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Great places for dessert after dinner?

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Long time lurker here. I have a birthday trip planned for Chicago July 9th-11th. We will be staying at The Acme. On the 10th we have everything planned, lunch at Topolobampo, dinner at 42 grams, and possibly a night cap at The Berkshire Room if we are up for it. The 9th is a little up in the air though.

We are looking for a place that has a variety of great desserts that we can sample after dinner. I don't think we are looking for anything specific in the dessert itself. In the past we have done the Tru dessert tasting and Hot Chocolate. We are pretty open on traveling far in the city if it's a worthwhile destination, but near our hotel can sway our decision a bit. We also haven't quite pinned down dinner (maybe Boka since we enjoyed The Lobby on our last visit...), so if you have a suggestion for a great place that also has great dessert options, I'd love to hear it. We don't have a set budget or a preference over dressy vs. casual.

Edit: we will be arriving in Chicago at 3pm so we will have plenty of time to make just about anything work. Also, we have tossed around the idea of early drinks at The Aviary then wandering to somewhere in that area on foot if someone has suggestions on that.

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  1. >> We also haven't quite pinned down dinner (maybe Boka since we enjoyed The Lobby on our last visit...), so if you have a suggestion for a great place that also has great dessert options, I'd love to hear it.

    Recently I had dinner at North Pond, and it was thoroughly fantastic in every way, my best dinner of the year so far. I was especially impressed with the desserts - not that you can find great desserts elsewhere, but these seemed unusually creative as well as amazingly delicious, and you don't often find both in the same place. With the exception of Alinea, these were the best desserts I can remember having at any restaurant anywhere. Of course, North Pond is best known for its exquisite setting in the middle of the park, facing its namesake pond, with the city skyline looming over the opposite shore. (When reserving, request to be seated in the front room with the full-length windows.) I have enjoyed the cuisine from Lee Wolen too - including dinner his last night at the Lobby last December - but my dinner at North Pond was even better. North Pond is the recipient of one Michelin star and chef-owner Bruce Sherman won the James Beard Award a year ago. The restaurant's website is at www.northpondrestaurant.com and you can read the review I posted, with all the details about my recent dinner, towards the end of the lengthy post at www.chow.com/topics/976337#8953769

    Finally, if you're really looking for the most amazing, unusual, and delicious desserts in Chicago, you absolutely MUST go to Bad Wolf Coffee between 10:00 and 10:30 a.m. This is a coffeehouse with a limited selection of pastries, but those pastries are amazing. Jonathan Ory, the owner, has a fine dining background, and is turning out pastries every bit as good as Dominique Ansel in New York. His caneles come out of the oven at 10:00 a.m. so go shortly thereafter so you can get them warm and fresh, the most amazing caneles you'll ever have anywhere. His kouign amann is better than Ansel's and will open your eyes to just how good that pastry can be. Same for his Paris-brest. He only has about six pastries available on any given day but gosh they're amazing. It's right next to the Paulina stop on the CTA Brown Line and is closed on Tuesdays. www.badwolfcoffee.com

    1. Happy early birthday.

      I am as huge fan of Chef Wolen and Boka, so if you enjoyed what he did at the Lobby you likely will be extremely happy at Boka. Boka has good desserts, but I enjoy sister restaurant Balena's even better. They are just a block away from one another, so my wife and I often eat savories at Boka and then take a quick walk to Balena and sit at the bar there for dessert and/or an after dinner drink. The bar staff is so friendly there and excellent cocktails and dessert.

      If you opt for Aviary instead some good venues within a short walk for dinner would be Publican (farm-to-table), La Sirena Clandestina (Spanish), Embeya (Modern Asian fusion) and another of my favorite venues, Moto (modernist cuisine; lengthy tasting menu). Since you mentioned desserts, the pastry chef at Moto, Claire Crenshaw is amazing - some of my favorite all-time desserts have been consumed at Moto (she used to be the pastry chef at Tru). In the past Moto has occasionally offered a dessert tasting - so if you want to skip savories you may be able to work something out with them, especially on a weeknight.

      Stephanie Izard's Girl & the Goat might be an option too if you are willing to try and snag a seat in the bar/lounge area (where you can order off the full menu). Her sister venue, Little Goat Diner (across the street from Girl & the Goat) has one of my favorite desserts, a pork ice cream milk shake with homemade toffee.

      Grace (which IMHO has become the best restaurant in Chicago) is also in walking distance of Aviary, but pricey at $205 per/person for food. The tasting menu includes three dessert courses and mignardises and I love the pastry chef there.

      Eataly is extremely close to your hotel and does have a number of different dessert offerings (a pastry shop, a gelato venue, and a nutella bar). If you do savories elsewhere, that is definitely somewhere you can go afterwards to sample a bunch of sweets.

      For what it is worth, I prefer Berkshire Room to Aviary; while Aviary has the flashy, whimsical, unique cocktails I dislike their "ticket" system, find their drinks overpriced and quite frankly think the cocktails are generally better (though not nearly as flashy/exotic) at Berkshire Room. I do prefer going to Berkshire Room earlier in the evening as it becomes a bit too clubby of an atmosphere sometimes as the night progresses. Wonderful bar staff at Berkshire room - so recommend grabbing seats at the bar if available so you can interact with them. I highly recommend the Weston (a wheated bourbon based cocktail with Dark Matter coffee essence and cherry pipe tobacco essence - my favorite cocktail I have ever consumed) and their Pappy Van Winkle barrel aged negroni. Berkshire room opens at 4pm and Aviary at 6pm, so you could always try to do both.

      One other option is Nico Osteria; Amanda Rockman is the pastry chef there and is often regarded as Chicago's best. I have not dined there myself, but have enjoyed her desserts when she previously worked at L2O and Balena. For savories they offer upscale Italian food and are located in the Gold Coast neighborhood. I am not sure how busy they are on weeknights, but it might very well be possible to just go in for desserts.

      Have a wonderful trip!

      1. Cicchetti is a fine new restaurant (across the street from Tru), however their desserts are stellar. Their pastry chef was recognized as Jean Banchet Pastry Chef of the Year in 2013 and was also recognized as a "Best New Pastry Chef" by Food & Wine.

        She has a coffee and donuts dessert that's just terrific.