[Skip to Content]

Plan a romantic date night in the Loop

Posted  20 months ago  in  Trending, Eat & Drink, Arts and Culture

2 MIN READ – Love is always in the air downtown in the Loop, whether it’s Valentine’s Day or any other time of year. If you’re looking to plan a romantic date, there’s no better place. Whether you want to keep things casual or treat your partner to a special night they won’t forget, we’ve got just the romantic date idea for you.


Experience a month of romance with The Allegro Royal Sonesta this February and receive a bottle of bubbly, plus chocolate strawberries and an assortment of petit fours from local French pastry shop Vanille Patisserie, on arrival. Learn more. For love in the air at Royal Sonesta Chicago Downtown receive a bottle of Chandon Champagne, plus a four-piece box of chocolate from Chicago-based luxury chocolatier, Vosges, on arrival. Learn more. Or, for a romantic escape at Royal Sonesta hotel outside of the Loop, check-in at Royal Sonesta Chicago River North and receive two bottles of our custom pre-mixed Concierge Cocktails hand-selected by their team, perfect for a pre-dinner aperitif in your room! Learn more

Check out other hotels in the Loop for more staycation options here.


Whether you're planning a night out or in, consider a Chicago classic located in the heart of Chicago's Theater District, Petterino's is the perfect destination for any date night. Amid caricatures adorning the walls, sink into their booths and indulge in timeless Italian flavors while sharing a bottle of wine ​or sipping classic cocktails. Don't forget dessert,​ their signature pionono is worth saving room for. Learn more.

Under the glow of the James M. Nederlander theater, The Dearborn is the perfect destination for date night or your next pre-show meal. The spacious dining room full of creative cocktails and dishes that lean into Midwestern seasonality provides everything you’d want while enjoying a special evening with your special someone. Learn more. 

Have a taste of some of the ocean's finest at Ocean Prime with its Valentine's Day feature. Enjoy Broiled Sea Bass served over cauliflower puree with sauteéd haricot verts, toasted garlic fingerling potatoes and roasted tomatoes, finished with orange vinaigrette and topped with caviar. Learn more

shop 'til you drop

Valentine’s Day is almost here! Whether your V-Day plans include a romantic date night out or a cozy night in with your love, pick up the perfect Valentine’s look at Primark on State Street. Put the finishing touch on your hot date outfit with Primark’s sexy red and black lingerie sets, or get ready to cuddle up on the couch with your boo in adorable loungewear. Whatever your Valentine’s Day entails, Primark will have you feeling the love. XOXO! Learn more

‘Wow, you’re so cultured!’

Love is in the air and theatre in the Loop is the destination for romance! Broadway In Chicago presents a fantastic lineup for your special night out: "Hairspray," the Tony Award-winning musical comedy phenomenon. It's 1960’s Baltimore! Traci Turnblad sets out to dance her way onto TV’s most popular show. Can a girl with big dreams (and even bigger hair) change the world?; "Teatro ZinZanni," Randolph Entertainment LLC presents a new cast of characters performing astounding acts and bringing audience members a unique, immersive dining and live entertainment experience; "The Play that Goes Wrong" is a play that introduces "The Cornley University Drama Society," which is attempting to put on a 1920s murder mystery, but as the title suggests, everything that can go wrong… does, as the accident-prone thespians battle on against all odds to get to their final curtain call; "Come From Away," this true story of the small town that welcomed the world has won Best Musical all across North America and is The New York Times Critics’ Pick; and "The Simon & Garfunkel Show," the immersive concert-style theater show chronicles the amazing journey shared by the folk-rock duo, Paul Simon and Art Garfunkel. Learn more

Visit the Museum of Illusions for a date night this month. Take advantage of their online 50% off ticket special on February 14 for Valentine's Day. Tickets will also be 20% off every Tuesday in February. Learn more.

Exclusive Loop deals, recommendations, and news direct from Chicago Loop Alliance.