First Date Spots: 10 Places to Meet, Talk, and Linger in Chicago

Walk through Lincoln Park Conservatory for a relaxed daytime date, with plants to look at and talk about along the way. The visit takes you through four display houses: the Palm House, Fern Room, Orchid House, and Show House.

Admission is free. The conservatory is open Wednesday through Sunday from 10am to 5pm and closed Mondays and Tuesdays.

Walk the half-mile loop together at Promontory Point, a Hyde Park lakefront spot with Chicago skyline views. You can reach it from the Lakefront Trail.

Bring a picnic in autumn if you want to linger at the point. You'll find it at Lake Michigan and 55th Street.

Build wine or food stops into a first-date walk along the Chicago Riverwalk. The route follows the river from Lake Street to the lakefront through four districts: The Confluence, The Arcade, The Civic, and the Esplanade.

Public art, including ART on theMART, lines the path, with Dine, Explore, and Adventure sections to explore. Walking is free, no reservations are needed, and hours are 6am to 11pm.

Settle into a coffee date at Gaslight Coffee Roasters in Logan Square, where reclaimed wood and vintage lanterns give the shop a homey, rustic feel. For pour-overs, the beans come from the shop's own roaster or from guest roasters.

Pastries and donuts from local bakers give you something to eat if the conversation runs longer than one cup.

Pair a walk on The 606 with coffee or a nightcap at Ipsento Coffee 606 in Bucktown. Retractable windows open onto the neighboring park and Spire Garden.

Try the signature Ipsento espresso drink and mini donuts. A drip coffee costs $3.75, a latte $5.50, and a matcha latte $6.50.

Meet over seasonal cocktails at The Violet Hour in Wicker Park, where a single entrance leads to three candlelit salons and a long marble bar.

The bar program has won a James Beard Award. It is open daily from 5pm to 1am, with reservations available through the website.

Take in Millennium Park and Lake Michigan over drinks at Cindy's Rooftop, a restaurant and bar at the Chicago Athletic Association hotel. The terrace sits beneath a glass atrium on the 13th floor.

Reservations are encouraged and open 14 days ahead, while walk-ins are welcome if you decide on the day. It stays open until 12am on Fridays and Saturdays.

Choose Penumbra for an intimate first-date dinner in a dimly lit Logan Square wine bar and steakhouse. Start with the approachable by-the-glass list, or explore the longer bottle list if you want to linger.

The menu includes steaks, seafood, and vegetarian dishes. Come on a Wednesday between 5pm and 6:30pm and wine by the glass costs half price.

Have a first-date dinner in Bistro Campagne's ivy-and-brick courtyard, or settle into the dark-wood dining room inside. The French bistro is in Lincoln Square.

Book a table through the website for any night except Monday, when the bistro is closed.

Share fondue and conversation at Geja's Cafe in Lincoln Park. Swiss Gruyere cheese fondue begins the meal, followed by entree fondues with shrimp, scallops, lobster, chicken, or beef. Belgian flaming chocolate fondue is served for dessert as a classical or flamenco guitarist plays.

Booths sit behind small curtains, lit by little beyond the fondue flames. An average meal costs $35 and up per person, with a credit card required to reserve.