If you’re not a fan of Bloody Marys, chances are high that you haven’t had a good one -- for the record, your collegiate concoction of watered-down V8, well vodka, and a celery stick doesn’t count. Luckily, Bloody evangelists and converts alike can flock to the 11 best boozy tomato cocktails around Chicago.
Yes, you’ve heard about the first-class burger and it lives up to the hype, but the signature Bloody Mary is a stunner by its own right. Piled high with homemade pickles, this marriage of V8, Tito’s, horseradish, and black pepper packs a sweetness that balances the spice. Pro tip: it gets seriously crowded here, so you may want to stake out the bar to get a front-row seat for Bloody Mary slinging and cheeseburger grilling.
It’s no surprise this Big Easy-inspired Bloody would be big on flavor and spice. Lemon and Crystal hot sauce flavors take the stage, with house-made Worcestershire and fresh horseradish playing back up. The result? A simply fresh and spicy tomato flavor. If that’s not enough, the complimentary beignets will have you jonesing for another visit.
Saddle up for a Coyote Ugly-esque brunch vibe -- this BBQ joint offers the city’s best Bloody Mary bar, hands down. And thankfully, it gives directions along the way. Choose your rim, then your booze. If you’re bold, we recommend whiskey or tequila to complement the smoky BBQ spices of Bub’s house mix. Next, garnish like crazy with roasted peppers, shrimp, pimento cheese-stuffed olives, mini grilled cheeses, and more, and grab yerself a High Life pony. Giddy up.
Damn right, your grandpa would have hung out at Dove’s. With its old-school counter, wood paneling, and jukebox, this diner will make you forget what decade it is, apropos because its Bloody is timeless. It’s mixed with CH vodka and finished with smoked black pepper, celery and root bitters, and a simple lemon, lime, and celery garnish. It's simple, smoky, and spicy, thanks to the house-made and appropriately nicknamed, ahem, “grandpa mix.”
You gotta love a boozy tomato cocktail that’s delectable and distinctive without all the frills. The Board & Beer Bloody Mary at this Longman & Eagle sister restaurant is understated and well balanced, yet big on horseradish and spicy flavor. And, for your friends who can’t handle the magic of a Bloody Mary, there’s an impressive beermosa cocktail menu.
South Loop, Lincoln Park
The Serious Bloody Mary at this Jewish deli-meets-diner is seriously delicious. Big on tomato taste, it’s tangy, spicy, peppery, and heavy on celery salt in a good way. They’ll ask to upgrade to premium vodka, but it’s thick enough that you don’t need it. Unless you’re fancy. The garnishes aim to please with a celery stick, lemon, olives, salami, Swiss, and a cute Eleven City flag. If you love it, you can buy the mix for around $7 and DIY at home.
Every once in a while, you find a brunch cocktail that truly marches to the beat of its own drum. The Hair of the Goat Bloody Mary at this Stephanie Izard outpost is just that. It’s smoky, spicy, and full of pickled flavor, a mash-up of cultural tastes that just works: pickled onion juice, kimchi, masala, and miso. The generous size makes this Bloody a superb value.
Ordering a Bloody Mary or Bloody Maria seems like a rookie move when you’re at a bar (and inn) that’s venerated for its whiskey selection. Order yours with whiskey and you’ve got yourself a Bloody Lawrence (known as Bloody Larry to his pals).
Get ready for love at first sip. You’ll swoon over this Bloody Mary’s decidedly fresh and briny flavor, made more distinctive with a heavy dose of cumin. The garnishes are quite dreamy as well with crispy bacon, cucumber, a blue cheese-stuffed olive, a standard green olive, celery, lemon, and lime. We’d be soulmates if there had been TWO blue cheese-stuffed olives.
You COULD do the Bloody Mary cart. But what’s the fun in that when you can wrestle 32oz of the Sumo Mary? This beverage-and-meal-in-one is Chicago’s most ridiculous Bloody Mary because it’s ridiculously amazing. With a unique Asian flavor, its massive garnishes include a baked Alaska crab roll, a Chinese duck bao bun, pork belly, grilled cheese with tocino, oshinko, roasted potatoes, shishito peppers, lumpia, Chinese broccoli, and bacon.
If it’s actually a nice summer day in Chicago, take advantage by setting up shop at this biker-ish joint’s rooftop patio and work your way down its legendary Bloody Mary menu. There are eight in total, ranging from the classic Road Rash, to the spicy Smokin’ Salma, to the smooth gin-cloaked Bloody Queen, to the smoky Scotch-filled Deliv’rance.
1. Au Cheval800 W Randolph, Chicago
2. Big Jones5347 N Clark St, Chicago
3. Bub City435 N Clark St, Chicago
4. Dove's Luncheonette1545 N Damen Ave, Chicago
5. Dusek's1227 W 18th St, Chicago
6. Eleven City Diner1112 S Wabash Ave, Chicago
7. Little Goat820 W Randolph St, Chicago
8. Longman & Eagle2657 N Kedzie Ave, Chicago
9. Summer House Santa Monica1954 N Halsted St, Chicago
10. Sunda110 W Illinois St, Chicago
11. Twisted Spoke501 N Ogden Ave, Chicago
This upscale West Loop restaurant is known for its European flair and sophisticated American diner-style eats. Au Cheval usually has a wait out the door at peak dinner hours because it's home to iconic signature items like the fried house-made bologna sandwich and the so-called single burger, which actually comes with two thin patties and is topped with American cheese, house Dijonnaise, pickles, and if you know what's good for you, the optional bacon and fried egg add-ons. The brasserie-like space includes an open kitchen and a bar where local, domestic, and international beers are all on tap.
