As soon as the warm weather hits in Chicago, the whole city heads outdoors wherever they can. We have to make the most of every beautiful minute of this summer weather! This also means that date nights can move out from the usual bars and restaurants, and out into the fresh air for nights on patios, rooftops, and more. To make your planning easier, we have the best spots to spend your summer date nights, and get your romance on.
The first date is always the toughest to plan. You don’t want to go too over the top, or look like you’re trying too hard, but you still have to impress. So instead of going over the top, go to the top…of the Hyatt Centric in the heart of the Loop! AIRE is the rooftop terrace in the heart of the city, which makes it an easy place to meet for a work week happy hour. Get your first date off on a great foot under the stars! They have a chic ambiance with fun décor, and beautiful downtown views. They have plenty of small plate options to share with friends (or your date!) and an great list of craft cocktails and wines that you won’t want to miss!
The Terrace is known city-wide for its amazing views of the skyline from sixteen stories high. Right along the Chicago River, you and your date can cuddle up around the fire pits that warm cool summer nights, and take in their newly planted garden. This is the perfect spot for a special occasion date like an anniversary! We recommend the Watermelon Salad, or their Sliders with six year aged cheddar, and pair your meal with the appropriately titled “Gleaming of Passion” cocktail, made with vodka, vanilla, coconut, passion fruit with an egg white meringue.
Want to get to know someone better without the pressure of a more formal date? Grab a few friends for margaritas and see how a group date vibe goes! Located in Old Town, this spot knows what it’s about. They have a taco-focused menu, and they’re doing it, they’re doing it well. We also recommend the Blueberry Mint Margarita, which is the perfect balance of sweet and tart. You could walk in for tacos, and walk out with a new love!
If you’re looking for a fun, day-date activity, the riverboat architectural tours are a great way to get to know both your hometown and your date a little better. This is also the perfect date for the busy couples, as there are cruises all throughout the week, so you have plenty of scheduling opportunities. You can see the city move from day to night at sunset on the Twilight CAF River Cruise nightly at 7:30 pm., or get your artiste on at the Capture Chicago Photography Cruise on the weekends. They will also be having a celebratory, summer, kick-off on June 1st to kick off Pride Month and celebrate love, unity and equality. There will be champagne, a ceremonial flag raising on Chicago’s First Lady, and lite bites! The event starts at 5:30 pm and there is a complimentary 20 minute cruise at 6 pm, so we’ll see you there!
There might not be a lot of drive-ins downtown, but that doesn’t mean you can’t see a movie under the stars! There is, of course, this year’s schedule of Movies in the Park, which has a pretty awesome line-up for 2017 (think La La Land and Hidden Figures, plus throwbacks like Jumanji and even North by Northwest). They’re perfect for a lounging, picnic evening outside. However, if you want to take your movies to new heights, ROOF on theWit also offers Monday movie nights all summer long, also showing favorites like La La Land on June 26th or the seductive 50 Shades Darker on Augst 28th.
Few patios have the same level of romance of this West Loop spot. Set back from the street, you and your date can stroll along cobblestones, and under tea lights towards a patio champagne toast. The romantic vibe is completed by a touch of Parisian glamour, with stylish antique mirrors, tassels, and frames throughout the intimate candle lit venue. If your guy is trying to impress you, this patio will take any date night up a notch. It’s also the perfect spot for a girl’s night out, if you want to leave the guy at home!
“A guy walks into a a bar…” And that bar is RAISED! The sign that greets you when you walk into this fun indoor/outdoor space is a perfect sign that you’re meant to meet your date here. The regular menu at Raised features American bar food with a twist, focusing especially on shareable plates – ideal for mixing and mingling! The space invites you to sip, savor, and see the city all in one spot. A glass wall gives stunning view of the skyline and Chicago River from the indoor bar, while the outdoor area has fresh flowers, fire pits, cabanas, couches and an outdoor bar. After going to a Lollapalooza event here last year, our team has been hooked.