Are you looking to celebrate a special occasion dinner, like a birthday or an anniversary, but you’re looking for something a little different from the “greatest hits” from the food critics’ most lauded restaurants? Trust me, I’ve been there. After years of picking special occasion restaurants based on the number of Michelin stars (Chicago has 25 starred restaurants), I decided I wanted something to open up my Chicago special occasion dinners possibilities to all the other delicious restaurants in the city. Chicago is an incredible foodie city, filled with outstanding food in unexpected places. I have eaten at a lot of restaurants throughout the city and the neighboring suburbs, and I discovered several amazing restaurants that are worthy of a celebratory meal.
We have a ton of birthdays all clustered at the same time of the year, which makes this time of year especially busy. In December and January alone, we celebrate my birthday, Dave’s birthday, my brother’s birthday, and my sister’s birthday. This year, Dave and I did Whole30 during our third anniversary, so we decided to also celebrate a belated anniversary dinner in December. Given the fact that we had so many birthdays to celebrate at once, I decided to share my rationale behind picking special occasion restaurants and final choices of Chicago special occasion dinners for December 2017 and January 2018.
My criteria for these five Chicago special occasion dinners:
- Classy atmosphere. If I’m celebrating a birthday or an anniversary, I want it to feel special. I love a good slice of pizza as much as the next person, but a pizza joint does not provide the upscale atmosphere I prefer for a special occasion.
- Outstanding service. When celebrating a special occasion, I don’t want there to be any unwelcome surprises. I don’t want to show up to dinner with an inattentive server who fails to acknowledge the birthday or anniversary. I do want a service experience that attends to everyone’s comfort and makes sure the guest of honor feels special.
- Affordable. You may define it differently, but I define “affordable” as restaurants with entrees available for under $30. (With five Chicago special occasion dinners over the course of a month, this was a key criteria this year.)
1. The Bristol – Located in Bucktown
The Bristol is an outstanding local restaurant located in the Bucktown neighborhood of Chicago. The Bristol has delectable American cuisine, particularly recognized for handmade pasta, their farm-fresh produce, and the basque cake dessert. Executive Chef Todd Stein (follow him on Instagram here: @cheftoddstein) emphasizes fresh locally farm-sourced ingredients. The menu is veggie-forward, including dishes like the charred cauliflower, endive salad, and mushroom risotto. If you enjoy lighter fare alongside your heavier meat and seafood, The Bristol is a perfect dinner spot. Actually, part of the reason we chose The Bristol to celebrate Dave’s birthday with his parents because Dave’s mom is a vegetarian, and the menu provided plenty of delicious options for everyone. The Bristol recommends sharing plates for dinner for a communal dining experience. Everything on the menu is so good that you’ll welcome the opportunity to taste as much as possible. For a table of four, they recommend three starters, two pastas, and two entrees. We ended up ordering one additional pasta (the single yet tantalizing raviolo), and it was the perfect amount of food. The highlights from our meal were the monkey bread with dill butter, the pork tenderloin, the raviolo with ricotta, farm egg, and brown butter, the cacio e pepe, and the acclaimed basque cake. The service was also impeccable. The staff at The Bristol made Dave feel so special from the start of the meal to the end. The meal began with personalized menus that said “Happy Birthday Dave!” and ended with a trio of birthday desserts for the table (including a lit candle for the birthday boy). We ended our meal with perfectly brewed earl gray tea from La Colombe. As far as Chicago special occasion dinners go, The Bristol deserves your consideration. You can count on The Bristol to make the dinner special for your guest of honor, and the food will be outstanding. Click here for their brunch, dinner, and drink menus.
