Chicago’s best happy hours under the sun

By Anthony Todd

There’s nothing better than drinking outside in the summer—except drinking outside in the summer when the drinks are cheap. Thankfully, plenty of Chicago restaurants have combined amazing sunny spaces with cheer-worthy happy hour deals to create an irresistible combo. Here are some of our favorites.

Boleo
Boleo’s epic, South American–themed rooftop is the perfect spot for a downtown drink after work. It’s even got a retractable roof, so no matter the weather, you’ll feel like you’re in a tropical paradise filled with plants, Latin music, and delicious cocktails. Every Wednesday and Thursday from 5 until 8 p.m., take part in their #8for8 promo, where eight items off of their menu are just $8—and there are plenty of drink specials to keep you satisfied.
Neighborhood: Loop MAP

Nellcôte


Nellcôte
Nellcôte’s interior is so pretty and bright, it’s easy to forget they even have a patio. But they do—and wrapping around the building, it’s absolutely dripping with beautiful hanging plants. Every weeknight from 5 to 7 p.m., you can get one of their awesome pizzas (they mill the flour in-house) and a Modelo beer for just $10—a perfect treat for a beautiful weekday night.
Neighborhood: West Loop MAP

Mon Ami Gabi
Mon Ami Gabi is celebrating the summer of Rosé! In their walled-in, secret-garden patio in Lincoln Park, they’ve got a special new all-rosé bar to quench your summer #roséallday thirst. The patio opens early—at 3 p.m. on Friday, Saturday, and Sunday—and offers an array of specials, including charcuterie, truffle frites, and more. Plus, full dinner service starts at 5 p.m., so you can cruise right into your weekend date.
Neighborhood: Lincoln Park MAP

Derek Richmond
Bar Lupo


Bar Lupo
Bar Lupo’s patio, on a somewhat sleepy section of Huron Street, is a great spot for some Italian drinking. Luckily, they’ve got some great deals, too: from 3 to 6 p.m. each weekday, join them for “Aperitivo,” their Italian happy hour. Choose from a variety of $4 beers and wines, and $5 rotating spritzes. Pair the drinks with their awesome (not discounted, but it’s only $8) ricotta toast with truffles and honey, and you’re pretty much set for the night.
Neighborhood: River North MAP

Castaways Bar and Grill
Castaways isn’t exactly a fine-dining destination, but there is literally no way to get closer to the water at a bar in Chicago—it’s right on the beach. They’ve also got some pretty great drink specials, especially if you can go early on a Tuesday, when you can sip on $5 margaritas from 5 to 9 p.m. It may be the slowest night of the week, but this is a deal you should definitely take advantage of.
Neighborhood: Lincoln Park MAP

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