Visiting Chicago? 6 Things to do in the Windy City

Visiting Chicago? 6 Things to do in the Windy City

Visiting Chicago? 6 Things to do in the Windy City
24th June 2021

Filled with iconic buildings, incredible corporate spaces, and boasting a booming business climate, there are many reasons to visit Chicago - whether travelling for business or leisure. When it comes to the list of things to do in Chicago the choice is endless, but we’ve done the leg-work for you and selected six activities perfect for filling your free time when visiting Chicago on business.

1. Explore Navy Pier

Navy Pier Chicago
With attractions for all the family, Navy Pier is a popular destination for tourists and locals alike

Stretching 3,300 feet across Lake Michigan, Navy Pier is a monumental structure providing over 50 acres of attractions and amenities. Famed for its 196 foot Ferris wheel, the pier has many rides for all ages to enjoy, but is also home to numerous bars and restaurants with spectacular views across the water. The pier can also be explored by Segway for the more adventurous visitor, and is a superb setting for New Year’s Eve as spectacular firework shows dominate the skyline. For those looking to explore Lake Michigan, the pier is also a good point from which to embark on a sightseeing cruise, such as the impressive Tall Ship Cruise which runs day and night across the majestic waterfront.

2. Wander around Grant Park

Buckingham Fountain things to do in Chicago Grant Park
Buckingham Fountain in Grant Park provides a stunning backdrop for photographs of your stay

With over 300 acres of green space to explore, Grant Park is well worth a visit (or several) during your stay in the windy city. Being located in the central business district, the park is ideal for lunch breaks and after-work strolls when visiting Chicago on business. Affectionately known as ‘Chicago’s front yard’, Grant Park was named after President Ulysses S. Grant whose success as Commanding General in the Civil War won him much popularity both in Chicago and across the United States. The park’s most famous feature is perhaps Buckingham Fountain, pictured, which was inspired by a similar fountain at the Palace of Versailles. A perfect spot for a photo to commemorate your trip.

3. Walk the Bloomingdale Trail

Chicago street walk
While walking the streets of Chicago has its charms, the Bloomingdale Trail offers a more relaxed experience

In our blog detailing the best outdoor spaces in New York, we mentioned the High Line walk – converted from an old freight line. Not to be outdone, Chicago has its own converted walkway in the form of the Bloomingdale Trail. Originally a rail line constructed in 1873, the three mile route provides a stunning walkway frequented by cyclists, runners and dogwalkers. Offering a different perspective on the city, the trail is a great way to stretch your legs and take in the surrounding scenery – certainly one of the most relaxing things to do in Chicago during your stay.

4. Take in the views at the 360 Chicago Observation Deck

observation deck skyscrapers things to do in Chicago
The 360 Chicago Observation deck towers above the city affording stunning views in all directions

Another way to experience the majesty of Chicago’s cityscapes is, of course, from above. The 360 Chicago Observation Deck can be found on the 94th floor of the John Hancock Center, 1,000 feet above the city streets - providing sublime, uninterrupted views of the city scape and beyond. For those seeking adventurous things to do in Chicago, the deck also features ‘Tilt’, a ride that allows visitors to ‘lean’ out over the city streets and peer through reinforced glass! Not for the faint-of-heart, the deck also features a well-stocked bar - Bar 94 - so you can calm your nerves after your heart-stopping ride.

5. Enjoy a show at The Chicago Theatre

visiting Chicago The Chicago Theatre
The iconic Chicago Theatre is a must-visit during any trip to the city

Built in 1921 as a flagship Balaban and Katz movie theatre, The Chicago Theatre is today one of Chicago’s most recognisable buildings. These days, the building is used exclusively as a performing arts venue for plays, comedy shows, music concerts and sporting events. Having closed down in 1985, the theatre reopened in 1986 with a performance by none other than Frank Sinatra. Other famous figures to have performed in the venue include Liza Minnelli, Bob Hope and Steve Lawrence. Whether you intend to see a show when visiting Chicago or not, a trip to the theatre to see the incredible architecture alone is a must.

6. Hit the Jazz Joints

Jazz players Chicago
Jazz and Chicago go hand in hand

Chicago is famed for its jazz heritage, with the music genre still playing a major part of the city’s culture and nightlife. A trip to the city wouldn’t be complete without visiting some of its most famous jazz clubs and soaking up the atmosphere. The Green Mill was once frequented by the likes of Al Capone, but since the 1980s it’s been home to some of the best jazz players in the circuit. A more low-key venue which favours progressive, avant-garde jazz performances is Constellation - perfect if you take your jazz seriously. If an impressive cocktail menu is your idea of a good time, head to California Clipper – a wildly popular cocktail specialist bar with supporting performances by some of the city’s leading jazz troupes.

