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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How to spend 5 days in Chicago

You’ve done the sensible thing and decided to spend 5 days in Chicago. Fantastic! The US ‘second city’ has a range of attractions that many other destinations simply can’t compete against – from magnificent art galleries to lake shore beaches. With a 5 day Chicago itinerary you’ll have the time you need to take in the city’s atmosphere alongside its landmark buildings. You’ll also be able to enjoy some of the city’s more off-beat things to see and do. For a round up of all that’s going on in Chicago, check out our favorite way of spending 5 days in the city. Day 1 – Downtown Chicago With your first hours in Chicago, it’s a good idea to get to grips with the downtown area – otherwise known as the Loop. The location of many of the city’s major landmarks, you’ll be spending much of your time here so it makes sense to get a feel of what’s located where. Whilst one of the most walkable cities in North America, you’re not going to want to wear out your shoe leather on day 1. Nor are you going to want to tackle Chicago’s public transportation, so instead head to one of the dozen stops included on the city’s Hop-on Hop-off sightseeing bus. The whole circular tour lasts for two hours and is accompanied by an audio narration providing a perfect introduction to the city. However, it’s unlikely you’re going to be able to avoid jumping off at a couple of points of interest. North Michigan Avenue – better known as the Magnificent Mile – is one of the city’s top places to be, blending suited office workers with luxury brands, much-loved restaurants, historic landmarks such as the Old Water Tower and views from 1000 feet up from the floor-to-ceiling windows of 360 CHICAGO in the John Hancock Center. Showing all that Chicago has to offer, it’s just a short stroll to the Museum of Contemporary Art – turn off on either East Pearson Street or East Chicago Avenue to get there for an afternoon amongst the greats of twentieth century art. Day 2 – Lake Michigan You will have already seen its vast expanse from 360 CHICAGO, but day 2 gives you the chance to explore the Lake Michigan shoreline. Start to the north of the Loop in Lincoln Park for views of western lowland gorillas and kangaroos at Lincoln Park Zoo. Then soak up the sun on North Avenue Beach (weather permitting). If you can tear yourself away from the beautiful setting, keep the shoreline to your left as you wander south back into the Loop by way of the upmarket Gold Coast neighborhood. On reaching Navy Pier, there are further options for taking in the Chicago skyline, by slipping into one of the gondolas of Centennial Wheel, which rise to a height of almost 200 feet. Swap gondolas and sidewalks for the lakeshore cycle track by picking up a bike at the pier’s Bike and Roll rentals. Ease yourself into the saddle by making the short journey to Chicago’s Museum Campus, incorporating the Field Museum, Shedd Aquarium and Adler Planetarium, either one of which will round off the afternoon hours with aplomb. Day 3 – Chicago from the water You’ve taken it in from high up and cycled along it, so there’s nothing more to do than get onto the water and explore Chicago from another angle, especially if your visit to the Shedd Aquarium gave you a feel for life in and on the waves yesterday. Unveiling hidden gems amongst the world-famous landmarks, taking a cruise along the three branches of the Chicago River is like slipping through the city’s two centuries of history. Its shift in architectural styles reveals itself as you cruise the calm blue waters beneath bridges and past structures including the giant art deco Merchandise Mart building and Willis Tower – for many years the tallest building in the world. Follow the river to its natural conclusion and you’ll find yourself floating on Lake Michigan. A Skyline Lake Tour does a similar job to river cruises, but arguably on an even greater scale. Departing from Navy Pier, tours take in the lakeshore forming the natural eastern boundary of the Loop, with commentary providing interesting tidbits of information, such as the fact Batman’s Gotham City is based on the skyscrapers of Chicago. But for an extra-special tour on the water don’t miss your chance to board Windy, Chicago’s official tall ship. With its sails filled with the wind the city is famous for, you’ll tack across Lake Michigan in a fashion almost entirely unchanged since the birth of steam. Day 4 – Chicago culture and more Keep up the pace of your Chicago in 5 days trip by starting day 4 with a few hours in another of the city’s top museums – the Museum of Science and Industry. A great choice for all the family, there are plenty of interactive exhibits, alongside flight simulators, important landmarks in transport and a gallery of exquisite model ships – should your trip aboard the Windy have gotten you hooked on all things nautical. Continue your exploration of Chicago’s culture by seeing a show. The Second City theater is well-known in comedy circles as the place to head for improv and the chance to catch the next big thing before the rest of the world. The Chicago Theater has a busy schedule of plays and pop concerts. Failing that, it’s also possible to head behind the scenes with a Chicago Theater Marquee Tour. Then enjoy a bite to eat. AT&T Plaza beneath the Cloud Gate sculpture in Millennium Park is home to an open-air restaurant during the warmer months of the year – replaced by one of the city’s top skating destinations during the winter. Day 5 – Get active End your 5 days in Chicago by mixing up the museum visits and river tours with some physical activity. Maggie Daley Park – immediately east of Millennium Park – has plenty of ways to do this, from free climbing walls and tennis courts to a skating ribbon from November to March. If you need a breather, there are shady groves for picnics in the sun, alongside one of the finest children’s playgrounds we’ve seen rising high above it all. One of Major League Baseball’s oldest arenas, Wrigley Field is a must-see for sports fans. Home of the Chicago Cubs, there’s no better way to understand the city psyche than attending a game. Alternatives include basketball from the Chicago Bulls and ice hockey from the Blackhawks both at the United Center. Save on admission in Chicago Sounds expensive? 5 days in Chicago doesn’t have to be! Go City lets you enter many of Chicago’s top attractions and landmarks with incredible savings versus advertised prices. It means you can do much more on your trip to Chicago than you thought you could without having to worry about your bank balance once!
Ian Packham
Navy Pier and Centennial Wheel in Chicago
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Navy Pier thrills: Centennial Ferris Wheel vs Flyover in Chicago

