Winter adventure: Chicago

A little bit of background

If you've just come to this post, it's one of a series on our 2016 winter adventure. You might like to read the LA prelude post first, as it gives some background on the trip and documents our stopover in the city on the way to Chicago from Australia.

I've given my overall reflections on our experience of Chicago at the end of this post. Check out my post on NYC for my reflections on what the winter experience meant to me.

Chicago wanderings

Coming from a hot place in the Southern Hemisphere, I'd always wanted to experience a white Christmas and proper winter. Our (W= husband; E= 16-year-old daughter) winter adventure took us to Chicago, NYC and Washington DC in December of 2016. I'm writing this post in 2024 but I still recall the intense cold we experienced in all three cities. We'd never felt anything like it before! That said, we were absolutely enthralled by the snowy landscapes, something that feels very otherworldly to us. So...be prepared for lots of pictures of snow in this post!

Travelling to Chicago

We were all super excited to be heading to Chicago, flying overnight on Sunday December 18, 2016 from Australia via a day's stopover in LA. We flew with Delta via Detroit, scheduled to arrive at Chicago O’Hare at 8.05am the next day. We ended up diverting to Denver as a passenger on our flight became quite ill and had to be stretchered off by paramedics. The passenger was sitting a few rows in front of us, and we could see that a doctor on board was assisting while we waited to land in Denver. It looked quite serious.

Delta booked us on the next available flight to Chicago. I remember that the airline was efficient in sorting out all the passengers. I know Delta comes in for a fair amount of criticism, but we had no issue with them. I mean, it wasn't the airline's fault that a passenger took ill!

We had our first glimpse of snow on the ground, as you can see from this shot taken from the plane as we landed in Denver. Super exciting!

We had enough time for breakfast at the airport in Denver. We found a diner, at E's request, and had a heart-attack-inducing breakfast. I remember ordering eggs on toast and the toast came out dripping in butter. American food!

I can’t recall what time we got to Chicago, but it was some hours after our originally- scheduled early morning arrival. We took the train from O’Hare into the city, and we were again treated to glimpses of snow.

Our first experience of snow

It was a shock to the system when we left the station to walk the short distance to our hotel. IT WAS COLD! I mean, cold like we had never felt before. It might sound odd, but it was such a thrilling new experience for us to be THAT COLD and in the thick of a recent heavy snowfall.

This is the first photo of me in the Chicago snow!

Our home for a week in Chicago

We stayed in a hotel located at 201 E Delaware Place, at the top of the Michigan Avenue, the main street in central Chicago. We were one block away from North Lake Shore Drive that sits alongside Lake Michigan. The hotel was the Raffaello at the time but I think it might be the Gale Chicago Hotel now.

We found it to be a good option, largely due to its location as we were easily able to walk everywhere and there was a grocery store across the road. The three of us slept in the same room but it was a decent size. We had a small fridge and microwave, and the rooms were nice. The best part was the view of the snow-covered streets below, as you can see in the two shots in the below collage.

The bottom two photos were taken from the hotel website; the other three are mine.

We had seven nights in Chicago with five days to explore + Christmas Day. There are loads of things to do in the city area, but we were so fascinated by the snow that we spent most of our time stomping around in it and immersing ourselves in the experience.

I know we only saw a small snapshot of the city, but I absolutely loved it. The winter experience, the city centre architecture, and the stunning snowscapes have left a lasting impression.

Snow and more snow...

I’ve waded through a bajillion photos of snow to make some collages that best represent my memories of our week in Chicago. Was it cold? Yes, it absolutely was, and miles from our own experiences of winter. That said, we were suitably rugged up and we coped once we started walking around and became used to it. There’s also something about a heavy snowfall that lends a certain crispness and beauty to the landscape. The snow feels cleansing and creates a sense of having stepped into another dimension. We felt like we’d climbed through the wardrobe and had landed in Narnia!

These photos were taken during our first full day in Chicago, after some shopping on Michigan Avenue. Yeah, we were just a bit excited to be experiencing snow! I’m sure locals who must contend with all the inconveniences heavy snows brings each winter feel differently, but to us, it was an incredibly magical experience.

