MostBest Chicago | Date Night Destinations

There are over 116 date night destinations in Chicago. Feeling overwhelmed? MostBest knows the Top 3.

Trying to plan a special night with your sweetheart but are coming up short? Let us tell you the best date night spots—all you have to do is make the reservation.



via Flickr user lobstar28

Boasting a Michelin star and a James Beard Award, you’d be hard-pressed to find a place more elegant and refined than North Pond—perfect for impressing someone special. The view of the pond is gorgeous, and dishes like Foie Gras Crème Brulée and Smoked Beef Tenderloin are guaranteed to impress.

Make a reservation, cozy up to your sweetheart, and dig into the refined fare of North Pond.

We Love Their: Foie Gras and Lime, Lamb and Snap Pea, Bleu Mont Dairy “Bandaged Cheddar”

2610 N Cannon Dr
(773) 477-5845



via Flickr user Kimberley Vardeman

Trying to sweeten up your date? Head to Mindy’s Hot Chocolate, whose dark wood interior mirrors the rich, sinful treats that you’ll find inside. They serve everything from milkshakes and hot chocolate to decadent desserts, all of which are perfect for sharing. Try the Chocolate No. 1, a mind-blowing concoction of caramel, chocolate, and pretzel.

Mindy’s makes for a sweet night that neither of you will forget.

We Love Their: Hot Chocolate, Chocolate No. 1, Brioche Donuts

1747 N Damen Ave
(773) 489-1747



via Flickr user Benny Wong

Maude’s Liquor Bar is more than just a bar—this cozy restaurant serves up some truly decadent French dishes. Between the multi-level dining area and dim candlelight, you and your date are sure to enjoy a great conversation over dinner.

Wine and dine your date with an exquisite meal and delightful cocktails at Maude’s Liquor Bar.

We Love Their: Roasted Bone Marrow, Brussels Sprouts, St. Germain Fizz

840 W Randolph St
(312) 243-9712