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. These are the best places for casual drinks in River North. At least start here before saying screw it once you hear D Wade 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 drunks session with some wagyu beef sliders and flatbreads. Ten out of ten people that live or work in River North have been on a first date here.
If you want a glimpse into what River North was like as little as fifteen years ago before all the trendy restaurants and fancy clubs, just walk into Rossi’s Liquors. It’s a dive bars among dive bars, and it’s a dying breed in the neighborhood. From the outside, Rossi’s looks particularly neglected because most everything else around it is so nice, but it’s really no different than your typical neighborhood watering hole throughout the rest of the city. Stop by Rossi’s for cheap beer and a low-key time.
Not that River North needed a new cocktail bar, but we’re not complaining about the addition of Arbella. It’s high ceilings, brick walls, and colorful murals make it a comfortable place to sit, and the cocktails are fun and interesting to spice things up a bit. The menu reads like a map of the world in alcohol form, so try something you’ve never had before like a Funky Chicken, a-rye based drink with Mexican spices involved.
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.
We’ve generally found that people either love Boss Bar or absolutely hate it. Guess which side we fall on? Boss Bar was our home base for a while when it was still a total dive a few years back. And while a recent expansion and makeover has made it nicer than it used to be, the older part is still similar. Boss Bar mainly has the look and feel of a dive in River North, but the fact it’s open until 4-5am every night of the week attracts a lot of different people. You’ll get everything from industry folks, after-work 9-5 people during happy hour, and those shuffling out of Paris Club next door at 3am on the lookout for one more drink that’s inevitably a bad idea.
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.
Public House isn’t necessarily the best at anything, but it’s really good for a lot of situations. It’s trendy compared to your typical sports bar, but casual for River North. There are plenty of TVs if you want to catch a game. And the bar food is above average. All of these things make it an overall great utility bar in River North, which is why we recommend keeping it in your back pocket if you’re around Hubbard Street.
A sleek and trendy bar on Hubbard St., Celeste manages to keep the douchiness in check. Post up at the bar or a table on the first floor for quality cocktails, hit the rooftop for a serene space when it’s nice outside, or head to the newly remodeled second floor that’s now called Disco late at night if you want to dance. Celeste is ideal for being a little more upscale without getting stuck-up about cocktails, and that’s a good balance for River North.
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 Tavern has just the right amount of old man cranky tavern on the corner vibes, while still managing to be cool. The building was built approximately a million years ago in 1872, and it’s been a bar and restaurant for almost 100 years. Not only did it survive prohibition, but the basement functioned as a secret bar during those times. Today, the secret basement bar is a separate area known as The Drifter where you can get creative cocktails and catch a burlesque show. But we rely on the main floor of Green Door, where it’s always a laid-back good time.
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. But 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's a great spot to get a little loose on the dance floor if you've outgrown the days of Social Twenty-Five across the street.
Like The Broken Shaker, The Berkshire Room is a bar in 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.