Things to Do in Chicago for Valentine’s Day

If you are visiting Chicago in February with your special someone, here are some ideas for romantic things to do in Chicago for Valentine’s Day. Skip the stale candy hearts and cheesy greeting cards this Valentine’s Day and create a lasting memory instead! Experience Chicago’s seductive side with our recommendations on the coziest restaurants, romantic hot-spots, and a few wild cards!

Check out our Chicago Visitors Guide, with budget advice, travel guides, and information about local Chicago attractions

Chicago view from Signature Room Hancock tower



Enjoy stunning views of Chicago at the Signature Room

On top of the Hancock building on the 95th floor you can take your date to the top of the clouds and have drinks or even dinner at the Signature Room. While the place is upscale and you are partly paying for the great view, food is not half as bad here. Just remember to bring your photo IDs to be allowed up the elevators and to plan in some time waiting in line for a table upstairs. Ladies, in the meantime while waiting in line, check out the restrooms for a spectacular view out of those big windows.


Chicago Ice Skating Go Ice Skating in Millennium Park (FREE through March 6th)

What’s more romantic than ice skating with your crush in the gorgeous Downtown Loop? Millennium Park’s McCormick Tribune Ice Rink on Michigan Avenue between Washington and Madison, has free admission through February, and provides skate rentals for just $12. Open on Valentine’s Day (Sunday) 10am-9pm.


Check out the Cupid’s Undie Run (charity run, Feb 13th at 12pm)

It’s not a ‘real’ run, you don’t have to do it in your undies, it’s a non-traditional date (bring friends!), and it benefits finding a cure for neurofibromatosis (NF). Party at John Barleycorn at noon, run at 2pm, and return to celebrate some more! More information about Cupid’s Undie Run, including registration/volunteering can be found on the website.


Chicago Blues player


Let your love speak through the blues

You are in the capitol of blues, so why not check out one of the many blues clubs and listen to some great live music with your sweet someone. Check out the B.L.U.E’s website if you need more convincing. We have also listed the best places to listen to blues in Chicago in our Chicago Blues blog.



Eat Your Heart Out

Many restaurants have created an exclusive menu for Valentine’s Day Weekend, and OpenTable has all of them listed here. It might be overwhelming to see all of the choices, but OpenTable lets you choose the perfect restaurant based on cuisine and location, and gives you access to hundreds of reviews!

  • romantic dinnerOur top romantic choice would be Boka, winner of the Jean Banchet award for “Restaurant of the Year” in 2015. Boka will offer an exclusive tasting menu of 6 courses for $125 per person on February 14th.
  • Looking for casual and affordable, without sacrificing taste? Go to Latinicity, a brand new restaurant in Block Thirty Seven that offers a food hall of Latin-fusion dishes in the South Loop! Sample from several stations, and share with your date. Our favorite dish is the Arroz Aeropuerta ($14) at the Chaufa-Wok station.


Chicago riverwalk


Take a romantic walk at the Riverwalk 

If it’s not too cold, enjoy the breathtaking scenery of great architecture and take a relaxed stroll along the river. If you are planning on impressing your date with knowing all the buildings along the water, consider taking a walking tour with us. Free Tours by Foot runs tours all year round.





Take your date to a concert, a show, or to the theatre

  • Valentine’s Love Affair (concert, Feb 13th at 7:30pm, tickets start at $80.50)
    Enjoy an evening of R&B, jazz, and soul with Kenny ‘Babyface’ Edmonds, R&B legend and winner of 11 Grammy Awards. Joined by Ledisi, and Eric Benet to perform at Chicago Theatre on Saturday the 13th at 7:30pm.
  • Romantic Sonatas (concert, Feb 14th at 3pm, Feb 15th at 7:30pm, tickets $38, Students $10)
    Rembrandt Chamber Players present Romantic Sonatas, a concert pairing flute, oboe, cello, and piano from composers Bach, Schubert, Widerkehr, and Rachmaninoff. Two concerts at separate locations, with a post reception free of charge. Tickets are available online here.

    • Nichols Music Hall, Evanston on February 14th at 3pm.
    • PianoForte Studio, Chicago on February 15th at 7:30pm.
  • Chicago TheatreChicago Theatre Week (discounted plays/musicals Feb 11th-21st, tickets $15-$30)
    How lovely! Valentine’s Day falls right at the time of Chicago Theatre Week, with 100 events at extremely low prices thanks to the League of Chicago Theatre and Choose Chicago. Choose your date night and see what’s playing. You’ll find plays, musicals, concerts, and improv shows!
  • If you are interested in a drama with music: Check out Goodman Theatre’s Another Word for Beauty.
  • For interactive comedy, we recommend Bible Bingo at the Royal George Theatre.
  • Pro tip: These ticket deals are exclusively offered between February 11th and 21st. After that, the same shows will be regular price; you’re saving 50% or more on ticket costs by going now!