PACKET POSTCARDS: How To Spend 72 Sublime Hours In Chicago
Unique pizza, world-class art and watching the Bulls with a hotdog in hand. These are just three reasons why I think Chicago is a perfect spring city break...
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The best way to stave off jet lag after a nine-hour, early-morning flight to Chicago from Heathrow? Make a beeline for the nearest pizzeria, then head over to the United Center for a Friday-night Bulls basketball game. That’s what we did when we booked a last-minute long weekend to the Windy City last April. I’d visited with my parents about 20 years earlier, but back then I was mostly excited about seeing the stomping ground of the Midwest emo bands I loved (American Football forever). This time there was a firmer itinerary: pizza, art and sport (my other half had found the one weekend of the year when Chicago’s pro basketball, ice hockey and baseball teams were all playing home games).
I love New York, but feel like many Brits often forget there are other Stateside cities to explore. Chicago is certainly more affordable – and it’s got the history, architecture and restaurants to match NYC. With a film camera loaded with LomoChrome Metropolis in hand, we spent three days jumping on and off the L. It was sunny. It snowed. We didn’t want to leave – but we did manage to cram in a wild amount from Friday night until Monday afternoon. From bars to museums, here’s everywhere I loved across America’s third-largest city…
EAT & DRINK
Deep dish. That’s what you’ll get at a Chicago pizzeria. It’s key you remember that when you first order a pizza pie each (you’ll get laughed at) instead of splitting one with dual toppings. Pizano’s on Madison was our aforementioned first pit-stop. In the Loop neighbourhood, it’s one of the oldest pizza joints in town, and this is not a place to rush – each pie takes 20 minutes in the oven and will be blisteringly hot when it arrives at the table. It’s worth the wait: we went for the Jeweler’s Special, a classic combo of sausage and hot giardiniera (Italian-style pickles) that was just the thing to sink into after a day of plane snacks.
But then we made it to Pequod’s in Lincoln Park, heading there after the ice hockey on Sunday night. A staple since 1970, it’s mainly walk-ins, so we waited in the bar next door until a table was ready, and – again – it was worth hanging around. Now knowing to split one between two, for my half I opted for green olives, onions, green peppers and pepperoni, and it was sensational. The crispy edges! Pequod’s pizzas are known for their caramelised crusts and they didn’t disappoint.
Pizza isn’t Chicago’s only native dish. In fact, most locals we spoke to said they were much more likely to eat Italian beef sandwiches on a regular basis. If you’ve watched The Bear, and remember the restaurant as it was when Carmy inherited it from his brother, you’ll be able to picture the scene. Al’s Beef was the first sandwich shop we tried, on our way back from the baseball at Wrigley Field. We ordered the classic: a white sub, filled with thinly-sliced roast beef and more of that hot giardiniera, before the whole thing was simmered in gravy. It was as messy as it sounds – and just what we needed after a few pints.
Johnnie’s Beef is a little further out of the way, but completely worth a detour. In Elmwood Park, you’ll find this no-frills, almost diner-like sandwich shop on the side of a busy road. Thankfully, we arrived when there wasn’t a huge queue, but we still had plenty of time to shuffle along, debating our order and watching the chefs grilling veggies and dunking the rolls into the gravy. Again, we went for the classic beef with hot peppers – and I think Johnnie’s beat Al’s by a mile. We also ordered its signature shaved ice with lemon, which was beyond refreshing, even in early April. I practically danced out of the door with the brown paper bag of food.
I also need to shout out L&L Tavern, an excellent cash-only dive bar we nipped into for a swift drink to break up the long cold walk between Wrigley Field and our hotel. We planned on bar hopping for a bit after the Cubs game, but ended up spending our entire night here, partly thanks to the lovely barmaid who, as soon as we sat down, handed us black coffees laced with whisky to warm us up. It also had a well-stuffed and well-used jukebox: we waited over two hours for my chosen song to come on before giving up and heading home. Still, it was a fun place to hang out (even if we did discover while there that it used to be one of serial killer Jeffrey Dahmer’s bars of choice!).
