Love Thy Neighborhood

Up in Rogers Park, it’s easy to find things to do. Perhaps not the first place many think to visit on a weekend day off work, Chicago’s northernmost neighborhood has a little bit of everything, from tapas restaurants and trendy coffee shops to lakeside relaxation and charming avenues. Today, we’re going to get a taste of Rogers Park by embarking on an excursion via the Red Line. We’ll stop to pursue antiques, pick out new books and be introduced to witchcraft — all right after fueling up at a cozy, plant-filled cafe.

Stepping into Lincoln Square is like stepping into Chicago’s own fairytale small town. The main strip along Lincoln Avenue has the charm of a European village, with open plazas where locals gather, vintage lampposts casting a warm glow, and storefronts with colorful awnings inviting you in. This guide will lead you through some neighborhood gems, starting with a shop that embodies Chicago’s quirky, no-nonsense pride, stocked with cheeky souvenirs and local art. Next, step back in time at a 19th-century apothecary filled with rare European skincare treasures and a staff that makes every visit feel personal. Finally, end your day with a cone from a plant-based creamery that’s mastered oat-based decadence.

A lot of record shops in Chicago are worth visiting, but none are as memorable as the one you’ll be visiting in this guide. It doubles as a “Museum of Curiosities” complete with taxidermy creations, a room on cults and secret societies, and a John Wayne Gacey exhibit (featuring none other than a recreation of his death row prison cell). To continue the theme of lesser known, more eccentric Bucktown gems, you'll dine at a retro pizza joint with a 1980s theme and enjoy a beer at a wonderfully quirky bar and live music venue with a long history in the neighborhood.

Greektown is a unique gem of a neighborhood, rich with Greek food and community. Located just west of downtown, it’s a place where Old World traditions mix with modern-day culture. To get to know the area, you’ll fuel up with coffee, take a stroll in a park and end with a traditional Greek dinner.

Andersonville is a literary hub, where bibliophiles and casual book browsers alike will delight in a variety of distinct bookstores. This exploration brings you to three unique shops, just half a mile away from each other. You’ll grab coffee at a theater-focused cafe, wander a few blocks to a feminist bookstore and end at an oasis for used and rare books.

To follow this guide, you’re heading south to the historic and beautiful Bronzeville neighborhood. Combining books, music and history, you’ll expand your mind and latch onto some shining nuggets of Chicago history. What could be better? Oh, and then you’ll follow it up with a glass (or bottle) of wine and a lovely meal at one of the neighborhood’s premiere eateries.

Remaining frugal in a city like Chicago can be a tough task, but it’s not impossible. To prove it’s doable, we ventured to Lincoln Park, a notably expensive Chicago neighborhood, to craft a memorable outing on a $10 budget. You’ll start by grabbing a coffee drink in a small coffee shop, followed by a trip to a classic Chicago-style establishment for a bite to eat. You’ll then head to a French-inspired dessert shop before ending the day with a tour of a historic Chicago architectural monument. Plus, all are within walkable distances from one another. You won’t have to break the bank to enjoy a day in the city.

As one of Chicago’s most ethnically mixed neighborhoods, West Ridge is a melting pot of cultures and flavors. This diversity is perhaps most prevalent on Devon Avenue, where global cuisines blend seamlessly with a strong community feel. Tonight’s escapade gives you a sampling of the area’s eats and treats along a stretch known as Little India. You’ll feast on vegetarian food, indulge in dessert and take in some live music at a neighborhood bar.

Home to the University of Chicago, Hyde Park is undoubtedly the city’s ideal hub for intellectuals. To tap into your inner highbrow academic, take a trip through the neighborhood for a bookish day filled with daydreaming and fantasies about your other life as a poet or professor. Start at 57th Street Books, then take an obligatory walk around the gothic campus and finish the night with delicious Italian food at Ascione Bistro.

It’s not hard to love Andersonville. It’s a charming North Side pocket of eclecticness and eccentricity just waiting to be tapped. This neighborhood is worth a meandering walk down Clark Street punctuated with sweet treats, quirky thrift finds and a delicious cocktail. In this guide, find a serendipitous balance of all three at a gluten-free bakery, a locally beloved thrift store and an inviting cocktail bar.

Ravenswood, Wrigleyville’s cozy sibling to the north, is home to Chicago’s Malt Row. With Ravenswood Avenue hosting more than 10 craft breweries and distilleries, hitting them all in one go could be quite the doozy. Instead, this guide focuses on two spots for a chill evening of snacks, digestifs and, beer.

Pilsen is a mecca for vintage shoppers and the plan for this guide is to bounce around to four different shops, each with a different era of fashion and merchandise in mind. But before the shopping spree begins, you'll start the day with chilaquiles and coffee at small countertop diner that's been run by a mother and son team for over 30 years.

