Ambiance Matchmaking Meet Attractive Singles
Ambiance Matchmaking Meet Attractive Singles

Chicago's Top 7 Summer Date Ideas

Ahhhhh, Chicago in the summertime is magical. We are lucky to be laden with so many great summertime dating activities. This list includes our top seven favorites for creating the perfect date night (or day). Take your pick and start planning!

1. Saturday Morning at the Farmer’s Market

Chicago is dotted with Farmer's Markets spearheaded by city locavores. These fresh markets setup shop on Saturday mornings between the warmer months of May and October. Roll out of bed and migrate over to find popup shops full of seasonal veggies, baked goods, fresh cheese, and flowers. Are top picks for farmer's markets are:


The Green City Market is tucked inside the south end of Lincoln Park. Its vendors boast some of the best local products, from Wisconsin's Nordic Creamery––specializing in goat milk cheeses, butter, ice cream, and brats––to Cookies and Carnitas's offerings of tacos, chilis, and hot sandwiches. You can even get your knives sharpened by Sharpening by Dave, but we don't recommend showing up to your date with a large knife.


The Plant is a groundbreaking food production space designed to be a net-zero, closed loop system. This is the only farmers market in Chicago where you’ll find small batch coffee, gourmet mushrooms, kombucha, naturally leavened bread and fresh greens being sold in the same space they’re produced.

2. Randolph Street Market

The Randolph Street Market Festival is home to the world-renowned Chicago Antique Market, Indie Designer Market, Modern Vintage Chicago and the Holiday Market. As seen in Travel & Leisure, the NY Times, Lucky Magazine and featured on TV news shows and web casts, the Randolph Street Market Festival is one of Chicago’s most happening monthly parties!

3. Navy Pier’s Ferris Wheel

The 3,300-foot-long pier on the Chicago shoreline of Lake Michigan is a destination in its own. But when you add the magnificent 196-foot ferris wheel to the mix, it’s a combination you can’t beat for a magical date. When you’re done with your romantic gondola ride, head to the nearby beer garden for a nightcap.

4. Millennium Park Summer Music Series

Millennium Park is considered the world’s largest rooftop garden, spanning 24 acres of Grant Park. The park itself is a great date idea due to sights such as “The Bean,” Crown Fountain, Lurie Garden, and the Ice Rink in the wintertime. However, our favorite park feature is the Pritzker Pavilion, which serves as the new home of the Grant Park Symphony Orchestra and Chorus and the Summer Music Series, the nation's only remaining free outdoor classical music series. Check out the schedule and start planning!

5. Cub’s baseball game

Attending a Cubs game at the famous Wrigley Field should be experienced at least once. Grab a hot dog, a bag of peanuts and an Old Style beer before heading in. The post-game neighborhood-wide party can get rowdy, so walk a mile to Lincoln Park for a nightcap instead.

6. Check out a festival

Chicago is laden with street festivals during summertime. Each neighborhood has its chance at the spotlight, featuring its own theme: wine festivals, beer festivals, food festivals, live music festivals… you name it! We personally love The Taste of Chicago, deemed the world’s largest food festival (hurry, it’s happening this weekend!)
Find a festival

7. Architectural boat tour

Take a cruise along the Chicago River while taking in the magnificent architecture. There’s no better way to see the city, learn about Chicago’s history, and watch the fireworks. There’s a slew of boat tours available, but we recommend the Chicago Architecture Foundation River Cruise. Go on their Twilight River Cruise to see more than 50 buildings bathed in softer light, all while sipping a cocktail from their full-service bar onboard.
Book a tour

More City Guides

7 Ways To Meet Singles In Chicago in 2023

Seven great ways to meet singles organically in Chicago.
Read more

Anthony Bourdain's Chicago Picks

Tony's culinary and cultural aptitude combined with our dating expertise.
Read more

Chicago's Best Date Restaurants

We carefully selected Chicago's best restaurants for the perfect date night based on atmosphere, crowd, menu, and neighborhood.
Read more

Chicago's Best Date Spots

Chicago’s best date spots for any type of craving; tacos, burgers, oysters, pizza, you name it!
Read more

Chicago's Best Rooftop Bars & Restaurants

Chicago's most romantic rooftop bars and restaurants for your perfect date night.
Read more

Chicago's Michelin Restaurants

Michelin is the most prestigious restaurant-rating system in the world, and Chicago is full of Michelin restaurants. Get ready for an experience!
Read more
magnifiercrossmenu linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram