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Wintertime Date Ideas for Chicagoans

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Dating in Chicago in the winter can require a little creativity. I have a handful of wintertime date ideas for Chicagoans that will make sure your weekends are filled with fun (and food). I created seven different date ideas that pair an activity with my favorite thing – food. I tried to pick accommodate a wide variety of interests, cuisines, and budgets so there would be something for everyone. Hopefully these suggestions make your winter a little bit better.

Ice Skating in Millenium Park (from above)

1. Ice Skating! Chicago has several ice skating rinks, so why not go skating, work up an appetite, and then grab some grub?

Parson’s Chicken & Fish installed a synthetic rink so you can skate if the weather is on the warmer side. Fuel up first with Parson’s brunch. You can’t beat their Chicken & Waffle which is served with a sunny side up egg, and then hit the rink. You can bring your own skates, but some are also available for rent. If you get cold, warm up by sipping glühwein by the fire pit.


You could visit the Ice Ribbon at Maggie Daley Park or the Millennium Park Rink, and then feast on burgers at the nearby Shake Shack. This ice rinks are free if you BYO Skates, which means that this is a date idea perfect for people on a budget. The Ice Ribbon is a favorite among locals since skating through its winding curves offers a little more excitement than skating around an oval rink. The Shake Shack on Michigan Avenue tends to be less crowded than the other location, but I promise that the Shack Burgers, Cheese Fries, and Milkshakes are just as amazing.

Or, visit the animals at the Lincoln Park Zoo, skate at the Farm at the Zoo, and walk over to the J Parker roof and take in the view while you sip on cocktails. The J Parker roof top is enclosed in glass, it’s basically like being in a snow globe with views of the city.

Art Institute Lions

2. Explore the Art Institute and admire the view of the bean, Millennium Park, and the lake from Cindy’s – it’s simply magical at night. The Art Institute boasts one of the country’s largest collections of Impressionist works, plus a big Van Gogh exhibition exploring his bedroom paintings opens to the public on February 14th, making this a fun date option for Valentine’s Day!

AMC Auditorium

3. Dinner at a movie at Latinicity and AMC at Block 37. Latinicity is one of my favorite places to go on a date because you don’t have to exactly agree on what you want to eat. The food hall has over 90 menu items! I love their tacos and tortas, but they have sushi, stir fry, burgers, and more. After dinner, head upstairs to the new AMC. This isn’t your typical movie theater – the chairs are giant recliners that go so far back you can almost lay down, you can reserve your exact seat in advance, and they have a full menu and you just hit a button to get a server’s attention. Did I mention they have a full bar? And, you might want to save room of the s’mores milkshake.


4. Cheer for the Bulls or Blackhawks, and dine on Big Star Tacos or Leghorn fried chicken. I just went to my first ever NHL game at the United Center and I couldn’t get over how much team spirit Chicago has for the Blackhawks. The other thing that impressed me was the food. Good luck deciding between tacos from Big Star and Leghorn’s fried chicken, and don’t forget to wear red, otherwise you might stick out a little.

RPM Italian

5. When Chicago gets especially grey and gloomy, cheer yourself up with dinner and a show. This winter you can choose between Beautiful – the Carole King Musical, Matilda (an adaptation of the Roald Dahl book, If/Then, Cabaret, 42nd Street, and more. For dinner before the show, head to RPM Italian, one of my favorite special occasion restaurants – and definitely try the fried artichokes. The restaurant is just a short distance from the theaters, and they have some of the best pastas in Chicago, or if pasta isn’t your thing head to RPM Steak down the block instead.


6. Sometimes it is just too cold to go outside in Chicago. Fortunately, there are many food delivery options in the city, so when the sub-zero temperatures hit you can order in and throw on a movie. I have a few movie and food combinations for you to try. Order the cheeseburger and buffalo chicken tacos from Velvet Taco and watch Chef.

Or, if you are wine lovers, grab a bottle and watch Uncorked. The Esquire channel show follows a group of Sommeliers as they prepare to take the grueling Master Sommelier Exam. Don’t have cable? Watch Somm on Netflix instead.


7. If you want something to do this Sunday – go to Donut Fest at Chop Shop in Wicker Park, it’s an activity and a meal all in one.

This post was sponsored by RentPath, all opinions expressed are my own.

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