2. Roanoke – Located in the Loop
Roanoke Restaurant is an American restaurant located in the Loop (by Madison and LaSalle) near several theaters in the heart of the Loop. It’s an obvious choice of the potential Chicago special occasion dinners, particularly if you’re planning on seeing a show at one of the many nearby theaters. (I’m still kicking myself for not knowing about Roanoke when I saw Hamilton at the CBIC Theatre!) Roanoke has a sophisticated atmosphere–perfect for a classy dinner for a special occasion. There are also a lot of different seating options available throughout the restaurant. They are equipped to host any size of group dining up to 150 people! So, if you want to invite all your friends to a birthday dinner, rest assured that Roanoke has you covered. We opted for an intimate dinner for two to celebrate my belated birthday. Roanoke nails my top three categories: classy atmosphere, outstanding service, and affordable. Our exceptional server led us to an private two-person booth toward the back of the restaurant. While there were people dining around us, we felt like it was just the two of us with the high-backed booths. We started our meal with cocktails from the drink menu. The highlight was the Landmark Old Fashioned with tea drip infused old forestor bourbon, turbinado syrup, and bitters. Roanoke has a unique apparatus used to infuse liquors (like the forestor bourbon) with different flavors, including tea. I would sit at the bar just to watch this infusion take place in real time! Next, we ordered the meat and cheese board for a starter. The selection of cheese for the day was delicious and paired well with the mostarda, house pickles, and toast points. This was a fabulous indicator of the outstanding dishes to come. The standout dishes the rest of the meal were the wheat berry salad, the rotisserie porchetta, and the macaroni & cheese side dish. (The tasso ham, blue cheese, cheddar, gruyere, holy trinity, and panko breadcrumbs together made one of the best mac & cheeses I’ve tried in Chicago.) In addition to the reasonable prices, we were also impressed by the ample portion sizes; we actually had leftovers to enjoy the next day. Our lovely server surprised us at the end of the meal with a huge ice cream sundae with a candle, and she even sang happy birthday to me! It was the perfect end to a perfect birthday dinner. Click here for their full brunch, dinner, and drink menus.
3. fourteensixteen – Located in La Grange
fourteensixteen is a New American restaurant with locally sourced ingredients located in Chicago suburb of La Grange, about 25-minute drive from downtown. Even though La Grange is located in the suburbs–not the actual city–this Chicago special occasion dinners post wouldn’t be complete without a nod to the neighboring suburbs. The restaurant is located in the downtown area of the town, which is easily accessible by the BNSF Metra line (zone A-C Ventra ticket from Chicago to Aurora). Most of the ingredients in the food are sourced within 300 miles of the restaurant, and the menu changes depending on the seasons. While some of the dishes we enjoyed for this special occasion dinner may not be available when you dine in, I’m confident in Chef Bret Bohning’s ability to create outstanding dishes–regardless of season. fourteensixteen has some of the best dishes I’ve had outside of the city limits, so I knew I wanted to return to celebrate my sister’s birthday. Even though we dined in on a weeknight, fourteensixteen was filled with people for dinner, so make sure you make a reservation! The building is an industrial rustic space with a dining room, bar, lounge, and rooftop terrace. For dinner, we dined in the dining room near the kitchen, where we could see everything being cooked through a large glass window. The tastefully rustic space was decorated with class holiday decor, which enhanced the special occasion ambiance of the meal. We started out our meal with a round of drinks. The “Thanks Champagne!” with St. George Terroir Gin, Cayenne Syrup, Lemon, and Perlage Prosecco had a delightful kick to it while still maintaining an overall pleasant sweetness. We decided to let Chef Bret Bohning decide on the rest of our meal by doing the “Chef’s Tasting” option on the dinner menu. The chef decides on four courses for the table, keeping in mind any dietary restrictions/preferences of the diners. Chef Bret did an outstanding job selecting dishes for everyone that met all of our preferences. Since I do not eat meat, he sent out another fish dish while Dave and my sister enjoyed the meat. Each dish was better than the next. We savored each bite of each dish. My absolute favorite dish of the evening was the gnocchi with Italian white truffle, parmigiano-reggiano, chestnut, and parsnip. The flavors of everything completely blew my mind, and I was immediately wistful upon finish the last bite. Pastry Chef Ruby Rodriguez created an outstanding beet dessert for us to share, which was almost too beautiful to eat. It was an inventive take on beets, including beet merengue, chips, and cake. Following the dessert, our meal ended with a special round of port for us in celebration of my sister’s birthday; it was my favorite glass of port to date! We were so pleased with the birthday dinner; I recommend you consider venturing out to La Grange to experience it for yourself. Click here for the full dinner menu.
