3 cost-friendly neighbourhoods that show Chicago’s charm

A home designed by Frank Lloyd Wright in the Beverly neighbourhood of Chicago, Illinois. The best discoveries in this area are the architectural gems and beautiful homes.
A home designed by Frank Lloyd Wright in the Beverly neighbourhood of Chicago, Illinois. The best discoveries in this area are the architectural gems and beautiful homes.PHOTO: NYTIMES

CHICAGO (NYTIMES) - No travel assignment is ever straightforward, but reporting on the place you grew up presents specific challenges. Walking along the bungalow- and tree-lined streets in the Beverly neighbourhood of southwest Chicago, where I lived until second grade, a fog of memory followed me as I passed businesses my family used to frequent and the houses of old neighbours. 

I scarcely recognised Sutherland Elementary School, a red and white brick structure on my block. The house where I lived as a child was equally foreign, and seemed tiny, like a dollhouse.

The other side of this mild nostalgic angst is the joy of discovery: The privilege of being able to explore old stomping grounds with fresh eyes (and a few decades under the belt). That’s exactly how I spent the better part of a week in Chicago, a city defined by its 77 distinctly demarcated community areas, which in turn houses dozens of additional neighbourhoods, each with its own particular nuance and local spirit.

I chose three – Beverly, as well as Lincoln Square and Roscoe Village – as the lenses through which I would rediscover the city that played such a large part of my childhood. The best part? Keeping expenses low without sacrificing enjoyment. My time in the Windy City, which included a historical walking tour, free dance classes and delicious food and drink, cost me a pittance.

1. Lincoln Square 

I started in the most northern destination of my Chicago adventure, the epicentre of which is where Western meets Lincoln and Lawrence avenues. That confluence is made blessedly less hectic by Lincoln becoming a narrow one-way street, creating a small oasis in the city lined with businesses focused on serving the neighbourhood as well as plenty of green spaces. 

A focus on local ownership “really makes Lincoln Square feel like its own small town”, said Elizabeth Bracken, a scenic designer and neighbourhood resident I met through Barrel of Monkeys, a non-profit theatre we’ve both worked with.

Cafe Selmarie, which opened in 1983 as a small bakery and coffee shop, has grown along with the neighbourhood, which has come into its own as a destination for artists and young families. It’s a cute, all-day cafe (closed Mondays) but the ideal time to pay a visit is burger nights on Wednesdays. 

I downed a thoroughly enjoyable burger dressed with Brie, bacon and caramelised onion, alongside a nutty, deep-amber Domaine DuPage French-style country ale, all for US$15 (S$20.40). I picked up a loaf of banana bread (US$4.15) for the road, and wasn’t disappointed.

Nearby is Gene’s Sausage Shop, a big, bright market and deli that’s hiding a secret: a wonderful rooftop where you can enjoy different beers, wines and snacks. It was a secret to me, anyway. 

I arrived there one weekend to meet up with some friends and it was packed with hungry revellers enjoying a sunny, breezy afternoon. 

“Number 46!” bellowed the young man behind the counter and I picked up my order of crispy potato pancakes (US$6), Sao Paulo Sandwich (US$9) and pasta salad (US$3) to go along with a refreshing Wittekerke Belgian white beer (US$6).

I’d recommend everything but the sandwich, which was a sad couple of pieces of fried mortadella and provolone cheese. The food (cash-only on the rooftop, by the way), though, is incidental – it’s more about the good vibes and camaraderie of drinking on a rooftop with friends, and there was plenty of that to go around.


The gate to Lincoln Square. A neighbourhood resident said the focus on local ownership “really makes Lincoln Square feel like its own small town”. PHOTO: NYTIMES

Other highlights of that stretch include a cute toy store, Timeless Toys, with a weekly kids’ story time, and a cosy book store called The Book Cellar. 

Beyond plenty of books and multiple events and readings every week, the independent seller has beverages, including beer and wine, to accompany your browsing. I got an iced coffee for US$2.20.

If you’re feeling crafty, it’s worth stopping into the Gallimaufry Gallery, which has been run by Pat Rodarte and Michael Merkle for over 40 years (15 in its current location). 

They source pieces from artists both local and throughout the country. I picked up an attractive oversized market bag printed with a colourful map of Illinois for US$19.50. 

“It’s like a little hamlet,” Rodarte said about the neighbourhood. “The community is very supportive.” 

