Chicago, IL

Best Places to Celebrate a Romantic Chicago Valentines Day

Natalie Frank, Ph.D.

If you are In Chicago on Valentine's Day, here are some of the best activities and places to go
Photo byKumar's Edit/flickr (CC BY 2.0)

Valentine’s Day is only a week away. The Second City is filled with romantic activities to please both you and your other half. If you are just getting to know someone, there are plenty of options to learn more about them and deepen the connection. Celebrate Valentine’s Day in Chicago with these fun, romantic activities.

Mystery Picnic

If you are looking for some adventure this Valentine’s Day, a Mystery Picnic is just what the doctor ordered. Mystery Picnics are self-guided tours of the city or neighborhood where your destination is a secret. You only learn what the location of the picnic is by solving clues and riddles together. Each clue will take you through scenic areas to local artisan shops where you will receive different food and drink items. The last clue will lead you to your destination where you will hold your picnic and enjoy the artisans fare that you have gathered. There is also a stay-at-home adventure with hours of Valentine-themed activities and adventures couples can do together. Along with the main menu there are vegetarian, vegan and gluten free options. Just add on the Valentine’s Day Edition when checking out. There are locations in and around Chicago, including Lincoln Park, Evanston, and Naperville. Tours with picnics take about 3-4 hours though you can take as long as you’d like. You can also select the adventure to give as a gift.


Tours for couples are $110 for the All Inclusive Picnic and $165 for the Exclusive Experience plus $18 for the Valentine’s Day upgrade.

Candle Light Valentine Dessert and Dance Tango

There isn’t a more romantic dance than the tango. If you’ve always wanted to learn to Tango, there couldn’t be a better day than Valentine’s. Lessons are held in a candle lit studio and taught by a professional dance teacher. Bring a bottle of your favorite wine to sip during class or accompany your dessert. Romantic music is played throughout the night. Prices include a private tango lesson for two and dessert. This is a 21+ activity.

Dates: Feb. 10th through Feb. 17th

Time: 4:00pm to !0:00pm (preferred time)

Location: Sway Dance, 3317 W Irving Park Rd, Chicago, IL 60618

Cost: $75 for two

Valentine’s Candlelight Concert: Romeo and Juliet and More

Enjoy a romantic, candlelit live concert featuring the music of Romeo and Julien in a multi-sensory musical event performed by the Metropolis String Quartet. There’s no worry of fire, as the candles are fireproof.

In addition to Romeo and Juliet, the tentative program includes a mix of romantic favorites including:

  • Romeo and Juliet (Fantasy Overture) - Tchaikovsky
  • Music from West Side Story - Leonard Bernstein
    • Maria
    • Somewhere
    • Tonight, Tonight
  • Love Story - Taylor Swift
  • Somewhere Over the Rainbow - Israel Kamakawiwo'ole
  • Music by The Beatles
    • And I Love Her
    • In My Life
    • All You Need is Love
  • Send My Love (To Your New Lover) - Adele
  • Sweet Child O’ Mine - Guns N’ Roses
  • Theme from Love Story (1970) - Francis Lai
  • Kiss from a Rose - Seal

Dates: Feb. 14th through Feb. 15th

Time: 6:30. 8:45

Location: Cafe Brauer 2021 N Stockton Dr., Chicago, IL 60614

Cost: $60 (Zone A), $70 (Zone B)/per person

Valentine’s Day at the Field Museum (Free)

If you have always wanted to visit Chicago’s Field Museum, Valentine’s Day is the perfect time to go. Admission will be free on Valentine’s Day, from 9:00am to 5:00pm (last admission at 4:00pm). The Field Museum is one of the largest Natural History museums in the world.

Tour the dinosaur exhibits and catch a view of the Titanosaur, the largest land animal ever to walk the earth, listen to local stories of the Calumut region, experience an 19th century Pawnee earth lodge, learn about the changing face of science and if you are a jewelry fan then the gemstone exhibit and Hall of Jades are for you. There are also many other exhibits you can tour with your better half at the Field Museum.

Tickets for Free Days are available to Illinois residents only and cannot be reserved in advance or bought online. Show your proof of Illinois residency to a Visitor Services staff member for free admission.

Date: Feb. 12th, Valentine’s Day

Time: The museum is open 9am to 5pm (last admission at 4pm)

Location: Chicago’s Museum Campus, 1400 S Lake Shore Dr, Chicago, IL 60605

Cost: Admission normally varies but will be free for Illinois residents on Valentine’s Day, 2023.

Visit the Most Romantic Places in Chicago

If you want to spend Valentine’s Day with a group of friends this tour is for you. The Guided Tour “Love Stories of Chicago” will take you to the most romantic locations in the city while a local guide tells you about the love stories associated with the city’s streets, buildings and parks. Listen to tragic stories that will break your heart, hysterical stories that are sure to make you laugh along with saucy, a little naughty stories that will spice up your night. The guide will also tell you about the best date locations and where you want to take the most romantic selfies to remember your experience.

Dates: Feb. 8th through Feb. 14th

Times: 10:00am, 12:00pm, 2:00pm, 4:00pm, 6:00pm

Location: Millennium Park, 201 E Randolph St, Chicago, IL, 60602

Cost: $339.50 for up to 15 people

Name a Cockroach/ Adopt a Penguin at the Brookfield Zoo

Location: 8400 W 31st St, Brookfield, IL 60513

Few birds are cuter than penguins and what’s more romantic than adopting one for you sweat heart this Valentine’s Day. If you are still searching for the perfect gift for Valentine’s Day, the Brookfield Zoo will let you adopt a penguin for Valentine’s Day. Penguins are the lovebirds of the Antarctic, with the male returning to the same female year after year.

You can adopt famous penguin couple Patty and Valentino. Valentino is particularly special, as he was born on Valentine’s Day in 2011. You can receive an adoption certificate, penguin plush, and tote bag celebrating your penguin.


  • Certificate of Adoption- $35
  • Certificate of Adoption and penguin plush - $59
  • Certificate of Adoption, penguin plush, and tote bag - $75

On the other end of the spectrum, if you haven’t been able to get over an ex but desperately want to, name a cockroach in their honor. The Brookfield Zoo will let you name a Madagascar hissing cockroach after your annoying ex for Valentine’s Day and receive a certificate you can hang in your home.

Cost: Name a cockroach and receive a certificate - $15

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