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The Windsor

Perfect For: Wasting Your Time and Money

The Windsor

Ah, tourists. Aren’t they adorable? While their actions, such as intentionally spending time at Navy Pier and taking endless selfies in a mirrored bean, might confuse us, we still want to protect these gullible little lambs from the ruthless Chicago wolves. That means we steer them away from scary things - Navy Pier on sunny days, Hancock/Sears on cloudy days, or the Taste of Chicago every day. It’s also our duty to show them the good parts of our food scene, and not let duds like The Windsor ruin a good thing.

The Windsor is smack dab in the middle of Streeterville, one block off of Mag Mile inside of a Hampton Inn. We should have known better right then. Walk in, and you’ll get a feel for what Applebee’s will look like when it rebrands in five years. It’s trying to follow the overplayed rustic yet chic formula of so many before it with lots of wood and lots of exposed bulbs. The problem is it feels like a cheap imitation of the real thing. There’s a huge bar up front with a couple of dining rooms in the back, and the acoustics are quite poor as it’s trying to be both a trendy restaurant and a raucous bar.

The food tastes like a product you’d get at mid-level chain restaurant. Some things don't taste like they were made fresh, some things are boring, and some are just plain bad. While the service is truly great, it’s not enough to overlook disappointing food.

Tourists will wander in here simply because of its location, but help them. Warn them. Steer them back around to Purple Pig or Joe’s. Or for the love of God at least send them to Portillo’s. Do your civic duty as a Chicagoan - don’t let someone wander in here and think this is what Chicago food is all about.

Food Rundown

Buffalo Cucumbers

Exactly as advertised. Cucumbers with bleu cheese and really, really spicy buffalo sauce. Eh.

K Town Short Ribs

Short ribs covered in a spicy soy-ginger marinade with asian slaw. The soy-ginger marinade is solid, although not spicy as advertised, and the ribs are pretty tender.


There’s just no way this was made fresh. It tasted like it had been premixed, sitting in a fridge for a day. We’re guessing it was.

Berkshire Pork Chop

This chop with mashed potatoes is supposedly the star of the show. Unfortunately, they ran out. This has been a common theme, and it feels like more of an inventory issue than a “these things were so wildly popular that we ran out” issue.


Twirly pasta in tomato sauce with parmesan and bacon. It’s nothing to write home about.

Prime Rib

Served with au jus. This is terribly dry and a real letdown since The Windsor advertises their rotisserie options.

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