Chicago, Illinois: best places to eat and drink

Heritage Bicycles and Coffee - for coffee

Hand-crafted coffee and bikes go hand in hand at this friendly Lakeview neighbourhood coffee/bike shop. Beautiful vintage-inspired bikes are built on site and can be customised to order.

The coffee shop is a high-ceilinged open space with reclaimed timber tables and homemade chandeliers. Order an expertly made cortado and one of the best cinnamon buns we’ve ever tasted from local West Town Bakery. You can even grab a growler (four pints) of cold brew coffee to go.

Floriole - for pastries

Owner Sandra started Floriole as a pop-up at Chicago’s famous Green City Market, selling two or three pastries each week from a put-up table. Now the business has a permanent, Lincoln Park, home and is a must-visit for brunch.

As well as beautiful patisserie – we tried the kouign amann and the delicate passion fruit tart – there are savoury offerings of pretty tartines topped with trout and pickles and some killer sandwiches – try the turkey, avo and bacon club on delicately toasted brioche with roast tomato aioli.

Band of Bohemia – for a boozy brunch

Chicago’s first Michelin-starred brewpub is probably not what you’d expect. Step through an unassuming yellow door on Chicago’s ‘Malt Row’ (in Ravenswood) and, inside, you’ll find a vast space that stylishly manages to mash up its former factory architecture with granny-chic decor and a functioning microbrewery and restaurant – think chintzy fabrics and chandeliers alongside exposed ceiling pipes, vats of beer (brewed with food in mind) and a wood-burning grill.

Head here for brunch; try the likes of caviar crepe cake with smoked sturgeon, creme fraîché and cultured butter or shrimp and heirloom corn grits with gravy and swiss chard. Order the beer pairing and work your way through a delicate, light brew made with jasmine rice and Vienna malt, through to moody Bruja - A Witches Wheat made with beetroot, orange, chicory and wheat.

Dovetail Brewery - for craft beer and a tour

A 15-minute walk from Band of Bohemia (this isn’t called Malt Row for nothing) brings you to Dovetail’s taproom (as well as plenty more breweries and distilleries). This is where traditional techniques meet new thinking, resulting in European-style craft beers that have an American flavour. Try the hefeweizen with its nose of clove and taste of mandarin, or an auburn rauchbier that smells like a heady mash up of smoke, maple, bacon, chocolate and beachwood. Or, if you’re feeling really experimental (and it’s on), ask for the Dovetail X01, a blend of smoked lager and Belgian-style sour – complex and a contender for the best-tasting, unusual beer you can buy in Chicago.

Deep dive into beer geekery on Saturdays at 11am, when the team host a 90-minute tour of the brewery for just 15 bucks (the price includes three beers and a closer look at their specialist equipment including Chicago’s first ‘coolship’ - no spoilers, you’ll have to visit to find out more). If you’re hungry there’s a choice of pretzels, cheese flights or landjäger sausage, otherwise you’re welcome to BYO.

Ema - for lighter, meat-free lunches

Vibrant colourful small plates with a Mediterranean twist make up the eclectic menu at Ema. This light and airy neighbourhood restaurant is dedicated to cooking California-style so local veg are a highlight and there are plenty of non-meat options.

Inventive dishes include tarted-up hummus with toppings of fresno chillies or spicy harissa lamb served with puffy homemade pitta, roast romanesco cauliflower with homemade yogurt and local honey, and grilled octopus with fried kale, fingerling potatoes and preserved lemon vinaigrette. Portions are a bit more delicate than your regular US super-size so there is scope to try quite a lot of the menu.

Katherine Anne Confections - for chocolate

For a sugar rush with a twist visit Katherine Anne Confections in the trendy Logan Square neighbourhood. Chocolate truffle flavours change with the seasons but expect unusual flavours like goats cheese and walnut or basil. The caramels are also really popular (don’t miss the rosemary and sea salt).

Buy your goodies to go or sit in the small, pretty shopfront and have a cup of Katherine Anne Confections’ famous hot chocolate. The rich liquid is made with only melted chocolate, milk and cream, and topped with gooey marshmallows or whipped cream. If you can’t decide between the different flavours order a flight of three mini cups and try varieties like salted caramel, Mexican and chai.

Forbidden Root Brewery - for the best beer snacks

Built on the site of an old theatre, the bar at this brewery has quite a dramatic feel to it and the beers are showstopping to match. In early American brewing, aromatics and botanicals like ginger, dandelion and burdock were in common use. Forbidden Root used this as a starting point for their brewing so each of the company’s beers contains subtly interesting layers of flavour; try Money on my Rind, with its notes of grapefruit and juniper in a wheat beer, or WPA, which uses wild botanicals such as elderflower and marigold as the base for a pale ale.

The food is as inventive and flavour-packed as the booze – bar snacks include Korean chilli popcorn, ’nduja sausage with pickled mustard seeds and honey, and home-made beer cheese spread. Small sharing plates include malted lamb ribs with tamarind glaze and sesame, and mussels cooked with Wildflower Pale Ale.

Pequod’s Pizza - best for deep-dish pizza

After much searching, and eating, we can confirm that Pequod’s Pizza, on North Clybourn Avenue, is the best deep-dish pizza in Chicago. Some (pedants) will argue it’s not technically traditional – thanks to its caramelised cheese crust and crown (all down to an ingenious sprinkling of cheese around the deep-sided dish before it’s baked) – but if this is wrong, we don’t want to be right. It’s fluffy, crispy, sloppy and supremely cheesy all at once – aka deep-dish pizza heaven.