That first day we discovered the Potbelly chain of restaurants that serve delicious high-quality, mindfully-sourced salads, hot sandwiches and soups.  We had lunch there a few times during our trip, including in Milwaukee and Washington DC. The restaurant was founded in Chicago in the 1970s and now has over 450 stores across the US and one in London, Toronto and Gurgaon in India. We were amazed to see people eating salads when we ate at the Chicago Potbelly. We couldn't fathom it in the freezing weather!

Photo taken from the Potbelly website.

There had been a huge snowfall the week before we arrived, closing O’Hare Airport and generally causing chaos. We benefitted from that snowfall as we were able to wander around the snow-covered streets. The thick layer of snow stayed around for most of the week we were in the city.

Here's E, doing her best impression of a snow angel. She really got into the spirit of things in Chicago and didn't seem bothered that we spent most of our week just stomping around in the snow. I love the snow angel photo!

The below collage features my favourite shots of all the photos we took. The stunning snowscapes in the city centre and the icy Lake Michigan took my breath away. Apparently, the average surface water temperature of the lake can fall to minus 7 degrees Celsius during winter, but rarely freezes over completely. The lake was 90% ice-covered in the 2013-2014 winter, though. Constant wind and wave movement tends to inhibit ice formation. We were lucky enough to see the beautiful wonderland of ice even if the lake wasn't completely frozen.

I was particularly struck by the winter light in Chicago. I hope these photos go some way to capture the light at that time of year. The sunlight set against the buildings along Michigan Avenue was really beautiful. Michigan Avenue creates a funnel of tall buildings and the way the light catches the windows on the buildings is stunning. The reflections of light on the building are also pretty.

Chicago is known for its architecture and the city certainly lived up to my expectations in that regard. The city is the birthplace of the American skyscraper, and it is still home to one of the largest and most diverse collections of skyscrapers in the world.

The Chicago River is another main feature of the city. It’s a system of rivers and canals with a combined length of 250km that links Lake Michigan and the Mississippi River basin and eventually the Gulf of Mexico. The river is a beautiful part of the city as these photos show.

We were fortunate to see the river in its icy winter state. Sections of the river completely freeze over during winter although the water continues to flow under the icy surface. The icy river is stunning despite the brutal weather that causes it. We'd never seen an icy river before, so this was a new and fascinating experience for us.

My photos don’t really capture just how cold it was, but they do give you some idea of how rugged up we were as we explored the Chicago River Walk. We took breaks throughout the day by heading inside to cafes and shops as all the buildings are super warm inside. It's just a matter of peeling off layers when coming in from the cold and steeling yourself to face it when you head out again.

Navy Pier

One of the major attractions in Chicago, and indeed in the entire Midwest, is Navy Pier. The pier is 1km long and sits on the shoreline of Lake Michigan. At the pier there are shops, cinemas, live theatres, kids’ rides and attractions, restaurants and parks. It originally opened in 1916 to serve as a dock for freighters and passenger ships. Indoor and outdoor expositions and pageants were held there. The pier was given its current name in 1927 to honour WWI naval veterans. During the Second World War the pier was used as a naval training centre, but it was later redeveloped as an entertainment hub.

Honestly, Navy Pier is pretty much just a flashier version of the piers in England – think Brighton and Blackpool – although I imagine it’s a fun place for families with small children. The best part of our visit was the 2km walk from our hotel that took us along Lake Michigan. Here’s a selection of shots from our walk, again allowing us to immerse ourselves in a winter snow experience.

How cool is this: A beach in winter! This is Oak Street beach, on North Lake Shore Drive on the shores of Lake Michigan, not that far from Navy Pier. The beach is close to the road and there was nothing to stop us from accessing it, other than the deep snowfall.

We wandered around the pier for a bit and had lunch at a lovely bowl place we found in the food court. We bought tickets for a cinema showing there but there was a technical issue that prevented the showing from going ahead. We took the refund and the new tickets that the cinema issued and watched two films later in the week at a cinema off Michigan Avenue.

A collection of my favourite shots of the pier.

Here we are in front of the crazy mirror that we found near the giant ferris wheel. There's a great view of some of the city buildings in the background! I tried looking the mirror up to write this post, but I can't seem to find anyone information on it. Perhaps it was just a one-off attraction at the time we visited.

Chicago pedway tour

The only paid attraction we did during our week in Chicago was a Pedway walking tour. The Pedway is the underground tunnel network that connects the city buildings, used by residents during winter to stay out of the brutal weather. It was definitely a quirky thing to do – so on brand for us – but interesting to walk through the tunnels and learn something of the city’s history. I’d booked it as I was fascinated by the concept of a city needing underground tunnels because of the harsh winters.

