The Outdoor Happy Hour Guide

Where to get cheap drinks when it’s warm out.

Imagine with us: It’s a warm, breezy weekday in pre-pandemic Chicago. The clock strikes 5:17 pm. You still have some client work due, but it can wait till you get home.

You leave the office, smirking as you wave goodbye to your coworkers. Unbeknownst to them, you’re going to meet some actual friends (whose company you genuinely enjoy), for discounted drinks, maybe a few wings, and dollar oysters - all shared while sitting within six feet from each other. You split the tab and head home, floating on a cloud of cheap rosé, deep-fried goodness, and pleasant conversation. Life is good.

Now wake up. Except for the dollar oysters and discounted drinks, things are different now. But Happy Hour doesn’t have to be. Here’s a list of 16 Chicago spots that are still doing great Happy Hour specials outside.

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The Outdoor Spots

When: Monday-Friday 4-6pm, all day Sunday.

The Deal: $20 Pitchers, $5 Select Drafts

West Loop brewery and taqueria, Cruz Blanca, has $20 pitchers and $5 select drafts. As a bonus, there are even a few TVs inside you can see from the patio - perfect for mindless staring while contemplating the state of the world. And Leña Brava, (which is right next door and from the same team), also has a decent Happy Hour. There you can try their featured tostadas while drinking $6 glasses of rosé.

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Kennedy Rooftop


When: Monday-Wednesday, 4-6pm

The Deal: $3 Off Signature Cocktails

You can get $3 off signature cocktails at the Kennedy Rooftop in Wicker Park. Come for the cocktails, stay for the leafy-backdrop/neon sign you’ve been seeing all over your feed. Don’t forget your cute masks and those socially distant happy hour hashtags.

When: Monday-Thursday, 4-7pm

The Deal: $4 Select Draft Beer, $6 Draft Wines, $8 Select Cocktails

Time Out Market has eight restaurants under one roof, so it’s a good option if you need some variety after being stuck working from home all day. And if you spend $12 from any vendor, you get drink discounts: $4 select draft beer, $6 draft wines, $8 cocktails, and complimentary fountain drinks.

When: Monday-Friday 3-6pm

The Deal: $5 Small Bites, $8 (or less) Drinks

Happy Hour at Avli is an excellent opportunity to sample a variety of Greek drinking bites. Try small plates like kataifi prawns and taramosalata, while enjoying their selection of Greek liquors - like ouzo, mastiha, and tsipouro.

When: Tuesday-Thursday from 4-pm

The Deal: $7 Cocktails and Bites

Serving up Mexican-inspired drinks and dishes, Pilsen restaurant La Luna offers $7 cocktails and rotating specials. And Wednesdays they have $1 oysters and $6 glasses of cava - both perfect for enjoying on their sidewalk patio.

When: Monday-Friday 4-6 pm

The Deal: 1/2 Priced Bottles of Wine & Select Cocktails

Despite the name, Machine Engineered Dining & Drink isn’t known for heavy metal music and industrial decor. Instead, thanks to the attached flower shop, Machine’s known for having beautiful floral arrangements and equally pretty cocktails. And during the week you can try a couple discounted drinks, and split (or not split) a bottle of 1/2 priced wine with a friend.

When: Tuesday-Saturday, 5-6 pm

The Deal: 1/2 Priced Bar Snacks, $5 Beer, and $7 Select Cocktails

Like its regular menu, Funkenhausen’s Happy Hour is a little German, a little southern, and a lot of meat. You can snack on rib tips, spicy smoked chicken leg, a hot schnitzel sandwich, and wash it all down with a $5 Krombacher pilsner.

When: Tuesday-Friday 5-6 pm

The Deal: 1/2 Priced Bar Snacks and $7 Cocktails

Argentinian steakhouse El Che offers 1/2 priced bar snacks and $7 cocktails - a good enough deal to get you in the door. But while you’re there, you should also check out their meat market, which has a bunch of fresh steaks, sausages, and chops. It’s almost the end of the grilling season, and you can use their dinner menu for some flame-charred inspiration.

When: Tuesday-Friday 5-6 pm

The Deal: 1/2 Priced Beer, Wine, Cocktails, And Bar Snacks

It’s a tiny window of time, but from 5 pm till 6 pm Duck Inn has 1/2 off their entire menu of beer, wine, cocktails, and bar snacks. And if our track record at weddings with an open bar is any indication, a lot of damage can be done in an hour.

When: Monday-Friday 3-6pm

The Deal: Discounted Sake, Beer, and Yuzu Margaritas

As it starts to get chillier, a ramen Happy Hour might be just the thing to warm up your week. Ramen-San offers discounted sake, beer, and yuzu margaritas every weekday from 3-6 pm.

When: Wednesday-Friday 4-5:45pm

The Deal: Specials on Bar Bites, Beer, Cocktails, Wine

Virtue’s Happy Hour, aptly named Pot Liquor Time after their collard greens (which you should totally try), features lots of tasty deep-fried southern delicacies like pork cracklins, buffalo mac and cheese bites, chicken-fried cauliflower, catfish sliders, and an impressive selection of booze. And it’s all priced under $8.

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When: Wednesday-Sunday 5-7pm

The Deal: $30 Unlimited Chaat and Sangria

Vermilion’s Happy Hour is a $30, and a combination of unlimited chaat (like pakora, pani puri, and kale bhel) and spiced sangria.

Land & Lake Kitchen


When: Daily 4-7pm

The Deal: Specials on Snacks, Beer, Cocktails, Wine

Land & Lake Kitchen is one of those rare restaurants that manages to have a large patio and a three-hour-long Happy Hour where nothing on the menu is over $10 - right in the middle of the Loop. Even if you’re not in the neighborhood for work anymore, this spot is worth visiting.

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