Here’s what you want: an outdoor date night. Here’s what you don’t want: to share a picnic table with six strangers, or sit on a sidewalk patio where you’re going to see multiple dog owners cleaning up after their pets. Here’s what you should do: read our guide to the 17 best places for a romantic summertime meal.
Update June 10th, 2020: After months of being closed, Chicago restaurants have been allowed to reopen. Check out the list of Chicago Restaurants Reopened For Outdoor Dining for up-to-date info.
the Outdoor spots
The tables inside this cute little restaurant are so close together that if your date involves a whisper argument, everyone will hear. Luckily for you and anyone who doesn’t want to hear a discussion of what happened last night, the back patio is huge. It’s also very private and includes enough string lights to charm the confrontation right out of you. Order a bruschetta flight (you can choose five different types for $12) and a polenta board to share (our favorite is topped with a venison bolognese). Then round things out with a pasta, like the penne arrabiata or one of the handmade specials.
This is a small Filipino restaurant in Wicker Park that has a dimly-lit interior and a cute back patio. Sitting back there feels a little like you’re having dinner on the deck of a Wicker Park single-family home you’ll never own. This means you can enjoy dishes like kinilaw, chicken adobo, and a fantastic sisig without worrying about a mortgage or whether the squirrels are getting into the garage.
The back patio at Piccolo Sogno is the standard by which all others are judged when it comes to a romantic dinner outside in Chicago. It’s surrounded by trees decorated with lights, and there’s enough space between each table that you won’t be able to tell whether the people around you are getting engaged or divorced. It’s good for any kind of date, too - from an early-in-the-game dinner to a “let’s finish this bottle of wine before we go home to the kids” situation. All in all, a true date night utility player.
Date nights don’t always start out perfectly - maybe someone is running late, or you’re having a very polite argument about street parking. But the upbeat environment at Mi Tocaya, not to mention the excellent Mexican food, will help all that disappear. Especially if you try your best to sit on the relaxing outdoor patio, on a quiet corner in Logan Square. The only thing to disagree about once you’re sitting down is your order. (And where to go for Thanksgiving - it’s never too early to start that conversation.)
Bistro Campagne’s courtyard is charming, with brick walls, ivy, and lots of plants and trees. It’s also one of the best-kept secrets in Lincoln Square, which means the crowd, to the extent that there is one, is mostly regulars. Stick with French classics, like escargot and boeuf bourguignon, and congratulate yourself on venturing out of your neighborhood. Or being lucky enough to live nearby.
La Storia in the Gold Coast rivals Piccolo Sogno for string lights - the decorations on the front of the building suggest that someone took full advantage of the discounted Walgreens seasonal aisle on December 26th. The courtyard patio, on the other hand, is peaceful and charming. And the Italian food is great, particularly their housemade pastas. The atmosphere is nice, but still relaxed, so this place works for a casual date night but also something a bit fancier.
The outdoor patio at Mott Street is quiet and serene, making this an ideal place to try and get to know someone. Plus, the Asian fusion food is delicious - try the kimchi empanadas or the catfish claypot. If your date goes well, come back sometime for brunch and get the burger (which is otherwise only available at the bar).
The rooftop patio at Taxim in Wicker Park should definitely be on your summer to-do list. It’s surrounded by uplit brick walls from adjacent buildings, and there’s a nice outdoor bar area. The outside (like the inside) has an upscale feel, so this is a nice neighborhood choice for a weekend date night. The Greek food is consistently good - there’s really no wrong way to order, but you should make sure to share one of their pastry appetizers (like leek and goat cheese in homemade phyllo).
A lot of restaurants talk about serving “farm to table” food, but Homestead On The Roof takes it a few steps further than most - they grow their own vegetables and herbs in their rooftop garden. And this place really hits its stride in the summer, when that garden doubles as an outdoor seating area. Come here if your date really likes to know where her basil was sourced from, or if you’re the type of couple who gave out sunflower seeds as a wedding favor.
You never got around to planning that romantic getaway to Galena. Don’t feel bad - when you’re eating on the enclosed backyard patio at The Duck Inn in Bridgeport, you can forget you’re in the city. Order anything involving duck (including the whole rotisserie duck, which needs to be arranged ahead of time), or the chef’s tasting - five courses for $66. Just make sure you have enough time to hang out after dinner and have drinks. The space has fire pits and comfortable chairs that will make you want to stay a while.
Vincent is hiding on a side street up in Andersonville, so it’s a perfect date night spot when you want someplace that isn’t ridiculously crowded. And it just so happens that the street it’s on is tree-lined and not very busy, so you can sit outside in peace. The menu is New American, and has a whole section dedicated to different preparations of mussels (whatever else you order, you should really get at least one mussel dish to share).
“Outdoor dining” in River North often means sitting at a tiny table about two feet away from the street. But not at Tanta, which has a rooftop bar and dining area. This is always a fun restaurant with a lively scene, but it’s best in the summer. Mentally plan your eventual honeymoon with this person over tasty Peruvian food and cocktails.
If you don’t get out to Lincoln Square much, you’re missing out on Gather. This place has great food as well as a fantastic covered back patio. Come here on an early-in-the-game date (or even if you haven’t met this person yet). The seasonal menu of new American food will please just about everyone, and even the boring-sounding dishes (like the broccoli) end up being interesting. Which is good, since there’s a chance your date won’t.
The courtyard patio at Blue Door is one of the most relaxing outdoor seating areas in the city. So it’s a good place to practice hanging out with someone you can imagine sitting on a front porch with in about 50 years. Come here for seasonal salads and comfort food like fried chicken. Talk about the good old days, when we had to hang up the phone to be on the internet.
Sticking a few tables on a busy sidewalk typically doesn’t count as a quality outdoor experience. And while that’s technically the set-up at Ema in River North, the fact that the area in question is walled off with fencing and plants makes it feel more secluded than your average sidewalk patio. Sit outside and share Mediterranean small plates. You’ll have just enough exposure to the energy of downtown, without having to be bothered by tourists asking directions to The Bean.
We really like the American food at Giant in Logan Square. The one issue is that the space is too small, meaning that sometimes you can’t get in here last-minute. This changes in the summer, when the patio is open. Come here for date night and order any type of pasta, like the tagliatelle with crab and uni butter. The casual space works equally well for a double date.