Doughnut Vault, Black Dog Gelato, Alliance Bakery, Hot Chocolate, Atwood Cafe Chicago IL

Having just returned from Boston a week earlier the turnaround time for yet another trip to the Windy City was short, but with NEXT reservations and a trip to the Rookery as well as Wright’s Home, Studio, and Walking Tour of Oak Park as the impetus for the trip and two of my very favorite people coming along for the ride I knew it would be a whirlwind of great memories. As the reigning champion on my list of favorite Breakfast/Brunch cities and resting near the apex of best dining cities overall the question of where to eat was harder than it should have been, but after much debate three breakfasts, two lunches, and two dinners made the final cut along with a number of snacks in between.

Having gotten up at my traditional “insane” hour according to my mother for a nice run our departure from her home in Northwest Ohio would precede sunrise by a few hours and making great time our arrival to Chicago would not only beat the rush hour traffic, but also leave us waiting outside our first stop before the doors opened…in a line of about ten that would subsequently grow to thirty or more at a relative newcomer to the local food scene; The Doughnut Vault.

Located in a doorway off North Franklin and open from “Tuesdays-Friday starting at 8:30am until we run out. And Saturdays at 9:30am until we run out” The Doughnut Vault is the brainchild of Brendan Sodikoff who also owns Chicago’s “Gilt Bar” (and a pretty impressive resume including time with Keller and Ducasse) and although there have been some detractors calling his success yet another food fad, it is hard to argue with lines greater than twenty deep ever since opening in April and having never been “wowed” by a doughnut I took my place in queue as we watched the metermaids do their thing.

With the line growing slowly the doors would open at 9:30 on the dot and as mostly locals and regulars stood at the front it would be no time at all before we found ourselves before a nice young woman dancing to cheesy 80s music and with a quick exchange of “What can I get you?”, “One of each.”, “Good choice – $14, cash only.” we were on the street again with a big box of doughnuts including a Gingerbread Stack, Old Fashioned Buttermilk, Vanilla Glazed, Chocolate Glazed, and Pistachio Glazed – all still warm – and all shockingly delicious despite my previous convictions about fried dough.

Beginning first with the gingerbread stack – three “smaller” doughnuts (IE a normal sized doughnut like you might get from Dunkin) – these were the heaviest of the quintet and but despite the cakey texture they were anything but oily, instead similar to a coffee cake and loaded with spicy notes, cinnamon, and sugar. Moving next to the Buttermilk – another dense cakelike doughnut, smaller (and cheaper) than the others – something like a cruller but with tangy notes, a melt-in-the-mouth glaze, and not a bit of greasiness. Last but not least – the glazed trio – each at least twice the size of a “normal” doughnut yet nearly as light as a glazed Krispy Kreme with a wispy yeasty interior contrasting with a slightly crisp sugary shell first coated in the same glaze as the buttermilk but then with an additional layer of flavoring – each delectable but most impressive the Pistachio with subtle smoky notes and bits of crushed nut for texture; easily on par with the best baked breakfast goods I’ve had in Chicago and well worth both the $3 and getting out of bed early enough to avoid the line.

With sightseeing consuming much of our first day a second snack stop on this trip to Chicago was another relative newcomer to the scene – this time in the frozen variety from Black Dog Gelato, a small shop in the Ukrainian Village that wasn’t necessarily “on our way back” from Oak Park, but a relatively short detour hopefully well worth it for those of us with an eye for esoteric ice cream flavors. Oft raved by local gourmands and sourced by local chefs for their dessert menus it was with luck that we not only found Black Dog to be unbusy, but also that we found free parking right next door.

With twelve flavors on rotation and three young ladies working on cookies and house-whipped cream in the back it was without delay that we were greeted and with The Shins playing overhead our smiley server suggested to “let me know if there’s anything you’d like to taste” before we even made it to the counter; and taste we did, making it through ten of the flavors before we finally decided to order three small ($4.75) cups with two flavors in each and a clear predilection for sweet meets savory.

Beginning with the one flop, at least to me, Mexican Hot Chocolate was simply one of those flavors that worked as a small bite but when served in quantity proved to be not only overwhelming but damned hot. Creamy and textural to be sure it was just too much on its own, but vastly improved when mixed with Salted Peanut – a mellow and smooth flavor somewhat akin to the inside of a peanut butter cup but far more buttery. Moving on to “safer” but delectable options, Butterscotch Bourbon Pecan and Pistachio would both taste very much like their namesake ingredients with the Butterscotch tasting largely like a southern-style pecan pie rendered into a silky dense gelato. Finally, amongst the more interesting and challenging flavors, Goat Cheese-Cashew Caramel and Sesame Fig Chocolate Chip would prove most delightful – particularly the sesame fig chocolate combination which was equal parts sweet and savory, smooth and crunchy but a bit less dense than I’d have expected from gelato – perhaps a good thing considering the amount of eating we did on this trip, but overall enough to make me say I appreciate what Black Dog is doing but I wouldn’t go out of my way for it at such a high price point.

