The West Loop has a disorienting number of great restaurants, and picking out a place to go on a date in the neighborhood can be overwhelming. But we’re here to help you sort through it all. Whether you’re trying to impress a potential partner with a low-key bar or you finally found a babysitter, use this guide to find the perfect date spot in the area.
OK this one might take some planning since Monteverde gets booked up quickly. And for good reason, this spot has some of the best Italian food in the city. Every pasta dish here is fantastic, in particular the cacio e pepe, which is a menu staple. But the non-pasta is great, too (try the stuffed cabbage appetizer or the pork shank), and what makes this place even better is that you can buy their fresh pasta, sauces, and pantry items to take home.
photo credit: Kim Kovacik
Trivoli Tavern is in Gin Alley, and from the same team as Au Cheval and Green Street Smoked Meats. This means they have a twinkly lit cobblestoned patio. Or you could sit inside, where it’s dark and full of overstuffed leather furniture. The menu has a lot of dishes you’ll find at their other restaurants. They serve upscale bar food like fish and chips, handmade pastas, steaks, and a very good burger. This place works well for a date, or anytime you can’t get a reservation at Bavette’s or Gilt Bar.
The West Loop has more restaurants run by former Top Chef contestants than any other neighborhood in Chicago. Our last count was eight, and they’re all operating within two blocks from each other. And, despite our trust issues with reality shows, they’re all really good. Rose Mary, a Croatian spot, is another one of those restaurants. They have things like a refreshing and flavorful salad with tomato, farro, and asparagus, a delicious crni rizot that tasted like it was made with stock from the tears of a hundred lobsters (that’s a compliment), and incredible pastas. Most dishes range from $10-$25, and it works for a casual date.
Alla Vita in the West Loop is always buzzing with staff, and everyone from couples to small groups. And the space is impressive— decorated with hanging plants and a very cool fabric wave ceiling. Plus, it’s roughly the size of Terminal 2 at O’Hare but with way better food. This Italian spot is from the same chef as Boka, and while the menu isn’t going to blow your mind with creativity (it’s mainly pizza, pasta, and a handful of entrees) it is delicious. The cacio e pepe ricotta dumplings can only be described as “sexy”, the pizza has a chewy crust, and the chicken parmesan stays crispy even while sitting in a rich tomato sauce.
You can come to Perilla for their fantastic Korean BBQ (most tables have a gas grill), or you can focus on the other dishes—like the spicy fire chicken, dumplings, or the kimchi pancake, which is one of the best in Chicago. As far as Korean BBQ goes, this upscale place is pretty sedate. You’ll be grilling your own meat to a quiet indie rock playlist, surrounded by other couples on dates silently grilling away and people that clearly just came from the office.
The Loyalist is the casual French restaurant and bar in the basement of Smyth. And while the food here is good (with dishes like foie gras-filled eclairs and gnocchi a la Parisienne) the main reason is to come here is for the outstanding burger. The patty is made from a mixture of chuck, short rib, and bacon, giving it a light, smoky flavor and incredible richness. The cheese is gooey and the caramelized onions are plentiful. In other words, even if the date is bad at least this will be good.
El Che Steakhouse & Bar
This Argentinian spot is fun and a little loud, with a live-fire grill putting out some delicious food in the open kitchen. Everything that grill touches is worth ordering. We like the steak, but don’t overlook the grilled oysters or sweetbreads, and breaking up the meat-fest by ordering plenty of sides is a good idea. El Che works for a group since everything is easy to share, but it’s great for date night, too. No matter why you’re here, it’s an easy place to have a good time. And in case you want to try grilling some stuff yourself, they sell meat and various other things in an online market.
When all else fails, Avec. You can never go wrong here, and we encourage you to visit Avec every now and then to remind yourself how reliably outstanding it is. New menu items keep the romance alive and interesting, but it’s the staples like chorizo-stuffed bacon-wrapped dates and the taleggio flatbread that we’ll always come back for.
Duck Duck Goat
This is the Chinese restaurant follow-up to Girl & the Goat and Little Goat. Like everything in the goat empire, Duck Duck Goat is a fun spot with good food. Here, you’ll find Chinese food with twists—like glass noodles with blueberries. Of course, several dishes have goat in them (like the duck and goat spring rolls). Also worth noting is that their takeout window Bao Bing has great desserts in case you want to stroll around the neighborhood with some sesame soft serve.
Dinner at Aikana in the West loop might make you forget that we live in a city that necessitates owning a floor-length puffer coat. This upscale Latin American restaurant is filled with hanging basket lights and tropical plants, and the menu focuses on food from Central and South America. You’ll find dishes like lime-cured wagyu on top of a crispy rice cake, mote and chorizo mixed with an incredible poblano salsa, and the churrascaria, which includes your choice of meat, tubers, arepas, and a few other sides that are perfect for two people to share.
This upscale cocktail bar and restaurant is from the owners of Oriole, a fancy and expensive tasting menu spot that’s right next door. This place has wonderful cocktails, coffee drinks, and small plates. All the dishes look pretty and artistic, and you’ll find delicious options like tamago and tonakastu sandos, karaage, and yakisoba.
Even by West Loop standards, this place is a scene. The good news is that Aba is a scene that comes with fantastic food. It’s always crowded, but the space is beautiful, and there’s a huge rooftop patio that’s perfect for hanging out over drinks (even during the winter). And as with its sister restaurant, Ema in River North, a lot of things on the Mediterranean menu are meant to be shared.
This is one of the only spots in the city that specializes in okonomiyaki - savory Japanese pancakes topped with things like shrimp, chicken, and beef. Gaijin has a few different varieties to choose from (for example “Hiroshima-style” where the batter is layered with yakisoba), and we like them all. Be prepared, though—this small place gets very crowded. So definitely plan on making a reservation.