There are many more things to do in Chicago beyond our top six suggestions – so don’t put off your business trip to the city any longer. Browse our selection of serviced apartments in Chicago or read about some of our favourite corporate housing options from our portfolio.


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When it comes to power house cities for fashion there are only a...

What is Leeds Famous for? 11 Fascinating Facts about Leeds

There’s more facts about Leeds than the average person knows about,...

A Guide for Your First Business Trip to Tokyo

A city notorious for its towering buildings, teeming streets and...

Wining and Dining in Paris – Our Top 4 Restaurants in Paris

Internationally renowned for their prowess on the fashion scene, the...

Sights in Tokyo - The Top 7 Must See Places in Tokyo

The capital of Japan is truly a marvel, mixing both the technological...

The 6 Best Conference Venues in Leeds

The largest city in West Yorkshire, Leeds has one of the most diverse...

One Day in Hong Kong: 8 Top Things to See & Do

Boasting the world’s 35th largest economy, low taxation and a strong...

Hong Kong Cuisine – What to Expect on Your Business Trip to Hong Kong

Due to the region’s long history of being an international port of...

12 Surprising Facts You Probably Never Knew About Zurich, Switzerland

The picturesque city of Zurich is renowned for being the financial...

The Surprising Stories behind New York’s Most Famous Buildings

New York’s iconic skyline is known the world over, emblematic of...

Relocating to Zurich: Why Zurich is One of the Best Cities to Live in the World

Be it the city’s fascinating Roman history, breath-taking...

Manchester's Universities and their Impact on Business in the City

Manchester: birth place of the computer, industrial revolution and...

23 Fascinating Facts About Hong Kong That Might Surprise You

Hong Kong is a unique, cosmopolitan region which fuses together...

Is Zurich a Boring City? 8 Reasons We Think Not

Upon discovering that the city is consistently voted as one of the...

After work drinks? The five best beer gardens in Manchester

The return of the pub - beer garden style. With the easing of...

Our Favourite Restaurants in New York for a Corporate Dinner

The sheer number of New York restaurants at the disposal of corporate...

The 5 Best Outdoor Spaces in New York

The Big Apple, global hub of business and commerce and home to Wall...

The Best Beaches in Sydney to Enjoy in your Free Time

Australia is revered for its thousands of miles of golden coastlines....

Best Outdoor Spaces London has to offer in spring

After a colder, darker, and – let’s face it - bleaker winter than...

Business Trip to Dubai? 5 Things you need to know

Upcoming business trip to Dubai? This is the desert city where...

Singapore Cuisine: Your One Stop Business Travel Guide

The delectable delights on offer in the restaurants and food stalls...

Things to do in Munich: Christmas Markets and More

As we have previously established, there is much to do in Munich when...

What to do in Munich, Germany on Business

The third largest city in Germany, Munich also boasts the strongest...

Edinburgh Conference Centre and More Top Business Venues

Edinburgh continues to be considered as one of the top corporate...

The Happiest Place to Live in the Capital: Richmond Upon Thames

Richmond upon Thames is an area with a lot to shout about, being...

Corporate Housing: The Growth in Demand in the USA

In many ways, the term ‘corporate housing’ is interchangeable with...

The Best Canary Wharf Restaurants for London Business Travellers

Staying in Canary Wharf on business and in need of a venue to take...

Things to do in Edinburgh at Night on Business

With signs of civilisation dating back to 8500 BC, Edinburgh is...

Australian words and phrases: visit Sydney with confidence

Sydney is a city so brimming with vitality and energy that many regard...

Living in Canary Wharf: The Bonuses and Benefits

Comparing those working in Canary Wharf and those living in Canary...

The Growth of Richmond Business: A Corporate Destination

Within Richmond, business has prospered in recent years, enabling the...

Why Business in Copenhagen makes it an Important European City

Often described as the gateway to Scandinavia, Copenhagen has long...

10 facts about Copenhagen, Denmark you probably didn't know

Copenhagen is a city defined by its vibrancy, energy and...

Top Ten Things to do in Berlin on your Business Trip

One of the most historically and culturally significant cities on the...

Berlin Film Locations: A Love Affair with Cinema

Berlin is a city filled with iconic landmarks and idiosyncratic...

What to do in Copenhagen at night: rollercoasters, opera and more

When on a business trip to Copenhagen, we know you’ll have a busy...

Relocating to Berlin - SilverDoor's Top 5 Useful Tips

Relocating to Berlin is becoming an increasingly popular option for...

