If the success of date night revolved around spending a lot of money, 99% of us would be single. Be smart, be strategic, and go out to a meal that has good food and good vibes without breaking the bank. We’d say just be yourself, but, let’s qualify that and say only be the good parts of yourself.
Here are 16 affordable restaurants that will win over any date.
La Scarola721 W. Grand Ave.
It's best to put yourself and your date in a situation where you can both loosen up, and La Scarola will help you do just that. It's our favorite old-school Italian spot where you can settle in over a bunch of pasta and wine. And the key to any successful relationship is more wine.
Pizza for a date? Oh yes, pizza for a date. If you're going out with someone who doesn't like pizza, then you shouldn't be going out with that person at all. Spacca Napoli is the perfect Neapolitan style pizza place where you can easily have a conversation, but it's also upbeat enough so you don't have to worry about awkward silence. If the date sucks, at least you'll be eating some of the best pizza and burrata in town.
Southern Comfort isn't just a sh*tty liquor, it's a lifestyle. And while Chicago is as Yankee as you can get, Big Jones is bringing a bit of Southern charm to Andersonville. You're charming in your own right, so show that side of yourself over a meal here.
Date night doesn't have to be so serious, so keep things lighthearted and fun at Kimski where you can bond over Korean-Polish bar food and quality drinks. If poutine with kimchi beer gravy doesn't set you up for a successful night then it was doomed from the start.
There's something we like to talk about here at The Infatuation called The Feel Good Factor™. The Feel Good Factor™ is reserved for places that make us happy, and Topo Gigio is one of those places. It's easygoing Italian food in a friendly and familiar environment. You'll be happy, your date will be happy, and hopefully the two of you will live happily ever after. Good luck.
There are a lot of great Indian restaurants in Chicago, but none are really great for a date night. But Pub Royale is perfect for a date, and it's serving Indian-inspired food with a British pub vibe. Eat some mussels with naan and cucumber raita alongside the delicious house cocktails, and then try and taste your date's tongue.
If you’re caught in between wanting to take someone to dinner or drinks, hedge your bet at Moneygun. It’s a cool cocktail bar in Fulton Market that will make you seem in the know, but there’s also a menu with reasonably priced small plates and a couple sandwiches. If things are going well, suggest sharing food. If he or she is a vegan, skip the food and run as fast as you can. Sorry, vegans.
Nature is fantastic, particularly in a city. And by nature we mean a patio in the midst of a lot of concrete where you can sit outside and enjoy nice weather. So take this potentially special person to St. Lou's Assembly, the 1950's style meat and three cafeteria that has a great backyard. An entree and three sides is less than $20, and it will hopefully lead to a blossoming courtship like Danny and Sandy on a summer night.
Nothing says romance like a fine Italian restaurant, but fine Italian also screams expensive. Go with the in-between Italian instead, meaning nice enough to sit and hang but not so nice it’ll bleed you dry. That’s what makes Davanti in Little Italy an ideal date spot - it has the charm of a classy Italian restaurant without the high costs. Hopefully your date has similar style.
Before you start planning trips to the Greek islands with someone you barely know, test the waters over Mediterranean food at Ēma first. A few small plates like spicy hummus, crispy halloumi and dates, and chicken kefta are a much more reasonable commitment than a couple of plane tickets.
Cold Storage won’t be affordable if you blow all your money on a couple dozen oysters, but everything else on the menu is very reasonable. Stick to the plain pieces of fish, sandwiches, and a few other entrees like clams and chorizo while you sit at the bar and try to figure each other out. Then again, oysters are an aphrodisiac, so you can always go that route.
Hit 90 Miles to do it big on a Friday or Saturday without having to spend your entire month's paycheck. The Cuban entrees are all less than $20, music is lively, and it's BYOB. Bring a decent bottle of red to mix with their great sangria mix and don't be afraid to share your feelings.
Mott Street isn't a guaranteed cheap meal, but there are are a lot of ways to pull it off. You only need a good mix of three or four shared plates to fill you up, and the interesting Asian flavors make that more than possible. Try the "everything" wings that taste like an everything bagel, kimchi and oaxaca cheese empanadas, and boat noodles in a beef shank broth that are incredible. The dining area is usually fun and loud, but there's an excellent patio that's more quiet.
Everything about Ixcateco is a steal. It's high-end Mexican food like [Frontera}(http://www.theinfatuation.com/chicago/reviews/frontera-grill) (the chef started there), but in a bit more casual environment and at half the price. Share quality entrees like carne asada or chicken in mole for less than $20, and take advantage of the BYOB policy. Spend a little extra on a nice bottle to prove you're practical and not cheap.
Keep it simple with a tried and true cocktail bar like Scofflaw. The drinks are excellent, the bar food is always way above average, and they serve free chocolate chip cookies at midnight if you can make it that far. Hopefully you can make it that far because chocolate chip cookies should be the key to anyone's heart/pants.
Nothing will impress another person like proving you can eat a couple pounds of brisket. Alright, maybe not, but that doesn't mean you can't take a date to Green Street Smoked Meats. The Texas-style BBQ spot has a cool warehouse vibe where you can eat casual food off a tray and linger for drinks at a picnic bench. Not the creepy kind of lingering, but the let's keep hanging out and keep talking to each other lingering.