48 hours in Chicago: the ultimate two-day guide

How to make a whirlwind trip to the Windy City a breeze


A storm was brewing in the Windy City. Thunder rumbled overhead as a steady stream of lightning strikes illuminated the night sky. I was soaked in seconds in the downpour as I clambered from my Uber into the welcoming warmth of Lou Malnati’s Pizzeria. Considered the oldest family name in Chicago pizza, their legendary gut-busting deep dish had long sat on my foodie shortlist. A buttery, flaky crust bathed in sweet, plummy tomato sauce, gooey mozzarella and generously adorned with home-made pepperoni. Enough said. “Welcome to Chicago, baby. We Fed-Ex pizza anywhere in the country,” said the waitress. Hungry yet?

Chicago felt feisty and I had little more than a 48 hour stopover to experience her. Having recently been awarded 2017 Restaurant City of the Year, and nabbing the titles of Best Big City in the US and Best City for Having it All, plus being home to avant-garde chefs earning James Beard accolades, and the centre of the world of architecture and design during the Chicago Architecture Biennial, America’s third-largest city is bubbling.

On top of this, Elon Musk has just been selected to build a futuristic US$1 billion underground transit system that will whiz people from Chicago’s downtown Loop district to O’Hare International Airport travelling at 240km/h, cutting travel time to 12 minutes, from the current 30-45. In partnering with O’Hare’s planned US $8.5 billion expansion, it will continue to propel Chicago’s economic prosperity.

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I’m enjoying yet another music-themed trip Stateside, having only just experienced jazz and Creole music in New Orleans, Lafayette and the ultra-cool city of Asheville. Coming here, I was interested to absorb how the blues had transplanted to Chicago, creating a hotbed of creativity for musicians, real and raw like the city itself. I headed to one of the few blues clubs left in the city - Buddy Guy’s Legends.

Offering live streaming concerts, this true local landmark has hosted blues greats like Stevie Ray Vaughan, B.B. King, Willie Dixon, Bowie, Bo Diddley and The Rolling Stones. It’s a place where modern mingles and colludes with the ghosts of Chicago’s past.

The walls are adorned with items from Buddy’s personal collection of accolades and gifts; think guitars, trophies, awards and photographs. There is a reminiscent menu of Louisiana style Cajun and soul food, including gumbo, jambalaya, chicken, ribs and po’boys.

I ordered a Buddy Brew (Guy’s craft beer), found a pew and enjoyed the live evening act of Jimmy Burns. His soulful vocals and harmonica and guitar skills had my body unconsciously swaying to the beat. I caught Jimmy later at the bar where he told me his influences run deep: Muddy Waters and the Soul Stirrers are just a few examples. “With music, you have to find your own groove. If I feel good, the audience feels good.”

With a reputation for design and a penchant for hospitality, Chicago hosts a plethora of splendid breweries (over 100 independents), restaurants (more than 7,000) and hotels - from thrifty-chic to downright luxurious. The scene is booming. Among the new hotel openings are Hotel Zachary, The Ace Hotel, Marriott Marquis, The Rose and Viceroy Chicago. Additionally, the Ritz-Carlton Chicago recently completed a $100 million renovation.

The Blackstone Hotel however, was my chosen abode. It has a long standing place in U.S history, playing host to 12 consecutive US presidents, remaining the preferred choice of diplomats and dignitaries alike. Recently refurbished, it rocks a Grand Park-side location. I woke up the next morning to a sensational view of Lake Michigan, sunny skies and 24 degrees.

As a big breakfast fan, the day began at Kanela Breakfast Club, voted Best Breakfast in Chicago by USA Today. Their local, organic, Greek-inflected American creations are how to do breakfast the right way. I deliberated for an age between lemon blueberry pancakes or red velvet French toast. I opted for both. When in America, go large.

One of the coolest things about Chicago is the river flowing through the heart of it, and so, an hour later, I was floating beneath the city’s biggest buildings on a 75-minute Shoreline Sightseeing Architecture River Cruise - voted last year as the most popular tour in America. Fresh air. River breeze. The sun on my back. A metropolis bustling with energy and innovation. It’s a great way to see a city raised on mighty industry, and a natural relief from vertical construction.

Tour guide Ash relayed ribbons of information at great speed. We passed the soaring neo-Gothic Tribune Tower, stately bridges, bustling waterfront eateries and slick high-rises – corporate businesses, luxury apartments - many were under construction. Hedge fund billionaire Ken Griffin recently splurged on the most expensive home ever sold in Chicago, paying around $58 million for the Penthouse of No.9 Walton.

I learnt how Chicago rose from the ashes of the Great Fire of 1871 to become the birthplace of the skyscraper and the home of modern American architecture. You will see over 40 landmarks along the way and no doubt take plenty of Insta-worthy snaps. There are breakfast and lunch cruises and classic lake and firework tours and wine tastings available too.

In a city of sweeping vistas, everyone wants to be on top. I made the most of the clear skies and headed to the 103rd floor for a Birdseye panoramic at The Ledge, Chicago’s highest observation Skydeck to soak up the 50-mile views. Tip: opt for a weekday (I was up and down in 30 minutes) in order to miss weekend queues.

