Chicago: The City by the Lake – A Guide to the Windy City

Chicago Skyline

Located on the shores of Lake Michigan, Chicago is a vibrant city that offers something for everyone. It is often called the “Windy City” and is known for its stunning architecture, rich cultural scene, and diverse culinary offerings. Chicago is home to some of the world’s tallest skyscrapers and has a thriving music scene with numerous jazz, blues, and gospel clubs. As the second largest business and financial centre in the US, after New York, Chicago is a bustling city that is both exciting and welcoming. Whether you want a romantic getaway or a cultural adventure, Chicago is a great choice to add to your USA travel list.

Chicago Cubs
Image: Choose Chicago

The thwack of the bat on ball sends the crowd into delirium, us included, with the battered ball sailing over the fence at the famous Wrigley Field, home to the Chicago Cubs. A sea of people wearing Cubs colours – blue and red – jump up and down as if zapped. We find ourselves joining in, doing high fives with the total strangers around us. They explain the rules, tell us which hot dog is best, where to go and what to see in town, and are incredibly friendly.

The field is fascinating because it is smack bang in the middle of suburbia. In fact, so close that people have built mini grandstands above their houses and sell tickets to watch the game. Wrigley is a special place – one of only two baseball fields to still have a manual scoreboard. Being there to watch the Cubs play at Wrigley Field – named after THE Wrigley of chewing gum fame – is perhaps the most romantic experience of our week, and there are plenty.

Chicago is a big surprise on many fronts. I had no idea that Lake Michigan was so big, so blue and so beautiful, with 26 miles of white, sandy beachfront. I was unaware that Chicago has one of the best laid out cities in the world – thanks to a cow, or a person, starting a fire in a barn back in 1871. Thanks to the fire, Chicago got to start over, and the result is beautiful parklands, glorious museums and galleries and some of the best architecture in the world.

Chicago Cubs Wrigley Stadium

Park Life

We spend many hours wandering through Grant Park, with its magnificent sculptures, art installations and gardens. Along with a few honeymooners, we take reflective selfies in the archway under the Cloud Gate – which everyone calls The Bean, mainly because it looks like a coffee bean – and marvel at the Frank Gehry-designed, Deconstructivism-styled performance stage. It is something to behold. So is the Crown Fountain, with two enormous towers that project the faces of Chicago citizens as well as a reflection pool. We stroll further south alongside busy Michigan Avenue, past the Art Institute of Chicago with its guardian lions out the front, the many huge sculptures, and in the southwest corner, the Agora art installation. Agora consists of over a hundred, nine-foot tall headless cast iron torsos. They are posed in countless directions, symbolising the idea of going everywhere and nowhere at once. Besides the Bean, this is probably one of the most photographed places in the city.

Chicago white whale
Image: Choose Chicago

Also in Grant Park is the Shedd Aquarium, where we make friends with one of the most beautiful creatures imaginable. We sign on for the Beluga Encounter, donning waders and interacting with these unusual small whales, trying a few training techniques – there are no fancy tricks here, just techniques that allow the staff to do health checks on the whales – and touch their skin. Wonderful for honeymoons, a couples holiday, or you can even pop the question poolside, with the option of champagne and strawberries.

Image: Choose Chicago

For a romantic experience on high we visit the Skydeck, on the 99th floor of the 108-storey, 412-metre Willis Tower. The views are outstanding, but for something really special, go out on The Ledge – glass boxes that extend over a metre outside the building. It is quite scary stepping out on the glass floor, seeing nothing under your feet except the bustling city streets, far, far below. There is a photographer on site, and it’s worth buying the photos as they are much better than what you can get yourself. We did it in the day time, and again at night – both are spectacular. The Ledge has hosted many proposals and weddings – with the wedding photos certainly something different.

Image: Choose Chicago

All Aboard

When your feet are firmly planted back on ground level, set off for a leisurely cruise up the river on the Chicago Architecture Foundation cruise with Chicago’s First Lady Cruises.

We settle down on the deck for the 90-minute tour with a smattering of honeymooners, couples, backpackers and holidaymakers from all over world. We hear a fascinating commentary on the city’s history, along with descriptions of the more interesting buildings as we go by – and there are plenty, including the Wrigley Building, Trump Tower, the Boeing building and the Chicago Tribune. We glide along all three branches of the Chicago River, under 13 of the river bridges, and get a good feel for the layout of the city centre while seeing all of its skyscraper stars. You can even see the glass boxes of The Ledge, hanging out of the Willis Tower. They look rather high from down here.

Image: Choose Chicago

Not so high anymore is an old United Airlines Boeing 727 which hangs in The Museum of Science and Industry on the lakeshore. We board the plane and take a seat, joined by a young couple from Nebraska on a romantic escape. We joke about how much room there was in the aisle in the old day and check out the cockpit, looking down over some of the other exhibits, including a 999 steam locomotive. There is so much here you need a day to see it all, with the highlight for us exploring a German U-505 submarine, captured by the Americans in 1944.

