15 EPIC Things to do in Chicago [2019 • Insider Guide!]

Last Updated on

15 EPIC Things to do in Chicago [2019 • Insider Guide!]

sWith world-class museums, Michelin star restaurants, award-winning theatre shows, and some epic skyline views, Chicago is one of those places that truly has it all.

But too much can actually be too much. With a seemingly endless list of exciting things to do in Chicago that are all just as amazing as the next, how do you choose?

Well, we’ve done our research. This handy behind-the-scenes guide written by our team of experts will let you in on Chicago’s best-kept secrets. We’ll reveal the very best things to do in Chicago whether you’re going solo or with friends, family or your significant other.

From fun and romance, to free and family-friendly, here are some unique experiences you can look forward to when you visit Chicago…

Quick Answer – Best things to do in Chicago

Fun Things to Do in Chicago

Whether you’re a first time visitor or a seasoned traveller, you’ll always find new and fun things to do in Chicago. Need a few ideas? Here are our suggestions: 

#1 – Biking, Bites and Brews

Biking, Bites and Brews 

The most rewarding end to a day of exercise is some well-earned food, and a bike tour of Chicago combines the best of both. Cycle through the city’s lively streets with perfectly timed breaks along the way to sample some of the city’s famous cuisine, from deep-dish pizza to flavour-filled Chicago-style cupcakes.

Learn how to make hot dogs the local way and refresh yourself with three samples of traditional craft beer – exercise has never been so easy!

But it’s not just the local food that makes biking such a fun thing to do in Chicago. You’ll also pass famous city landmarks, such as the Wrigley Field stadium and Lincoln Park, and explore the upmarket Gold Coast neighbourhood with a local guide to tell you all about it.

#2 – Crime and Gangster Tour

Crime and Gangster Tour

Chicago has a peculiar and rather sordid history filled with mobsters and gangsters from Al Capone to ‘the Untouchables’. And you’ll have a chance to delve into the dark secrets of Chicago’s criminal underworld on this exciting 90-minute tour!

Escape the Windy City’s unpredictable weather on a climate-controlled bus. Along the way, you’ll enjoy drive-by views of some famous city landmarks, such as the Chicago Criminal Courthouse where some of history’s most notorious cases were tried.

And if you appreciate architecture, you’ll be in your element witnessing the contrasting buildings in Chicago’s River North, Gold Coast, Old Town, and Magnificent Mile as you pass them by.

It’s the perfect way to explore the scenes of some of Chicago’s most infamous crimes – fortunately, many years after the fact – including the Holy Name Cathedral, Clark Street Bridge, the Biograph Theatre, and the site of St. Valentine’s Day massacre.

#3 – Visit a Secret Bar

Visit a Secret Bar, (Photo Credit-boingboing.net)

Photo credit – Boingboing.net

Chicago’s speakeasy bars are built for romance for those in the know. And the best part about these bars is that not everybody knows about them which – you guessed it – means fewer crowds!

The city is teeming with secret bars hidden in unusual places with secret entrances you can walk past time and again unless you know exactly where to find them. While Chicago’s speakeasies don’t quite offer a just-for-two experience, they’re definitely close enough.

Head to the Ladies Room tucked away in the back of a bakery, Chicago Magic Lounge found within a Laundromat or Violet Hour which can be found by locating the secret door handle on the wall mural on Damen Avenue.

Romantic Things to Do in Chicago

With extraordinary skyline sunsets, it’s as though Chicago was built for starry-eyed couples. If you’re planning a treat and you need some ideas, here are the most romantic things to do in Chicago: 

#4 – Watch the Sunset from the Chicago Observation Deck

Watch the Sunset from the Chicago Observation Deck

What’s more romantic than watching the sunset 94 stories above the city? We can’t tell you!

From the top of the Chicago Observation Deck, you’ll enjoy sensational 360-degree views across the towering skyscrapers of Chicago, four neighbouring states and the waters of Lake Michigan. Don’t miss the chance to stop for a drink at Bar 94, the highest bar in Chicago. It’s the perfect way to see the sights and city lights of Chicago at night!

And, because we know waiting in queues tends to take the romance out of the situation, your ticket allows you to skip the queues. Don’t forget that while you’re here, in the heart of Chicago, you’re perfectly placed to enjoy a meal and a glass of wine along Magnificent Mile, one of Chicago’s premier dining districts. Bliss!

#5 – Soak in the Aire Ancient Baths

Soak in the Aire Ancient Baths,

Photo credit – Michiganavemag.com

Embark on a sensory couples’ spa journey at Chicago’s Aire Ancient Baths.

With a focus on bath rituals and techniques from the Roman, Greek and Ottoman empires, this romantic thermal experience includes a choice of six thermal baths, including a hot bath, ice bath, and a saltwater floatarium.

Submerging yourself in each thermal bath offers its own unique health benefits, from increasing your blood circulation to getting your heart rate pumping.

