Tips on enjoying Chicago's nightlife as recommended by Maddie Rish, a Chicago native and nightlife enthusiast. Maddie is part of the founding team of Everfest, the world's festival authority and largest festival community. Festivals were her first love - next came red wine, craft beer, writing and travel.
Chicago is one of America's most important cultural hubs, with a partying scene that is just as diverse. With a dizzying array of things to choose from to do, here are the local insiders' top picks of what's hot in Chicago Nightlife.
Best happy hour spot: Division Ale House
1942 West Division Street
If you can believe it, there was a period of time--we’ll call it the dark days--when happy hour, by definition, was banned by law in all of Chicago. I suppose there were some concerns about people drinking excessive amounts in too short a time - weak, I know. But fear not, happy hour enthusiasts. This past summer, Governor Bruce Rauner signed a bill that allowed the return of happy hour drink specials all across Illinois (thanks, Bruce!). If you’re looking for one of the best happy hour spots in The Windy City, I’d recommend Division Ale House - a friendly, Irish neighborhood bar in the heart of Wicker Park. Ale House has super authentic Irish vibes, an epic food menu and the following happy hour deals to start off your Chicago nightlife experience:
- Every Monday through Thursday from 6-9pm: $416oz draft beers, $4 cocktails and $5 wines by the glass
- Every Friday, the bar offers a $20 meal package, which includes a dank Certified Black Angus burger with choice of side and Bud Light drafts (also from 6-9 pm)
Best live music venue: House of Blues
329 North Dearborn Street
The House of Blues is a famous staple in Chicago’s live music scene, drawing in epic acts across all genres. With a capacity of 1,300 people, the venue is pleasantly intimate but full of vibrant, tangible energy. The sticky floors and tight crowd is more than worth it for the up-close-and-personal concert experience. On top of frequent local acts, big name artists make a stop here every so often to take a break from their arena-filled tours (I’ve seen STS9 here 3 times). Come to the House of Blues if you’re down to get a little rowdy and experience one of Chicago’s most beloved venues.
Best spot for drunk munchies: The Weiner’s Circle
2622 North Clark street
Ah, good ole’ Wiener’s Circle. The quintessential gathering spot for hungry partiers as they stumble out of the bars at 3 am. The Wiener’s Circle is a place locals hate to love and love to hate – but alas, it remains as one of the go-to spots to satisfy our drunken cravings. And for visitors – well, you simply don’t have a choice.
To understand the true spirit of The Wiener’s Circle, you have to go there and experience it for yourself. But for now, the next best thing is to hear the outrageous stories involving the establishment. Talk to locals, and they’ll tell you about the time they got into a tift with the ladies behind the counter (this is more common than not). Others will tell you about the time they ordered a ‘chocolate shake,’ which is a far cry away from the ice-cream based treat you’re used to. However, if you asked me, I’d tell you my own story of the time my friend picked me up, threw me over his shoulder, and dropped me on the cement by the Wiener’s Circle picnic tables while a hoard of late-night eaters watched. By the time I was able to stand up, it was blatantly obvious that I had a badly broken collarbone - but in the spirit of the Wiener’s Circle, I downed two double cheeseburgers before considering a hospital visit.
So, if you really want to tackle this establishment like a local, there’s four things you need to know:
- If you go on a weekend night, you will wait in line. But it’s worth it. So worth it.
- Drunk or sober, you will order the char dog or the cheddarburger and it will be everything you’ve ever wanted.
- Ask for a “chocolate shake,” but when you do, don’t expect the traditional icecream-based treat. Brace yourself for something a little more along the lines of, well, you’ll see. But don’t say I didn’t warn you.
- Try not to take it too personally if the ladies behind the window are a little bit rude. It’s part of the experience. Just don’t end up like this guy, who learned his lesson the hard way.
