Restaurants in the Loop tend to be terrible or overpriced - often both. So the decision to eat in this neighborhood is usually based on necessity, not choice. Perhaps you have a business meeting, an event downtown, or some visitors who think there’s a containment field surrounding The Bean. The good news is that while good spots here can be hard to find, they do exist. Here are 12.
If you’re having a business dinner with out-of-towners, going to a Chicago steakhouse is usually a safe bet. And Prime & Provisions is where to go when you’re in the Loop. This place is hard to classify - it’s not as iconic as Gibsons, as trendy as RPM, or as corporate as Chicago Cut. But it still serves fantastic steak, along with options like seafood, fried chicken, and a giant piece of bacon topped with maple syrup and dark chocolate. Plus, the upbeat space is huge and full of giant booths - two good indicators that you’re in a genuine, accept-no-substitutions Chicago spot.
On weekends and weeknights, sections of the Loop feel eerily deserted, kind of like the opening scene of 28 Days Later. There just aren’t many good reasons to stay in the neighborhood once you’re done with work. But dinner at Fisk & Co in the Hotel Monaco is a valid one. Their specialty is mussels, and you can get them served in a variety of different broths (like white wine or green curry). The rest of the menu is seafood-focused as well, with raw bar selections and entrees like a prosciutto-wrapped bass. It’s a great option for a casual business dinner or a mid-priced meal by yourself at the bar.
If you miscalculated how long mini golf at Maggie Daley Park was going to take and are now in a hunger-induced fugue state, the Loop is a minefield of bad decisions. Avoid going someplace like The Corner Bakery because now (in your vulnerable condition) it seems like the easiest choice. You need to know about The Dearborn, an easy-to-like spot with a well-rounded American menu that works for a lot of occasions. It’s nice enough for a business dinner, but still casual enough for lunch after that Segway tour you took with your parents. Plus, the space is huge, with multiple rooms that work for large groups or couples on a date. Order the pork belly appetizer and any of the salads, then make sure someone gets a cheeseburger - it’s really good.
Your friend’s bachelor/bachelorette weekend is finally here, and the good news is that it’s in Chicago, so you don’t have to fly anywhere. But this also means you’re now responsible for showing off the best parts of the city while making sure no one passes out on the roof of a double-decker bus. Put dinner and drinks at Cindy’s on the list. It’s on Michigan Ave on top of the Chicago Athletic Association, and has beautiful views overlooking Millennium Park and Lake Michigan. It’s particularly good for groups, with a lot of dishes designed to be shared among three or four people. The food probably won’t blow you away, but the atmosphere makes up for it.
In addition to Cindy’s, there are actually a lot of other great spots at the Chicago Athletic Association, like The Game Room (a cocktail bar) and this place, an upscale restaurant on the second floor. The main design elements at the Cherry Circle Room are dark wood, overstuffed leather chairs, and a huge fireplace. It reminds us of a fancy turn-of-the-century lodge, and the rustic menu (with plenty of roasted meat) fits the ambiance. It’s perfect if you’ve ever wanted to join a secret society without needing to learn a bunch of passwords and handshakes.
Hotel restaurants are a way of life in this neighborhood - it’s something you just have to accept. Cochon Volant is another one, underneath a Hyatt hotel. This spot is designed to feel like a French brasserie, with vintage-looking marble tables, a bakery counter, and a menu full of French food. It does a good job of temporarily helping you forget that the neighboring stores include a Starbucks, Dunkin Donuts, Wendy’s, Noodles & Co., and McDonald’s. Get their cheeseburger royale - it’s excellent.
Chicago is an old city full of activities like architectural boat tours and visits to the places where mobsters used to hide out. And if you want to continue this historical theme, consider eating at The Berghoff. This German spot opened in 1898, and still has an old-school bar/tavern feel. You can expect dishes like wiener schnitzel, sauerbraten, and a pretty fantastic reuben sandwich. Come here for a casual meal with someone who just spent the day listening to a tour guide talk like Al Capone. And hope they’re not inspired to practice their new gangster impression, or it’s going to be a long meal.
The Gage is our top choice in the Loop for bar food. The menu is full of elevated classics, like bison tartare, poutine, and entrees like fish and chips. Since this spot is right across from Millenium Park, you can also plan on it being full of tourists. But at least they’re the cool kind of tourists who know where to go for a good meal.
Acanto is a small, upscale Italian restaurant from the same people who own The Gage, and it’s right next door. This place has great housemade pastas, so focus on those when you’re here. Although you should still make sure to get one of their pizzas - there are two on the menu, but there’s typically another on special that you should try.
Cafe Bonhomme is owned by the same people as Beatnik in West Town. And much like Beatnik, Bonhomme puts a lot of effort into its atmosphere. It’s meant to feel like a lively European cafe (so it can get a little loud), and it has an eclectic menu, with dishes like beet hummus, crab brandade, and curried meatballs. Come for drinks and small plates to celebrate the end of your internship.
Steadfast is in the Kimpton hotel, and this place really feels like a hotel restaurant. For example, you have to leave the restaurant, climb two flights of stairs, and go down a long hallway to get to the bathroom. That aside, this is still a good option for a fancy meal in the Loop. They have prettily plated entrees, caviar service, and a tasting menu option - five courses for $75, or seven courses for $115. If you commit to that, just try to remember to pee ahead of time.
If all else fails, there’s always the Shake Shack at the bottom of the Chicago Athletic Association. Sure, the the line goes out the door at peak times, but it’s worth it for crinkle cut fries and a consistently great cheeseburger.