5 Romantic Chicago Restaurants that Will Impress

Whether you are hoping to impress a date or you simply want to treat yourself to a great meal and some cocktails in a lovely yet quiet setting, below are five romantic Chicago restaurants that should be on your must-do list:


Homestead On The Roof


What:  A rooftop oasis which is hidden above

Roots Handmade Pizza in West Town.  The main space sits alongside an outdoor patio with an organic garden which supports the seasonal menu.  The food and cocktails feature Homestead On The Roof’s fresh herbs and vegetables. The outdoor deck with romantic lights is perfect for lounging under the moon on warm summer nights.  I loved the salmon crudo with pastrami spices and the eggplant with quinoa tabouli, English cucumber, and white bean puree.  The cocktails and wine list are excellent.

Where:  1924 W. Chicago Ave (Take the Blue Line to the Chicago ‘L’ stop and transfer to the #66 Bus going west toward Austin).



Romantic Chicago Restaurants Homestead On The Roof garden


Romantic Chicago Restaurants Homestead On The Roof menu


Romantic Chicago Restaurants Homestead On The Roof patio


Romantic Chicago Restaurants Homestead On The Roof in West Town


Romantic Chicago Restaurants Homestead On The Roof in Chicago




What:  Herb is not only one of the five romantic Chicago restaurants that will impress, it is the best Thai restaurant in Chicago.  There, I said it!  Chef Patty incorporates a healthy, holistic approach to cooking with both familiar and harder to find ingredients in her eye-popping plates of color. The three-course and five-course menus are a great deal, but everything on the menu is available a la carte.  I loved the herbaceous, crispy betel leaves with ginger, peanuts, lime, toasted coconut, shallot and caramel palm sugar sauce.  Betel leaves are very high in calcium and other nutrients, and Chef Patty is shipping them in from Florida.  The pork spring rolls and pork belly entree are also too beautiful to eat, but once you start, you will want to order more!  Do not leave Herb without trying dessert.  I thought the warm mango sticky rice was light, lovely and romantic.

Pro Tip:  Herb is  BYOB only.  The do not have a liquor license so come prepared!

Where:  5424 N. Broadway (1 block west and 1.5 blocks north of the Berwyn ‘L’ stop, along the Red Line)



Romantic Chicago Restaurants Herb restaurant



Romantic Chicago Restaurants Herb Thai restaurant



Romantic Chicago Restaurants Herb restaurant menu



Romantic Chicago Restaurants Herb in Edgewater



Romantic Chicago Restaurants Herb restaurant in Chicago



Geja’s Cafe


What:  This incredibly sexy restaurant in Lincoln Park offers just the right amount of atmosphere and fun with fondue and wine to cause a spark between you and that special some (or a group of friends).  There’s plenty of candlelight and ways to get tactile with your food here.  It’s a great spot if you’re headed to a show at the Park West theatre nearby.

Where: 340 W. Armitage (Take the #73 Armitage bus east from the Armitage ‘L’ stop on the Brown line.  Or take the #22 Clark bus).


Cafe Marie-Jeanne


What:  A French-inspired brasserie located in the Humboldt Park neighborhood on Chicago’s northwest side.  Cafe Marie-Jeanne makes my list of romantic Chicago restaurants because it evokes the “open all day” cafes you find in Paris.  Come for coffee and breakfast at 7 am and work on your laptop until it’s time for lunch or dinner.  This place is the French version of Pleasant House Pub in the Pilsen neighborhood which gives the nod to those fantastic British pubs that can easily become an all-day affair.  Cafe Marie-Jeanne is a transportive experience where you can enjoy some quiet time, connect with friends and family or the one you wish to woo.  The cocktails are delicious, and the specials change often.  On a recent visit, I enjoyed the crispy sea bream with in-season asparagus, as well as some smoked trout, gravlax, pickled veggies, cream cheese and sliced potatoes.  Delicious!  In fact, Cafe Marie-Jeanne loves its smoked fish and smoked meats.  I will be back for the decadent brunch, pastries, and soups.  C’est si Bon!


Pro Tip:  Cafe Marie-Jeanne has a $32 prix-fixe menu on Wednesday and a $20 burger, beer and fries special on Thursday.


Where:  1001 N. California Ave (Take the Blue Line to the California ‘L’ stop and transfer to the #52 Kedzie bus toward 63rd St.)



Romantic Chicago Restaurants Cafe Marie Jeanne cocktails



Romantic Chicago Restaurants Cafe Marie Jeanne Humboldt Park



Romantic Chicago Restaurants Cafe Marie Jeanne menu



Romantic Chicago Restaurants Cafe Marie Jeanne Chicago



Mad Social

What:  This sleek and sexy spot in Chicago’s West Loop is romantic first and foremost because it is a bit south of the madness on Randolph St.  (See what I did there?)  Who needs all of those looky-loos crowding your romantic moment?  The globally inspired menu at Mad Social has Midwestern roots.  The plates here are meant to be shared, but on a recent visit, I romanced myself with some seasonal bruschetta with asparagus.  I also recommend that you take advantage of Mad Social’s Happy Hour Specials like the excellent half-priced meat and cheese boards on Thursday!  


Pro Tip:  Make sure you identify the Happy Hour specials at Mad Social from 5 – 7 pm.


Where:  1140 W. Madison St. (3 blocks south and 3 blocks west of the Morgan ‘L’ stop, along the Green and Pink Lines)



Romantic Chicago Restaurants Mad Social West Loop



Romantic Chicago Restaurants Mad Social


Do you have a list of favorite romantic Chicago restaurants you like to frequent?  Leave me a comment so we can discuss!

In keeping with the spirit of Feeding Off The Rails, I encourage you to leave your car at home and take the ‘L’ and buses to these 5 Romantic Chicago Restaurants. Save on gas. Avoid traffic, road rage and parking.  Reduce pollution. Don’t drink and drive!

Looking for other great Chicago restaurants?  Check out Chicago’s best Italian restaurants and best Latin restaurants.