An Ultimate Guide For You To Celebrate Valentine’s Day in Chicago

Planning for the big weekend? Let us help! After putting together a dinner date guide, we are now moving on to pop-ups, events, and special happy hours! Oh, you’ll also find Valentine’s weekend hotel deals in Chicago toward the bottom of this article. So, if you are trying to figure out how to celebrate Valentine’s Day in Chicago this year, look no further! We’ve got the best info for you.

Valentine’s Day Pop-Ups and Events

jojo's candyland valentine's popup
Image Credit: Jojo’s ShakeBAR

Visit the Candyland at JoJo’s ShakeBAR

JoJo’s Candy Land is an immersive dining experience that brings everyones’ favorite childhood board game to life! Decked out with enormous gummy bears, gigantic lollipops, and massive glowing gumdrops, JoJo’s heated Candy Land tent is the perfect accompaniment to the delicious diner food.


As Chicago’s signature Valentine’s Day spot, JoJo’s does not skimp on the festive treats. The Love Shake is sure to steal your heart with the perfect blend of raspberry and red velvet cake topped with a chocolate-covered heart pretzel, a full slice of raspberry drizzled cheesecake, a decadent chocolate-covered strawberry, and finished off with a giant heart-shaped “Be Mine” sugar cookie. But don’t forget about the Love Shake’s other half, the Cupid’s Cocoa. This Red Velvet flavored Hot Chocolate topped with heart marshmallows, a chocolate-covered pretzel and pink chocolate dipped s’mores is sure to make you feel all warm and fuzzy inside.

Reservations are available on OpenTable. Walk-ins are welcome too! Also, Valentine’s Day Menu is available until February 20.

free pool valentine's day date in Chicago
Image Credit: aliveOne

Valentine’s Music Trivia Date at aliveOne

2683 N. Halsted St. Chicago, IL 60614

A fun Valentine’s Day outing for couples and groups, aliveOne will host FREE Valentine’s Music Trivia from Whaddayaknow! Beginning at 8 p.m. on Monday, Feb.14, guests will also enjoy FREE use of their pool table. The Lincoln Park neighborhood bar that combines the very best of music and spirits will offer specials like $6 The Becky cocktails with Tito’s, La Croix Pamplemousse, fresh lime juice and demerara syrup.


Additional specials include a half-price happy hour from 5 p.m. to 7 p.m. and a $7 PBR and whiskey shot combo. Guests will also enjoy emo music like Fall Out Boy, Taking Back Sunday, Blink 182, and Dashboard Confessional all night.

estelles valentine's day wine event
Image Credit: Estelle’s

Annual “Wine About Your Love Life” at Estelle’s

2013 W. North Ave. Chicago, IL 60647


On Valentine’s Day, the bartenders at Estelle’s will be ready to lend an ear as they invite Chicagoans to cozy up to the bar for their annual “Wine About Your Love Life” night. Half-price glasses of wine will be available all evening for $7 each (normally $14), and selections include Beckstoffer ’75 Company Cabernet Sauvignon, Planet Oregon Pinot Noir, Lobster Reef Sauvignon Blanc and Nomadica Rosé.

Additional specials will include half-price happy hour from 4 p.m. to 6 p.m. and half-price burgers. Candy hearts will be available for customers if they want to give a “sweet” special message to their Estelle’s crush.

remedy wine
Image Credit: Remedy

Enjoys a Special Valentine’s Day Happy Hour at Remedy

2013 W North Ave, Chicago, IL 60647

Chicagoans looking for a casual Valentine’s Day night out can enjoy half-price happy hour from 4 p.m. to 7 p.m. at Remedy in Bucktown. Half-price house cocktail options include the Rhubarbarella with Aviation gin, Aperol, lemon juice, rhubarb bitters and simple syrup, the Passionably Late with Chinola passion fruit, Aviation gin, lime juice, and soda water, and the Winthrop with Tito’s vodka, limoncello, creme de violette, lemon juice, butterfly pea tea, and vanilla, and more.

rambler drinks bingo
Image Credit: The Rambler

Bachelor’s Bingo at Rambler

4128 N. Lincoln Ave. Chicago, IL 60618

Guests are invited to get their group dates together to play The Bachelor-themed bingo at The Rambler in North Center on Monday, February 14 at 7 p.m. The grand prize winner will receive a prize pack featuring roses, champagne, fancy chocolates, rosé wine and more. Specials will include $20 Bottomless LaMarca Mimosas, $4 High Noon Flavors, and $7 Strawberry Kiss cocktails. To reserve a table, email


Valentine’s Cruise by City Cruise

City Cruises is running a special early bird promo for those looking to book now by saving 15% on Valentine’s Day Weekend Cruises using promo code VDAY15 upon checkout! Love is in the air and on our waterfront this Valentine’s Day with City Cruises Chicago. Patrons are invited to celebrate love between Friday, February 12th through Monday, February 14th abroad one of their four dinner or brunch cruises.

With onboard packages and upgrades to choose from, sweethearts can expect a delightful plated or buffet-style meal along with a sweets arrangement, onboard entertainment, and a cash bar, all while sailing along Chicago’s River or lakefront for the best views of the city. Make this Valentine’s Day unforgettable!

celebrate valentine's day candelight concert
Image Credit: Fever Chicago

Go to a Candlelit Concert

You don’t need to know all things classical music to enjoy the evening; simply sit back and savor the stunning pieces you’ll hear. Walk into one of Chicago’s historical buildings where the walls will be flickering by candlelight to create a magical atmosphere. Prepare to be taken into the clouds with these most treasured masterpieces!