One lifts you above Lake Michigan, the other sweeps you over it; we compare vibes, energy, food spots and more near these Navy Pier favorites.
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Things to do in Chicago for Christmas

Christkindlmarkets, snow-covered streets and stunning seasonal light displays means we’ve probably already successfully answered the question ‘should I visit Chicago in December?’. Filled to brimming with festive fun and events unique to the most wonderful time of year, Christmas in Chicago is a period that will bring a smile to the faces of all but the grinchiest of grinches. Looking for things to do in Chicago at Christmas? Look no further than this round up of the very best! What to expect from Christmas in Chicago Part of what makes the city such a fantastic December destination is Chicago’s Christmas weather. Snowy and cold, it’s exactly what many of us want – and expect – from the festive season. Daytime temperatures aren’t all that different to what Santa’s elves will be used to at his North Pole workshop, with highs of 35°F. They regularly drop below freezing by night to averages of 23°F. Clearly, you’re going to want to ensure you’ve packed your woolens. On the plus side, December is the second-driest month of the Chicago year, with just a couple of inches of rain – and up to eight inches of snow. Skies are largely clear, making days sunny and crisp. Another part of what makes Christmas in Chicago so special is the city’s collection of long-held seasonal traditions, discussed in more detail below. Brighten the winter nights with Chicago’s seasonal lights You don’t have to look far in central Chicago to get your fill of Christmas lights once the sun has set over the shores of Lake Michigan. In addition to its Endangered Species Carousel and Lionel Train Adventure rides, Lincoln Park Zoo sparkles with over 2.5 million bulbs, incorporating several scenes that move to music. Head south from the zoo and you’ll soon end up on the Magnificent (or Mag) Mile, which is a blaze of lights adorned to its trees from an impressive switch on festival in the last week of November right through until New Year. Millennium Park in the Loop – part of Downtown Chicago – has been the location of the city’s official Christmas tree since 2015, although the tradition goes back more than 100 years. However, it has to compete for attention with the avant-garde lighting installations that appear at Chicago Botanic Garden at about the same time. The nearby Daley Plaza hosts a Menorah lighting at the start of December – complete with donuts – for anyone celebrating Hanukkah. Grab your chance to do some last minute shopping Daley Plaza is also one of Chicago’s top seasonal shopping locations since it’s home to the city’s German-style Christkindlmarket. Visitors are free to peruse the selection of local sellers, whose stalls are packed with decorations, clothing accessories and their fair share of sweet treats and mulled wine – rather than the Chicago-style pizza you might plumb for at other times of year. The Bridgeport Art Center’s Renegade Craft Fair is another bastion of independent sellers, with around 250 displaying their wares, which range from bespoke pieces of jewelry to stylish household items sure to add a little je ne sais quoi to your abode. Keep your ear to the ground from the end of November, and it’s more than likely you’ll also hear word of the large number of pop-up one day or weekend markets taking place in and around attractions right across the city. Don’t forget about the city’s all-year shopping options in all the excitement of the season. If just one destination is worth mentioning it’s the Magnificent Mile, defined as Michigan Avenue between Oak Street and Michigan Avenue Bridge. Whatever your budget, you’ll find something to suit here, from well-known department stores to luxury brands Burberry and Tiffany & Co. There’s also a branch of Macy’s at Water Tower Place, although many prefer the holiday windows of the historic Macy’s store on State Street. Show off your skills on the ice The start of winter sees a number of free ice rinks appear in the city, including not one but two within proximity to Millennium Park. The first is the McCormick Tribune ice rink nestled beside the steamy windows of the Park Grill restaurant and the stainless-steel Anish Kapoor sculpture known as ‘the bean’ but officially called Cloud Gate at the heart of AT&T Plaza. The second is Maggie Daley Park Skating Ribbon next door. A sort of wide skating track, it winds its way through the park with its backdrop of downtown skyscrapers, past snowy pine trees and outdoor climbing walls awaiting the warmer weather. But if ‘the bean’ has you yearning to discover more of the city’s art, look no further than the Museum of Contemporary Art, whose permanent collection includes around 2,500 individual works by twentieth century greats including Andy Warhol and Jasper Johns. Take in the exhibitions and shows Many of the city’s other museums also get into the holiday spirit. The Museum of Science and Industry – whose rather staid name is contrasted by the hands-on modern attractions within – hosts their annual Christmas Around the World exhibition, which now also includes the winter celebrations of non-Christian cultures from Diwali’s birthplace of India to China’s Spring Festival commemorations. Christmas shows in Chicago are also a big part of the scene in December in the city. One of the biggest hubs for theater in the US outside of New York’s Broadway, companies big and small go all out to wow their audiences, whether that’s through Christmas classics such as performances of A Christmas Carol or the Nutcracker, or newly written plays that will tug at the heartstrings. If people watching is more your thing, and the wintry streets don’t provide the opportunity, you could do far worse than head to nightspots of North Clark Street such as Simon’s Tavern. Often voted as the city’s best bar, it has been serving up tots of its signature glogg (mulled wine) for nine decades. Save on Christmas in Chicago When it comes to winter wonderlands, the US doesn’t get much better than Christmas in Chicago. And when it comes to making the most of your time – and budget – in the city, things don’t get better than Go City. Offering up great discounts on many of the city’s top attractions even over the festive season, travel with Go City and you can save big on entry to attractions you were planning to visit anyway. Now that’s a Christmas gift everyone would surely love to receive!
Ian Packham

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