Let me plan your date


Amber Stoutenborough

Millennium Park’s ice skating rink is open from November 19th to March 6th for the public.

Ice Skating + fine dining

Whether it’s for Valentine’s Day or just a cute date with a friend, let me plan your date in the city that will be magical enough to keep them impressed for the rest of the year. Since most of the dates have been close to Lincoln Park, I wanted to venture out to the Loop and visit what Chicago is most known for during the cold winter seasons.

McCormick Tribune Plaza

While normally considered an activity meant for Christmas time, ice skating is open until March 6 at the McCormick Tribune tower and the perfect opportunity to show off your skills to your date or hold them close to you if you need a little extra help gliding across the ice. The rink itself is free but to rent skates they cost $13 weekdays and $15 during weekends. The hours are 9:30 a.m. to 9 p.m., so go in the later afternoon to watch the sunset while you flirt your way through the cold. Once you get too cold or grow hungry, head on over across the street to the second part of the date.

Chicago Athletic Association

Just across the street is one of Chicago’s most prominent hotels and one of my favorite spots to impress people. Start off after your skate date and order some drinks while you take in the Victorian style of the drawing room, filled with comfy couches and walls of stained glass and books. This spot is the perfect chance to cuddle up by the fire and enjoy some one-on-one. After the first drink, head upstairs to the top floor, which features a restaurant called Cindy’s, where you can enjoy a nice dinner and a view of the city skyline and lake. Cindy’s is ready for the perfect romantic date for an inexpensive, fancy occasion and free view of our favorite city.