If you’re feeling especially romantic, you can sign up for the ‘Red Wine Bath Experience for Two’ which also includes a dip in a wine bath made from Spanish Ribera del Duero red grapes, followed by a one-hour massage with grape seed oil. And a facial to boot. Don’t knock it ‘til you’ve tried it! 

#6 – Star-gazing at the Adler Planetarium

Star-gazing at the Adler Planetarium,

Photo credit – Adlerplanetarium.org

Okay, so visiting a planetarium might not sound like your ideal date night, but spending an evening at the Adler Planetarium is actually one of the most romantic things to do in Chicago.

Located on the edge of the Museum Campus peninsula, it has arguably the most incredible views of the city skyline. In fact, many couples get their engagement and wedding photos taken here. Who knew?

But it’s not just the exterior of the Adler that attracts Chicago couples but also the interior with its astonishing opportunities for star-gazing. The planetarium hosts a monthly Adler After Dark series where you can learn fascinating facts about the night’s sky, along with some complimentary wine and beer. We’re sold!

Best Things to Do in Chicago with Kids

Chicago is effortlessly family-friendly with a plethora of activities and attractions to keep kids of all ages busy. Here are the best things to do in Chicago with kids:

#7 – Ride the Centennial Wheel

Ride the Centennial Wheel

Wow the kids with sky-high views of the Windy City safely inside the climate-controlled Centennial Wheel. Towering almost 200 feet above the Navy Pier, you’ll have 360-degree views of Chicago and Lake Michigan. As the experience is just 15 minutes, it’s the perfect way to keep the kids entertained, even those who bore easily.

As the wheel revolves three times you’ll get to focus your attention on different parts of the city, including downtown Chicago, the Navy Pier, Chicago River, and Lake Michigan. Plus, you’ll skip all the queues with the Fastpass Express Ticket option – perfect for families!

With cubicles that are cooled in summer and heated in winter, this is one of the best things to do in Chicago with kids all year round.

#8 – Chicago Children’s Theatre

Chicago Children’s Theatre,

Photo credit – thorntontomasetti.com

In a city that’s known for its theatre, it’s only fitting that they’d cater for little ones too.

The Chicago Children’s Theatre is the largest of its kind in the city with a reputation for immersive theatre that all kids, even those with autism, vision or hearing difficulties and Down syndrome can enjoy. Not only does the theatre put on shows tailored to children, but it also has some impressive four-dimensional sets and life-sized puppets that the entire family can appreciate.

The theatre has been busy over the last decade with 17 world premieres such as A Snowy Day with Beatrix Potter, The Houdini Box, and Mr. Chickee’s Funny Money.

Watching a show is also a great way to support the local community. Your entry fees help the company in their goal to provide free tickets to over 5,000 low-income students in the Chicago area each season.

#9 – Movies in the Park

Movies in the Park

Not much beats an outdoor movie night – especially if it’s free! The ‘Movies in the Parks’ program has over 200 movie screenings planned throughout Chicago’s neighbourhood parks every summer.

Whether you’re into Hollywood blockbusters or family classics, you’re sure to find a movie you like. Popular past favourites have included Home Alone and Jumanji. Screenings usually start around 8.30pm in the evenings when the skies start to darken. Take a look at the MyChi Parks app for the latest line-up.

If this sounds like a bit of you, you may also want to check out the Millennium Park film series held at the Jay Pritzker Pavilion between July and August. The 2019 summer line-up includes 10 Things I Hate About You, Pan’s Labyrinth, and the Muppet Movie screened on a 40-foot LED screen.

Things to Do in Chicago at Night

The fun doesn’t stop when the sun goes down. There’s so much to keep you busy 24 hours a day in the Windy City, from bedazzling theatre shows to Michelin star dining. Here are our favourite things to do in Chicago at night:

#10 – Stroll the Magnificent Mile

Stroll the Magnificent Mile

Photo Credit – Choosechicago.com

As Chicago’s alternative to Paris’ glamorous Champs Elysees, the Magnificent Mile is simply astonishing when it’s lit up at night. Stroll hand in hand down this impressive avenue that meanders 13 blocks from Oak Street in the north to the glittering banks of the Chicago River in the south.

There are all sorts of activities and entertainment to stop and marvel at along the way, whether you’re looking for a romantic spot to have dinner or the best bar in Chicago for live music and dancing.

Those couples looking for some late-night retail therapy are in luck. The Magnificent Mile is the best spot for it as most shops only close around 9pm.

 

Recommended Reading – The 5 Best Neighborhoods in Chicago, Illinois (for all budgets!).

#11 – Secret Food Tour

Secret Food Tour 

From epic Chicago-style food to Michelin star cuisine, Chicago is a foodie’s paradise. Dig into deep-dish pizza, Chicago-style hot dogs, finger-licking good donuts, and Italian beef sandwiches (it may not sound like it, but these bad boys actually did originate in Chicago all the way back in the 1930s).