Insider's Guide to Berlin for Successful Business Travel

Berlin is a key travel destination in Europe, and in fact, tourism in...

A fascinating whistle-stop tour of historic Sydney

Today, Sydney is Australia’s largest and most populous city: an...

Singapore relaxes travel entry restrictions

SilverDoor welcomes the news this week that some entry restrictions...

The Most Amazing Serviced Apartments Berlin has to offer

Berlin is an economic power-house, not only within Germany but in...

14 Fascinating Things You Didn’t Know About Belfast

A city full of character, wit and charm, Belfast is widely becoming...

20 Things You Didn't Know About Chicago

The third-largest city in the US, Chicago represents a key national...

5 reasons Seoul is a key business destination

Becoming the world’s fourth-largest metropolitan economy in 2014,...

The Ultimate Guide to Melbourne's Neighbourhoods

Many who are visiting Melbourne for the first time find the prospect...

Business trip to San Francisco Bay? 6 tips you need to know

San Francisco has an international appeal to business travellers and...

The best after-work hangout spots in Amsterdam: bars, clubs, restaurants

When on a business trip to Amsterdam, your time does not have to be...

The Top 16 Things to Do In San Francisco Bay When on A Business Trip

When travelling on business to San Francisco it’s important to break...

7 Tips you need to know when travelling to Melbourne on business

With the number of professionals travelling to Melbourne on business...

Relocating to Amsterdam? 6 Things you need to know

Relocating to Amsterdam is a popular option for many businesses,...

The Top 7 Restaurants in Amsterdam for a Successful Business Lunch

Coming towards the end of another decade, globalisation has further...

Why is San Francisco a great city to live in and for business?

San Francisco is home to remarkable views of the world’s greatest...

Europe's Greenest City: The Top 5 Reasons Why Amsterdam is an Eco Capital

With cycling being the city’s main form of transportation, it’s no...

Why is business booming in Liverpool?

The significant rise of business opportunities in Liverpool has been a...

The great Australian debate: is Melbourne better than Sydney?

It’s a debate that has never truly been settled – which Australian...

The top 21 things to do in Boston when travelling on business

Boston, Massachusetts is a pioneering city in the US and is known as a...

What You Need to Know When Relocating to London After Brexit

By Francis Buchanan With the UK’s new Brexit deadline edging ever...

The 7 Best corporate serviced apartments in Liverpool

Liverpool is host to a constant stream of visitors throughout the...

Where to stay in London? The Top 5 Trending London Districts for Serviced Accommodation

Since its earliest development, London has been integral to...

22 Things to do in Sydney, Australia: for free, at night, on the wild side and more

Easily identifiable due to its distinctive Opera House and Harbour...

Capitalising on Brexit: The Rise of Frankfurt’s Financial Sector

By Francis Buchanan In light of Britain’s Brexit saga, a number of...

The 8 Best Restaurants in Aberdeen

Widely known as Scotland’s industrial powerhouse, Aberdeen is a city...

10 Free Things to do in New York City

The shimmering lights of New York City attract millions of visitors to...

Top 11 Things to Do in Aberdeen

A historic city in northeast Scotland, Aberdeen is a hub of tourism,...

10 Iconic US Cities by Industry

The nature of the industry in America has changed considerably over...

Business Trip To Singapore

SilverDoor in APAC As Singapore is one of the leading financial hubs...

Trips to Take From Singapore

Singapore is known for being one of the most innovative finance hubs...

Why New York is the Most Popular Business Travel Destination

In a study conducted earlier in 2019, New York was named the world’s...

Chinese New Year in Singapore

Chinese New Year 2023 is almost upon us. Also known as Lunar New Year,...

Top New Developments in Manchester

Manchester is a city on the brink of change. As one of the fastest...

A Business Travel Guide to Manchester

Staying in Manchester, England As the birthplace of the Industrial...

Celebrating Christmas in the USA

America is a huge, multi-cultural melting pot of different cultures...

Best Places in London to Celebrate Thanksgiving

Thanksgiving is a huge cause for celebration in America, and, as a...

11 Places That Have The Same Name in Britain and America

The reason behind why so many place names in America are the same as...

The Best Vegetarian and Vegan Restaurants in London

Green-eating is all the rage right now. More people than ever are...

Top International Destinations to Relocate to

We live in a world where people are constantly on the move, shifting...

Revealed: The Best City In The UK To Launch A Start-Up

Going it alone and starting up your own business is no easy feat and...

20 Of The Best Expat Blogs To Follow In 2018

Taking the plunge and becoming an expat can seem like a daunting task,...