I checked out the Chicago History Museum’s shrine to the musical greats who shaped modern soul. The ‘Amplified: Chicago Blues’ space is dedicated to a period of evolution of the blues. In 2016, the museum acquired the collection of Raeburn Flerlage. A Chicago-based photographer, whose photographs – taken on city streets and recording studios, neighbourhood clubs and artists’ homes – offer a snapshot of those who shaped the music and shared it with the world.

I learned that blues was a perfect fit for Maxwell Street, a one-of-a-kind marketplace on the Near West Side, where artists peddled their talents while bargain hunters bartered for deals. While skill was measured by tips, the noisy scene forced musicians to be loud, bold and experimental. Little Walter for example, amplified his harmonica and changed blues history. I came away with an appreciative full glass of background insights into the city’s soundtrack of today, courtesy of migration, contracts and hometown labels.

Now firmly in the mood for music, munch and waterfront dining, I lunched at River Roast, where award-winning chef Tony Mantuano and recipient of the James Beard Foundation Award for Best Chef Midwest, is at the helm. Meat, fish and veggies are roasted and carved table-side and there’s a variety of large tables perfect for jubilant dinners with friends. The Golden Gobbets (fried chicken with honey) to start had a terrific punch and the Lobster burger with smashed avocado was absurdly good.

Believing in having your cake and eating it, naturally I opt to finish with the waitress’ carrot cake recommendation. Carrot cake is the ultimate guilt-free option you would think. At River however, wrong. The ginormous, yummy scrummy wedge in front of me was eight creamy layers high. Winner.

Their popular Blues & Brunch available on Saturdays and Sundays requires reservations two weeks in advance and is a sweet nod to Chicago’s immersive music scene. The after-work set on Thursday nights are championed by two suits at the next table, “there’s no better place in the city to kick-start the weekend on a Thursday.”

So how does a Chi-Town rookie navigate the city? I asked a local and took a free guided walking tour of Millennium Park with ‘Chicago Greeter’ and local resident Marcia Aduss. This year-round curated service offers the opportunity to explore different avenues within the city and is available in 10 languages. “There are hundreds of free cultural programmes including concerts, exhibitions, festivals and family activities. Year-round free entertainment at your fingertips, where else would you find that?” she asked.

In the evening I dined at Sapori Trattoria. The popular Italian joint was bustling ��� business meetings were underway in one corner, a date in another and birthday and family celebrations a plenty. The atmosphere was happy, warm and the menu made me drool. Homemade pasta stole the show; the veal meatballs and spicy Italian sausage were mighty, topped with a puddle of parmesan.

Try out world-famous blues nightclub Kingston Mines, whose stages have been graced by the likes of Koko Taylor and scores of musical names. A bulging, well stocked bar greeted me. Neon fairy lights provided an amusing touch and iced beers for the tables are served in funky tin buckets. Onto Joy District for cocktails and late night dancing, then Logan Square for Rosa’s Lounge, followed by The Green Mill Cocktail Lounge for intimate late night jazz with the wonderful Patricia Barber Quartet. Founded in 1907, its old-school. No cards, cash only.

The late night before had me waking up at 11am, just in time for lunch at Dusek’s Board & Beer. Named Best New Restaurant and awarded one star in the Michelin Guide Chicago for the last three years running, the awaiting table was filled with beer-centric menu pleasers of curried chicken with watermelon radish and feta and iron roasted mussels. My heart feels giddy merely thinking about the warm ricotta beignets enriched with blueberry jam and toasted almonds, and the free-flowing vin rose.

After five beignet portions, I later discovered Record Row. Home to record distributors and independent recording studios including Chess Records, well-known artists such as Chuck Berry and Etta James contributed to its legacy. Chess Records is no longer active but the building, home to Willie Dixon’s Blues Heaven Foundation, is a fantastic museum with adjoining Blues Garden, featuring live performances that are free to the public every week throughout the summer. Dixon’s vision was to encourage a new generation of blues greats and to provide for the on-going welfare of senior Blues musicians.

“I can’t help but think of all the musicians who came and rang the doorbell, hoping to get an opportunity to sit down with one of the Chess Brothers or my late father, Willie Dixon, for a possibility to record. It’s a place where many blues musicians cut their teeth. It was a home away from home for many,” said an audio recording of Willie’s daughter, the late Shirley Dixon.

Today’s Chicago is more Bugsy Malone than Al Capone. Next time, I’ll be sure to take a walk on the wild side and experience the old haunts and hear the exploits of 1920s gangsters Capone, Dillinger, Moran, and the rest of the band, courtesy of Untouchable Tours: Chicago’s Original Gangster Tour.

In the words of Rat Packer, Sinatra: “Chicago is my kind of town.”

Norwegian operates a daily flight direct from London Gatwick to Chicago, with a fleet of brand new Boeing 787 Dreamliner aircraft featuring two cabins – premium and economy. Fares start from £150 one-way and £280 return in LowFare economy and £499 one-way and £909 return in premium including all taxes and charges, subject to availability. To book visit norwegian.com/uk or call 0330 828 0854.

Stay at the Blackstone Hotel from £142 per night in low season and from £435 per night in high season; theblackstonehotel.com

For more information on Chicago check out choosechicago.com, or for information about travel in the United States generally, go to VisitTheUSA.co.uk

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