Freehand Chicago - for cheap digs and sustainable cocktails

If Cocoa Puffs-infused old fashioneds, espresso martinis made with leftover Nicaraguan coffee grounds, or mescal shot glasses made from dehydrated waste lemon and lime skins sound like your cup of tea, then the award-winning Broken Shaker cocktail bar inside the Freehand boutique hostel is worth seeking out.

There are always two off-list cocktails to choose from – spot them on the coasters – and expect a sustainable and delicious approach to mixology from the enthusiastic team. If you need a place to stay, too, then look no further than the stylish rooms here. You can bunk-up, hostel-style, stay in a private king or queen room hotel-style, or rent out the penthouse.

Cruz Blanca - for Mexican food and Mexican beer

With nearly one brewery for each of the 77 neighbourhoods in Chicago, there’s a lot of beer to try in the Windy City. But, for something a little different, head to the 10-barrel brewery and taquería Cruz Blanca in the cool West Loop district.

Explore the range of modern Mexican lagers, barrel-aged brews, bright IPAs and tropical, lip-puckering sours (we loved the Electric Flamingo, a fruited Berliner with fresh mango sweetness and a gentle tang) alongside a menu inspired by the southern Mexican state of Oaxaca. If you’re in a group, order the giant tostadas – crisp tortillas filled with cheese, beans and a selection of toppings from Florida pink shrimp to Gunthorp smoked pork loin or Oaxacan chorizo.

Other places to eat and drink in Chicago

Chicago Distilling Company - for hard liquor

If you fancy a bit of the hard stuff, visit the Chicago Distilling Company for a tasting. The company’s small-batch whisky, bourbon, gin and vodka is produced on-site by descendants of original Midwest moonshiners. You can buy a bottle to take away or just work your way through the spirits section in the buzzy bar. There are also regular tours/tastings with the owners to guide you through the art of brewing your own.

Piece Pizza and Brewery - for pizza, beer and basketball

Pizzas here are served with four bases – white, red, BBQ or New Haven (that’s tomato sauce and no mozzarella but with extra olive oil and parmesan) and come in three sizes. After choosing your base you then add whichever toppings you fancy. The pizzas are designed to share and they are HUGE (three of us ordered two mediums and we couldn’t finish them).

The large open space is made up of large communal benches and has a beer hall/sports bar-type atmosphere with screens showing local basketball and baseball games lining the walls. Watch them while sipping a craft beer that’s been brewed on site: there are usually seven on tap at one time – try the Astronaut Haus, a citrusy American Pale Ale. Famous fans have included Anthony Bourdain and Dave Grohl.

Vice District Brewing - for small-batch beers

This small-batch brewery in the Chicago South loop is owned by two Chicago South-siders whose aim was to provide a friendly, diverse, inclusive space (it’s both dog- and family-friendly) for the neighbourhood.

There’s no food on offer but you are encouraged to order in from local restaurants (ask the barman for recommendations). The beer selection is seasonal and, as everything is brewed in small batches, it can change month to month. We loved the Coconut Porter – a dark, chocolatey beer with a subtle creamy coconut accent.

Swift & Sons - for steak

Chicago is famous for its steak joints and Swift and Sons is one of the swankier offerings. This huge dining space is in the former meatpacking district and has a grand gentleman’s club feel to it – think curved leather booths, warm wood and shiny brass fittings and soft lighting. It’s the sort of place you’d expect to find Don Draper of Mad Men nursing an Old Fashioned. The travelling cocktail cart is definitely worth trying, too – have your martini mixed table-side and get a little history lesson on the drink thrown in.

The menu is a surf-and-turf dream with spankingly fresh oysters, shrimp, king crab and lobster to order individually or on groaning platters. Steak is the real star here, though, and you’re guaranteed a perfectly cooked strip, rib eye or porterhouse. It’s not cheap but portion sizes are hefty (the New York Strip is a whopping 16oz/450g) so split a steak and order a couple of sides (we liked the crispy brussels sprouts with soy and lime, and the spiced cauli gratin with parmesan). Sauces come on the side – try the umami-rich oxtail marmalade.

Portillo’s - for hot dogs

Chicago hot dogs are unlike any other American-style versions thanks to their multitude of toppings (affectionately known as “dragging the dog through the garden”). Head to any of Chicago’s Portillos (we loved the character of the River North branch) and get your dog (inside a soft poppy seed bun) layered up with mustard, relish, celery salt, onions, tomatoes, pickles and peppers. Ketchup is an absolute no-no. Seriously, don’t ask; you’ll only offend.

The Doughnut Vault – for donuts and coffee

If jet lag keeps you awake, make the most of it and head out early to North Franklin Street, in the River North district, to beat the crowds and catch the daily specials at The Doughnut Vault before they sell out. The team here specialises in old-fashioned donuts, which are more cake-like, with rough edges and a crisp exterior. Expect flavours including key lime, strawberry crumble, and pink lemonade and decent drip coffee, too.

Words | Janine Ratcliffe and Laura Rowe

Images | Adam Alexander, Anjali Pinto

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