There are literally hundreds of date spots in the city, some better than others.
These are my opinions.
Check back for post-date reviews.
Glenn’s Diner is right under the brown line at Montrose. Their awning claims “The Best Food in the World” and I certainly wouldn’t throw the first punch over that disagreement. With a unique combination of entrees and an entire section of their menu devoted to cereal, Glenn’s covers all the bases. With your everyday cereals like Chex all the way to seasonal holiday cereals and even a few I hadn’t heard of before, I was sufficiently impressed. In plain juxtaposition to their cereal collection and all-day-breakfast menu, Glenn’s also offers an incredible selection of scrumptious sea food. Their menu is lengthy and overwhelming but spattered with notably well written content and reads more like a beautiful book than a listing of food. With a decent wine selection on hand and a great collection of desserts, Glenn’s won me over instantly. Date or no date, I will certainly be back again, perhaps solely for the Count Chocula.
**Photo borrowed from Glenn’s Facebook page
The Lincoln Park Zoo
• I mean, they have otters. What more could you ask for on a first date?
DMK Burger Bar (Lakeview)
• Great burgers that you can eat while still looking decently respectable? I vote yes.
The J Parker (Lincoln Park)
• Ultra-trendy rooftop bar with an interesting cocktail list and an unbelievable view of Lincoln Park that will blow you away at sunset.
Tavernita (River North)
• Delicious food, amazing cocktails, ambiance that will make you wonder if you’re actually cool enough to be there…
Howells and Hood (Mag Mile)
• A rather impressive beer list, wine by the beaker and the largest patio I’ve yet to find in Chicago? Sign me up!
Bar on Buena (Buena Park)
• Snag a seat at the bar on a Wednesday, enjoy a craft beer and split a giant bowl of all-you-can-eat mac and cheese. It just sounds too good to be true, doesn’t it?
Webster’s Wine Bar (Lincoln Park)
• Friendly staff, a beautiful collection of wine, and a lively-yet-intimate atmosphere. Aim for earlier in the evening so as not to run the risk of finding yourself table-less.
• A little loud and certainly very casual but great for a good beer and some nibbles if you want to keep things low key.
Atlas Brewing Co (Lincoln Park)
• Atlas lets you try samples of beer so commitmentphobes (or beer ignoramuses, like me) can experiment. The environment is laid back and casual.
The Matchbox (River West)
• This place has quite the reputation and I’d say “intimate” is an accurate word, but on a first date I like to be on the same level as my date. Literally. It’s awkward if you can’t get two seats at the bar and one person has to stand :-/ maybe that’s just me.
Rocks (Lincoln Park)
• Good for pretty decent bar food and a good selection of drinks. If you’re going for this option, stick to it in summer when you can take advantage of their great patio!
Haymarket Pub & Brewery (West Loop)
• A solid selection of house-brewed beers available in adorable 4oz sample cups so you can try a variety. Standard bar food.
Zocalo (River North)
• Good food, great drinks, upscale ambiance. Just don’t over indulge in the delicious margaritas!
Brownstone Tavern (North Center)
• I’m always a fan of a Four Corners restaurant but it’s certainly more sports bar than date spot.
Trader Todd’s (Lakeview)
• Honestly, there are few things I love more than karaoke but there is a time and a place for everything. A first date is not the time or the place (and yes, someone did take me to a Karaoke bar on a first date)
Cullen’s Bar and Grill (Southport Corridor)
• Pleasantly standard. Standardly pleasant. I might grab a drink here with friends out of convenience but I wouldn’t try to impress a date with it.
Some places are awesome but not first-date appropriate. If you find yourself with a keeper (or, I mean, on date 3 or 4) give these places a try.
Rose Angelis (Lincoln Park)
• Rose Angelis is for lovers. Or anyone you really like. Great Italian food with a definite homemade feel. Incredible specials, great desserts. Love love love it.
404 Wine Bar (Lakeview)
• Cozy, homey, rustic, delicious. A great selection of wines and fantastic nibbly bits. One of my favorite first date spots in the city but certainly with a heavy romantic vibe. Could be great for an intimate 2nd or 3rd date for a lil wining and dining.