Valentine's Day weekend in Chicago: Top concerts, theater and live events

If you’re planning a Valentine’s date in Chicago, the city’s live-event calendar does a lot of the heavy lifting. From massive concerts and must-see theater to comedy shows and electric sports atmospheres, there’s no shortage of ways to make February 13–15, 2026 feel special with no prix-fixe dinner required.

Must-see Chicago concerts for Valentine’s weekend

These concerts set the tone for a memorable Valentine’s weekend in the Windy City.

Chicago Philharmonic Orchestra at The Auditorium Theatre (Feb. 13)

The Chicago Philharmonic performs a romantic and dynamic concert at The Auditorium Theatre, featuring a mix of classical masterpieces and contemporary favorites perfect for a date-night outing.

Justin Furstenfeld at House of Blues Chicago (Feb. 13-15)

Singer-songwriter Justin Furstenfeld performs in the intimate House of Blues Chicago — great for couples who enjoy heartfelt, acoustic‑leaning rock.

Jaap van Zweden at Symphony Center (Feb. 14 & 15)

Jaap van Zweden conducts the Chicago Symphony Orchestra with violinist Himari performing works including Bruch’s Violin Concerto and Mozart’s Jupiter at Symphony Center, making it a perfect romantic Valentine’s weekend concert.

Chicago theater for a romantic Valentine’s weekend

These musicals and plays are ideal for a romantic evening out.

The Outsiders at Cadillac Palace Theatre (Feb. 13-15)

The Outsiders plays in Chicago over Valentine’s weekend, bringing the classic coming-of-age story to life on stage for fans of drama and nostalgia at Cadillac Palace Theatre.

Hamnet at The Yard at Chicago Shakespeare (Feb. 13-15)

Hamnet at The Yard at Chicago Shakespeare is a critically acclaimed stage adaptation of Maggie O’Farrell’s bestselling novel about family, love, loss, and resilience.

Hamlet at Courtyard Theater at Chicago Shakespeare (Feb. 14)

Hamlet is playing at Chicago Shakespeare Theater’s Courtyard Theater with a special abridged 75‑minute adaptation, making it a great romantic Valentine’s weekend matinee option in Chicago.

Chicago comedy for a Valentine’s date night filled with laughs

If laughter is your love language, Chicago’s comedy scene offers the perfect Valentine’s date night alternative to the usual dinner plans.

Josh Johnson Stand‑Up at The Chicago Theatre (Feb. 13-15)

Comedian Josh Johnson brings his nationally touring stand-up show to The Chicago Theatre, offering a hilarious and unforgettable Valentine’s weekend date night.

Sheryl Underwood at The Auditorium Theatre (Feb. 14)

Sheryl Underwood, the Emmy-winning comedian and host of The Talk, brings her sharp, witty, and unapologetically bold humor to The Auditorium Theatre, offering a laugh-out-loud Valentine’s Day experience perfect for couples who enjoy edgy, relatable comedy.

Jessica Kirson at Riviera Theatre (Feb. 14)

Comedian Jessica Kirson brings her high-energy, hilariously self-deprecating stand-up to the Riviera Theatre, delivering a bold and unforgettable Valentine’s Day night of laughs.

Why buying Valentine’s Day tickets early for live events is crucial

Valentine’s Day weekend puts major pressure on Chicago’s live-event calendar. Popular concerts, comedy shows, and sporting events often see a rush of buyers as soon as the weekend approaches, with prime Friday and Saturday night tickets disappearing first.

Locking in tickets early gives you:

• First pick of the best seats

• Better pricing before demand spikes

• More flexibility across dates and start times

• Confidence that your Valentine’s plans are set before options narrow

How to buy Valentine’s weekend tickets on SeatGeek

SeatGeek makes it easy to browse, compare and book live events across Chicago for Valentine’s weekend. Here’s how to line up the perfect night out:

1. Start your search Visit SeatGeek's website or open the app, then you can either: • Enter the artist, show, or sports team, then filter results by Chicago and the dates February 13–15, 2026. • Click on the "Chicago" city page and filter events for "This Weekend" or "Next Weekend."

2. Size up your options SeatGeek highlights tickets with a Deal Score, helping you spot strong value quickly. Narrow your choices by price range, seating section, row, or number of tickets.

3. Choose where you want to sit Select a listing to explore the interactive seating map. For most events, you’ll be able to preview your view before committing.

4. Confirm the details Review the event date, time, ticket quantity, and pricing. SeatGeek displays all-in prices upfront, so there are no last-minute surprises.

5. Check out and get ready Complete your purchase and receive your tickets via mobile delivery or email. Add them to your wallet or print them out so your Valentine’s weekend plans in Chicago are officially locked in.