Chicago, IL Dating Guide
Chicago’s North Side delivers fresh and unforgettable date options for every kind of couple. From jazz-filled lounges and candlelit dinners to creative cafés and scenic strolls, this 2025 guide offers ideas that go far beyond the ordinary. Whatever your vibe — playful, romantic, spontaneous, or laid-back — there’s a perfect spot on this list to spark a real connection.
Geja’s Café $$-$$$
Enjoy romantic fondue dining by candlelight with live flamenco guitar in a cozy, timeless setting—perfect for a special night out.
Cost: ~$60–$100 per person (fondue dinner + wine)
Ella Elli $$
Stylish and softly lit, this Mediterranean-California fusion spot offers sharable plates and craft cocktails near a fireplace.
Cost: ~$40–$65 per person (small plates + drinks)
An elegant, intimate bar with a great selection of classic and modern martinis, perfect for a flirty first date or pre-dinner drinks.
Cost: ~$15–$30 per person (2–3 drinks)
A rustic-chic café known for its house-roasted beans and hearty brunch offerings like duck eggs Benedict and charcuterie plates. The inviting interior, adorned with baroque wallpaper and taxidermy, provides a unique backdrop for a relaxed and intimate date. Perfect for people-watching or deep conversations over expertly crafted coffee.
Cost: ~$10–$20 per person (coffee and brunch items)
The Hideout Inn $-$$
Eclectic music venue in a quirky house-like building—catch indie bands, comedy sets, and more in a fun, laid-back space.
Cost: ~$10–$25 per person (cover + drinks)
Get ready to laugh at one of Chicago’s top comedy clubs featuring local and national comedians nearly every night of the week.
Cost: ~$20–$35 per person (tickets + minimum drink)
Biking, walking, or skating through scenic nature paths—ideal for active, low-cost quality time in the fresh air.
Cost: Free
A lush, tranquil greenhouse escape showcasing exotic plants and blooms—quiet, beautiful, and great for wandering and chatting.
Cost: Free
Sip classic cocktails while soaking in world-class live jazz at this storied 1920s-era speakeasy haunt.
Cost: ~$20–$35 per person (cover + drinks)
Explore iconic art galleries after hours for a calm and cultured date—especially good for weekday evenings.
Cost: ~$25–$30 per person (entry fee)
Candlelight Concerts by Fever $$
Attend a classical or contemporary music concert bathed in candlelight inside a unique, intimate setting.
Cost: ~$30–$45 per person
A creative and community-driven café that doubles as a hub for local artists and entrepreneurs. Enjoy unique, Filipino-inspired drinks like the ube or burnt vanilla lattes while browsing handcrafted goods and catching occasional pop-up events. The cozy, eclectic atmosphere fosters meaningful conversations and connections.
Cost: ~$5–$10 per person (specialty drinks and pastries)
