This chic steakhouse is a nod to old-school dining, with white tablecloths and a fantastic selection of drinks, but it’s taken a modern approach with rich, purple walls, candelabras, and a dark, elegant ambiance — plus the bar is just stunning. Grab a seat there if you can to people watch, and chat over some great apps and drinks. (A must-try? The Heart in a Cage, which has earl-infused Grey Goose (!!!), spiced raspberry, lemon, and egg white.) This would be a great pick for a smaller, more intimate group of friends who want a well-crafted meal to go along with their catch-up and cocktails. And don’t miss out on the seafood tower — it’s a must-have. 

From the owners of Concrete Cowboy comes a new River North concept in Clutch. Grab your friends and come early before the crowds for dinner (you won’t go wrong with the classic Clutch burger and truffle fries), and stay for the dancing and cocktails. Order a pitcher of the Wild Ginger Mule for the table and ring in the holiday season the best way you know how.

You’ll be hard-pressed to find a more diverse cocktail menu in all of River North. Arbella specializes in “global” cocktails, all inspired by regions around the world and their flavors. Your group of friends will want to settle in for an around-the-world spirited tour, starting with a few vodka cocktails. Start out easy with the Pretty in Pinkish cocktail, a ginger and rhubarb-infused vodka cocktail with hibiscus and grapefruit mixer, and work your way up to the Aren’t You a Fineapple, a mix of vodka, bianco port, pineapple, chile syrup, pepper ice, and Red Bull yellow edition.

Come for the Instagram-worthy decor, stay for the awesome drinks and food. The nautical theme is carried throughout the River North restaurant and bar, and it even features a “rosé all day” sign that you’ll surely see in many a social media post. But the drinks and food are also standouts — we say get some photos and drinks to start the night off right. And you don’t have to stick to rosé; there’s also some great cocktails on the list, including the brunchtime Hampton Bloody Mary, made with their house-made Bloody Mary mix and vodka. Pssst… there’s also a newer Streeterville location that’s worth checking out. 

Another River North haunt, this gastropub and sports bar has all the things you need for a good time: good food, plenty of space, and a great beer selection (over 100 beers and some booths even have their own tap!). Don’t miss out on the amazing cake shakes, which are milkshakes topped with a slice of cake, and make sure to order a Pear of Kings cocktail, featuring Grey Goose La Poire, Ty Ku Black, St-Germain, lemon, and lemon-lime soda. Hang out with friends at brunch or get some dinner before hitting up the spots in River North — but like most places in the area, it also can get rowdy at night, so you might just want to stay awhile and make a night of it. 

Located in the LondonHouse Chicago hotel, this sleek establishment has three levels of drinking and dining with indoor (and outdoor, weather permitting) seating and great views. LH on 21 is the indoor lounge on the 21st floor that has an industrial look and feel, with plenty of big tables and seating for all your friends and family. Call ahead for reservations to ensure a great spot, and do yourself a favor and order a Moscow mule made with vodka, Owen’s Ginger Beer, lime, soda, and mint. 

Located at the top of theWit hotel in the Loop on the 27th floor, this beautiful bar has floor-to-ceiling windows and a glass roof that give you uncompromised skyline views. If you go before sundown, you’ll get to see the beautiful interior sparkle that much more — at night, the place gets livelier, often with rotating DJs and live music sets, and they’ll open up the space to create more room to dance. You can go ahead and order bottle service of Grey Goose for a good time, or order from a bevy of cocktails, including the Breaking News with Wolf Spritzer that features Grey Goose, blueberry-infused St-Germain, grapefruit shrub, pamplemousse La Croix, and sparkling wine. Make sure to check out the calendar before heading there (they do host events), make a reservation, or go on the early side to pick the best place to perch.