If you’re looking for real Southern comfort in Chicago, then Big Jones in Andersonville is for you. The menu is filled with authentic Lowcountry dishes adapted from antique cookbooks, like cornbread muffins taken from an 18th-century plantation recipe and traditional Cajun gumbo. The sustainable menu changes seasonally, but no matter what, expect the signature fried chicken every night. Big Jones’ weekend brunch is also a stunner, especially if you nab a table on the back patio.
Nashville comes to River North through the doors at Lettuce Entertain You’s Bub City, whose award-winning barbecue, 100-plus whiskey labels, and live music can make you forget about that deep Chicago chill. The all-American bar brings the heat from down South with dishes like barbecued brisket (get the burnt ends), fried chicken sandwiches (the Original 8 Buck Cluck is best served with a side of those aforementioned burnt ends), spoonbread, and baby back mac & cheese. To drink, you can sip on anything from a can of Bud to a pour of Pappy Van Winkle himself. Enjoy live country music multiple nights a week, and be prepared for a rowdy dance party.
One Off Hospitality's 41-seat counter service restaurant pushes Southern-inspired Mexican cuisine like chicken fried chicken smothered in chorizo verde gravy, smoked brisket taco Norteño, and chili con carne, along with craft cocktails and tequila galore.
Helmed by Longman & Eagle's Jared Wentworth, this Michelin-starred restaurant in Pilsen serves upscale American pub food. Dusek's takes everything you love and makes it better, whether that's cooking French fries in beef fat or topping a juicy hamburger with bacon marmalade and serving it on a house-baked pretzel bun. There are more than two dozen beers on tap -- some are from Chicago, others are from abroad -- and daily beer specials. The late-night menu serves the aforementioned burger and fries until 1am every night.
A matrimony of the Jewish delicatessen and the old-school diner, Eleven City Diner's a greasy spoon sans the grease, with awesome double-decker sandwiches and generally huge portions of pretty much everything.
Right across the street from its upscale sister Girl & The Goat, Stephanie Izard's Little Goat is an all-day upscale diner that serves insanely creative takes on classic American comfort food. Split between a sit-down restaurant and a bakery, Little Goat is the place to go for over-the-top breakfast (breakfast spaghetti, banana peanut butter waffles), exceptional burgers (you can choose between a beef, goat, and veggie patty), and crazy desserts (smoked pork & toffee crunch milkshakes, Cheez-It sundaes). If you can't sit and stay -- or handle the long weekend waits -- then hit the "Grab and Goat" take-away area.
Longman & Eagle, the Michelin-starred gastropub in Logan Square, has an exclusive whiskey selection (clocking in at over 400 labels), a craft cocktail menu, and an extensive beer list all fit for the most pretentious of drinkers, in the least pretentious of atmospheres. Longman takes a flavor-forward, honest approach to eating and drinking, and because it doesn’t accept reservations, there is always a wait for brunch, happy hour, and dinner alike. (And it is always worth it.) While whiskey may be king, the regional American fare has just as much to offer, hence the Michelin star. The menu changes often, but expect anything from beef tallow beignets and veal brains to wild boar sloppy joes, chicken and waffles, and a burger that, if you know what's good for you, you will order.
From Lettuce Entertain You, Summer House Santa Monica brings Chicago a much-needed dose of SoCal flavor. The restaurant goes full force with its Angeleno theme, from the beach house-meets-garden party decor to the expansive list of California wines. Seafood and vegetable plates shine on the menu -- which also includes tacos, sushi, and burgers -- but the most notable dishes, like wild mushroom enchiladas and king crab orecchiette, are found under the speciality "Things We Love" section. Pro tip: top off your meal with a bacon chocolate chip cookie from the bakery counter at Summer House's sister restaurant, Stella Barra Pizzeria, which is right next door.
Toeing the line between swanky hotspot and sophisticated dining destination, this Asian fusion concept from Rockit Ranch Productions is a worthy choice for an undeniably hip meal out in River North. The menu offers some seriously interesting eats (duck breast kimchi, oxtail pot stickers) and includes sushi, sashimi, and plenty of wok dishes. The beer list is heavy on the Asian pours, and there are sake and speciality cocktails as well. Sunda's decor feels just as sleek as the menu with polished black bamboo and high wooden tables.
In case the exterior motorcycle art and bike handlebars on the front door didn't tip you off, Twisted Spoke is a biker bar. The West Town hangout is beloved by Chicagoans of all stripes thanks to a massive selection of whiskey and beer, legendary Bloody Mary menu, rooftop garden, and sinister bites like barbecue nachos and fried jalapeño poppers. Of all the things that make Twisted Spoke stand out though, it's the weekly Saturday night "Smut and Eggs," when you can order breakfast food and watch porn. Um.