2. Roscoe Village 

I was energised enough to walk a mile and a half south to Roscoe Village. The “village” in the name says a lot; on the train overpass at the Ravenswood intersection are painted the words “The Village Within the City”. 

Its main drag, along Roscoe Street between Western and Ravenswood avenues, is less than 2km and can be traversed in about 10 minutes – past small businesses, cute wood-framed and brick houses and plenty of families and pets strolling the main commercial drag. 

A self-guided garden walk (organised by the neighbourhood association), where locals opened up their backyards to curious wanderers with green thumbs, was a great way to explore the area by foot.

Those small businesses include some great vintage and thrift shopping. Shangri-La Vintage gives a sense, unlike many other stores I’ve visited, of actually being carefully curated by the owner. 


Shangri-La Vintage in the Roscoe Village neighbourhood of Chicago. Exploring Lincoln Square, Beverly and Roscoe Village is a way to keep expenses low without sacrificing enjoyment of the city. PHOTO: NYTIMES

“We’re dressing up like the ‘Stranger Things’ kids for Comic-Con!” one shopper explained as she was pawing through some ‘70s and ‘80s-era shirts. I found a great Chicago Bulls hat from the glory days of the late ‘90s for US$13.

For those on a slightly tighter budget, and with a lot more patience, there’s Village Discount Outlet just down the street. 

While sections of the store looked like an earthquake had hit it, there are treasures and deals to be found throughout the considerable sprawl. I needed a pair of athletic shorts, and picked up one for a few bucks.

There’s quality sustenance to be found, too, when you need a break from shopping and garden-hopping. 

Turquoise Restaurant was marred by slow and indifferent service when I visited with my family but offered an incredible deal on brunch. For US$20, diners get fresh bread served with honey and butter, hash browns, two kinds of omelettes, Turkish sausage with eggs, meatballs, a cheese platter, crepes and fresh fruit. 

It’s an astounding amount of food, most of it quite good, so come hungry. Did I mention you get tea or coffee, too?

If you’re in the mood to go in a slightly different direction, The Region offers Northwest Indiana-style hamburgers – a style I wasn’t even aware existed. 

The distinguishing characteristic is that the burger is pressed thin on the hot griddle until its edges become crispy and caramelised. The  Regionette (over 110g for US$5.50; just under 200g for $8.50) made me wish I’d found out about this style sooner. The chilli cheese fries (US$5.50) with homemade chilli were a delectable mess.

3. Beverly 

That wasn’t the only revelation of the trip. When I went down to 95th Street to explore my old Beverly neighbourhood, the discoveries kept coming. 

The Purple Cow, a bovine-themed ice cream parlour I remember as a favourite birthday party destination for neighbourhood kids, was long gone. 

But Top Notch Beefburgers, opened in 1942, was still alive and kicking; the US$5.67 cheeseburger with a thick slice of tomato and raw onion hit the spot.

The best discovery, though, was a wealth of architectural gems and beautiful homes I was too young to appreciate (or even notice) as a child. 


Signs at Janson's Drive-In in Beverly. There are plenty of cheap eats in this neighbourhood. PHOTO: NYTIMES

On Longwood Drive, Frank Lloyd Wright’s Raymond W. Evans house lords over the area atop a modest hill. 

The 1908 Prairie School structure (and its neighbours) are well worth a peek – just be respectful as it is a private residence.

I found a wealth of local architectural information at the Ridge Historical Society on South Seeley Avenue. 

The Tudor Revival-style Graver-Driscoll house, in which the Society is located, is worth checking out in its own right. 

But the real find was a copy of a hand-scrawled architectural tour, available in printouts on oversized pieces of paper. 

I spent the better part of an afternoon exploring not just the Frank Lloyd Wright landmarks (the H. Howard Hyde and Guy C. Smith houses on South Hoyne Avenue) but also those of Walter Burley Griffin, a one-time Wright employee who designed the Australian city of Canberra. 

Griffin’s Prairie School contributions are visible throughout the area, but are mostly focused on West 104 Place – a small street with at least a half-dozen structures bearing his design.

Most eye-opening of all was the Vanderpoel Art Association, an astonishing (and free) assortment of American impressionist art crammed into a modest-sized room in the field house at Ridge Park. 

Full of day-campers and running kids, the rec building seemed an unlikely place to hold a priceless art collection, including works by Grant Wood, Ernest Hennings and John H. Vanderpoel himself. 

But, after straying into the gymnasium a couple of times, I finally found it: a plain room packed to the gills with striking art pieces.