswood Chicago

From ‘90s up-and-coming neighborhood to today’s laid-back residential district, Ravenswood sits in Chicago’s North Side about 500 meters from Lake Michigan’s Montrose Beach. Often spoken about together with its Lincoln Square enclave, Ravenswood is well-connected by metro to the delights of downtown. You won’t find too many places to stay, but head in this direction and you will find a fantastic riverside area and a fine selection of places to eat and drink among cleverly repurposed historic structures dating from around the time of the Great Fire in 1871. Looking for things to do in Ravenswood Chicago? Here’s our guide to the area’s top attractions. Parks and gardens in Ravenswood Chicago With a name such as Ravenswood it’s fantastic to see that green spaces still play a significant part in life in the neighborhood. They comprise a mosaic of public gardens situated at each cardinal compass point. The smallest, on the eastern edge of Ravenswood, is Chase Park, a fun place to get a little physical activity since it contains an outdoor pool, tennis courts (which can be enjoyed from M Bakery) and a running track. Although it also contains an outdoor pool and tennis courts, River Park has a more natural appearance. Taking in North Shore Channel Trail and popular with dog owners, it occupies a beautiful part of the banks of the Chicago River. Welles Park has a historic bandstand-style gazebo, and an indoor pool. Just outside the official boundaries of Lincoln Square and Ravenswood, Rosehill Cemetery is a charming spot from which to take in some of Chicago’s history from a personal perspective. Dating from 1859, its 350 acres contains the graves of North Side residents spanning over 150 years, including soldiers who fought on both sides during the American Civil War. Down time in Ravenswood Whilst its parks and gardens are an awesome addition to the neighborhood, Ravenswood is really known for its post-work and weekend hangouts. Of a long list of places to shop, Ravenswood’s resident bookworms highly recommend The Book Cellar, whose welcoming vibes extend as far as an onsite café where you’ll find a range of sandwiches, soups and freshly-ground coffees. ENJOY, An Urban General Store is one of those treasure trove stores you can’t believe your luck in discovering, with shelves loaded with quirky gifts, cards and stationery. Meanwhile, the thrift store Village Discount Outlet’s humble exterior belies a constantly changing stock of one-of-a-kind second-hand items as kind on the budget as on the planet. When hunger makes its presence felt look no further than River Valley Farmer’s Table, whose mid-morning locally-sourced breakfasts are rapidly gaining legendary status. If you can’t find a spot at this farm-to-table restaurant and grocery store head instead to Pastores Brunch, one of a clutch of favorites on North Lincoln Avenue. For drinks, the Sixth makes for a classy cocktail bar with a cool urban feel. Decked out in black with yellow highlights, this LGBTQ+ friendly location has a bar menu encompassing not only the classics but some homegrown inventions too. Or there’s O’Shaughnessy’s Public House, taking the stereotypical Irish bar to new places and Wolcott Tap, whose atmosphere is second to none and beer list one of the best in town. Things to do in Ravenswood Saved from demolition by community pressure, the Davis Theater has been entertaining Ravenswood with first-run movie screenings for over 100 years. The longest continuously operated movie theater in Chicago, its matinee screenings are particularly good value. Elsewhere, the stage at Chicago Magic Lounge always seems set for slight of hand par excellence, whilst its speakeasy style harks back to the dark days of gangland feuds between Al Capone and Bugs Moran – culminating in the St Valentine’s Day Massacre. It may not be the Field Museum, but the Swedish American Museum does a good job of detailing the influence of Swedish immigrants to the Ravenswood area. Alongside its royal seal of approval – King Carl XVI Gustaf attended its opening ceremony – its collection includes personal objects, paintings and stories. Similarly, the DANK Haus German American Cultural Center aims to preserve the unique cultural contribution of German immigrants through a series of rotating displays and temporary exhibitions from German artists. Not to be missed in Ravenswood The heart of Ravenswood and Lincoln Square is Giddings Plaza, a pedestrianized road of just 20 meters or so. What it lacks in size it makes up for in community spirit, being the place to head to meet up with friends before delving into one of the small boutique stores that surround it. During the festive season it’s the location of a large Christmas tree and the sound of live music often drifts away from it in the warmer months thanks to a summer concert season. Lillstreet Gallery is more gift store than art center these days, though it’s still one of the best places in northern Chicago to check out the work of the next generation of makers – and help them on their way to success with a small purchase. With your help, their work could one day make it into the hallowed halls of the Museum of Contemporary Art, alongside Pablo Picasso and Andy Warhol. To peruse another form of art – the skill involved in the production of whiskies and other spirits – look no further than Koval Distillery’s regular tours. Heading behind the scenes of the first distillery to set up shop in Chicago since before the prohibition era, you’ll get insight into the grain-to-bottle ethos and the chance to sample some of the resulting award-winning concoctions. Make your money go further Just a small part of the North Side, there are still plenty of things to do in Ravenswood Chicago. Alongside Lincoln Square, this neighborhood provides a contrast to the bustle of the Magnificent Mile downtown. Whether you arrive by metro, Uber or rental bike, be sure to travel with Go City. Our passes are a simple way to save on trips to Chicago and cities worldwide, giving incredible savings on admission to many of the top attractions around.
Ian Packham
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Best walks in Chicago