If you’re looking to treat yourself then Michelin star dining in Chicago is not to be missed! There are as many as 25 Michelin star restaurants to choose from here, an impressive list that includes Band of Bohemia, the only Michelin star brewpub in the world!

For something different and a decent mix of the above, why not book a secret food tour of Chicago and test out all the cuisine this city is so famous for? But shhh! Keep the destinations a secret!

 

Looking for a great deal on a hotel? Read our guide to the best hotels in Chicago (no matter your budget!)!

#12 – Watch a Theatre Show

Watch a Theatre Show 

You simply cannot plan a trip to Chicago without dedicating an evening to the theatre. The city is teeming in talent, and theatre productions vary from famous Blockbuster shows and award-winning comedy to Broadway that will knock your socks off.

The Blue Man Group is a mixture of Chicago’s best with an amazing cast and more than a touch of comedy. But one thing is for certain: you need to grab these exclusive tickets in advance! Dubbed “brilliantly revamped” by the Chicago Tribune, it’s a well-loved show that’s often sold out.

Luckily, if you book your Blue Man Group Chicago tickets early, you’ll get your tickets to this four-star production at a price that’s seriously hard to turn down!

Free Things to Do in Chicago

Not everything in Chicago involves taking out your wallet. There are plenty of free things to do in Chicago, from picturesque walks, to complimentary activities and events pretty much every day in the summer months. Here are our tips: 

#13 – Stroll the Chicago Botanic Garden

Stroll the Chicago Botanic Garden

Photo credit – chicagobotanic.org

The Botanic Garden is one of the top free things to do in Chicago. The only thing you have to pay for is parking so find an alternative way to get there – walk, bus, or cycle – and the experience will be completely free of charge!

The 385 acres of scenery is a great way to escape the concrete jungle and enjoy a day out in nature. And with 2.5 million plants of 10,000 species in 25 natural gardens as well as some record-breaking bird sightings, you’ll have plenty to keep you busy! Pick up a free map from the walking centre and explore to your heart’s content!

While there are two restaurants available, if you want to save more money, there’s a picnic area where you can relax and enjoy your own packed lunch.

 

MUST READ – Heading to Chicago next? Check out our post about some of the most fun day trips from Chicago!

#14 – Free Guided Walking Tours with a Local

Free Guided Walking Tours with a Local

Chicago locals love their city and they’re more than happy to show you around their much-loved local hangouts in 25 neighbourhoods around Chicago. The Chicago Greeter program connects new travellers with a local-living volunteer who takes you on a free guided walk of the city.

Each tour is completely tailored to suit you with two to four-hour tours covering everything from history, to culture, architecture, and hidden gems. Perfect for first-time visitors and solo travellers, it’s a great way to explore the city with a new friend.

Not sure what you want to do? You can also sign up for a Greeter’s Choice tour where your greeter shows you their personal favourite things to do in Chicago. There are family-friendly and LGBT-friendly tours available, and all tours include a free bus and train transit pass.

#15 – Free Activities in Millennium Park

Free Activities in Millennium Park,

Photo credit – choosechicago.com

Strolling through Millennium Park is pretty much a rite of passage in Chicago – you can’t not do it.

Covering just 24.5 acres, it’s actually quite small but within its borders you’ll find an impressive array of sculptures, including Cloud Gate (known as  ‘the Bean’ the locals), the Crown Fountain, and the central Millennium Park Monument.

Discover ‘a city within a garden’ at the Lurie Gardens or simply show up and take part in the wide variety of park activities and events available free of charge.  In the summer months, there are free concerts, movie screenings and exercise classes held in the park, while in winter you can enjoy free ice skating – a tradition that’s been celebrated for nearly two decades!

Free ice skating lessons are available an hour before the ice rink officially opens on Fridays, Saturdays and Sundays, as well as during Chicago Public School’s winter holidays. 

That’s it!

Chicago is a city for explorers and adventurers and we hope you’ll enjoy uncovering the best things to do in Chicago in our handy insider guide.

From bike tours to botanical gardens, fantastic food to family fun, the city is yours to explore! And while each and every activity and attraction has something unique to offer, we think a Crime and gangster tour is the best thing to do in Chicago if you’re looking to uncover the city’s sordid history.

But whatever you do, whether you’re travelling with friends, going solo or looking for something to do with the kids, you’re promised a bucket-list topping adventure in the Windy City.

What are you waiting for? It’s time to discover Chicago!

*** Some of the links on Hotel Jules are affiliate links, which means if you do make a purchase, we may make a small commission (at no extra cost to you.) Thank you for using our links! Your support keeps the site going***

About the Author Aaron Hovanesian

Born in Los Angeles, Aaron Hovanesian is one of the original staff writers for Hotel Jules. Having backpacked the world as a young man, Aaron now prefers to travel the world in luxury, proudly staying in the world's most amazing hotels and properties. When Aaron is not traveling he lives in Western Colorado he can be found brewing his own beer (probably an IPA) or spending time with his two amazing golden retrievers.