Top 12 Singapore Lifestyle Blogs

Singapore is a country best explored on foot, but how are you to know...

Which Cities In The UK Could You Live On Minimum Wage In?

The National Minimum Wage in the UK for over 25s increased to £7.83...

12 Free Things to Do in Singapore

Singapore may be one of the most expensive places to visit, but that...

Top 10 Event Spaces in The City of London

After an event space for a meeting or office bash? Look no further...

Top 6 London Pubs on the River

When the weather's warm and you're feeling thirsty, nothing quite...

Life As An Expat...5 Individuals Share Their Experiences

Moving abroad can be life changing, whether it’s for work, family or...

Lions of London: 6 of the Most Famous Lion Statues In London

Lions are an important part of Britain’s identity. The Barbary lion...

Top 10 Jogging Routes in London

Jogging is an excellent way to keep fit. It’s safe, simple, easy to...

Important Upcoming Projects and Developments in Aberdeen

These are changing times for Aberdeen. The Granite City is right now...

Top Things to Consider When Relocating to London

So, you’re decided to move to London: home of Big Ben, red telephone...

Top Things to do in Edinburgh and Glasgow

Scotland is a country definitely worth visiting. All the wonders of...

The Aberdeen Renaissance: Why Change Is On The Way For Scotland's Granite City

By Anton Constantinou If you thought Aberdeen had lost its place as a...

Top Nine Best Ranked Places in Britain

Make no mistake about it - Britain is a diverse place. Different areas...

Tried and Tested: Amsterdam

We love Amsterdam, so much so that we recently visited the Dutch...

Starting a business in Singapore

So, you’ve decided to start a business in Singapore. What better...

The Evolution Of The Dubai Skyline

In the last 50 years or so, Dubai has undergone a rapid...

An Industry Guide to London

By Anton Constantinou Few cities around the world can compete with...

Best Aparthotels in London’s Most Exclusive Postcodes

Looking for somewhere special to stay in London on your next business...

Top Seven Business Lunch Destinations in London

Not all important business decisions are made in a boardroom. Getting...

24 Things You Shouldn't Do On the London Underground

If you’ve ever been to London, there’s a good chance you’ve...

9 of the Best Motorway Service Stations in the UK

As one of the world's leading serviced apartment providers, we've done...

16 things you didn't know about Milton Keynes

There’s more to Milton Keynes than meets the eye. Now in its 50th...

Top restaurants in London's business areas

By Anton Constantinou Knowing where to eat out in London can prove...

Best specialist supermarkets in London

By Anton Constantinou Modern day food shopping in London is not what...

The SilverDoor Board To London Serviced Apartments

As one of the most iconic board games, Monopoly invites players to buy...

Singapore Area Guide: where to eat, drink, stay and conduct business

Singapore is an international city and sovereign state located in...

What to remember when relocating to London

Relocating to London can be a daunting task but, by getting the basics...

A Business Travel Guide to Canary Wharf

Over the last few decades, Canary Wharf has transformed from simply a...

New York City Guide

New York is said to be the largest and most popular city in the US....

Edinburgh City Guide

Edinburgh has a wealth of history and is a world-class business and...

London City Guide

London is the capital city of the United Kingdom (UK) and also one of...

The Ultimate Madrid City Guide for Business Travellers

The capital of Spain, Madrid, is the largest city in the country....

Hong Kong City Guide

Hong Kong is the Special Administrative Region of China, and lies...

Relocating from Poland to the UK

I left my home city Szczecin in Poland seven years ago. I came to...

A Business Travel Guide to Dubai

Staying in Dubai, UAE Despite its humble beginnings as a fishing...

Why do expat assignments fail?

Serviced apartments are an important piece in the complex jigsaw of...

Berlin City Guide

Berlin is the capital city of Germany and accounts for one of the...

Zurich City Guide

Zürich is the largest city in Switzerland and is located near the...

Dublin City Guide

Dublin is located on the east coast of Ireland. Following the...

Relocating from the Netherlands by Kristel Horst

I moved from Oldenzaal, Netherlands, to London in 2009. I was working...

Relocating to the home of cricket by Joanna Cross

From the moment I arrived as a fresh-faced Aussie girl, I knew England...

Paris City Guide

Paris is famous for being a hub of culture; the city has welcomed...

Relocate to the land of opportunity

On average, 1 in 30 people living in England and Wales will...

The best London boroughs for families

If you’re thinking about relocating to London with a family, you...

The 10 friendliest countries for expats

Moving to another country can be one of the most rewarding experiences...

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