Chicago’s Ultimate Valentine’s Day Guide

Valentine’s Day is right around the corner, and whether you’re in a committed relationship or just committed to having a good time, we know that you deserve some love this year.

And while, yes, it can certainly be hard to find the right place to go on Valentine’s Day in a city with so many romantic restaurants, events, and attractions, there’s truly no need to fret – UrbanMatter is here to help.

This is your Ultimate Valentine’s Day Guide.


Parties & Bar Crawls

Photo Credit: Art Room Events

Step in the name of love.


Restaurant Specials

Valentine's Day Guide
Photo Credit: The Publican

Deep breaths, everyone – this one’s gonna be a doozy.

  • The Albert – The Albert is cooking up a special Pre-fixe Valentine’s Dinner Menu for all lovers out there. Indulge in their 4-Course Chief’s Tasting menu, featuring East Coast Oysters, Onion Tartine, Love is a Drug chocolate mousse dessert and more. The price is $65 per person, with a $45 wine pairing option.
  • Ella Elli – For $95 per person, partake in a four-course, prix fixe meal from this romantic getaway, known as the “Most Romantic Restaurant in Illinois”. Reservations can be requested here.
  • Shaw’s Crab House –  Their menu is featuring a Surf and Turf duo with a sliced 14 oz prime NY Strip Steak served with truffle butter, roasted cipollini onions and a Whole Maine Lobster Thermidor, all for $150. If you’re looking for a brunch affair, attend their Cupid’s Brunch on Sunday, February 10th. Reserve here.
  • Booth One – Booth One is spreading the love with a luxe prix-fixe menu of seasonal specialties. The menu is $55 per person. More information here.
  • Summer House Santa Monica – Looking for a sweet treat for your sweetie? Summer House is selling their special Valentine’s Day sugar cookies for $4.95 all week.
  • Naoki Sushi  – For $95 per person, Chef Naoki is offering an a la carte menu along with hosting a special Omakase at the sushi bar. Reserve here.
  • The Dearborn – From February 14 – 17, enjoy their Valentine’s Day specials that include house-made charcuterie for $19, Roasted Saddle of Lamb for $45, and their mouth-watering Rum Baba for $15.
  • El Che Steakhouse & Bar – The February 14th, this restaurant will be offering discounted sparkling wines and Champagnes, such as the Blanc de Blanc “Bubbles for Two” for $50, and the 2016 Clos Cibonne, Cotes de Provence rose for $65.
  • Travelle at The Langham – Get “A Four Course  Love Story” for $95 per person. Check out their special Valentine’s menu here.  And of course, reserve now.
  • LH Rooftop – Enjoy this cozy indoor restaurant and fall in love all over again with a lovely three-course American cuisine with for $65 per person. Reserve here.
  • Lawry’s The Prime Rib – Lawry’s is having a romantic Valentine’s Day Dinner for $150 per couple. Make your reservations here.
  • The Publican – For $65 per person, treat your loved one to a multi-course tasting menu, showcasing all of The Publican’s best flavors. Menu and reservations are provided here.
  • Mercat a la Planxa – For $145 per couple, enjoy an authentic, Spanish, four-course Valentine’s Day dinner from February 14 – 16th. Reserve here.
  • The Signature Room – Offering a four-course prix fixe menu from 5-10pm is the luxurious Signature room for $125 per person. Feature items include Braised Short Rib, Half Roasted Chicken, Grilled Filet of Beef, Roasted Rack of Lamb and more. Contact info available here.
  • Geja’s Cafe – Get a full week of Valentine’s day goodness at this classy Old Town restaurant. Starting on Monday, February 11th Geja’s will feature a number of romantic events including a Celebration of Marriage discount dinner, a Valentine’s Day Lunch of Romance and a special prix fixe Valentine’s Day dinner menu. More information and reservations available here.
  • Kizuki Ramen & Izakaya  Prix fixe menus include an appetizer sampler, entree, and dessert for $80 per couple. You can also purchase a white rose bouquet for your honey for an extra $40, ya know, if you’re feelin’ fancy. Tickets available here.
  • North Pond – Nothing says “I love you” quite like dinner with a view. And this one is spectacular. The 5-course tasting menu on the 14th starts at $125 a person with optional wine pairings for $60. Make reservations here.
  • GT Prime – Love abounds in this cozy, dark lit restaurant in River North, perfect for a romantic getaway with bae.
  • The Promontory – A delicious menu AND R&B soul? Sounds like a perfect night out to us.
  • Maple & Ash – Dine in at this upscale steakhouse on the Gold Coast at 8 West Maple Street for an extra-special Valentine’s Day.


Drink Deals

Valentine's Day Guide
Photo Credit: Publican Anker, courtesy of Christiana Forsberg


What To Do

Valentine's Day Guide



Valentine's Day Guide
Photo Credit: Chicago Pork Chop
  • Heart Shape Chocolate Cake from Portillo’s – Portillo’s annual heart-shaped cakes are back again! For just $19.49 you can get one of the restaurants famous chocolate cakes in heart form, available for both delivery and pick up.
  • Cindy’s – The Chicago Athletic Association’s iconic rooftop transforms into the dreamy Bows and Eros for the season, serving amazing sweet treats for Chicagoans of all kinds to box up and take home.
  • Valentine’s Day Sugar Cookies from Summer House Santa Monica – Did someone say $4.95 sugar cookies? I’m there.
  • Mindy’s Hot Chocolate – Not only is this Wicker Park favorite offering reservations for a romantic V-Day, but you can also pre-order ombre chocolate covered strawberries or assorted chocolate brittles for pick up on the big day.
  • Flowers For Dreams – Go classic and send an arrangement of beautiful flowers to your partner in crime.
  • Or…you could always try these creative gifts!


Anything we missed? Got a tip on a fun or romantic Valentine’s Day event that you want everyone to know about? Tell us below!


About Author


Leave a comment