We’ve all been there. Your finance friend wants to grab a happy hour beer near the office. Your Hinge date wants to meet for a cocktail near their apartment. You have a networking event at Merchandise Mart. We know you’ve avoided the usual River North bar scene since St. Patrick’s Day 2010 – the day a nineteen year old puked on your shoes at 2:00pm on Hubbard Street. The red ropes, the suburban crew going out HARD – it’s just not for you anymore. You’ve grown up. Your fridge is covered in so many wedding invitations it’s like a goddamn Paper Source showroom. You’ve got accent pillows, a Sam’s Club membership, and are saving up for a Dyson.
Yet here you are, because for one reason or another it makes the most sense. So what do you do? Trust us, you can get through River North unscathed and in a relatively adult fashion. We can’t promise that you won’t get cat-called by some gelled v-neck bros or stepped on by a herd of bachelorette parties on the way to Howl At The Moon, but once inside, you’re safe.
These are the best places for casual drinks in River North. At least start here before saying screw it once you hear Joakim Noah is at Paris Club.
The ground level bar in the Hotel Palomar has a bit of hotel vibe going on without being too weird. It also has great snacks if you want to turn up your drinks session with some wagyu beef sliders and flatbreads.
Even if you have a token Southern friend, odds are the majority of your crew is originally from above the Mason-Dixon Line. We point this out because Midwesterners inevitably look awkward in a country style setting on Hubbard Street, which means you’re not fooling anyone with that flannel shirt and ripped jeans, girl from the North Shore. This Southern style barbecue restaurant and bar may be commonplace in Nashville, but it’s a unique breed here, so take advantage of the live country music and whisky list throughout the week.
Technically on the eastern side of Michigan Avenue, Howells & Hoods is close to being in River North. And that’s good enough for us, especially with its big space, big patio, and even bigger beer selection. It’s on the Magnificent Mile without being too touristy, and it can accommodate both small and large groups last minute. You’re probably reading this because you’re bad at planning, so consider a move to Howells & Hoods.
Yes, a tiki theme in a basement is a little weird. Yes, Three Dots and a Dash is often crowded, a little pretentious, and pricey. But it’s fun if you’re willing to have fun with the theme. Reserve a table to ensure some space, or commandeer seats at the bar like Captain Jack taking control of the Black Pearl. The ridiculous drinks served in everything from skulls to treasure chests are unique.
Citizen is perfect for escaping the general absurdity of River North. Head a bit west to the quieter part of the neighborhood where you’ll find a casual bar in the midst of apartment and condo buildings. Come here with your Tinder/Hinge/J-Date/Christian Mingle/Farmer’s Only/E-Harmony/Match.com/OkCupid date who lives or works nearby, and make sure to hit the rooftop bar if it’s nice out.
A sleek and trendy bar on Hubbard St., Celeste manages to keep the douchiness in check. The first floor bar is where you want to be, and the cocktails they are dishing out are rather good. Celeste is ideal for being a little more upscale without getting stuck-up about cocktails. Check out the secluded rooftop garden when it’s nice outside.
Pops Champagne is nice and all, but go to the basement bar, Watershed, instead. It’s way more laid-back than the upstairs champagne bar. It also has a better drink selection, which makes Watershed a much better place to get cozy with a date or catch up with a couple of friends
Green Door has been standing in the same place for approximately a million years, and it’s about as quintessential Chicago speakeasy as you can get. We’re not exaggerating either. The place was built in 1872 right after the Chicago Fire, and 2015 minus 1872 equals one million years old. Green Door is ideal for beers, burgers, and a secret bar downstairs called The Drifter that was once an actual speakeasy during prohibition – there’s a lot of history here.
25 Degrees is one of our favorite utility spots in the neighborhood. It’s unpretentious and has a few TVs so you can catch a game without being engulfed in a standard bro bar. The kicker is 25 Degrees serves excellent build-your-own burgers with a ton of great ingredients. It’s more bar than restaurant though, so feel free to go there whether you want food or not.
The former Tokyo Hotel was a creepy place that looked like the home of ghosts and murderers. Luckily, The Freehand Hotel came in to save the day and renovate the building, and they opened up a pretty cool bar inside. The Broken Shaker is a small area in the back of the main floor that feels like 80’s Miami tiki hut meets grandma’s living room. Sounds weird, we know, but it 100% works.
Henry’s has slowly won us over. Having a pool table right next to the front entrance is a little impractical for both those playing and everyone walking by, but aside from that it’s a good spot to hang. The basement area called The Rec Room feels like Hugh Hefner’s modern library with a small dance floor, and it makes for a good transition move if things loosen up a bit.
Like The Broken Shaker, The Berkshire Room is a bar in another recently renovated River North hotel – the Acme Hotel. Unlike the Broken Shaker, The Berkshire Room is more of a refined cocktail lounge. It’s a great date night spot, especially if you want to drink some interesting cocktails.
JIMMY at the James Hotel is great for an intimate setting. Pull your best 2015 version of the old yawn, whoops, there goes my arm over your shoulder trick. You can also have serious conversations with old friends. Either way, know that the only thing sharper than the cocktails will be the wardrobe of the crowd.