Dating can be hard, but luckily for you, you’re dating in a city that has some of the best food, beer, and entertainment options in the world. So start by counting your blessings, and then dive into this article to plan that perfect date for your current, soon-to-be, or hopeful significant other!

One: Bobby’s Bike Hike – Bike Tour!

There are few things more invigorating than biking the Chicago lakefront, the gentle breeze cooling you down as you glide alongside the beauty of Lake Michigan. The sight is breath-taking, and it’s even more special with a special someone! Bobby’s Bike Hike offers a lakefront neighborhoods bike tour that will take you past various sights including the Gold Coast, Lincoln Park Zoo, and North Avenue Beach. Looking for something a little more private? Bobby’s also rents out bikes so that you and your date can explore Chicago on your own. If you thought a lakefront ride was romantic on a standard bike, you should try it on the tandem bike they offer for less than $25 an hour!

People jumping during a bike tour of Chicago

*Photo courtesy of Bobby’s Bike Hike,


Two: Jazz at the Museum of Contemporary Art!

Founded in 1967, the Chicago Museum of Contemporary Art is among the world’s largest contemporary art venues. During the summer, their “Tuesdays on the Terrace” concert features the top Chicago jazz musicians. Not only is the outdoor concert free, the museum collection is as well for Illinois residents on Tuesdays! That makes this a high-class experience for a low-budget price, casual enough for a first date while establishing that you’re cultured. Order delicious food like lobster rolls and BBQ chicken at the terrace (as well as beer, wine, and cocktails), and let a sultry saxophone do the smooth-talking for yo

People enjoying live jazz music during Tuesdays at the Terrace

*Photo courtesy of Ashlee Benes, Tuesdays at the Terrace


Three: Movies in Millennium Park!

For movie lovers, Millennium Park is the place to be. The Millennium Park summer film series screens free movies on Tuesday evenings with a lineup that includes romances like “10 Things I Hate About You” and “Love, Simon,” action movies like “Black Panther,” and foreign language films like “Pan’s Labyrinth.” Bring a blanket and some BYOBooze, then watch the screen intently (or ignore it altogether). It’s a lovely opportunity for a homemade picnic. And if you want to extend the date after the film, you’re right in the heart of Chicago near some of the best bars and restaurants. Some recommendations include Ema for Mediterranean food or Pinstripes for drinks and bowling.

Millenium Park Summer Film Series in Chicago

*Photo courtesy of Choose Chicago,


Four: Soak up some Vitamin D at the Beach

Your first few dates were probably more formal: going to events, trying out a new bar, and basically finding excuses to meet up with the person. By the tenth date, you don’t need such a formalized activity. You clearly enjoy hanging out with each other, so it’s time for something casual. Why not hit one of Chicago’s amazing beaches? Soak up the sun, swim around, and then destroy your date in beach volleyball. (Or let them win, if playing nice is your thing). Some great beaches include Oak Street Beach, North Avenue Beach, and Loyola Beach. Whichever spot you choose, don’t forget your sunscreen!

Things to do in Chicago, Chicago Beaches

*Photo courtesy of Realcity online:

Five: Dancing in Grant Park

What’s more romantic than “dancing cheek to cheek?” SummerDance in Grant Park is the perfect time to get your Fred Astaire/Ginger Rogers groove on. Even when you’ve been married for twenty years, you can’t deny the power of two people moving as one. Never danced before? No problem! These free dances include lessons prior to the shindig. And because it’s outside with 4,900 square feet of space, you don’t have to worry about being cramped or smelling other peoples’ dancing fever. The money you save here means you can splurge a lil’ bit on a fancy dinner by the Chicago river.

Couple dancing on the dance floor in grant park

*Photo courtesy of Choose Chicago,


Six: Garfield Park Conservatory

Floriography- an ancient way to say, “I love you” without saying, “I love you.” If you have trouble getting those words out, head over to the Garfield Park Conservatory. Wanting to take your relationship to the next level? There’s nowhere better to propose than amidst the sweet, perfuméd air of these luscious gardens. Let the Conservatory send you back to Shakespearean times, when lovers stood upon balconies and serenaded each other with sonnets. The Garfield Park Conservatory is free all year but stay away if your date has pollen allergies.

couple walking through the plants at Garfield Park Conservatory

*Photo courtesy of Jasmine Nicole


Seven: Baseball game – Chicago Cubs or White Sox!

If you’re both into baseball, then a baseball outing is a guaranteed home-run! But make sure you both root for the same team, or the date might go foul. Tickets vary greatly in price, so you can decide whether to make this a cheap get-together or something more special. If you can eat a Chicago dog in front of your date, it’s a relationship meant to last.

Things to do in Chicago, Wrigley Field

*Photo Courtesy of Barry Bloom

Eight: Neighborhood Street Festival

When you’re in a polyamorous relationship, ticket prices add up and dinner-for-two just doesn’t cut it. But neighborhood street festivals only get better when more people attend. More people means more local food samples means more flavors to be shared. One or two people dancing by the music truck (because there’s always a music truck) can be awkward, but 3+ is instantly a party. Neighborhood street festivals are a great way to know your neighborhood better, or acquaint yourself with somewhere new. Check out Pilsen’s Taco Fest, Roscoe Village’s Burger Fest, or the weekly Argyle Night Market.

Street performers in colorful costumes at Mole de Mayo

*Photo courtesy of


Nine: Full Moon Jam

Fan the flames of love by the blazing fire of Chicago’s best pyro dancers. Once a month during summer, drummers and fire dancers congregate on Foster Beach to celebrate the full moon in its maximum glory. The Full Moon Jam is free to attend and a great spot for a picnic. This is a fun date for any stage of a relationship, but it’s especially helpful early on during the awkward phase. If you run out of things to say, there’s no uncomfortable eye contact because you can just watch the dancers! Stop by Asia on Argyle beforehand for some delicious bubble tea or banh mi. And no need to worry about getting singed; the dancers stay within a cordoned-off area. The only thing set aflame will be your date’s heart!

4 fire blowers in Chicago

Photo by Ryan Brandoff, courtesy of


Ten: Chicago Riverwalk

Why are Paris and Venice some of the most romantic cities in the world? The rivers, of course! But if flying to Paris for the day seems a little too extravagant, the Chicago Riverwalk has a myriad of romantic options like boat tours, fishing, and riverfront restaurants. Or you can check out Urban Kayaks and rent tandem kayaks for just $30 an hour.

Chicago River river front with green umbrellas

*Photo courtesy of Choose Chicago,

As you can see, Chicago offers a ton of options. You can never go wrong with a fancy restaurant like Alinea or a nice, craft brewery like Goose Island, but if you’re looking for something different, we hope this list helped. Of course, ten suggestions don’t begin to cover everything that’s available. What’s your favorite date spot in Chicago? Let us know in the comments below!