Great coffee and women’s business in the Windy City: AWNY’s Guide to Chicago

As that great woman Calamity Jane once said, the Windy City is indeed mighty pretty, and it’s perfect for a long weekend getaway.

As a silver lining to being built on a swamp, downtown Chicago boasts a series of waterways that lend themselves to stunning views. Having been razed to the ground by fire in 1871, Chicago is the home of the world’s first skyscraper, along with some of the finest examples of modern architecture.  You’ll also find a strong supportive community for women-owned businesses, several Aussie and Kiwi cafes for a cup of our finest – and then there’s the food.  Pack good walking shoes, and loose pants.

Chicago street art
The famed Chicago sign, Logan Square, Chicago. Photo: Sara Denby

Fortify yourself for long days of sightseeing with a hearty breakfast, and I can heartily recommend Wildberry Pancakes & Cafe (recommended by a fellow AWNY) – no reservations, so arrive early. Miss Ricky’s at the Virgin Hotel was fabulous with breakfast cocktails like Beermosa (better than it sounds) and a spectacular Bloody Mary.

For a taste of home, we were fascinated to find Rice Krispie pancakes at Yolk, and flat whites at Colectivo Cafe, but imagine my Kiwi joy to discover a Mojo café – one of New Zealand’s best, and resplendent with four locations in Chicago!  A mandatory hit to start the day.

Rice Crispy Squares in Chicago, at Yolk
Rice Crispy squares available at Yolk, Chicago. Photo: Sara Denby

The architecture is the star of downtown Chicago, and a river cruise with the Architecture Foundation Center’s First Lady is highly recommended for the best views and expert commentary. The trusty Hop On Hop Off bus tour was great to get your bearings, but be sure to hop off at Millennium Park to explore its fascinating art installations and the iconic Cloud Gate – a mirrored bean-shaped sculpture that provides hours of selfie fun. It’s next door to the Art Institute of Chicago, which offers the perfect respite if that famed Chicago wind kicks in, and houses a stellar collection that includes American classics Nighthawks and American Gothic.

Ten minutes north of the city centre ‘Loop’ is the restored warehouse district of Fulton Market, which is now a hub for tech and media companies, and cheek-to-jowl with great restaurants. But we loved our day wandering through nearby Wicker Park – sort of what Newtown is to Sydney or Brunswick to Melbourne, and walking The 606 is Chicago’s answer to The High Line.

Many of its eclectic shops display the sticker ‘Women Owned’, as members of a robust collective of women and minority-owned businesses throughout the city, so do seek them out.  One of our favourites was the women-owned Bungalow by Middle Brow craft brewery and restaurant in Logan Square. Great food, cool vibe, and negronis with lager. Need I say more?  Hope not, because that afternoon is kind of a blur…

Women owned business sign in Logan Circle
Photo: Sara Denby

While Chicago is doubtless the home of many fantastic restaurants – I can recommend RPM Italian and Aba in Fulton Market – the jewel in the Chicago crown is its Deep Pan Pizza.  Love the idea or hate it, you have to try it.  So we visited Pequod’s Pizza in Lincoln Park, recently voted #1 in the city. I was a deep pan virgin and not too excited about it – but it was delish. Kind of like pizza on a thick biscuit base, definitely add the spicy sausage if you’re into meat, and make the trip to Pequod’s.  Excellent service – and great tips from staff on where the locals hang out.

This included the Old Town Ale House, a dive bar opposite The Second City comedy club.  Book ahead if you’re planning to take in a show there, and leave time either side to visit the Ale House.  It’s definitely worth a visit, if only to check out the questionable artwork (probably don’t take your kids…).

Deep dish pizza in Chicago
The Chicago special, deep dish pizza at Pequod Pizza in Lincoln Park, Chicago. Photo: Sara Denby

We were also lucky to see Will & Grace’s Sean Hayes star in ‘Good Night, Oscar’ at the Goodman Theatre.  It’s bound to transfer to Broadway and, when it does, go see it.  He’s incredible – with only the tiniest glimpses of Jack McFarland!

At the end of a long day sightseeing or before dinner at night, another local tip was to head up the Hancock Tower to the Signature Lounge bar. Not only does the price of a drink afford you the same stunning views as the 360Chicago observation deck above it, but the best vantage point is in fact from the ladies’ restroom. How’s that for supporting women’s business?!

Downtown Chicago
Chicago in April Photo: Sara Denby

Other honorable mentions to add to the growing list of Chicago must sees include Kingston Mines if you’re looking for a some live music at a rustic blues club, the Map Room; A Travellers Tavern with flags and beers from around the world represented, including stubbies of Coopers Sparkling for anyone craving a beer from home and Gibsons Bar & Steakhouse which has a large selection of Australian steaks and is an iconic Chicago steakhouse in operation for over 30 years.

Map Room, A Travellers Tavern in Chicago, cafe during the morning, bar afternoon onwards
Map Room | A Traveller’s Tavern in Chicago with flags and beers from around the world. Photo: Melanie O’Brien

Author: Sara Denby

Kiwi in New York, gender warrior everywhere.

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