Andersonville’s beloved dive bar, Simon’s Tavern, is one of the best places for a drink in Chicago. It’s friendly and no nonsense with the occasional band and well-curated jukebox. Simon’s has opened a back patio. Hopefully the good times will continue through the holidays when warm glogg will be poured and cookies handed out to customers.

Dovetail, part of “Malt Row” in Ravenswood, has created a beer garden right underneath the CTA “L” tracks. The brewery serves some of the city’s best lagers and is a wise stop to celebrate Octoberfest. Sidewalk seating available for walk ins, but the patio requires reservations.

This Irving Park bar has been a haven for craft beer drinkers back when folks were calling them the less trendy “micro brews.” While the beloved space isn’t welcoming customers, folks can order a variety of bottled drinks to take home online.

The East Room needed to mature; its owners were growing up. So they’ve created a back patio that focuses on natural wine. The picnic tables are comfortably socially distant, and the staff is kind. Customers can also buy wine to take home by using their smartphones.

Chicago has another new rooftop hotspot — this time above the legendary Second City comedy club in Old Town — in the form of the whimsical Utopian Tailgate. As the name suggests, the theme here is tailgate food, drink, and games, but with fun and weird twists. Brightly-colored decor, oversized games, and a wild menu that includes “munchie bowls,” a “gin & chronic” cocktail, “l’il kegs” and coolers of beer, and a large space with lots of sun are keeping it bustling in the winter.

One of downtown’s last dive bars is still fighting. While patrons can’t enjoy the new flooring the owners installed, they can grab a to-go drink and enjoy at along the nearby Chicago Riverwalk.

The timing for this outdoor venue was perfect in Fulton Market, a huge venue surrounded by shipping containers that made it perfect for social distancing. Chicagoans will want to at least visit Recess once before winter snow makes it unbearable. Sample large-format cocktails served in mini water coolers, and enjoy the unique view of the city. Reservations recommended.

Julia Momose’s drive helped ensure state lawmakers allowed bars to sell to-go cocktails, which isn’t a small task. The star bartender, and her partners at Kumiko, continue to sell to-go drinks that are expertly mixed and balanced. Momose is trying to bring Kumiko’s unique experience home and even offers craft ice to those who want to go the extra mile. While Momose and her staff can’t pour customers flights of customized drinks at home, this is the second-best thing.,

The busiest patio in Pilsen (which also has plans to open in Lincoln Park), serves plenty of margaritas inside a boisterous space that draws younger customers. Expect to wait in lines on weekends.

Kenny Johnson has brought his Little Italy bar to the South Loop. This is a full-service restaurant with a popular weekend brunch on a sidewalk patio. There’s also large windows that allow customers to seek cover if needed. Reservations are available via Tock.

Osito’s, which opened in 2019, is geared for the rain with tent and heaters for outdoor service. Find an array of fancy liquors like mezcal and tequila, and a great selection of beer. Osito’s also sells food, including tacos. Reservations via OpenTable. They have offered to-go cocktails and growlers. Check with management to see if they’ll return.

Inside the Sophy Hotel, Mesler Kitchen has become a community meeting space along busy 53rd Street in Hyde Park. This isn’t a normal hotel bar. It’s well designed and comfortable. A covered sidewalk patio provides outdoor space and two cocktails are available to go. Reservations via Resy.