4. Tuscany – Located in Little Italy
Tuscany Restaurant is an Italian restaurant with locations in Chicago, Oak Brook, and Wheeling. My friend first introduced me to Tuscany a few years when she had her bridal shower at the Oak Brook location, and I loved the food there. This year, I decided I wanted to try out Tuscany again–but this time at the Little Italy location in Chicago. I picked this special occasion dinner for my brother’s birthday because he absolutely loves Italian food. I was initially a little nervous about any comparisons he might make between Tuscany and the food he ate in Italy earlier in the year. I knew Tuscany was good, but how could it possibly compare to Italian food in its country of origin? Well, after enjoying several dishes at Tuscany, my brother was raving about the food by the end of the meal. “It’s even better than most of the food I ate in Italy!” he declared. Yes, it was that good. The space managed to be both formal and classy while also feeling positively cozy. The beautiful decorations for the holidays helped create a festive, celebratory ambiance. The service throughout our meal was personable and attentive, which really made it stand out compared to many other places we’ve dined. Our lovely Italian server made excellent recommendations for food and drink; he did not steer us wrong! We split a bottle of red wine for the table based on our server’s expert recommendation. Our server also brought a huge basket of bread and created an amazing dip by crushing fresh garlic tableside and mixing it with olive oil and parmesan cheese. It was hard not to fill up on the bread because it tasted so good–especially when doused in the flavorful garlic dip. Thank goodness for our server’s recommendations because everything looked delicious on the menu. We decided to order a few pasta dishes to share, then entrees to enjoy individually. Of the dishes we tried, we could not stop raving about the raviolini pera with roasted pear, parmigiano, toasted nuts, sun-dried tomatoes, and mascarpone cheese. It was absolutely decadent–so much so that I recommend it as a shared dish so you still have an appetite to enjoy dessert! I also loved the polpi (spicy grilled octopus) antipasti with tri-colored salad and balsamic vinaigrette. I’m really picky about octopus because it’s one of my favorite foods, and Tuscany passed with flying colors. My brother also raved about his filettini con funghie e patate all’erbe (seared beef tenderloin with crispy potato and wild mushrooms, malbec reduction, and toasted sage). Our wonderful server surprised my brother at the end of the meal with a cannoli with a candle in it! The meal went as wonderfully as I could have hoped, and we all left smiling from ear to ear. I highly recommend going to Tuscany for authentic Italian cuisine; they will make your special occasion special! Tip: There is a parking lot connected to the restaurant for free, easy parking! Click here for the full lunch, dinner, wine, and dessert menus.
5. Stock and Ledger – Located in the Loop
Stock and Ledger is a newly opened upscale American restaurant located in the Loop on the corner of Madison and Dearborn. Stock and Ledger prides itself in sourcing quality ingredients, including offering Antibiotic and Hormone Free (ABF) chicken, beef, and pork. They also are carefully to source fully sustainable seafood: seafood caught or farmed in an environmentally friendly way to help sustain the species. If you eat a gluten-free diet, Stock and Ledger even has a dedicated gluten-free fryer for the substantial gluten-free items on the menu. Chef Laura Piper was raised eating fresh ingredients, so her dishes on the menu strongly reflect that culinary upbringing. Dave and I decided to celebrate our three-year anniversary at Stock and Ledger because we had heard a lot of positive buzz, and we loved the idea of trying somewhere new for our special occasion dinner this year. Even though the restaurant had been open for less than a week when we dined in, the service was 100% on point. I often find that restaurants have a lot of training to do and other kinks to work out during the first several weeks of opening, but there were no telltale signs of that at Stock and Ledger. If I were not privy to its recent opening, I easily would have assumed it had been open for a long time based on how expert our server was in explaining the dishes. Out of the dishes we tried, the standouts were the mussels with Spanish chorizo, caramelized fennel broth, red pepper mayo, and crostini, the seared Great Lakes walleye with olive caper tapenade, potato chips, and dijon butter sauce, the flourless chocolate cake, and the chocolate peanut butter mousse dessert. I never would have considered eating potato chips with walleye, but it paired spectacularly. Our courses included an excellent combination of salty and savory tastes. We were so surprised with our server brought out a flourless chocolate cake with “Happy Anniversary!” written on the plate, plus glasses of rosé. It was the perfect way to end a delicious meal, and we could not be more grateful we decided to celebrate our anniversary at Stock and Ledger. Click here for the full lunch, dinner, dessert, specials, and happy hour menus.
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Disclaimer: While some meals were complimentary, all opinions expressed here are my own.
Karen says
I love Tuscany and The Bristol! Have not made my way to the others yet, but now I want to. Thank you for the informative article.
Claire Drake says
How hard is it to get reservations at The Bristol? I remember you mentioned on Instagram stories that there was a line at the hostess stand when you went on Friday night. Thanks!