Between the Windy City and the City that Never Sleeps, you’ve got plenty to choose from when it comes to great food and drink. But, when it comes to a great breeze and gorgeous views that aren’t overcrowded, there are a select few The James recommends.

We’ve compiled a shortlist of Chicago and New York City go-tos for outdoor dining and patio bars that won’t disappoint. Fresh local ingredients mixed with a bit of underground charm were considered, so be sure to grab cocktails and bites before the word gets out. 


Located at The James, this speak-easy-style spot is outlined by greenery, dividing guests from Rush Street. The space allows for 35 cocktail connoisseurs to enjoy the lounge’s peaceful patio. There is also bench seating where patrons can sip on beer, wine and bottled cocktails carbonated in-house.

Primehouse Ice Cream Pop-Up
Sundae’s are on Fridays this summer as the Primehouse Ice Cream Pop-Up Shop returns. Discover a new flavor each week for $5 a scoop and optional sundae toppings. Every Friday from 4 to 6pm through August 26 on The Patio.

The Long Room
This homey outdoor spot has an artistic feel and sociable mood, mixing regulars with revelers looking for something new to eat and drink.

RM Champagne Salon
Look close enough, and you’ll see an unmarked alley leading to cobblestone-laid parlor. Reminiscent of Paris, you’ll wash macaroons down with champagne under sparkling lights strung overhead.


David Burke Garden
The 130-person space is surrounded by herb beds and flowers and whimsically decorated with sculptures. Settling at the bar, patrons enjoy the signature sun-brewed iced tea with flavors Meyer lemon, hibiscus and ginger-peach. Snacks and starters are also available: tomato ricotta and eggplant trifle, tuna tartar tacos with whipped avocado and tomato gazpacho with watermelon and rock shrimp.

Mulberry Project
Though spending time in New York City is an escape in itself, sometimes a break from all the hustle and bustle is in order. This Little Italy bar’s "Tulum patio" feels like a little slice of solitude and Chef Carmine di Giovanni’s new dishes have already gotten rave reviews, including lobster sliders, chicken wings, and three types of grilled-cheese sandwiches.

This new restaurant has a 52-seat terrace that wraps around the corner of the Whitney Museum at 99 Gansevoort Street. Following its launch, only drinks are currently available outside, but full-service lunch and dinner menus are set to be announced soon just in time for spring.