To experience yet another form of transport, we take the city’s famous “L” elevated train line, now called the Brown Line, out to Armitage in Lincoln Park from historic Quincy Station. Armitage has some excellent quirky boutiques and galleries, and a charming café called the Blue Door Farm Stand. This is quite a find, with fresh, seasonal food and drink from local farms and farmers’ markets as well as from the restaurant’s namesake, Blue Door Farm, once owned by Oprah. It also has an artisan market with some beautiful handmade gifts and gourmet foods. They win me over when they had heard of flat white coffee and even make one, accompanied by the best piece of carrot cake – and probably the biggest – that I have ever had. It is well worth the train ride.

Image: Choose Chicago

Wine, Dine and Pizza

On any romantic escape, couples holiday or honeymoon for that matter, wining and dining is all important, as it is where couples can chat about what they experienced during the day, plan for tomorrow and just enjoy being in this cracking city. We try out several restaurants, bars and a few nightclubs, and also love room service, eaten wearing the stylish bathrobes in our suite at the Peninsula Chicago, one of many excellent hotels providing luxury accommodation.

For dining, we give a big thumb’s up to the Peninsula’s Shanghai Terrace, with divine dim sum and superb Cantonese-style dishes. We also really enjoy Goosefoot, with chef Chris Nugent presenting cuisine that looks as good as it tastes, Terrace Sixteen – a very swish two-Michelin star restaurant at the Trump International Hotel and Tower that serves award-winning Modern American cuisine complemented by gobsmacking views over Lake Michigan, Nico Osteria at the very swanky and cool Thompson Hotel which is hotter than Hades right now, and Epic Restaurant and Lounge, which wins us over with its pork belly starter and duo of duck (me) and roasted sea bass (him), for mains. The lounge menu is also excellent for a more casual meal and the service throughout the entire place is outstanding.

The Underground has it all going on – it is full of beautiful people so pick up some trendy threads at one of the boutiques along the Magnificent Mile and glam up bigtime. Of course, if loud music and bright lights are not your thing, there are plenty of uber-cool jazz clubs around town.

Visit Chicago: Fact File


The Peninsula Chicago is luxury accommodation at its finest and is an elegant cocoon of style and tranquillity well positioned just off the Magnificent Mile. 


Shanghai Terrace has spectacular food in a lavish interior. Goosefoot has divine cuisine and chef Chris Nugent can do things with chocolate that make you swoon. 


Skydeck at Willis Tower is the home of The Ledge. The Museum of Science and Industry is jam-packed with something for everyone. 

Don’t Miss 

The Architecture Tour with First Lady Cruises is definitely not just for those with a passion for architecture. It’s informative and very interesting and one of Chicago’s most popular tours. 

Couples Will Love

The Beluga Experience at Shedd Aquarium will have you falling in love with these exotic whales. 

The Chicago CityPASS contains prepaid admission to Shedd Aquarium, Skydeck Chicago with a fastpass entry, The Field Museum, the Museum of Science and Industry and either the Art Institute of Chicago or the Adler Planetarium. It will save you 50 per cent compared to normal box office prices.

Getting There 

Qantas flies to Los Angeles with connections to Chicago O’Hare Airport with American Airlines. 

Best Time to Go

The ideal time to visit Chicago is during the summer months of June to September. During this time, the city experiences warm and sunny weather, perfect for enjoying outdoor activities like live music events, neighbourhood festivals, and relaxing on the urban beaches. October is a great time for runners, as the city hosts the annual Chicago marathon. Visitors can enjoy the famous Chicago Blues Festival in June, while July brings the Taste of Chicago, a food festival showcasing local favourites. August is packed with events like the Lollapalooza Music Festival, the Chicago Jazz Festival, and the Chicago Air and Water Show. For those willing to brave the cold, December offers the Christkindlmarket, ice skating at the Maggie Daley Ice Skating Ribbon in Grant Park, and the opportunity to see beautiful Christmas lights at the Lincoln Park Zoo and Navy Pier.

How to Get Around

Getting around in Chicago is convenient and accessible thanks to its walkability and excellent public transportation system. The city’s train system, known as the “El,” runs above ground and connects various parts of the city, including downtown and the airports. Additionally, Chicago has an extensive bus network that can take you almost anywhere via public transit. Bus information can be obtained through text messages using the instructions provided at bus stop signs. Metered taxis are readily available downtown and surrounding neighbourhoods, but rideshare services like Uber and Lyft are often more affordable. Uber tends to be slightly cheaper than Lyft in terms of rideshare services, although this may vary.

Related: A Relaxing Driving Holiday Through Maine, USA

Leave a Comment

Scroll to Top