How to Spend Valentine’s Day With Your Girls in Chicago

How to Spend Valentine’s Day With Your Girls in Chicago

You’re cordially invited to replace that little black dress with a red dress.

It’s February. It feels like love is in the air—for your man, for your friends and for yourself.

I know that this holiday can bring anxiety for some, pure dread for others, and is basically a public service announcement for singles, for others.

If you want a man for Valentine’s Day, there’s still time.

But for those who would rather not be desperate or feel alone, there’re tons of ways to celebrate this all too familiar commercial holiday with your favorite girlfriends. After all, they are more likely to hang out with you for longer than your Valentine’s Day flavor of the week.

So, get excited.


Cupid’s Undie Run is an international fundraising event for Neurofibromatosis (NF) with a fun twist—you don’t have to wear pants. The one-mile race in Wrigleyville begins on Saturday, February 13, 2016, in Chicago.

  • Noon – Doors open & the party starts!
  • 1:00 PM – Awards ceremony
  • 2:00 PM – Cupid’s Undie Run
  • 3:30 PM – Earned “open bar” closes
  • 4:00 PM – Bag check closes, Cupid’s officially ends

Learn all the details about Chicago’s most liberating race. Hurry! February 4, 2016, is the last day to get discounted race tickets. xoxo



Don’t worry, the 17th Annual Screw Cupid Pub Crawl will put you in the Valentine’s Day spirit.

On Saturday, February 13, from 8:00 – 11:00 pm in Lincoln Park, enjoy a $20 meal package that includes:

Food buffets at each bar
Domestic drafts
Cupid Punch (Reviewed by Metromix)
Looping trolley transportation to all 5 bars

Best of all, this pub crawl includes drink tickets, which according to the CDC should not be more than 8 alcoholic beverages in a WEEK.

Get your tickets here. 

Accept The Final Rose from The Bachelor:

Laugh about love or accept the final rose in a night of improvised parody of ABC’s greatest dating show, The Bachelor. Special guest includes Ed Swiderski from ABC’s The Bachelor. Don’t miss a minute of the drama, the journey, or the obligatory jacuzzi scene at Under the Gun Theater.

Laugh About That Romance Novel:

Because there’re so many romances that occur at Book Club, Under the Gun Theater is making a whole play out of it in Smut! Improvised Romantic Comedy. The show has two parts. A member of the SMUT ensemble will have read a popular romantic novel and have prepared a steamy, but academic presentation distilling the STYLES, the THEMES, the MOTIFS and other words you heard in English class about that particular novel. Immediately after class, enjoy an improvised performance based on what they learned from the romance novel.

Tickets for both shows are available here. Each show is $12 or you can see both shows for $20. Tickets include a drink voucher.

Throw Your Own Galentine’s Day Party:

Oh, this will be fun because girl’s just wanna have fun. Throw a Valentine’s Day Dinner Party. Invite men, too, because well, we like men.

Send out invitations with a chocolate kiss on top. Wear a red dress.

Make some of these Valentine’s Day drinks.

And top it off with games like charades. And best of all, play secret admirer. I made it up, but it’s cute. Everyone draws a name from a hat and has to write a Valentine’s poem for them. They read it out loud and guests have to find out who their secret admirer is.

P.S. Mojo Spa has an all-inclusive Galentine’s Day party ideas from Netflix and Chill to sweet cocktails and the best beauty gifts for your best friends.


Take A Day Trip to The Vineyards:

How about a day trip to the vineyards?

Get you guy friends and girlfriends together for a day out of Chicago for an all-inclusive winery tour at four locations in Southwest Michigan. A tour guide will take you to four nearby vineyards and provide an Italian lunch to pair with the 20+ wine tastings of your choice throughout the day.

Wine Tasting Tours in Southwest Michigan with Cannonball Productions. Photo: Amanda Elliott
 The Southwest Michigan Wine Tour is an awesome Valentine’s Day plan because you don’t have to plan, you just get to enjoy.

Get your Cannonball Productions tickets for Michigan Wine Tours on February 13 or February 14, 2016. Roundtrip transportation from Chicago to Michigan is included.

Wishing you a fun weekend with your girls!

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