Night Crawler

For less than the price of a cup of coffee, you can go see one of the best improv shows that Chicago has to offer. This evening, you’ll sandwich that show between some delicious craft cocktails at a neighborhood watering hole and dinner at a quaint bistro with a Michelin nod, all within a four-block stretch on West Diversey Avenue.

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" bars. You'll start off the outing with Mexican food and a cocktail in a setting that’ll leave you booking a flight to Cabo. Not only that, but what looks like a normal restaurant from the outside is also home to a speakeasy open only on the weekends. The night will continue with another tucked-away bar where you'll enter a nondescript door lit by a sign with a small bird and question why you ever went to traditional, visible bars in the first place.

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 ideal place to spend a night out. Tonight’s classic Lakeview evening will bring you down the Southport Corridor where you’ll start with a drink at Corridor Brewery and Provisions before dinner and a show at Coda di Volpe and Schubas Tavern, respectively.

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 and Wicker Park neighborhoods. You'll start with dinner at a natural wine shop and restaurant for a meal that's described as a fancy picnic. You'll then take in a comedy show at a theater reminiscent of the 1920s Golden Age, featuring ornate Art Deco details, plush velvet seats, and gilded accents. Finish off the night with a drink and a game of pool down the street

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 right in the heart of Lincoln Park. It starts with dinner at an authentic Sichuan restaurant. After, you’ll find yourself at an iconic Chicago blues bar that’s been around since 1968. Finally, the night caps off with a drink and some dancing at a neighborhood watering hole.

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 BBQ spot, followed by a visit to a craft brewery known for its unique selection of beers. The night continues until the early parts of the morning at a nightclub with a history of hosting renowned DJs over the past decade. Surprisingly, all these hot spots are just a brief, 10-minute walk from the Red Line and within a two-minute stroll of each other.

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 comedy show. The performers here are the type where 1 or 2 years down the road you’ll be seeing them on a Netflix comedy special and you can brag to all your friends that you discovered them well before they got big. So kudos to your future self for being able to do that.

For a lot of Chicagoans, it's not about getting used to the cold-weather season but finding ways to cope with it until summer rolls around. This guide is one of those coping mechanisms. You'll spend the day jumping between pools, saunas, and heated relaxation rooms. In between, you'll stay warm with a sizzling bowl of kimchi soup and other Korean eats. 

Chicago's improv and comedy scene is unrivaled. You can find a show nearly every night of the week, but more often than not, that means hanging out somewhere in Lakeview, Lincoln Park, or thereabouts. For this guide, you'll catch a show on the other side of the Kennedy Expressway. You'll start a small theater in Logan Square making its own name on the Chicago comedy circuit. Afterwards, head up the street for late night patio drinks.

We've got a house party teed up in Humboldt Park. You're going to catch live music and comedy acts in the basement of a Humboldt Park home. Afterward, you're capping off the night at a local dive bar for a taste of the city's best sandwiches and experience that will leave you wanting more.

We've planned a whole night, all within a one-block radius right off the Damen Blue Line Station. It starts with New Haven-style pizza at a brewery with a 20-year history in Wicker Park. You'll then head around the corner, where if you can time it right, you'll have drinks and maybe a bit of karaoke at this bar with an early 20th-century vintage style. The last stop is a speakeasy behind a record store where you'll end the night with a giant cocktail served in a gauntlet.

10 pieces of Korean chicken, 30 plays, and 68 draft lines. That's the setup for this evening excursion in Andersonville. It starts with a late dinner featuring bubble tea and double-fried Korean chicken. You'll then go around the corner to watch not one, not two, but 30 different shorts plays crammed into one hour. Finally, you'll catch a night cap at a Belgian-inspired pub known for its 68 draft lines.

While the rest of the city sleeps, this guide has you going on a midnight escapade through Logan Square and Bucktown. You'll start at a late-night comedy club and then head down the street for post-show drinks at a chill neighborhood craft cocktail bar. After a long night of laughs and booze, you'll end with deliciously greasy burgers and hot dogs at a corner grill shack open until 3 am on the weekends. Here are the details.

We're taking you on nighttime adventure in Chinatown where you'll grab drinks in a backroom cocktail bar and then you'll have a family style Cantonese feast. Here are the details.

There's a large residential section of Bucktown with an eclectic mix of historic greystones, two-flats, and multi-million dollar modern homes. It's the type of neighborhood you can have fun aimlessly wandering around daydreaming about which home is perfect for you. What makes this neighbor even better are the randomly scattered corner bars. For this guide, you'll visit three of these corner bars with three different vibes.

In Rogers Park, there's a narrow cobblestone street full of shops and bars that feels more like old world Europe than it does Chicago. This guide has you spending the evening there drinking hot cocktails, playing old school arcade games, and catching a live jazz performance to cap off the night. Here are the details.

We visit the past and peer into the future all in one guide. You'll make your way to Evanston to visit Northwestern University. It starts with a tour of an art and history museum, and then you'll follow up with an astronomy lesson inside an open-air observatory. Between those stops, you'll grab a bite to eat at a chicken joint popular with students and locals alike. Here are the details. *Logistics note - This guide, in its entirety, is only good for Friday night as the observatory is only open to the public on Friday evenings.

Friday and Saturday nights tend to get all the glory, so we’re going to show Thursday night some love and paint the Uptown drinks, and dancing. Why Thursday? First of all, why not? But more importantly, it’s the only night of the week that Alan Gresik’s Swing Shift Orchestra plays at The Green Mill. You'll start with cocktails in the apartment lobby for craft cocktails and then make your way down the block for more drinks, live music, and dancing.

Every neighborhood has that one classic Chicago corner bar that everyone loves. For this guide, we're visiting three neighborhoods and their corner dives for an epic night of cheap drinks, pool, and good times. Here are the details.

We’ve got a full night of paranormal haunts and magic. It starts at a classic English pub in the heart of Lakeview, where the ghost of a young woman is sometimes said to have trapped people inside. After munching on haunted fish and chips and throwing back a few pints, you'll head to a close-up magic show in a small storefront theater. Here are the details.

The night starts and ends in Logan Square. We kick things off with a 3-hour wheel throwing workshop at pottery studio . We then decompress with your choice of 48 beers, wines, and ciders in a self-serve taproom. Things end the way any great night in Chicago ends -- eating burgers and fries underneath train tracks at midnight. Here are the details.

This guide is for the whisky connoisseurs out there. We're visiting a back room bar to peruse a list of over 400 whiskys and afterwards we head five minutes away for another round of rare spirits. But before all that, we've got to properly prepare ourselves by feasting on Asian versions of cheeseburgers and Italian beef sandwiches. Here are the details.

This guide has us in Lakeview and starts off with a nice wholesome evening of Korean fried chicken and cupcakes. Our wholesome night starts to take a turn when we make to a karaoke bar just down the street. With our night time debauchery fully underway, we end the evening at a basement dance club where we'll be kicking back cheap drinks to 90s/00s hip-hop. Here are the details.

It's the third Friday of the month and that means hundreds of artists in Bridgeport open up their studios to the public. Tonight we're headed to a few different venues that feature a wide range of multi-disciplinary artists with many hosting interactive demonstrations and special events inside their space. Here are the highlights.

Follow along with our shenanigans and embark on this 3-stop cocktail tour in West Town that ends with deliciously juicy burgers and whatever self-respect you may have left. Here are the details: