The Second City
With Valentine’s Day less than a month away, it’s time to start making your plans before spots and reservations fill up. Avoid the stress of scrambling last minute and look into one of these unique date options that are sure to impress your significant other. Here are Chicago Valentine’s Day date ideas at every price.



Chicago Valentine’s Day Dates UNDER $50


#DateMe: An OKCupid Experiment

Date Me

Attend this hilarious, award-winning comedy show at The Second City’s UP Comedy Club. This is an especially interesting and relevant option if you originally met your date through an online-dating site or app. Tickets are $26–$36.

230 W. North Avenue  |  312-662-4562



Drinks and Live Jazz Music at Andy's
Andy's Jazz Club

Andy's Jazz Club & Restaurant has a unique and romantic setting for a Chicago Valentine's Day date. Enjoy just drinks (admission from $10-15 per person) with the accompaniment of live jazz music at this historical establishment. Or enjoy dinner but be sure to make a reservation in advance — this will book up fast!

11 E. Hubbard Street  |  312-642-6805



UNDER $100


Romantic Dinner and Dessert at Mindy’s Hot Chocolate

Mindy's HotChocolate

Make a reservation at Mindy’s Hot Chocolate to indulge in a romantic and chocolate-infused meal. The menu is affordable, so it’s not likely to set you back more than $100 in total. Enjoy seasonal American fare for dinner, followed by rich and tasty hot chocolate for dessert.

1747 N. Damen Avenue  |  773-489-1747

Cupid’s Undie Run

Work up an appetite at Cupid's Undie Run Chicago before consuming mass quantities of chocolate. This scantily clad charity run is a fun event to partake in with your significant other. Not an athlete? Not to worry. The actual run is only about a mile, and proceeds benefit the Children’s Tumor Foundation. Early bird tickets start at just $35 each. Race begins and ends at John Barleycorn Wrigleyville.

3524 N. Clark Street  |   773-348-8899



Beer and Cake Pairing Class at Moody Tongue
Moody Tongue Brewery Chicago

Self-proclaimed sweet tooths and craft-beer lovers will enjoy this opportunity to indulge the senses right before Valentine's Day. If you're looking to celebrate a bit early, Moody Tongue is hosting a Beer and Cake Pairing Class for $50. It's an excellent opportunity to check out the surrounding Pilsen neighborhood, not to mention a good chance to learn how to pair flavors and aromatics. Cheers!

2136 S. Peoria Street  |  312-600-5111



UNDER $150


Valentine's Day Tea at Brindille


Start your celebrations early with a special French afternoon tea service at Brindille Chicago. Chef Carrie and Pastry Chef Craig are excited to announce this event, which is scheduled for Friday, February 10th, from 2 to 5 p.m. The price is $60 per person ($120 per couple), and seating is limited. RSVP by emailing

534 N. Clark Street  |  312-595-1616



Cooking Classes

If your significant other is the hands-on, creative type, a cooking class could be a great alternative to a more typical Valentine’s Day dinner reservation. Your meal will be that much more satisfying after you help cook it. Plus, you’ll pick up some skills that you can use to cook a romantic dinner at home the next week. Check out deals on Groupon for places such as Cook Au Vin, Cooked Chicago, and Cooking Fools, and make sure that the date you have in mind still has room for participants!


Which of these Chicago Valentine’s Day Date ideas is your favorite? Leave a comment below or tweet us at @ChooseChicago.