Best spot to grab a beer: Old Town Pour House
1419 North Wells Street
Located on bustling North Wells Street, this popular bar and restaurant is full of energy. If I had to guess why, I’d say it has something to do with the 90 unique craft beers they have on tap at all times. (Yeah man, I said 90.) Not only does Pour House have one of the largest draft brew collections in the United States, but they also happen to have one of the best beer lists in Chicago - and that’s not just my own opinion. Stop in at any time between lunch and bar close and you’re guaranteed a good time.
Best hangover cure: Tweet
5020 North Sheridan Road
It’s 11 am on Sunday morning, and you’re milking the only brain power you have left to figure out if what you’re experiencing is a severe hangover or just full-throttle inebriation lingering from last night’s shenanigans. At this moment, you’ll be thanking me for putting Tweet on your radar.
My memories of Tweet are characterized by spicy bloody marys, an endless flow of mimosas and a breakfast dish the size of a small human. The place is always packed, but you can wait for a table with an Ecstasy Bloody Mary from Big Chicks, the restaurant’s bar which has it’s own room in the building. You’ll leave Tweet with a food coma that’s equally as debilitating as your previous hangover, but I never said anything about the best food coma cure, did I?
Best Chicago festival: Lollapalooza
337 East Randolph Street
There’s a reason – many reasons, actually- that Lollapalooza draws in 120,000 festival-goers every year. First, there’s the consistently unparalleled lineups, which always include the biggest names in the industry across all genres. And then there’s the fact that it takes place in the heart of the city at Grant Park, making it one of the only festivals in the country with a clear view of the city’s picture-perfect skyline. Hit up Lolla for a weekend of beat-bumping chaos followed by massive after parties at some of Chicago’s hottest night clubs and music venues.
My favorite part of Lollapalooza is seeing how the city itself undergoes a complete transformation. Everywhere you go downtown, you see mobs of a smiling revelers buzzing about the weekend’s festivities. There’s a tangible excitement in the air that you only find in the Windy City.
Honorable mention: Taste of Chicago
Best craft cocktail spot: Barrelhouse Flat
2624 North Lincoln Avenue
If you have plans to party in Lincoln Park, Barrelhouse is the perfect spot to start or end your night (if you’re me, you’ll just never leave). This trendy establishment has two levels; head to the top floor if you’re on a date or looking for loungey vibes. Downstairs tends to get a little rowdier on weekend nights, with the occasional frat bros causing some sort of scene. This bar is open until 4am on Friday and 5am on Saturday, making it one of the few late night bars in the city that maintains its dignity after two in the morning. In addition to the cozy, trendy atmosphere, the craft cocktails at Barrelhouse are something to write home about. The bartenders certainly know what they’re doing and consistently serve up delicious and impressively artistic drinks. In a city where a decent martini typically costs $14 or $15, these $11 cocktails feel very reasonable.
Pro Tip: If you’re coming to Barrelhouse Flat, plan on eating dinner down the street at Lou Malnati’s. Why? It’s quite simple - you do NOT leave Chicago without trying Chicago-style deep dish pizza. You’d be a fool if you did. You don’t want to be a fool, do you?
Best boozy brunch: LOKaL
1904 West North Avenue
Photo credit: Trip Advisor
Who says the party stops at bar close? In Chicago, partying manifests in many forms - my personal favorite being the kind that involves delicious food and bottomless mimosas at the start of your weekend morning (or late afternoon, more realistically). Boozy brunch is somewhat of a mandatory happening in Chicago. Sort of like waking up and brushing your teeth, boozy brunch is one of those activities that’s permanently built into your weekend schedule.
Swing by LOKaL for a taste of what boozy brunch is all about. With locations in two of Chicago’s most beloved neighborhoods - Wicker Park and Lincoln Park - it’s no surprise that locals love this restaurant and lounge. Boozy brunch deals: $7 all you can drink mimosas (what?!), $10 Bottomless Bloody Mary’s (WHAT?!), and an epic food menu with the likes of nutella fritters and duck confit benedict. Need I say more?
Honorable mention: Little Goat Diner