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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A walker takes in Chicago's fall color
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Chicago in November

Visit Chicago in November and you’ll discover a city preparing itself for the depths of winter but not quite done with fall. Temperatures are generally healthy enough to allow you to still spend plenty of time outdoors, where it’s usually possible to see the last of the fall color or the first flurries of snow. As the days get shorter towards the end of November, there’s also the start of the Christmas festivities to look forward to as well as the celebrations around Thanksgiving on the fourth Thursday of the month. Wondering how cold Chicago is in November and what there is to do? We’ve brought together all the top tips so you need to look nowhere else. Enjoy the end of the fall color Chicago weather in November sees average daily temperatures rise to 50°F, equivalent to a cool spring day. Whilst you’ll want to wrap up warm, do so properly and just eight days of rain will mean you can get out amidst the city’s green spaces to take in the final days of reds, oranges and gold with the turning of its leaves. Should you choose, you could traverse Chicago’s shores on Lake Michigan without ever leaving parkland. A popular pick with those looking to get into the saddle of the city’s rental bicycles – but welcoming to walkers, joggers and skateboarders too – the Lakeshore Trail covers 18.5 miles. Starting at Edgewater Beach in the northern suburbs, it then runs south past many of the city’s top attractions. The first is the free-to-visit Lincoln Park Zoo, whose residents include great apes, big cats, a burr oak older than the city and the Lionel Train Adventure and Endangered Species Carousel rides. Further south lie other major things to do in Chicago in November including the magnificent Field Museum. As one of the largest natural history museums around, it is simply stuffed full of stuffed animals, cultural artifacts from across the globe and the famous skeleton of Sue the T-Rex – one of the most complete and best-preserved examples yet discovered. A short way across the state border, alternative vistas can be sought out at Indiana Dunes National Park. Situated close to the southernmost point of Lake Michigan, the park’s impressive dunes offer a wealth of walking trails, albeit without the fall color. Kick off the festive season Thanksgiving focusses very strongly on Chicago’s downtown areas. Taking place on the grid of streets which form immediately south of the fork in the Chicago River, the annual Thanksgiving Parade is a family-friendly affair which sees State Street taken over by giant helium balloons, dance troops and marching bands. Thanksgiving is also closely associated with the Black Friday sales. Still on State Street, there are a great number of smaller stores, whilst the Magnificent Mile boasts higher end boutiques, department stores including Marshalls and Nordstrom and several shopping malls. If you prefer the artisan touch, look no further than the Chirstkindlmarket that appears in front of Daley Plaza’s 50-foot tall steel Picasso sculpture towards the middle of the month. Its German-style wooden chalet-like stalls are awash with beautiful ornaments, jewelry and tasty treats. Alternatively, you might want to try your hand at another winter staple – ice skating. The city’s largest outdoor rink is the McCormick Tribune Ice Rink that sits beneath the gaze of Anish Kapoor’s Bean, although the Maggie Daley Park Skating Ribbon provides an attraction that’s a little more unusual, with a track winding through the tree cover twice the length of a lap around the Bean’s rink. Savor the views With such a long list of things to do in Chicago in November you shouldn’t forget to stop for a moment or two and take in the windy city in all its glory. One way to do this would be to give your feet a rest by opting for the Hop-On Hop-Off sightseeing bus instead. Taking in sights you might otherwise miss, it also connects up many of Chicago’s top attractions, including the Willis (Sears) Tower. Entering the history books as the world’s tallest building from its topping out ceremony in 1974 until 1998, it continues to host the highest observation tower in the United States – the Skydeck. From its 103rd floor vantage, visitors are able to take in no less than four states whilst feeling the building move in the wind at almost 1400 feet up. Giving the Willis Tower a good run for its money is 360 CHICAGO at 875 North Michigan Avenue. Although its views come from nine stories below the Skydeck, its wrap-around glass windows still have extraordinary panoramas over the city. Get better acquainted with the city’s art Art lovers don’t need to look far in Chicago in November to get a fill of their passion. For one, the city has a huge array of public artworks. As well as the giant sculpture by Picasso in Daley Plaza and Anish Kapoor’s Bean, Chicago also has outdoor works by Joan Miro, Marc Chagall and Magdalena Abakanowicz. The immense Merchandise Mart building comes to life with the world’s largest video installation, projected annually onto the side of the structure from September through November. There’s also an impressive array of murals covering the ends of buildings throughout the city. West Town Street has developed into a mile-long open-air gallery, with other works including the mural of local photographer Vivian Maier in Wicker Park and an unforgettably bright 100 foot image of American singer-songwriter Muddy Waters on North State Street. The pick of the galleries includes the Art Institute of Chicago. One of the largest museums of its kind, the 300,000 objects in its permanent collection spans the genres, ranging from native American textiles to contemporary photography. Making the most of Chicago in November With so much to see and do in Chicago in November you won’t want to waste a second. Skip the lines and save big on admission to many of the city’s top attractions with Go City. Then the only thing left to do is have an incredible time in one of America’s greatest destinations!
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.
Museum of Science and Industry
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Museum of Science and Industry Vs The Field Museum Comparison

