Destinations Winding Through the Windy City: Chicago in 3 Days

by Kevin Warwick | October 01, 2019

While Chicagoans abide by their well-known rivalries — between the city’s baseball teams; the North and South Sides — they’re also willing to talk up neighborhoods outside their own.


They may point a visitor to unpretentious Uptown, where a favorite local jazz club sits among ornate, old-school concert venues. Or maybe to up-and-coming Bridgeport, where an influx of innovative new businesses is updating its persona as a manufacturing hub. The neighborhood of Hermosa may even get a call-out, being the birthplace of a now-world-famous animator who launched an empire with a certain animated mouse. Really just because they’re happy they know.

Which is to say, Chicago, IL, is a city not only defined by its distinctive neighborhoods and the civic pride locals feel for them, but also by the idea of being part of the greater whole. It’s all very Midwestern.
 

Recently, the city has made big strides to further connect one beloved neighborhood to the next via improved pedestrian and bike paths. The CTA train system (known as the 'L') has long provided a perfectly nice option, but now there are more ways than ever to walk, bike, scooter or, yes, even kayak from one enclave to the next.
 

Bike or stroll along the 606, a former elevated rail line that re-opened in 2015 as a converted pedestrian path running nearly three miles east-west through Humboldt Park, Logan Square and Wicker Park. (There are rumblings it may soon expand east to the Chicago River.) Farther north near Lincoln Square, a boat launch at River Park is giving the bike-friendly North Shore Channel Trail a facelift. Then, of course, there’s the famous 18-mile-long Lakefront Trail running alongside Lake Michigan. At the end of 2018, it was rejiggered and separated into a bike trail and pedestrian trail to alleviate congestion.
 

Here’s a game plan for tapping into those distinctive neighborhood vibes over three lively days in Chicago.

Quote
Now there are more ways than ever to walk, bike, scooter or, yes, even kayak from one enclave to the next.
End Quote

Day 1: Circle the square


While the glitz and glamour of Chicago’s renowned dining and cocktail scene can be soaked up with a dozen or so reservations placed at popular restaurants in the ever-expanding Fulton Market District, it’s the neighborhood gems that often leave a lasting impression. 
 

Like Baker Miller, in Lincoln Square. Head here to fill up with enough delicious carbs to prompt a relaxed stroll through the quaint North Side neighborhood. Its biscuit is hardly humble sustenance — after a slathering of one of the from-scratch bakery/pie mecca’s decadent jams, the crumbly treat becomes a meal unto itself.
 

Travel back into old Europe at Merz Apothecary, a half mile north of Baker Miller and nestled within a plaza featuring German bars and restaurants that pay homage to the neighborhood’s roots. First opened in 1875, Merz moved and remodeled in the 1980s to resemble the ornate apothecaries of the 19th century. Today it doubles as a purveyor of herbal remedies, natural skin care products and a historical landmark of Lincoln Square.
 

Speaking of institutions, the Old Town School of Folk Music — now split into two halves that sit across from one another on Lincoln Avenue — presents a full roster of folk, world music, and indie rock concerts in a pair of intimate halls as well as classes for accordion, ukulele, guitar and dulcimer, among others. One-off workshops such as “How to Approach Learning a Jazz Standard” are also offered.
 

After all that, you may need a drink. Stop by one of Chicago’s original craft breweries, Half Acre, where the original taproom expanded to a brewpub in 2016. Some of the brand’s most popular beers (say, a Daisy Cutter IPA), as well as some of its more elusive labels, are available.

Exterior of Half Acre Beer Company in Chicago

Photo courtesy of Half Acre Beer Company

Day 2: Swing for the south side


If you only stay north of the Chicago equator (aka Madison Street), you’ll be doing yourself a disservice. South Side neighborhoods have been surging over the past decade thanks to new restaurants and businesses that have opened — with the neighborhood of Pilsen, home to a large community of Mexican families, leading the way.
 

A number of hotspots can be found along Pilsen’s 18th Street, which hums with art galleries, bars, restaurants and vintage clothing stores. Knee Deep Vintage is downright savvy at cherry-picking the best threadbare vintage tees and button-up western shirts. The shop is nestled just east of Thalia Hall, a gorgeous 1,300-capacity concert venue that’s a South Side gem and one of Chicago’s premier music venues. Take a quick glance at the calendar and you’ll be surprised by the variety of hip-hop, stand-up, experimental and emo acts represented. And the concert hall is housed within the same building as a punch house, a cocktail bar and an upscale restaurant. You never really need to leave.
 

If you must depart, grab a bite at HaiSous, a hip Vietnamese restaurant that has reason to flaunt its innovative street-style dishes and cocktails. Or if you’re looking for a heartier option, Pleasant House Pub on nearby Halsted Street specializes in “royal pies” — otherwise known as British-style handmade savory pies.

Table and chairs at the interior of HaiSous

Photo courtesy of HaiSous

Day 3: Livin’ it up in Logan


As one of Chicago’s most happening neighborhoods, Logan Square is at the forefront of the dining and cocktail scenes. That doesn't mean it’s devoid of daytime amusement.  Hop off the Blue Line at the Logan Square stop and work your way out from the home base of the Logan Square Monument. Also known as the Illinois Centennial Monument, it was built in honor of the state’s 100th anniversary.
 

Featuring a boulevard system that makes the neighborhood supremely walkable, Logan Square includes a number of inventive eateries. Fat Rice Bakery — connected to the renowned Macanese-inspired restaurant of the same name — is where people line up for one-of-a-kind treats such as the Chicago-style Hot Dog Bun and a Sesame Peanut-Butter Mochi.
 

Milwaukee Avenue, which cuts through the heart of the Square, is dotted with additional bakeries, breweries, bike shops and galleries. Case in point: Galerie F, which touts a variety of exhibits by artists that specialize in screen prints and street art. From there, meander just up the Avenue to Estereo, a casual joint with an open-air layout that presents a robust menu of southwestern-themed cocktails. Afternoon hangs here can easily drift into early evening.
 

While barcades are more norm than novelty these days, few have the luster and soul of Logan Arcade. It's thoroughly a vintage arcade first and craft beer bar second, designed to encourage geek outs and uniquely good times alike. Roll through on the right night and you can experience a live animatronic band playing punk-rock covers.

counter at Fat Rice Bakery

Photo courtesy of Fat Rice Bakery

Remember, visiting these three neighborhoods will provide you with but a glimpse of the wonders that await throughout Chicago. Let this guide be a jumping off point for many adventures to come. You’ll undoubtedly be surprised by how much is contained within the city’s borders if you just keep exploring.

Kevin Warwick

is a Chicago-based editor and writer who has spent over a decade covering arts and culture for publications like the Chicago Reader, Vice, Bandcamp, Reverb, Pitchfork, and Chicago magazine.