The tour group was small so it was easy to listen to the guide. Some of the architectural highlights are included in the below collage, plus the Macy’s store endpoint and its giant Christmas tree.

The Bean

The coolest thing in Chicago, I think, is Cloud Gate, known affectionally as the Bean. Cloud Gate is a public sculpture by Indian-born British artist, Anish Kapoor. It is the centrepiece of Grainger Plaza at the Millennium Park in the City Loop.

The Bean was constructed between 2004 and 2006 and is made of 168 stainless steel plates welded together. There are no visible seams on the polished exterior so it’s super shiny and reflective. The sculpture weighs 100 tonne and measures 10x20x13 metres. The Bean is a magnificent sight set in the foreground of Chicago’s stunning architecture.

The main shot in this collage is my favourite. The Bean is so cool!

Walking under the 3.7m high arch is a fun experience. The underside is the omphalos (Greek for navel), a concave chamber that distorts and multiplies reflections. It's rather surreal to walk under the Bean as I hope my cool shots show.

Can you spot us in the main shots?

Adjacent to the Bean is McCormick Tribune Plaza and Ice Rink. We loved watching the ice skaters on the outdoor rink, something completely foreign to us living in a hot place. We watched the skaters during the day and at night. And, no, we were not tempted to give skating a go. The last thing we needed was broken limbs on our trip!

Finally a proper Christmas!

Our trip was planned around the experience of a 'proper' Christmas. What I mean by that is one spent in the northern hemisphere, where it's cold and feels like Christmas as it should be. Christmas for us is searing heat and humidity and lots of plastic inflatable Santas!

Here’s a selection of the many Christmas trees we stumbled across in Chicago. The giant one in the lefthand side of the collage sits in the atrium of the 900 North Michigan shopping mall. The sparkly trees at the bottom of the collage were in front of the 360 Chicago Observation Tower near our hotel. The top middle photo is an example of the trees and night-time sparkles that were scattered around the central city area. The blue sparkly tree with E and me in the shot we found adjacent to the Bean and the outdoor skating rink. The other two tree shots were taken in different shopping malls.

A zoo in winter

Lincoln Park Zoo is located on the northern end of the city. The lights are an annual Christmas event, where one million lights are displayed throughout the zoo. There are also kids’ activities and food stalls. Thankfully, most of the animals are safely tucked away in warm shelters (not sure where, though). We walked the 8km round trip from our hotel one evening to check out the light display. Our walk gave us the chance to look back at the city and see it all lit up in its wintery glory. Super cool!

The shot in the centre of the collage is the view of the city from our walk back from the zoo.

Christmas day in Chicago

Our final day in Chicago was Christmas Day. We’d visited the famous Chicago Christmas market (Christkindl) during the week. I don’t seem to have any photos of our visit, but this one is from the Christkindl website.

It was super busy when we went to the market and not being into Christmas kitsch ourselves, we didn’t buy anything, but it was fun to walk around and get some of an idea of what these markets would be like in Europe. The Chicago version has been around since 1995 as part of the German American Chamber of Commerce of the Midwest activities to promote bilateral trade between the US and Germany.

We had a quiet, relaxing Christmas Day after our week of stomping around in the snow. I’d prebooked at Carmine’s and we walked over to the restaurant for our Christmas lunch. Carmine’s is an iconic restaurant in Chicago, part of the Rosebud group of Italian restaurants.

We had a very Italian lunch, complete with Christmas cannoli! (Top right photo from the restaurant's website.)

Milwaukee

We decided to take a day trip to Milwaukee on Christmas Eve. Why? It was a spur of the moment decision because we had a day with nothing planned and we thought it might be nice to see somewhere further afield. There’d been a fresh dump of snow in the area and this was incentive alone to make the trip.

Milwaukee is only an hour and a half by train from Chicago, following Lake Michigan north.

We travelled on the Amtrak Hiawatha (yes, that’s a thing!), the route that connects Chicago with Milwaukee, in a partnership between Amtrak and the Illinois and Wisconsin Departments of Transportation. There is some history to the service, historically operating since 1935 by the Chicago, Milwaukee, St Paul and Pacific Railroad, travelling between Chicago and the Twin Cities (St Paul-Minneapolis). The Hiawatha services were the fastest trains in the 1930s and 1940s. Amtrak took over the service in 1971 and today the Hiawatha runs only between Chicago and Milwaukee. Cool, hey?