Chicago’s embarrassment of cultural riches includes such venerable institutions as the Shedd Aquarium, Art Institute, Adler Planetarium, and home and studio of legendary architect Frank Lloyd Wright. The Griffin Museum of Science and Industry and Field Museum are two of the biggest, brightest and best such attractions in town. Between them this pair of cultural giants chart the entire history of this planet we call Earth, from weather systems and animal evolution to ancient Egyptian burial rites and the space race. But which should you visit when on vacation in the Windy City? We take a closer look at the Museum of Science and Industry vs the Field Museum, covering must-see highlights, best times to visit and how long you’ll need for each. Griffin Museum of Science+Industry: The Lowdown Vital Statistics: The Griffin Museum of Science+Industry (or MSI) is perched on a reflecting lagoon in Chicago’s Jackson Park, and housed inside the former Palace of Fine Arts, built for the Chicago World's Fair in 1893 and opened as a science museum in 1933. Inside, a collection of some 2,000 pieces celebrate the very best of human endeavor, ingenuity and achievement across 75 cavernous halls. The museum has plenty of pulling power, welcoming more than a million visitors every year, thanks to its hands-on exhibits, major touring exhibitions and epic five-story wraparound theater. The MSI in Brief: Anyone with even a passing interest in the technological progress of the human species through the ages will find much to enjoy at the MSI. Here’s where you can ogle the world’s first stainless steel diesel-powered train, get down and dirty in a full-size replica coal mine, step aboard a captured WWII German U-boat and poke around in a 13-foot interactive 3D heart. And that’s just for starters: there are also simulated storms, lunar capsules, a toy-making lab and a huge domed cinema showing immersive films that highlight the very best of the human race. And more! When to visit: Regular opening hours are 9.30AM–4PM daily, with extended hours during summer and school holidays. The museum is closed on Christmas and Thanksgiving. There’s at least a day’s worth of entertainment here, but four hours is enough to tick off the big-ticket exhibits. Avoid school holidays and summer if you don’t like crowds, as these are – perhaps unsurprisingly – the most popular times for families to visit. Visit the official MSI website for up-to-date information on opening hours and exhibitions. Field Museum: The Lowdown Vital Statistics: The Field Museum can be found on Chicago’s Museum Campus, a few miles north along the shore of Lake Michigan, neighboring the excellent Shedd Aquarium and Adler Planetarium. This epic natural history museum was largely conceived around exhibits acquired from the 1893 Chicago World’s Fair and first opened its rather impressive doors back in 1894. Since then, it’s gone from strength to strength, amassing a collection of around 40 million objects, specimens and artifacts, charting 4.5 billion years and drawing in over a million history-hungry visitors each year. The Field Museum in Brief: This one is a naturalist’s nirvana: nearly 500,000 square feet of preserved dinosaur skeletons, meteorite fragments, Ancient Egyptian mummies, animal dioramas, Incan and Aztec artifacts, intricate totem poles, and more magnificent historical artifacts than you can shake a giant T-Rex femur at. Fun fact: the phrase “the customer is always right” is attributed to Marshall Field, the 19th-century department store magnate who gave the museum its name and was its original benefactor. When to visit: The Field Museum is open daily from 9AM–5PM, with final admission at 4PM. It’s closed on Christmas and Thanksgiving. You could very easily spend a whole day or more exploring the collections here, but four hours should give you a decent overview of the highlights. Arrive for opening time to secure the most elbow room – the museum tends to be busiest from late morning until mid-afternoon. Get the latest exhibition information and further details on opening hours at the official Field Museum website. Field Museum or MSI: Which Should I Visit? These are two of the biggest, best and most family-friendly museums in Chicago, so we’d really recommend visiting both if you have time. Go Chicago attraction passes mean you don’t have to pick favorites either, as both the Field Museum and Griffin Museum of Science and Industry are included, alongside other Chicago must-sees like the Skydeck, Navy Pier Ferris wheel, Children’s Museum, and Shedd Aquarium. Find out more and choose your perfect Chicago attraction pass here. Museum of Science and Industry Highlights Must-see highlights of the permanent collection at the MSI include: The Pioneer Zephyr: the world’s first streamlined, stainless steel, diesel-powered train; a gleaming vision of the future of rail travel from way back in 1934. The Henry Crown Space Center: here’s where you’ll find all things intergalactic, including the Apollo 8 spacecraft, a lunar module, and Chicago’s largest immersive domed movie theater. Wartime wonders: fans of militaria can ogle the captured German submarine; there are also several US Navy warship models and fighter jet simulators. Science Storms: physics and chemistry collide in this fascinating multi-level exhibit, which features a Tesla coil, a tsunami tank, and Foucault’s pendulum. You’ll also get the chance to control a 40-foot-tall tornado. Coal Mine: ride the train through this full-scale mine replica, containing original 1930s equipment. Field Museum Highlights Don’t miss these wow permanent exhibits at the Field Museum: Animal Halls. The Field Museum is home to some of the most realistic animal dioramas on the planet. Case in point: Carl Akeley’s ‘Four Seasons’, depicting wild white-tailed deer across the seasons, is a veritable work of art. Also don’t miss: the fearsome man-eating lions of Tsavo and the polar bear protecting her cubs. Inside Ancient Egypt. Decipher 5,000-year-old hieroglyphs, worship at the shrine of the cat goddess Bastet and come face to face with ancient mummified people and animals inside an authentic Egyptian burial chamber. Roarsome Dinosaurs. Grab the selfie of a lifetime with Sue, one of the most complete T-Rex skeletons on the planet, and meet her plant-eating pal Máximo, an absolute monster at 122 feet long and 28 feet tall! A dino-mic duo indeed. Save on Attractions, Tours and Activities in Chicago Save money on Chicago attractions, tours and activities with a pass from Go City. Check out @GoCity on Instagram for the latest top tips and attraction info.
Stuart Bak
Stuart Bak

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