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Architecture,  Chicago,  History,  Monday walks

A stroll in Chicago’s Old Town

… it was said that all who lived within hearing distance of the church’s bells were Old Towners.

 Donna Gill, Chicago Tribune, December 4, 1967

Old Town is not, somewhat to my surprise, the old heart of Chicago, but rather one of its neighbourhoods. It takes its name from art fairs held in this area in the 1940s, ‘Old Town Holidays’. However, it is certainly home to many buildings older than most in the city. There are Victorian era houses and even one of just seven buildings to survive the Great Chicago Fire of 1871.

With my Virtual Tourist friends I joined a walking tour of the neighbourhood one morning to learn more. We started at Sedgwick station on the Brown line of the L. Come along with me to see what Old Town has to offer …

Mural near Sedgewick St station

Almost immediately we were on quiet streets that contrasted significantly with the bustle of the River North area where we were staying, just one stop away on the L. They were lined with lovely old houses, some wooden despite a ban on using that material following the fire. I got the impression that Old Towners like to defy the rules and conventions. The streets here don’t always follow the grid pattern of the rest of the city. And the area has often attracted those who seek an alternative lifestyle: hippies, gays and lesbians, sex workers, artists and performers.

One of the first buildings pointed out by our guide Giovina was a bar, the Twin Anchors, which Frank Sinatra used to frequent.

St. Michael’s RC church

This area was once home to many Native American nations, including the Potawatomi, Miami, and Illinois. It was an important trading centre for them due to its proximity to Lake Michigan. After their forcible removal from the land it was settled mainly by German-Catholic immigrants. They were responsible for building one of the neighbourhood’s gems, and certainly a highlight of our walk, St. Michael’s church.

A leaflet I picked up in the church starts thus:

On October 9, 1871, mid-morning, the great bells in St. Michael’s tower began to toll a warning, slowly, sonorously. It was a bright and dry day, a little more than two years since the dedication of the imposing new church.

The leaflet goes on to describe how, as the fire jumped the Chicago river and started to devour the buildings of the North Side:

‘the German parishioners filled the wood-cobbled streets and planked sidewalks, hoping the massive walls of St. Michael’s would resist the fire.’

Miraculously they did, although the other buildings on the site (convent, school) were destroyed and the bell tower had crumbled.

Two years after the fire, in October 1873, the church had been restored. Today it stands as one of those seven buildings in the city to have (more or less) survived the fire. We spent some time exploring the inside, where I loved the stained glass which I read later was imported from Germany at the start of the 20th century.

Old Town streets

From here Giovina led along some of the neighbourhood’s prettiest streets. We saw several studios of local artists which from photos she showed us looked lovely inside but which aren’t, unfortunately, open to the public. However there were some lovely ‘arty’ details to enjoy on the exteriors.

Indeed, everywhere we went there were lovely details to photograph, and a few that made us smile, including one house with a duck pond in its tiny front garden! Rich pointed out a couple of the tiny houses built soon after the fire to house those made homeless. My feature photo is of one of these.

Around Lincoln Park

We emerged from these picturesque streets on to a busy junction by Lincoln Park and the Chicago History Museum. Here Giovina showed us a large fragment of a building that had been destroyed by the fire. This ‘hunk of molten iron, stone, and brick’, as the Chicago Park District website describes it, has been mounted and displayed here as a symbol for the resilience of the city.

Large chunk of stone by a busy road
Fragment of a building destroyed by the Great Fire of Chicago

A short distance from here we came to the rather appealing Children’s Fountain, dating from 1982.

Turning back from the park again we came to one of Old Town’s most famous institutions, Second City. The list of comedians who have started their careers in its improvisation shows contains many of the biggest names in that business: Alan Alda Alan Arkin, Bill Murray, John Candy, John Belushi, Dan Akroyd, Mike Myers, Steve Carell, Tina Fey, Joan Rivers and many more.

Two ice cream scoops in a bowl
Ice cream in Jeni’s

At this point our tour ended and our group broke up. I had lunch with a few of my friends in one of the many appealing restaurants along N Wells Street.

After our meal we browsed some of its equally appealing shops. And we finished our outing in Old Town with ice creams at a great place, Jeni’s, with unusual flavours such as sweet potato and marshmallow. Jo needs cheering up at the moment so I hope finishing this Monday Walk with ice cream will give her nearly as much pleasure as cake!