Enjoy classic pieces such as Romeo and Juliet, Somewhere Over the Rainbow, and iconic Beatles lovesongs bathed in candlelight in the remarkable Stan Mansion. Drinks are available for separate purchases.

A Date in the Deep Ocean at Shedd Aquarium

1200 S Lake Shore Dr, Chicago, IL 60605

Gift the experience of a 75-minute encounter with a beluga whale in the chest-deep water or a shark feeding tour. Actually, how about a date with the adorable penguins? Shedd Aquarium has the perfect Valentine’s date planned for you and your loved one! Come live your mermaid dream here at Shedd Aquarium and watch how the entire vast ocean celebrates your love.

Try Partner Climbing at First Ascent

First Ascent believes adventure is essential to the human spirit, and that climbing is just the adventure for everyone. Well, we agree with that sentiment 100%. So, if you’re looking for something cool and different to do this Valentine’s Day, check out their partner climbing initiative. They’re also running a Buy One Get One day pass and rental gear special to make your day even better.

First Ascent currently has 5 locations: four in Chicagoland and one in Peoria, IL. Each location has a different layout and feature. Some have a heavier focus on bouldering, the others on climbing. So, do your comparison and find your favorite spot!

Plan A Romantic Staycation With These Valentine’s Hotel Deal

And, as promised! Here comes all the V-Day hotel specials for you to celebrate Valentine’s Day in Chicago in the most pampering way possible. After all, why not make it a full day when you have such amazing deals?

Love Nobu Package from Nobu Hotel Chicago

155 N Peoria St, Chicago, IL 60607

Looking for a romantic getaway in the heart of Chicago with ultimate privacy and relaxation? Love is in the air as soon as you step through the door at Nobu Hotel Chicago with amenities made for couples looking for an intimate weekend away, perfect for a long Valentine’s Day weekend.

Couples can unwind in Nobu’s various rooms and suites with teak soaking tubs, an exclusive Nobu bed, yoga mats, and traditional Japanese tea service, making each room the perfect spot to fall in love. Take a dip in the one-of-a-kind Tranquility pool and relax in the fitness center with sauna rooms ideal for unwinding and tranquility.

Romance & Rivalry Package from Radisson Blu Aqua Hotel

221 N Columbus Dr, Chicago, IL 60601

This year Valentine’s Day and the Superbowl fall only one day apart! Enjoy this rare weekend at Radisson Blu Aqua Hotel and book the “Romance & Rivalry” package that includes accommodations in the Presidential Suite and a welcome amenity of champagne and roses.

The package also features Valentine’s day dinner for two at FireLake Grill House & Bar with a romantic multiple course dinner in Upper FireLake, a bottle of premium wine, and two cocktails and chocolate-covered strawberries to go. The next morning begins with a game-day brunch in Upper FireLake where you will load up on your game-day food favorites including two cocktails and unlimited beer and wine.

Build Your Love at Royal Sonesta Chicago Downtown

71 E Wacker Dr, Chicago, IL 60601

Spend this Valentine’s Day at a riverside setting in the heart of Chicago! Spoil the one you love most with a stay at Royal Sonesta Chicago Downtown and indulge in some of the largest guest rooms the city has to offer. Reserve the hotel’s Valentine’s Day package that features luxury accommodations, a champagne bottle upon arrival, cupid-approved welcome amenity, and a “Build Your Love” itinerary for guests to choose their own romantic adventure.

Itinerary options include a private lingerie fitting experience, Champagne helicopter tour, or couple’s spa experience. You and your sweetheart will enjoy scenic views of the Chicago River and the spectacular cityscape while sipping on champagne from the comfort of your recently renovated room.

The Rose Hotel Chicago O’Hare

5200 Pearl St, Rosemont, IL 60018

Back by popular demand, the beloved ‘Room Full of Roses’ package is returning to The Rose Hotel Chicago O’Hare. Guests are invited to stay in the ultimate, over-the-top Valentine’s Day experience. Featuring a King suite filled to the brim with over 400 roses and complementary bubbles upon arrival, welcome amenities, and a complimentary breakfast in bed for two (courtesy of Thorn Restaurant & Lounge), this package is sure to make this Valentine’s Day the most memorable one yet. Rooms will sell out! Book your unforgettable stay here.

Escape to The Drake Oak Brook

2301 York Rd, Oak Brook, IL 60523

Escape the city this Valentine’s Day and plan a romantic weekend at The Drake Oak Brook. Spend a romantic evening under the stars by reserving a heated igloo that offers a blend of delectable cuisine and crafted cocktails or reserve the Champagne Sunday Brunch at the iconic Colonial Room. Book the “Couples Escape” package, which includes newly renovated suite accommodations, champagne breakfast in bed for two, one-hour in-room couples massage and late check-out of 2 p.m. Indulge in what your body and heart need this holiday at The Drake Oak Brook.

Book Valentine’s Getaway at Renaissance Chicago Downtown Hotel

1 W Wacker Dr, Chicago, IL 60601

Celebrate this Valentine’s Day with your lover in the heart of the city at Renaissance Chicago Downtown Hotel. Book the Valentine’s Getaway package from February 11 through 14, or even February 18 through 21 if celebrating later this year, and receive breakfast for two at Staytion Market & Bar and a late checkout of 1 PM allowing you to have a leisurely morning after spending the evening with your sweetheart. Don’t skip a visit to Raised Bar Chicago on the third floor of the hotel for craft cocktails and delectable dining. The cocktail bar will feature a special Valentine’s Day menu with signature cocktails and bites during the holiday weekend.

Featured Image Credit: Estelle’s