ART, SHOPS & EXPERIENCES
Is the Art Institute of Chicago the greatest art museum ever? I think it might be. My friend Zoë and I used to watch Ferris Bueller’s Day Off whenever we were getting ready for a night out. As part of Ferris and co’s escapades, the trio zip around the museum, taking in Chagall’s stained-glass window, Pollocks, Picassos and the stone lions that flank the entrance as a Smiths cover song plays. You can now use Ferris’s route to take in some of the gallery’s greatest hits. I knew that Edward Hopper’s ‘Nighthawks’ and Grant Wood’s ‘American Gothic’ were in there – and they were magnificent to see in person – but I wasn’t prepared to see world-class pieces every time we turned a corner. We had to rush around ourselves, as we didn’t realise it only opens at 11am on a weekday and had to get to the airport, but it was worth it just for some fleeting moments with the O’Keeffes and de Koonings.
If shopping is high on your city break agenda, earmark pretty Andersonville, the city’s historically Swedish enclave that’s now one of the coolest neighbourhoods in Chicago. Shops worth visiting include Rattleback Records, Raygun (a t-shirt shop that’s proud of the area’s LGBTQ+ roots), Scout antiques and Five Elements Home, a Japanese ceramics shop where I bought an amazing papier-mâché dragon. Across town, westernwear shop Alcala’s is a marvel. You can’t miss it, as there’s a life-size bucking horse on its roof. We headed in as we’d been tasked with sourcing a genuine cowboy hat as a family present but, even if you’re not on a mission, it’s worth a look through its rows of Stetsons, boots and accessories. We also spent a long time chatting to the Drake’s-clad fellas working in Independence, a USA-made menswear shop in Wicker Park – another neighbourhood you could easily spend a day mooching around.
We sacrificed the many bookshops of Wicker Park for a journey to the Frank Lloyd Wright Home & Studio in Oak Park (via Johnnie’s Beef). I love his works and have gone out of my way to visit some of his amazing homes in LA and Pennsylvania (I’ll probably do a post on Fallingwater one day), so it was amazing to see his first home and design studio, as well as the many Prairie-style houses he built around the Oak Park neighbourhood when he was first starting out. If you love art and design, this should be right at the top of your Chicago to-do list.
Netflix documentary The Last Dance was a lockdown favourite, so we were never going to go to Chicago and not watch the Bulls. The team might not be in the same shape as its 90s heyday, but a night at the basketball is still a lot of fun – watching flames shooting out as the Bulls entered the arena to ‘Sirius’ gave me goosebumps. The Bulls share the United Center with ice-hockey team the Blackhawks, so it was fun to see the same space in a new light two days later. Balancing a beer and bag of Combos in one hand while cheering on the winning team with the other hand made for the most fun Sunday night I can remember. The Cubs also won at Wrigley Field on Saturday afternoon, where a cloudy day couldn’t dampen a lazy few hours watching home runs, a historic catch by Cubs veteran Ian Happ – plus a number of crowd singalongs while IPAs and hot dogs were delivered to the stands.
In Chicago, even getting around is fun. The L’s brown line still chugs along the Loop (the elevated railway played a starring role in The Fugitive – not that I need an excuse to watch Harrison Ford in a film) and is worth doing. One of the best ways to take in all the city’s art-deco splendour is an architecture river cruise. You’ll float past the distinctive ‘corn on the cob’ car park towers and, round every corner, you’ll be greeted by another skyscraper that makes your jaw drop. But the way to see them all at once is from the sky. The Sears Tower is the most famous skyscraper, as it was the tallest building in the world until the 90s. It’s now called the Willis Tower, but its glass-bottomed Skydeck remains. I defy you not to get jelly legs standing on the invisible floor.
SLEEP
We stayed at the Chicago Athletic Association. This grand building is the former HQ of a historic gentlemen’s sports club and it has gorgeous, towering Gothic fireplaces, wooden staircases and original 19th-century tiles in all the lobbies and lounges. The hotel is right on the edge of Millennium Park, looking down onto Anish Kapoor’s mirrored Cloud Gate sculpture – affectionately called ‘the Bean’ by locals – and across to the shoreline of Lake Michigan. Jet lag did catch up with us by the end of the trip, but that was to our advantage – on our last morning we woke up at 6.30am and headed out, wrapped up against the first flakes of snow, to walk around the Bean without the crowds. It reflects everything around it: skyscrapers shrink in miniature, while up-close faces and bodies take on a haunted-house-of-mirrors distortion. It was a new way to see the city we’d fallen in love with – and a fun way to end the trip.
Thank you for reading this week’s email! Coming soon on Crisp Packet… the best restaurants I’ve tried this month, a new Sussex escape, plus March’s edition of The Multipack…
The L&L Tavern is such a great dive!