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The best (mostly free) ice rinks in Chicago — and places to eat nearby

Learn some of Aida Conroy's favorite spots for fall & winter in Chicago in this guest post from the November 2022 issue

Having lived in places with and without seasons, I think there's something special about the way they mark the passage of time. A lot of people associate Chicago with the cold, but I associate it with variety, because we experience this city differently at various times of the year. So many amazing things happen here during the winter, because when the city is blanketed with snow, we must specifically and intentionally find ways to stay connected. Cultural institutions are great gathering places, but as Aida Conroy points out below, there are also a lot of free things to do outdoors during the winter. Last time we caught up with Aida, we found ourselves in the transition between summer and fall. We visited the Logan Square farmers market, where we picked up some juicy tomatoes — “last of the season” — and biked to Comeciro Popular in Little Village. We even passed a park in full bloom. Now we find ourselves in an unseasonably warm transition from fall to winter, and we thought we’d check back in with Aida to learn some of her favorite picks for a cozy winter day.

— Abby Pucker

Hi, I'm Aida!

Photo courtesy of Jairo Granados-Cardenas

As a kid, one of my favorite winter activities was ice-skating. I rediscovered Chicago’s free rinks during the winter of 2020 when nearly everything else was closed. My new-at-the-time partner and I were hunting for outdoor activities to break up the monotony of Zoom meetings and cooking at home. Date night meant going to each of the city’s free outdoor rinks, then grabbing takeout at a local(ish) restaurant. Often, it was the highlight of my week: checking out a new part of the city, lacing up for $7, learning to skate backwards. During a time when social gathering was rare, I loved seeing people of all ages fumble around the rinks.

Here are my favorite ice rinks — all but one free — with a few places to eat nearby:

Warren Park Ice Rink, 6601 N. Western

  • Picking one spot on Devon Ave. for food is an impossible task, but I love Sabri Nihari for sit-down and Ghareeb Nawaz for takeout.
  • Wolfy’s for one of the best Chicago dogs in the city.

Wentworth Ice Rink, 5625 S. Mobile

Mt. Greenwood Ice Rink 3721 W. 111th St

  • Fill up with brunch at Bacon and Jam and then have a midday skate.

Midway Plaisance Ice Rink, 1130 Midway Plaisance North

McKinley Ice Rink 2210 W. Pershing Rd.

  • Don’t miss out on exploring the actual park :)
  • I always stop into La Placita (a supermarket with a counter-service restaurant) on 35th not because it is my favorite restaurant in McKinley Park but because I ate there all the time as a first-year teacher working a few blocks away.
  • Marz Brewing is just down 35th and has food on weekends.

Maggie Daley Skating Ribbon 337 E. Randolph St.

  • You have to reserve spots for this one and pay to enter, but you’ll be spoiled by its ice skating ribbon (NOT rink) and incredible view of the skyline.
  • Cindy’s to warm up with cocktails, followed by Avec for small plates and wine.

Photo courtesy of Jairo Granados-Cardenas

Photo courtesy of Jairo Granados-Cardenas