The second installment of our Date Night series finds Nia Magazine sitting high atop the broad shoulders of Chicago.

There’s no wonder it’s called the Windy City. Dazzlingly, vast adventure options can literally sweep a girl away. We have no complaints, however. It’s a great problem for a Chicagoan to have.

After all, more choices, more choosing. And it’s our hope that you’ll have many, many dates to plan.

Use our Date Night ideas to make each one an experience you’ll both have fond memories of. Choose one or mix-and-match a few.

And don’t forget, our suggestions are absolutely perfect for Girls Only escapades as well.

Whatever you decide, we’d love to hear about it. Happy dating to ya!

Date Night Chicago Edition: 25 Ideas to Spice Up Your Next One


Win all the way around when life-changing work allows you to acquaint yourself with your community and someone extra special.

  1. All for Good

Share an impactful experience with someone special all while making a difference in the world.

2. One Good Deed

Volunteer with One Good Deed Chicago for an opportunity to come together with fellow Chicagoans and your special companion for the good of your community.


This date isn’t just for book lovers. Casual and culture rich ambiance sets everyone up for conversations that nurture introspect and demand close, low talking. Add a little whimsy by downloading online couple’s challenges designed especially for flirty bookstore endeavors.

3. Myopic Books

So there’s this beloved couch, worn in by lovers of exploration and conversation that would perfect for your next date’s dialogue. Select something provocative from three floors of packed shelf space to dissect as a twosome.

4. The Book Cellar

Widely considered the pulse of Chicago’s lit world, you’ll have no trouble finding a date-worthy event to attend. Besides a stellar selection of books, fresh brewed coffee, and wine choices, you’ll find it’s a great place for warm socializing.


Close up of African American woman's bare feet with flower
Photo credit: Bigstock

Romantic relaxation will come easily as you indulge in stress-reducing specialties. Keep an eye out for online discounts for couples’ appointments.

5. Veola’s Day Spa & Wellness Center

This mother-daughter owned oasis specializes in uber chic stress relief and body renewal. State-of-art services, an on-site cafe, and private suites for couples make this full-service spa a premiere date option.

6. Bettye O’Day Spa

With an impressive variety of packages catering to every schedule and spa therapy desire, you’ll have no trouble coordinating a luxurious experience for you and your bae.


Keep that adrenaline surging in more ways than one, with heart pumping exercise and companionship.

7. Nike+ Chicago

From instructor to content, Nike’s diverse fitness experiences are top notch. Plan a date Monday through Thursday and you and your companion can attend a yoga, barre, interval training, or weekly wild card class together. Availability posts every Friday and classes fill up quickly, so make prompt registration a priority.

8. Soul Cycle

For fitness lovers, there may be few activities that are sexier or steamier than, soul engaging cycling by candlelight. Join the cult of soul cycle enthusiasts by conquering a class with someone you’d like to see sweat.


The daring at heart will enjoy these excuses to hold on tight to someone they adore.

9. NASCAR Ride Along

You can’t beat this adrenaline rush! A shot-gun ride with a professional driver at the Chicagoland Speedway will take your date to another dimension.

10. Tandem Skydiving

Take your date’s breath away in more ways than one with 60 seconds of free fall from 9,000 feet in the air at 120 MPH.


Beautiful dark skinned couple in love having a great time together man and woman enjoying each other young woman feeding man with dessert cake at their dating
Photo credit: Bigstock

Let your guards down as you become tourists for the day. Discover Chicagoan culture, food, wine, art, history and a bit more about each as well.

11. Chicago Prohibition Tour

For 3.5 hours, you and someone special can sip and sightsee as you immerse yourselves in an interactive history lesson about Chicago’s famed Prohibition era.

12. Walking Food Tour of Chicago

You and a guest can enjoy at least 7 food tastings as you explore deliciously historic Chicago neighborhoods.

13. Bikes, Bites, and Brews Tour

Awarded TripAdvisor’s 2014 Certificate of Excellence, this unique cruiser bike experience is a cool way for couples to sample all four Chicago food groups; pizza, hot dogs, cupcakes, and beer.

14. Revival Food Hall

2016 Jennifer Catherine Photography
Photo credit:; 2016 Jennifer Catherine Photography

Get lost for the day in this huge mecca of premier foods and spirits. Sharing all of the tastes Chicago has to offer is a great way to make your date feel special.


Tap into the cultural and creative passions of multicultural lives, with date night ideas guaranteed to help you discover more about yourself and others.

15. Private DJ Lesson

You and bae can show off or tighten up your DJ skills with help from some of the very best turntable experts at Jam Master Jay’s DJ Academy.

16. Create a Signature Scent

An experienced perfumer will help you and a companion create a fragrance to bottle and keep. This date is the gift that keeps giving.

17. Du Sable Museum of African American History


Quality time takes on a whole new meaning when it’s taking place within the majestic walls of this landmark. Celebrate the legacy of ancestors while creating one of your own with someone special.


Two of America’s favorite meals…either makes for excellent date cuisine. Whether you schedule it between other activities or as a stand-alone event, intimate dining is a surefire way to create sparks.

18. Peach’s on 47th

Wear your loose clothing and enjoy the ease of casual dialogue while dining on your favorite southern breakfast and lunch delights.

19. Park & Field

The vintage touches of their “Old-school gymnasium aesthetic” make for quaint and interesting conversations over a $30 gourmet brunch featuring bottomless Mimosas and Bloody Marys.

20. True Food Kitchen

Chicago’s newest brunch spot features dished based on the teaching of holistic and alternative medicine guru Dr. Andrew Weil. This vegan- and gluten-friendly dining experience will be a sexy and healthy one.

21. Sweet Maple Cafe

Considered home of one of the best breakfasts in Chicago, the modest atmosphere is a great backdrop for ‘getting to know you better’ discussions.

22. Two Fish Crab Shack

One of Chicago’s newest seafood boil hubs, Two Fish Crab Shack has received rave reviews from tasters. The casual atmosphere and succulent seafood encourage sleeve rolling, finger licking, and kicked-back conversation. Everything you need for a great date.


An after-hours rendezvous doesn’t have to be Rated R. Not necessarily. Chicago’s after-dark culture is impressively diverse. The following ideas are excellent ways to let stressors of the day fall away.

23. Adler After Dark

On every third Thursday of the month, Alder Planetarium hosts Adler After Dark; an evening of cocktails, appetizers and stargazing.

24. Late Night Laughs

Chicago comedy houses, iO Chicago and the Playground, keep the laughs coming long after other clubs have closed for the night. With late night hours on both Friday and Saturday, your weekend date is guaranteed to end with smiles.

25. Music Box Theatre


Midnight showings are pretty common and easy enough to locate these days. Take the experience to another level with one of two showings at Chicago’s famed Music Box Theatre. Picturesque facades make every viewing an open-air palazzo affair.

Ultimately, it’s the people sharing spaces with us that make our dates meaningful and special. They’ll be fulfilling experiences if we believe they are.

Find fun in any imperfections and choose to enjoy yourself. Everyone’s time is precious and not promised. Make intimate moments memorable one no matter what.

Do you have a must-add for our list? Send it on! Don’t forget to share your dating tales with as well. Cheers to you and great dating!

Date Night Chicago Edition: 25 Ideas to Spice Up Your Next One

RELATED ARTICLE: Date Night Atlanta Edition: 28 Ideas to Make Your Next Date the Best One Ever

We’re looking for Guest Writers to join our contributor team! Do you have something to share? Click HERE to find out how.