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 a...
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...
Wine and book lovers, especially fans of the two combined, this one's for you. You'll venture to Printer’s Row, a neighborhood near the South Loop tha...
We've got a short trip planned to Southwest Michigan for a quick weekend getaway. You'll layout on dunes along Lake Michigan's coast, drink whiskey wh...
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...
The night starts on an empty street surrounded by warehouses where you'll have cocktails inside a bustling taproom while a forklift might be operating...
Chicago’s Riverwalk is a labyrinth of life in the heart of downtown. The 1.25-mile-long path, which was expanded in 2016, offers unique city views an...
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 exp...
This lineup is for those in serious need of a dopamine hit. The night takes you along Division Street, where you’ll be surrounded by twinkly lights an...
Day one of your Saugatuck trip focused on enjoying locally farmed cider and exploring the bustling town by water. On day two, you’ll explore by sand a...
Drive south along Lake Michigan and you’re sure to pass through dozens of cute beach towns. But about 145 miles around the lake from Chicago, you’ll f...
Few things symbolize summer like ice cream and boating, and Chicago offers myriad options to embrace them both. The Chicago River cuts through the cit...
In a new addition to our “Known/Unknown” series, we’re heading to Michigan Avenue to pair a Chicago landmark with an overlooked place nearby. The firs...
This itinerary is part of our "Known/Unknown" series, where we pair a Chicago landmark with overlooked places nearby. For fans of literature and archi...
This is part of our “Known / Unknown” series. For each guide in this series, we pair a classic, essential landmark with an overlooked place nearby. To...
This guide is part of our "Known/Unknown" series where we pair an essential Chicago landmark with some more obscure spots nearby. It starts with a lei...
For this week's guide we're adding another edition to our Known/Unknown series where we pair a classic, essential landmark with an overlooked place ne...
We've got another guide to add to our Known/Unknown series where we pair an essential Chicago landmark with overlooked places nearby. Today we're on a...
As the summer heat hits Chicago, you’ll naturally be jonesing for two things: a sweet treat and time in the hot, outdoor air. In this guide, you’ll ge...
The weather warms up, so Chicagoans flock to the elevated 606 trail to get steps in and marvel at how lush the city has become. Today, you'll take in...
It’s springtime in Chicago, and that means the city is collectively regaining its will to live. To maximize your time in the sun and enjoy the city on...
We're taking a short trip outside the city to hike through a 2,500 acre forest preserve. We start by grabbing coffee at a quirky and retro coffee hous...
Access to nature can sometimes feel inaccessible if you don't have a car. But for this guide, the Metra is all you need. You'll take the UP-N line to...
Start your day at a sustainable farm, picking up fresh produce and sipping local coffee. Then, step into a neighboring nature preserve for an easy str...
It’s time for a change of scenery, so for two days this weekend, we’re heading north to Milwaukee — a mini Chicago, as some refer to it. The vibrant W...
About 18,000 years ago, Illinois and Wisconsin were covered under a big sheet of glacial ice. Eventually, these massive glaciers began to retreat, bu...
Imagine Chicago with mountains in the distance. Nobody would ever leave. While we don't have mountains, there are still places to hike to get some ele...
This guide has you hitting the road for a weekend trip out of the city. You'll visit Galena, IL, about a three-hour drive from Chicago and on the bord...
Did you know that just half a mile away from the bustling Magnificent Mile you can step back in time to an age of double-decker, decadent diners? That...
This guide is part of our Good Bites series, and we're venturing out to pick up fresh ingredients to make a classic BLT -- our summer sandwich of choi...
When the cold weather strikes, this guide has you cooking up some eats to keep warm -- or should I say hot -- hot pot that is. To get started, you'l...
We're taking the Red Line to go on a food expedition that starts in Chinatown and ends on the far North side in Little Saigon. We'll make a few stops...
When the weather finally turns for the better, a long walk through the city might just be what you need to shake off the winter blues. This guide take...
This night is about good eats and good drinks. You'll start things off with a dining extravaganza brought to you by a Michelin starred chef on a quiet...
Some of the best meals in Chicago can be found in nondescript, no-frills establishments, it turns out. This itinerary will guide you through exploring...
Lake Michigan and the downtown parts of the Chicago River may get all the glory, but the northern branch of the river is a stone you shouldn’t leave u...
Everyone knows humans don’t deserve dogs. But you can show some appreciation to your four-legged friend by bringing them with you on this dog-friendly...
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...
You want an unforgettable meal, so you head to Fulton Market. The main cobblestone street of the former warehouse district is littered with dazzling d...
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 t...
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 i...
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 d...
Tonight, you're going to head into Logan Square for dinner at one of the neighborhood's only rooftop patios and drinks at some "if you know, you know"...
Lakeview is an easy draw. Its proximity to the great Lake Michigan, seemingly endless options for food and drinks, and lively music scene make it an i...
Everyone knows Chicago is one of the best cities for food, comedy and drinks. Tonight, you’ll combine all three for a lively night in the West Town an...
It’s not uncommon to be overwhelmed by contemporary nightlife spots, so we're going to infuse the night with some rich, old-school history and rhythm...
After a week of being responsible and sticking to healthy eating, it's time to indulge a little. This guide kicks off at a fusion Chinese-Korean BB...
We’re going on a night time adventure in Roscoe Village for burgers, cocktails, live jazz, and a comedy show in the back of a bar. This isn’t any come...