This guide takes us to Edgewater for a quick afternoon trip. It starts at a place that's one part pie shop, one part bar, and one part elevated tavern food. Afterward, head across the street to Chicago's oldest antique store. Here are the details.

This is a classic neighborhood walkabout in West Town. It starts with coffee and shopping at a pandemic-inspired retail/coffee shop. You'll then grab a Filipino breakfast at at a place that's going on 30 years in the neighborhood. After, you'll visit a small art gallery focused on contemporary African and African diaspora art. Finally, it all ends with a few beers at a massive brewery nearby.

In this guide, you’ll be taking in the history of Edgewater which encompasses several smaller neighborhoods like Edgewater Beach, Edgewater Glen, Magnolia Glen, and Andersonville. You'll take this in both through a museum visit and boots-on-the-ground fieldwork. All good walks should come with rewards, though, and don’t worry: high-quality coffee awaits at the end of this excursion.

For this guide you'll be grubbing at the back of a Korean grocery store, and afterwards, you'll take some to-go dumplings and head down the street to one of the largest breweries in Illinois

Get your walking shoes ready, because we're going on an old fashioned neighborhood walkabout. The plan for the day is a one mile jaunt through Lincoln Park that's got a bit of an international flare. It starts with Taiwanese bubble tea, then olive oil and lemon drenched Greek chicken and fries, and we end the day at a Chicago apartment building from 1920's that's been converted into an art gallery and cultural center. 

We’re going music and book shopping in Andersonville today. The great thing about record stores and bookstores is that you don’t have to buy anything to enjoy yourself—browsing covers and reading back summaries, mind racing with anticipation of what’s contained—that’s its own fun. The difficult thing about records and books is you usually want to buy more than your wallet allows. Today, we’re looking at three different shops in Andersonville’s famed commercial district on Clark Street.

We're hopping on the Brown line for this guide to see what we'll find if we take it all the way to the last stop (Kimball).  Once you get off the train, you'll find yourselves in Albany Park, a neighborhood on Chicago's Northwest side that's a huge melting pot of various communities. Walk the neighborhood and you'll hear conversations in Tagalog, Spanish, Hindi, English, Urdu, Korean, Spanish, Bosnian, and tons of others being spoken. This guide gives us a small sample of this wonderful melting pot of a community where we can find classic Chicago hot dogs, a late night Mexican pastry shop, and coffee and cocktails all within a few blocks of each other. Here are the highlights.

We've got a lazy Sunday in West Loop on the books. The day starts a local non-profit bookstore to dig through their collection of new and used books.  You'll then take that new novel you picked up and head a few blocks to a coffee house run in partnership with a world-renowned Japanese latte-artist. The day ends in the same place, because in addition to being a coffees house, it's also a bbq restaurant and ramen shop. Here are the highlights.

Chicago's history has been shaped by different waves of immigrants from all over the world, and we're celebrating part of that history with a visit to Chicago's Ukrainian Village neighborhood. This neighborhood has been a central hub for Ukrainian-American's since the first mass migration of immigrants in 1870.  Our trip to has us taking in Ukrainian food, art, and history on this three-stop guide.  Here are the highlights.

This guide has you going on a classic neighborhood walkabout around Humboldt Park. It starts with a Coney Island hot dog at a corner hot dog shack. You'll then head to an occult bookstore for a tarot reading session. Afterward, you're breaking for apple pie at a throwback diner with some strong 1950s vibes. More shopping follows at a feminist-inspired gift shop. We end things at a neighborhood cocktail bar with a mix of art deco and modern Southwest design flair.

This guide takes you on a mini Swedish adventure in Andersonville that works great as a chill Sunday afternoon outing. This is a historically Swedish neighborhood on Chicago's Far North Side, and we'll be doing our best to immerse ourselves into the food and culture. Here are the highlights.

This guide has you strolling through fields of wild flowers and exploring an island nature preserve on the South Side. But before that, you'll grab brunch and beignets at a French cafe and then head down the block to a basement bookshop where you'll grab a book to take along our nature walk. Here are the details.

This guide takes us to Chicago's Bridgeport neighborhood, where we'll spend the afternoon doing a reverse progressive lunch. We start with dessert and scarfing down a paczki or two; we then grab some tavern-style pizza at an old-school neighborhood pizza place, and then we finish things off in a converted industrial space turned brewery.

This guide has us visiting Chinatown but we won't be getting there by car, train, bus, or bike. In fact, for our mode of transportation, we won't need roads. We'll be taking the water taxi to Chinatown for some deluxe dim sum. Here are the highlights.

Twenty-five years ago, on the southern end of the Roscoe Village neighborhood, an eight-block stretch of Belmont Avenue was home to 'Antiques Row.' At its peak, upwards of 30 antique shops and resale markets clustered along this one-mile corridor. Nearly every other shop was an antique shop. The scene then was like a bustling flea market with vintage furniture and knick-knacks pouring out the door and onto the sidewalk. But nothing lasts forever; shops closed or moved one by one, and today there are only a few left standing. You're visiting three antique shops that continue the legacy of Antiques Row, and afterward, we make our way to a local tavern to take stock of our shopping haul. Here are the details.

