Chicago, The Windy City: Where To Eat, Stay & Play

25 October 2018

Chi-town’s got it going on. The Midwestern mecca is the third largest city in the US, and it’s pretty impressive, with a booming foodie and festival scene, amazing art and architecture, a crop of cool hotels, and a lake smack-bang in the middle of it all. Here’s where to eat, stay and play in Chicago – the city that inspired one of the most ~interesting~ baby names in history.

Time your trip wisely! The city’s glorious in spring and summer, and downright miserable in winter. There’s a reason they call it the Windy City.

Chicago skyline


Forget about counting calories – Chicago is the land of deep-dish pizza, beef sandwiches and hot dogs, and you’ll want to indulge in all of those iconic eats. And don’t worry about squeezing into your skinny jeans: the city balances it out with brunch and fab farm-to-table spots.

But first, coffee…

  • Intelligentsia. With locations dotted around the city, you can wake up to Chicago’s craft coffee wherever you’re staying.
  • 3 Arts Club. Tucked behind the divine interior design store, Restoration Hardware, this courtyard café is cute AF. It also serves Doughnut Vault doughnuts – which will save you from lining up for them at their two stand-alone shops.
  • La Colombe. An all-American staple, this baby serves up organic coffee and has 5 cafes across Chi-town.
  • Sawada Coffee. This café rose to Instagram fame thanks to its Military Latte: a blend of matcha, espresso, vanilla syrup and cocoa powder.
  • Dollop Coffee. Start your day right with a honey cinnamon latte and a cheeky croissant. No regrets.

Chicago classics

  • Pequods. Italians, look away… In Chicago, deep dish pizza rules, and it’s exactly what it sounds like: thick crusted and oozing with cheese. Locals love Pequods because they add caramelised cheese to the pizza crust.
  • Gino’s East. Another contender for the best deep dish pizza, Gino’s is as gimicky as it gets, and we love it. Everything – from the walls to the furniture – is covered in graffiti.
  • Lou Malnati’s. Lou is a fierce competitor for the crown, too, and has pizza shops scattered all over the city.
  • Superdawg Drive-in. This old-school hot dog stand has been serving up Chicago Dogs for decades. This ain’t a regular hot dog: the frankfurt is topped with mustard, white onions, pickles, tomato and capsicum on a poppyseed roll.
  • Portillo’s. The Italian beef sandwich is a Chicago staple, and Portillo’s is one of the best. Otherwise, get your greasy fix at Al Beef, Jay Beef or Tony’s Italian Beef.

Pizza in chicago

Brekkie, brunch and lunch

  • Floriole Café. If you can’t go a day without an avo smash, head to this café-slash-bakery. It gets its ingredients fresh from the farmers market, and makes almost everything in-house.
  • Bernie’s Lunch & Supper. Debrief over brunch (and a bloody mary) at this bustling spot, and you’ll be ready for round two in no time.
  • Margeaux. When the weekend rolls around, go to this Parisian-inspired restaurant for a $30 bottomless rose brunch. ‘Nuff said.
  • Frontera Fresco. After shopping up a storm at Macy’s, stop by the 7th floor. Led by celebrity chef Rick Bayless, this eatery dishes up delish Mexican (try the tortas).


  • Clever Rabbit. Vegetarian? Treat yourself to dins at this elegant restaurant, which has a mostly vego menu and some of the most creative cocktails we’ve sipped (carrot margarita, anyone?).
  • Publican Anker. When you’re on the tight end of your budget, this lively gastropub will have your back.
  • Marisol. Located inside the Museum of Contemporary Art, this restaurant is a hit thanks to its share plate and the BEST risotto ever.
  • Girl & The Goat. This hot spot is Top Chef Stephanie Izard’s baby, and it’s booked out every night. The menu focuses on small plates, and has something for everyone.
  • Roister. At this restaurant, you can watch the chefs work their magic in the open-kitchen. The whole chicken with chamomile is insane.
  • Fat Baby Tacos. A taco spot that’s open from 2am-5am, Thursday to Sunday? GENIUS.


  • Ace Bounce. If – and only if – you want to get lit, this is the place. On Saturdays and Sundays, the bottomless brunch takes the neon bar to another level.
  • Up & Up. Go all the way up (sorry!) to this rooftop bar for sweeping views of the city and free-poured drinks. It’s perched atop the Robey Hotel.
  • Beatnick. When drinks turn to dranks, check out this chic cocktail bar. If you’re peckish, the roasted Lebanenese lamb with pistachio tzatki is next-level.
  • Blind Barber. ‘Murica nails speakeasies. In Chicago, make your way to this one, which is hidden inside a barber shop.
  • Proxi. Hello, happy hour! Dress to impress and make your way to this sleek cocktail lounge in the West Loop. The Aviary is another fun option that’s close to da clubs.

Skipped out on sightseeing? Tick the sights off your to-do list by grabbing a drink at Cindy’s or The Signature Lounge – both rooftop bars have panoramic views of the city.

Guide to Chicago


There are two ways to go about this. Settle on an area, then choose a hotel that’s close to the hotspots, or stay at the hotel you’ve been stalking on Insta. Either way, these are our top picks:

  • Freehand, River North – sceney, beautifully designed and affordable
  • Ace Hotel, West Loop –trendy, industrial-chic hotel in the nightlife hub
  • The Langham, River North – luxury hotel with all the trimmings, like a rooftop pool
  • Chicago Athletic Association, The Loop – gorgeous boutique hotel in downtown Chicago
  • Guesthouse Hotel, Gold Coast –this charming hotel is made up of one-, two- and three-bedroom apartments


Millennium Park. Get snap-happy at the city’s top tourist attraction. Millennium Park is home to The Bean – a silver steel sculpture that reflects the sky. If you visit Chicago and don’t take a selfie in front of it, the trip didn’t happen.

Skydeck. New York has The Rock, Paris has the Eiffel Tower… To get the sunset shot of Chicago, step out onto Skydeck, a glass ledge that juts out from the 103rd floor of the Willis Tower. This may be stating the obvious, but if you’re scared of heights, don’t do this!

Riverfront. Chicago’s lakefront is stunning, and the best way to explore it is by foot or bike. It’s lined with cafes, restaurants, bars and parks – make a pitstop at Olive Park for instaworthy views of the city skyline.

Wrigley Field. Catch a Cubs baseball game at this famous field. Before you head in, do as the locals do and get a beer at the Old Crow Smokehouse.

The Magnificent Mile. Splash some cash in the city’s biggest shopping district, which has a good mix of high street and haute shops. Then, wander along State Street.

And some culture…

Festivals. Chi-town has an insane festival scene. Music lovers, try to nab tix to Lollapalooza, the Chicago Blues Festival or the Chicago House Music Festival. Foodies, you’ll love Taste of Chicago and The Windy City Smokeout.

The Second City. This no-frills comedy club launched the careers of legends like Tina Fey, Joan Rivers, Stephen Colbert and Steve Carrell, so see a show for guaranteed LOLs.

Art Institute of Chicago. Whether you’re a culture vulture or someone who knows nothing about art, this museum is well-worth a visit. It houses some of the greatest, and most important art in history (like Andy Warhol’s). If art is your jam, you’ll like the Museum of Contemporary Art, too – it’s one of the biggest and oldest museums in the US.   

Frank Lloyd Wright tour. Love architecture? You can take a guided tour of the famous architect’s home and studio, or go all out with a tour of Oak Park, the neighbourhood that has the most Wright buildings.

 Words by Katia Iervasi.