For our finally mid-day bite in Chicago – this one on day two – we opted for an older member of the culinary scene that I’d actually walked into once prior during the Renegade Art Fair but neglected to buy from due to the line; Wicker Park’s own Alliance Bakery. Again scoring free parking and making our way to the shop with ease as hipsters and families alike dined on the sunny patio a stop at the window was mandatory first simply to witness the masterful cakes ranging from Green Eggs n’ Ham to Macaron towers to three tiered wedding cakes.

With the doors open letting in a cool breeze (and letting out the wonderful smells of butter and vanilla) we next made our way in to see what Chef Peter Rios and a team of youngsters (both in the kitchen and at the counter) had on display and after a few tough decisions we emerged from the shop to enjoy our choices on the patio.

Beginning first with the French classics, my mother selected two Macarons – one Blueberry Cheesecake and the other Passion fruit chocolate – both textbook in texture with a crackling shell giving way to lovely filling, but the Passion fruit Chocolate so cloyingly sweet that between two of us the $2 cookie went unfinished. Thankfully the Blueberry Cheesecake fared much better.

Moving next to two of the standards by which I judge a bakery my aunt’s and my selection were a Red Velvet Cupcake and the Dulce de Leche Bread Pudding. Beginning first with the cupcake, a $3.50 selection with good notes of cocoa and a tangy cream cheese frosting started out with a good base, but was unfortunately a bit dry – so much so that when my aunt took a bite the back half fell off landing directly on her chest; a comedic event to be sure, but not exactly the way a cupcake should be remembered. Moving next to the Bread Pudding which was served in a small tin topped with a sugar lacquered strawberry and powdered – it was dense and it was sweet, no more and no less but thankfully only $2.50.

With sightseeing, breakfasts, lunches, snacks and bites shared with the family while dinners were either with friends (NEXT) or flying solo (Avenues,) both nights of the trip would see me reconvene with my mother and aunt after dinner for dessert – a sweet ending to an evening pizza for them and a third or fourth bit of indulgence for myself (but who’s counting?) – and on the first night our target after drinks and bites at Aviary would be a place my aunt had always wanted to visit and a place that had for too long flown under my radar; Mindy Segal’s newly renamed “Mindy’s Hot Chocolate” on North Damen.

Described by optimists as an upscale café with great desserts and by detractors as an “overpriced urban bistro” with savories lagging far behind the sweets our trip to the four time Beard Award Nominee’s flagship admittedly came with a bit of warning – namely that the place can be wildly inconsistent, loud, and that after 9:00pm seating could be tricky – and after once again finding free parking (clearly our lucky day) we walked through the front doors to find two out of three to be true instantaneously; the place was deafening and our options for seating included the lounge or “about an hour for a table.”

With a quick glance to the ladies and a brief browsing of the depleted pastry case we elected for the lounge not only because it seemed quite and comfortable, but also because the clock was pushing 10:00pm and we’d not yet even checked into our hotel and without hesitation we were led to a cozy corner with long leather benches and appropriately low lying tables complete with silverware, candles, and water glasses that were filled without hesitation. Greeted next by our server, Laura K, we were asked if we’d ever visited before and on stating we had not she explained to us that each “dessert” was generally composed of two to three different items and we were left to decide – a process that took no time at all as we’d already researched the online menu en route to Chicago.

With orders placed and service appropriate but largely separated from the lounge throughout the evening the first item to arrive was a prerequisite given the restaurant’s name and although not quite as transcendent as that at Jacques Genin or LA Burdick the Black and Tan Hot Chocolate made of 1/3 hot fudge and 2/3 medium cocoa hot chocolate was certainly rich, creamy, and entirely too much for one person (especially after a full day of eating.) Sharing it around the three of us it was interesting to hear different impressions – all positive, but each catching different notes in the chocolate from vanilla to honey to fruit.

Moving on to the proper desserts – each priced at $11 – my mother’s choice was the restaurant’s signature “Chocolate #1(64%)” featuring a warm chocolate soufflé tart topped with salted caramel ice cream and a tuille of housemade pretzel; an exercise in balance and every bit worthy of its acclaim. Beginning first with the tart – hot, molten, and bitter – sure the concept of a lava cake is played, but as long as it made with great care and better chocolate it really doesn’t matter, especially when it is matched with extra sweet yet subtly saline ice cream and a crunchy salty sourdough pretzel for texture.

Moving on to my dessert, a seasonal option titled “My Honey Pie” and featuring “warm and luscious honey pie with honey-roasted peanuts, honey caramel, berry-rose syrup, graham cracker and ‘PB&J’ Ice Cream Sandwich this dish was another winner, but a case where one less ingredient could have been more. Beginning first with the pie – I love honey, I love peanuts, and I love caramel so it is needless to say that the warm gooey amalgam poured inside a thick buttery graham cracker shell had ‘had me at hello’ even before Segal crash landed a peanut butter and grape jelly ice cream sandwich directly into it. Already with a lot going on – fruit, honey, sweet, savory, hot, cold, gooey, and crunchy – the unfortunate aspect of this dish was not knowing when to quit, specifically in reference to the cloyingly sweet syrup whose perfume did nothing but distract from the pie’s nuance even though it was present in only a small quantity.