Think of Chicago and your thoughts either go to the racier parts of the musical and movie that share the city’s name, or major downtown landmarks. After all, there’s the views from the Skydeck of Willis Tower to look forward to, alongside the photographic opportunities around the Cloud Gate sculpture in Millennium Park. However, Chicago also has a wilder side. And it’s one that’s easily enjoyed on foot. From strolls of just a couple of hours to full-day hikes, we’ve brought together the very best walks in Chicago just for you! North Shore Channel Trail A multi-use trail – meaning you’ll more than likely encounter cyclists, joggers and skaters too – the North Shore Channel Trail picks up in the Lincoln Square area of Chicago’s North Side and follows a canal-like channel dug in the early 1900s towards its outlet at Wilmette. Passing through Stokie, its easy 13 mile total length takes in the 60 artworks of Stokie Northshore Sculpture Park and Evaston Ecology Center within the Ladd Arboretum as well as the beauty of the city’s north. The 606 Providing new opportunities for hiking around Chicago, the 606 was created out of an unused rail line cutting west-east through the Humboldt Park and West Loop neighborhoods for a little under three miles. Its former life as a railroad track means the gradient is almost undetectable, making it a great pick for families with young children in pushchairs and strollers. It’s also very readily accessible thanks to several entry and exit points. Also known as the Bloomingdale Trail after the name of the former rail line, this elevated greenway and linear park may remind some of New York’s Highline, though the 606 is almost twice as long. It takes its new name from the area’s zip code numbers. Lakeshore Trail With walking boots in hand – or on foot – you won’t want to miss perhaps the most scenic walking trail in Chicago, the 18 mile Lakeshore Trail. Taking in a mix of urban splendor, parkland, beaches and lagoons, it’s a highly-rated way of exploring the shores of Lake Michigan however much you decide to walk of it. And let’s face it, with the wealth of attractions on the trail’s doorstep, from North Avenue Beach to Centennial Wheel and the Shedd Aquarium, it could easily take you two or three days to tackle its entire length, recently split between designated walking and cycling trails. Deer Grove Situated on Chicago’s northern outskirts, Deer Grove’s two adjoining segments, Deer Grove East and Forest Preserve, form a winding system of footpaths. Those closest to the main entrances are paved, and total around four miles, whilst unsurfaced trails lead about the trees, prairies and ponds for a further ten miles across 2000 acres. The birdlife here is some of the best in the region, with other species of wildlife to look out for including the white-tailed deer after which the preserve is named. Waterfall Glen Forest Preserve A thirty minute drive outside of the city, which may not sit comfortably with everyone’s idea of walking trips, Waterfall Glen Forest Preserve has around 11 miles of mapped trails to choose between once you’ve arrived. Although it contains a small (artificial) cascade tumbling over some low rocks, it actually takes its name from a district board of commissioners’ president. One for nature lovers, its woodlands contain three quarters of all the plant species found in the region, alongside a long list of birds, fish, amphibians and mammals. Deep within its 2500 acres you’ll also find St Patrick Cemetery, which few others visit even on the busiest of days. The Magnificent Mile For urban exploration in its truest sense right at the heart of downtown Chicago there’s the Magnificent Mile. The honorary title given to the upper section of North Michigan Avenue, it runs from the Chicago River to Oak Street. Lined with mid-range and luxury stores, hotels and restaurants, it has some of the highest real estate figures in the US. It also boasts some of the city’s most famous landmarks, including the John Hancock Center – home to the 360 CHICAGO viewing platform. On the face of it, walking its length shouldn’t take you more than 30 minutes, but with so many store windows to check out and buildings to take in, it can take much longer than that. Save your stroll along the Magnificent Mile for later in the day, and if your feet are feeling tired, you can always make use of the Hop-on Hop-off sightseeing buses which ply the route instead. Midewin National Tallgrass Prairie Follow Route 55 southwest with the help of a motor engine and in around an hour you’ll reach Midewin National Tallgrass Prairie. Covering 19,000 acres of federally protected land, the prairie has over 20 miles of mixed use trails in addition to 12 miles of paths saved for hikers alone. Created out of an old army ammunition store with the aim of maintaining the region’s traditional prairie lands, since 2015 it has also been the home of one of the only wild-roaming bison herds in the country, totaling around 50 animals. They are allowed to move across roughly 10% of the prairie’s total area and are docile unless threatened. Morton Arboretum Walks If you’re a little nervous about heading into the wilds, Morton Arboretum makes for a great alternative. Forty-five minutes from the downtown neighborhoods, it has its own restored tallgrass prairie (minus the bison) as well as 16 miles of surfaced paths through burr reed marsh, woodland and landscapes of marginal lakes. Summer and fall see the arboretum host Theater-Hikes, where visitors walk between outdoor performances, whilst the Christmas period is given over to annual illuminations. Don’t miss anything with Go City The best walks in Chicago combine aspects of all the city has to offer to tourists young and old. Varying in length, difficulty and setting, they provide a different and often unique way of exploring the windy city. Travel with Go City and there’s also the chance to save when you stroll and stride. Many of the best walking trails in Chicago pass by the city’s bucket list attractions, so why not take a breather, skip the lines and save big on admission all at the same time?
Ian Packham
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The ultimate Chicago shopping guide: boutiques, big brands and bargains

Pack an extra bag. From makers' markets to the Magnificent Mile, here’s where to shop in Chicago for fashion, gifts, vintage and small-batch treats, plus those all-important coffee stops between stores.

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