Photo of the Amtrak Hiawatha taken from their website.

We took an early service from Chicago Union Station. The station itself is rather lovely, although it was almost empty first thing on Christmas Eve. There was no one much around generally on Christmas Eve, but at least there we no crowds to battle at the station.

We were surprised to find Milwaukee, a city of some 550 000 people, almost completely empty on Christmas Eve. It was an eerie feeling, walking around the snowy city when no one was around. The overnight heavy snowfall added to the sense of an otherworld.

The Milwaukee River is a beautiful feature of the city, especially in winter. This is us trying to navigate the Milwaukee RiverWalk. I remember it being super slippery. We loved watching the ducks on the river. Look at the adorable duck prints in the snow!

We found the Bronze Fonz near the RiverWalk, although it was partially covered in snow. The sculpture represents the iconic Arthur Fonzarelli character, played by Henry Winkler, in the television show, Happy Days, that was set in Milwaukee. As a child of the 1970s, Happy Days was a part of my (somewhat limited) television diet so it was kind of cool to see the sculpture.

I believe the sculpture was removed in February 2022 for maintenance. The bronze had begun to oxidise where salt has interacted with the metal. Lots of hands all over it plus the brutal weather had damaged its surface.

As mentioned, the centre of Milwaukee was empty. Weird! I liked the architecture, though. It was actually quite hard to find anything open. We managed to find a Potbelly for lunch and a department store where we did a bit of clothes shopping, but otherwise, it was very quiet.

The best part of our day was our jaunty trek around the harbour. Here are some of my picks of the shots we took of Lake Michigan. It was so beautiful in the snow and so empty of people!

We found the Milwaukee Pierhead Lighthouse at the harbour by chance, just south of the city. I love lighthouses! The lighthouse was established in 1872 and is still active, with its ten-sided lantern. The red building forms a stunning contrast to the pristine snow.

We also found these giant outdoor Christmas trees. What a cool find on our Christmas Eve wanderings! (Again, sans people. Where were they all? At home wrapping Christmas presents, I guess.)

Here's the Daniel Hoan Memorial Bridge, a tied-arch bridge that connects Interstate 794 in downtown Milwaukee to the Lake Freeway across the Milwaukee River inlet. It was originally called the Harbor Bridge but was later renamed after one of the longest serving city mayors. The bridge has been open since 1977. It's not a particularly pretty bridge, but the tied-arch is a bit nifty (whatever that means).

Milwaukee’s most iconic structure, and in deep contrast to the traditional architecture of the city, is the Quadracci Pavilion at the Milwaukee Art Museum along Lake Michigan. The pavilion was designed by Spanish architect, Santiago Calatrava, and completed in 2001. The funky bit on the top that you can see in the below picture is the Burke Brise Soleil, a moveable, wing-like sunscreen that sits on top of main structure. It has a wingspan is similar to a Boeing 747.

Milwaukee was a surprise bonus for us as we hadn't planned on going there, but we ended up having a lovely day in the snow sans people. The harbour area that we explored was stunning after the heavy snowfall, and we were treated to a different perspective on Lake Michigan.

Our Chicago experience

So that was our week in Chicago and the first leg of our winter adventure. We headed back out to O'Hare on Boxing Day to fly again with Delta to NYC. The next part of our winter wanderings saw us in NYC for nine days with a bonus day trip to Washington DC.

I loved Chicago, for its stunning architecture and the beautiful river and lake. No one will be able to convince me that it's not a magnificent city, even though I know it has its fair share of problems. There's a vibe to the city that resonates with me and it somehow seems authentic, owning its identity unashamedly. Chicago has a unique beauty with a distinctly European feel and even after only five days there, I fell in love with the city and its magnificent built and natural places and spaces.

I would love to go back in summer and see the city in a different season. There's so much to explore, and we only saw a tiny bit of it as we were hyper-focussed on the white Christmas and snow experience. If you can stand the brutal weather, it's worth a visit in winter just for the chance to stomp around in snow. Or perhaps that's just us, living in a hot and humid part of the world where Christmas is full of plastic inflatables, tacky Christmas lights, and draining heat. To have had at least one white Christmas in my lifetime was a real treat.