For the final dessert, my aunt’s (and the one I’d have ordered had she not,) “O’Dan-A-Banana” featuring a ‘nilla puddin’ icebox cake with ‘nilla wafers, cocoa nib ganache, vanilla bean pudding, bananas foster sauce, and a chocolate phosphate was everything I’d hoped for when planning to visit Hot Chocolate and then some. Beginning first with the phosphate – it was a textbook old school chocolate soda with a bit of extra thickness from the cream and although sweet the slight sour from the phosphate proved a perfect foil to the other half of the plate; a cake that would have been more appropriately described as a horizontal mille-feuille with alternating layers of thick banana pudding diving crispy house made wafers doused with caramelized banana chunks in a hot boozy sauce plus a bit of extra chocolate for good measure – all in all the best dessert I’d taste on this entire visit to Chicago.

With the bill paid and people still continuing to file in even as we exited the restaurant around 10:30 we thanked our server and again made our way to the street where a short drive would land us at our hotel exhausted, full, and happy to have experienced Segal’s intriguing concoctions even though not all were perfect and despite the fact that our ears were still ringing as though we’d just been to a concert as opposed to a restaurant (okay, slight exaggeration.) That said, having now experienced the scene at night I’d definitely not hesitate to return for brunch to see the savory side of the menu – and to try those brioche doughnuts the girl at the table next to us was eating.

Moving on to our final non-meal bites of the trip, the second night’s dessert setting would feature one of Chicago’s elder restaurants – The Atwood Café located inside the classic Reliance Building – a fitting end to a day that saw us spend most of our time downtown browsing Chicago’s iconic architecture from The Rookery to The Watertower and a distinct opposite from the loud cutting edge scene of the previous night at Mindy’s Hot Chocolate.

Making our way into the small restaurant by way of the hotel we were greeted first by tuxedoed door men and then by a friendly host named Patrick who would additionally act as our server for the evening. With the hour again past 10:00 we were told the main menu was no longer available and confirming that just desserts and coffee was our intent we were led to a nice four top in the middle of the heavily draped and upholstered room where we found both silverware and menus continuing the robust art-deco theme. With water poured and coffee offered and accepted by myself it was little time before our decisions were made and with a jovial “all the best choices” Patrick disappeared only to return moments later with both water refills and coffee warm-ups and once again ten minutes later with our dessert selections.

Without a bad sounding selection on the menu, the first dessert – my mother’s – would be the most “plain” yet at the same time perhaps the most intriguing, a dish called Buttermilk Pie with Huckleberry Compote. Described as being fashioned after something the pastry chef’s mother used to make at a diner down south and somewhere between tangy custard and sweet panna cotta baked into a soft shortbread crust this simple pie was topped with pan reduced huckleberries bursting with their juices and a dollop of whipped cream that served more to smooth than to sweeten – all in all this was diner food dressed up and down-home delicious.

Moving next to the more complex menu options, my aunt’s choice for the evening would be Red Velvet Cookie Dough with Goat Cheese Icing and Beet Puree – clearly another southern inspired dish, but this time reconstructed from the ground up with dollops of what literally tasted like chocolate chip cookie dough touched with cocoa and cream beneath inverted ice cream cones and resting atop a thick and tangy cream cheese. With the earthy flavor of beets both spread across the base of the plate and lacquering the inside of the cones this dish was far less sweet than what most folks would expect from Red Velvet (as popularized by the cupcake craze) but actually much more interesting though I must admit the texture of the cookie dough did get to be a bit much at times.

Rounding up the trio with my choice, a choice that would have been a no-brainer on any menu in America for me, Fig Bread Pudding with Lemon Basil Sorbet and Chantilly Cream was every bit as good as anticipated…or at least the Bread Pudding and Chantilly Cream were. Beginning first with the pudding – to be fair it was less bread pudding and more a traditional English Steamed pudding rich with both creamy and fibrous bits heavily accented with notes of honey, cinnamon, and brown sugar, but semantics aside it was great, especially when paired with the light and smooth Chantilly plus drizzles of honey fig sauce on the plate. Loving the bulk of the plate and really rather indifferent to the sorbet I’ll only note that while it didn’t really “hurt” anything, the sweet and savory concoction certainly did not compliment the dish in any conceivable manner and would have likely been served with another dish while pairing something more fitting with the pudding.

With no pressure to leave as Rat Pack standards played overhead we sat for a while enjoying our desserts while I sipped my coffee before Patrick would stop by again to make sure all was well and suggest we request the bill “whenever we were ready.” Another cup of coffee later and at this point not really making much difference in my fatigue the bill was next collected and paid with a sizable tip and after declining a cab since we’d driven we made our way to the streets which, save for the elevated train were largely quiet, and with my mother opting to drive I fell asleep almost the moment we got into the car – a well earned food coma if I do say so myself.