Guys, read and learn. My lady-friends and I have spilled our cheesy romance stories so that you can all receive helpful hints. If you have any questions, please leave a comment below, and Chicago gals will be happy to guide you in the right direction.

Romantic Hotel Getaway at the Trump International Hotel & Tower

This past Valentine’s Day, my boyfriend picked me up from my intramural bowling game (yes, I bowl, just not very well), and asked what I would like for dinner. I pondered and said I could make dinner, and he responded with a hotel key in hand, “How about we have dinner in our room at the Trump?” Well, duh, of course I said yes. I walked into the exquisite, one-bedroom suite (which is larger than my apartment, by the way) and walked over a pile of rose petals leading to the bed filled with my favorite snacks. We then ordered a bottle of champagne and strawberries, took a bubble bath, and lounged in the Trump robes and slippers for the rest of the evening. I loved my vacation destination.

401 N. Wabash Avenue
Chicago, IL 60611
(312) 588-8000

A Proposal at the Signature Room

A co-worker and good friend of mine named Ally came to work on an average Monday. Upon Ally’s arrival, her boss informed her that she had to go to a tasting at the Signature Room, but was unable to attend due to meetings. She casually asked Ally to go in her place, in which Ally accepted, but was not happy about it. For the next three days, she repeatedly complained to her co-workers and boyfriend that she was taking Friday off and had no time to get anything done. However, when Ally arrived at the Signature Room, in place of the catering team was her boyfriend waiting at a window table, ring box in hand, and a bottle of champagne. She said yes.

875 N Michigan Ave
Chicago, IL 60611-1894
(312) 787-9596

A Stroll Down Michigan Avenue

For a one-year anniversary, a great couple, Diane and Kevin, celebrated with a romantic dinner looking over Michigan Avenue at NoMi. Diane secured the private dining room all to themselves. The restaurant sent fresh orchids to be set up all down the center of the long dining room table with a bottle of wine for the couple to enjoy. After dinner, Kevin surprised Diane with a carriage ride down Michigan Avenue and ended the evening at the Dana Hotel & Spa in a corner room with floor to ceiling windows and a gorgeous view of the city. Nice team work you two.

800 North Michigan Avenue
Chicago, IL 60611
(312) 239-4030
Please note: NoMI is currently closed for renovations but will re-open soon. Check their website for availability.

Dana Hotel & Spa
660 North State Street
Chicago, IL 60654
(312) 202-6000

Chicago Blackhawks

(Credit: Getty Images, By: Abelimages)

Chicago Blackhawks

Sound unromantic? Not true. A friend of mine had his very first date with his now main squeeze at a Chicago Blackhawks game. What happened was this; she met all of his friends for the very first time at the place to be before a Blackhawks game – WestEnd. While he and his friends were all going to the game and she was just tagging along for drinks, his boss surprised him with one extra ticket. Six were in the suite and only two were in the 100 level, so guess which ones they got? He was teased the whole time with text messages from the guys overlooking the couple, but hey, it was worth it. She couldn’t keep the smile off her face the whole night.

1326 W Madison St
Chicago, IL 60607-1932
(312) 981-7100

United Center
1901 West Madison Street
Chicago, IL 60612
(312) 455-4500

Chocolate Class at Chocolate Academy

All women love chocolate, so my friend Lauren’s favorite date was a Chocolate 101 class at the Chocolate Academy. Just don’t do what they did and meet for coffee beforehand. Apparently, you are only supposed to drink water at room temperature or they will call you out for having a mug in hand. Strike one. Anyway, they learned all about how chocolate is made from start to finish, and then tasted about 20 different kinds of chocolate. Of course, Lauren was called on to tell the whole class what “notes” were detected, so she took a wild guess and said, “Earthy.” Her date was so impressed, so at the end of the date, she had to confess. Oh well, she felt smart while it lasted.

600 West Chicago Avenue
Chicago, IL 60610
(312) 496-7424

Alycia Nicole

Alycia Nicole

Alycia Nicole
is a concierge in the heart of downtown Chicago and loves being happily ever after.

Have a romantic story that you experienced in Chicago? Tell us about it in the comments section below.