  • SoyBend

    Great artwork in that mural. I liked your collection of small detail gems. Did you get a chance to go to a Second City show? Inside, it’s much smaller than I expected. The improv show we saw was hilarious. 🙂

  • Christie

    I never realized that German-Catholics immigrants settled in Chicago, I always lived with the idea that Chicago is more like full of Italian families🙂
    An interesting walk, thank you for taking us with you!
    Have a lovey day, xx

  • Alison

    Lovely photos Sarah and enjoyed exploring these streets with you. The buildings are beautiful and the churches stained glass windows are amazing. Looks like you had lots of fun over there.

  • Wetravelhappy

    Wow Frank Sinatra, I could imagine him belting ‘My Way’ in that bar.
    It looks like a pretty church, I can understand why it was the highlight of your walk. 🙂

  • Rose

    How sweet of you to cheer up Jo with ice cream. 😊 These images were wonderful and not what I imagine when I think of Chicago. We drove through there once several years ago, and saw mostly metal structures. The art and homes of this Old Town are just lovely. I especially liked the sign on the artist’s home in black and white letters – division/unity…

    • Sarah Wilkie

      Thanks so much Rose 😊 Yes, Chicago is largely built from stone and metal, wood was banned after the great fire – but somehow the people of Old Town got away with using it!

    • Sarah Wilkie

      Thanks so much 😊 I do like to look for different aspects of a city when I can, but this visit to Old Town was entirely down to our host Rich who suggested it – I would never have known to go there otherwise!

  • restlessjo

    If it’s good enough for Frankie…? And I do like the autumnal wreath. Nice idea! The stained glass is stunning, isn’t it? Do you still have the opportunity to write for Virtual Tourist, Sarah, or just go on jaunts with them? I don’t know why but I thought it had folded. Cheers for the ice cream. Probably more use to me than the lemon drizzle cake a friend just brought round. I’m having great difficulty opening my jaw and liquidised cake isn’t too appealing. Have a fabulous trip tomorrow!

    • Sarah Wilkie

      You’re right Jo, the Virtual Tourist website closed down – nearly seven years ago now! But a number of us have kept the core members largely together, mainly through a Facebook group (a few non-FB users also stay in touch the best they can). We still organise meetings, both big and small, and use the FB group to share photos and ask travel questions. And we’ve even been able to add a few new members, usually friends of existing members who come along to a meet and decide they want to get involved 🙂

  • Mike and Kellye Hefner

    What a great neighborhood, Sarah, and it looks like you had perfect weather for your visit. Since we’ve never been to Chicago, I had not heard of this section before, but I would also love to roam the streets there – with a guide, of course. I’m kind of in love with the altar and stained glass of St. Michael’s. I’m adding your posts to my Chicago to-do list.

    • Sarah Wilkie

      Yes, we were really lucky with the weather for most of our trip – just a few morning showers on the last two days. And I definitely recommend exploring Old Town if you visit Chicago Kellye – I’m sure you’d love it!

  • Richard Kolar

    Very good story on one of the many neighborhoods that make up Chicago. Although I personally have never lived in Chicago personally in my 71 years, my Polish ancestors came to Chicago in the 1880’s while my Czech and German ancestors arrived in the early 1900’s. I grew up in a nearby suburb of Berwyn, a very Czech and Italian community in the 1950’s and 1960’s which is now mainly Hispanic. It is always interesting to hear how people perceive Chicago either having never visited or only visited the main tourist areas. I’m glad members of our Virtual Tourist group got to see more of what real Chicago is like.

    • Sarah Wilkie

      I was really glad we got to see this neighbourhood as well as the downtown skyscraper areas of the city. It had such a great atmosphere – really the sort of place I’d happily live in!

  • Marie

    What a lovely neighbourhood for a stroll – I love all the wall plaques and tiles. Guided walks are great aren’t they – you come away with details you’d never spot on your own…


    I don’t think I’ve read any blog posts about Chicago apart from yours, so everything I read about it is all brand new. I know very little about it. Certainly I knew nothing of a German immigrant influence. On that sign of opposites, interesting to note that the positives are on the dark side…is that significant, I wonder?

Do share your thoughts, I'd love to hear from you!

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