The absolute highlight of my trip was eating at Schwa. Chef Michael Carlson and his brother Seth who run it are so punk rock that they don't even answer the phone, which makes getting a table difficult, yet weirdly fascinating. From the outside, Schwa looks like it has been condemned. Inside, the dining room is small and spare yet cozy. The formality of the service and menu (no orders taken until the whole party arrives, and the elaborate tasting menu) is juxtaposed by all the hot waiters in skater clothes and the blaring hip hop/heavy metal. The food is sublime. We did the 9 course tasting menu, which ranged from a very inventive bourbon Manhattan aperitif to the most unbelievable baked potato soup with crispy potato skin on the side (my favorite) with scallion purée and cheddar cheese. It’s classic American comfort food by way of Ferran Adria/Banksy/Tony Hawk. It’s off the hook.

Publican was another high point for me. It’s my ideal kind of menu, with oysters, roast chicken, fries, and lots of delicious sides. The room is big and light and open and our booth had little saloon style swinging doors on it for privacy. A great meal.

RL Restaurant, (yes that’s RL for Ralph Lauren) has the old-fashioned feel of an English club, with dark paint on the walls, leather seats, and art arranged salon-style on the walls. It’s a prime spot for ladies who lunch. I like to stop by here for their chopped salads, club sandwiches, and tomato soup.

This is a nice neighborhood place I went to for a simple Italian meal on my last visit. Chef Riccardo’s family-run joint has a plush tasting menu that is always a good option (especially if you’re very hungry, as portions tend to run large.) You definitely want to make a reservation, as it’s a small cozy space and it fills up on a nightly basis.

I stayed at the newly opened Elysian hotel and I loved it. I love a new hotel and they have really done it right. I loved its pared down aesthetic and its many shades of grey. It was chic and comfortable, and I also loved being in the heart of everything but not right on Michigan Avenue. The restaurant was delicious and the spa was lovely—I treated myself to a great massage before an overnight flight. Great service—elegant yet cool. I will definitely be back. The hotel has two restaurants and I stopped at Balsan for some great American bistro-style food, with oysters on the menu and flatbreads made in a wood burning stove.

For many years this was my all time favorite city hotel. The rooms and suites are spacious and beautifully turned down with great views of central Chicago. It’s definitely more of a traditional hotel with everything you’d expect—a great big pool, a wonderful spa, and perfect service.

Ikram is an incredibly special store with everything handpicked by Ikram Goldman, the owner who is known for, among other things, having styled Michelle Obama. I was so impressed by the beautiful space, all the one-of-a-kind pieces I found there, not to mention the spectacular jewelry. I found tons of interesting knitwear, lots of new designers I hadn’t heard of before and loved, jewelry and fun collaboration pieces like Rodarte’s line of sunglasses for Opening Ceremony (I bought two colors.)

Thanks to my friend Jessica, every time I go to Chicago I head to Blake, one of my absolute favorite stores in the world. They stock everything from Rick Owens to The Row to Marios Schwab, and round it out with more mid-priced brands like L’Agence (one of my favorites). The buyers have amazing taste; it’s hard not to fall in love with this place ....

Maybe it’s because it’s so damned cold in Chicago in the winter that the Moncler store here is one of the best in terms of selection. The Italian brand is famous for making winter outerwear, even big puffy jackets, look good.

I stopped here to buy a few things for my kids and loved their selection of cute and stylish clothing that kids actually want to wear. I especially liked their huge selection of jeans and casual play clothes, with brands like Splendid, Joe’s and J.Brand available. goop customers will receive a 20% discount when shopping on their online shop by using the coupon code: goop20!

I love going to Barney’s in Chicago. To start, the buyers at this branch are incredible at finding pieces that you often won’t find anywhere else. A huge plus, because Chicago tends to be more conservative, is that you can actually find runway pieces, as they tend to disappear lightning fast in New York.

Graham Elliot serves dressed-up American food using conventional ingredients to create unconventional combinations. His kitchen is a laboratory and the dishes that come out are completely original. The food and restaurant are elegant, but everything is set up and served in a relaxed, laid-back way.

Located within the new Hotel Palomar, Sable is the destination for a few drinks or a full meal. They serve gastropub dishes with an American twist, and a long list of wood-fired flatbreads. Their 14 page cocktail list is garnering plenty of attention too for a mix of old-fashioned drinks, new twists like their Ice & Fire, a tequila-based drink with Sriracha, cucumber, agave and fresh lime, and the longest list of options for a good ol’ Martini.

We hear great things about The Girl & The Goat, where craft is the key to every single one of the dishes. Chef Stephanie Izard separates food into three categories—meat, fish, and vegetables—with plenty of crossover in between. Combinations are unexpected and bold flavors abound, all with a feminine, comfortable touch. Don’t miss the selection of house-made breads served at the beginning of each meal, and if you’re a beer drinker, you will be pleased with their unusual collaborations with Three Floyds.

A collaboration between a chef and a wine connoisseur, Chef Tony Priolo and Ciro Longobardo opened Piccolo Sogno in 2008. The modern and rustic Italian food is all about the freshest, seasonal ingredients and Italian wines. The best seats in the house, especially in the summer, are in their quiet outdoor patio.

Nightwood’s handwritten menus are re-written on a daily basis, as the food served depends on the ingredients available from local farms and suppliers on that day. It’s a bit of a way’s to get to, as it’s located in Pilsen, but every single bite is worth the trek. On warm nights, the outdoor deck is an ideal setting, and in the winter, I imagine their simple and rustic décor makes for a perfect setting.

Another Chicago gastropub with great food and drinks available. You’re free to stop in for either or both, and are likely to be impressed. New at the Longman & Eagle are a few very affordable and sleekly decorated guestrooms, featuring the work of some great American craftsmen and designers.

My friend Julia recommends Arami for the freshest sushi in town. The Japanese dishes here are all authentically modern.

By far the best bbq in Chicago. The menu is short and, unsurprisingly, meat heavy but what makes Q special are the house wood-smoked meats and the distinctive rubs and pickles they concoct so consistently.

Davanti Enoteca
1359 West Taylor Street
+1 (312) 226-5550

Davanti, a fun wine bar which opened in September 2010, serves up a variety of rustic and regional Italian dishes. This is definitely a place to share plates and you can choose the size – from a vasi (a selection of spreads) to boards of appetizers, pastas or pizzas.

Next & The Aviary
955 W. Fulton Market

How could we do a Chicago newsletter without mentioning Grant Achatz, the Midwestern wunderkind of molecular gastronomy? He has recently opened up a new restaurant, Next, and bar, The Aviary. Expect flavors, textures and combinations that you’ve never encountered before. Next is an interpretation of French cuisine harkening back to 1906. The Aviary is more than a cocktail bar or lounge. It’s a lab. To get a coveted reservation (or a ticket, as the website indicates) sign up online.

Located in the hub of the art and design district, the Palomar is a modern, pet-friendly, eco-friendly, organic-oriented hotel that caters to active city visitors. The hotel organizes fun group exercise classes that include guided runs along Lake Michigan and ballet barre workouts on the hotel’s sundeck. Other novel perks are the in-room massages and yoga sessions available. And, if you travel with your pets, you’ll be pleased with all the amenities that they’ll enjoy. Sable, one of the best bars around, is just down the stairs.

Another solid option for a downtown hotel with all the good comforts and amenities. Plus a sleek, modern design makes it a Chicago oasis.