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 Chicago date for your current, soon-to-be, or hopeful significant other!

These are our top 10 creative date night ideas in Chicago (ideal for summer):

  1. Take a Chicago bike tour through the Lakefront Neighborhood
  2. Listen to Jazz at the Chicago Museum of Contemporary Art: “Tuesdays on the Terrace” concerts
  3. Catch a movie at the Millennium Park summer film series
  4. Soak up some Vitamin D at the beach with your date
  5. Bust out the dance moves at Grant Park
  6. Stroll through the Garfield Park Conservatory for a unique Chicago date idea
  7. Take your date to the ol’ ball game! Chicago Cubs or White Sox!
  8. Looking for a festive Chicago Date Idea? Attend a neighborhood street festival— Pilsen’s Taco Fest, Roscoe Village’s Burger Fest, or the weekly Argyle Night Market.
  9. There’s nothing like a full moon date night, complete with flames at the summer Full Moon Jam
  10. Chicago Riverwalk Date— Boat Tours, Fishing, and Riverfront Restaurants

One: Get Active On Your Chicago Date with a Lakefront Bike Tour!

There are few things more invigorating than biking the Chicago lakefront, the gentle breeze cooling you down as you coast alongside the beauty of Lake Michigan. The sight is breath-taking, and it’s even more special on a date! Bobby’s Bike Hike offers a Lakefront neighborhood 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? Rent bikes for the date 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!

People jumping during a bike tour of Chicago

*Photo courtesy of Bobby’s Bike Hike


Two: Jazz-Up Your Chicago Date Plans with an Outdoor Jazz Concert 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, but the entrance to view the museum collection is also free for Illinois residents on Tuesdays! This Chicago date night idea is a  high-class experience, low-budget, and is 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: Plan The Classic Chicago Date Night with an Outdoor Movie in Millennium Park!

For movie lovers, Millennium Park is the place to be for a summer date night in Chicago. 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 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 with Your Date

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 date itinerary. You clearly enjoy hanging out with each other, so it’s time for a more casual Chicago date idea. 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 in Chicago include Oak Street Beach, North Avenue Beach, and Loyola Beach. Whichever beach you choose for the date, don’t forget your sunscreen!

Things to do in Chicago, Chicago Beaches

*Photo courtesy of Realcity online


Five: Dancing Date in Grant Park

What’s more romantic than “dancing cheek to cheek on a date?” 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 date by the Chicago River.

Couple dancing on the dance floor in grant park

*Photo courtesy of Choose Chicago


Six: Stroll Through the Garfield Park Conservatory for A Unique Chicago Date Idea

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 for your next Chicago date. 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: Take Your Date To The Ol’ Ball Game! Baseball Game – Chicago Cubs or White Sox!

If you’re both into baseball, then attending a baseball game for a date 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-style hot 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: Festive Chicago Date Idea— 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, which 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 get 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: There’s Nothing Like a Full Moon Date Night, Complete with Flames— Attend the 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 an authentic Chicago date idea for the summer months. 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 Date— Boat Tours, Fishing, and Riverfront Restaurants

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 for your next Chicago date. Or you can check out Urban Kayaks and rent tandem kayaks for just $30 an hour for an adventure date idea!

Chicago River river front with green umbrellas

*Photo courtesy of Choose Chicago



As you can see, Chicago offers a ton of date ideas. You can never go wrong with a fancy dinner at a restaurant like Alinea or flight tasting at a craft brewery like Goose Island, but if you’re looking for a different Chicago date idea, we hope this list helped. Of course, ten Chicago date ideas don’t begin to cover everything that’s available.

What’s your favorite date spot in Chicago? Let us know in the comments below!