We're hanging out in Bridgeport and going on a classic neighborhood walkabout. It starts off with coffee at a beloved neighborhood cafe, and then you'll cut across three residential blocks to visit a public art exhibit and gallery. You'll then walk along one of the Bridgeport's main thoroughfares to grab a 3lb burrito at a corner super market. Things end at a rock quarry turned park with spectacular views of downtown.

This guide takes us to Chicago’s Southwest side. We’ll be exploring Little Village, or La Villita as the locals know it. Considered to be one of the city’s largest and most cherished Mexican-American communities, we’ll be getting a small taste of some of the local favorites, along with a peek into a newer establishment that is proud to call this neighborhood home. Here are the details.

We're headed to Chatham on Chicago's South Side. For this guide, we met up with Jahmal Cole, founder of My Block, My Hood, My City, a Chicago non-profit organization that works with students from under resourced communities, and takes them on city explorations throughout Chicago. He takes us around his neighborhood to grab giant donuts, have a plate of chicken and waffles, and tell his story.

This guide takes us to the heart of Hyde Park where we'll start the day with breakfast at President Obama's favorite diner. We'll then take a short stroll through the neighborhood and stop by a few interesting places nearby.  Finally, we finish the day with a some much needed quiet time in a tranquil Japanese garden that feels like an oasis in the middle of the city.  Here are the highlights.

No matter how long you've been in Chicago, the city's skyline and its architecture will always find a way to stop you in your tracks in a daze of wonderment. Maybe it happens during "Chicago Henge, " the twice a year phenomena where the sun sets in perfect alignment with downtown's grid patterned streets. Or perhaps it's during your daily commute on the Brown line when the train crosses the bridge over the Chicago river. For this guide, we’ll try to replicate some of those awe inspiring moments on a downtown tour where we’ll see the city from high above and walk down the halls of historic buildings. Here are the details.

For this guide we're headed all the way to 112th street on Chicago's South side where we'll tour a historic neighborhood and learn a little bit about one of the nation's first planned industrial communities.  While we're down this way, we're also going to visit a nearby smokehouse down by the river. Here are the highlights.

We're going to head to Oak Park to visit the home of the greatest American architect to have ever lived. From downtown, we're hopping on the CTA Green line for a short 30 minute ride to Oak Park where we'll be dropped off near the Frank Lloyd Wright–Prairie School of Architecture Historic District. This historic district, which covers a large chunk of downtown Oak Park and the surrounding residential areas, contains the largest collection of Frank Lloyd Wright designed buildings in the world. There's no way to see everything in one trip but you can follow along this introductory guide to get you started. Here are the details.

For this week's guide, we're headed to Little Italy on Chicago's Southwest side, and exploring it two different ways. It's kind of like a 'pick-your-adventure' type guide where you can choose to either dine on a plate of chicken picante at a classic Italian eatery and finish off at an Italian ice stand, or grab some picnic provisions at an Italian grocer and have lunch in a nearby park under the city skyline. Here are the details.

We're headed to Chicago's Southwest side, and spending the evening feasting on a mashup menu of Korean-inspired Polish food. We'll then walk down the street to visit an experimental cultural center that hosts a broad array of  events like festivals, performance art, comedy shows, and art exhibits.  Here are the details.

Andersonville is, without a doubt, one of Chicago’s most personality-filled neighborhoods. From its Swedish heritage to its catering towards the LGBTQ+ community, many people find it to be a great, community-oriented place to call home or turn into a regular hangout. It also houses a few spots unlike anywhere else in the city. The journey to this Northside neighborhood is filled with taxidermy, magic (literally), and  good drinks.

A good neighborhood is one that can offer entertainment and good hangs at any time of day. We love West Town for that. Its nightlife scene continues to build and bustle, but the streets definitely aren’t dead before the sun sets. We filled a recent Sunday with brunch, beer drinking and shopping along Chicago Avenue. It’s the perfect “Sunday Funday” to replicate if you’re looking to have a great time, but still be home by 4 p.m.

We're headed to Pilsen for this guide and doing a neighborhood walkabout to catch some of the sights and sounds of the area. The neighborhood is constantly changing and if you haven't been here in awhile, then you'll probably find something new the next time you visit. On the docket today is a Vietnamese coffee, a community bookshop, a local artist shop, a massive plate of deep-fried carnitas, and finally some churros to end the day. Here are the details.

We're spending the day getting cultured on a museum crawl on the South Side. We'll be visiting a fine arts museum on the University of Chicago's campus, then over to an independent museum dedicated to African American culture and history. Afterwards, we're walking up a tower to get a birds-eye view of Hyde Park, and finally we do what we do best -- eat some soul food. Here are the details.