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Chicagoland Club 50 — Ski & Sports was created especially to satisfy the preferences and lifestyles of adults over 50. We’ve developed our own friendly style of ski trips and year-round activities*.

Our 100+ members live in both Chicago and the suburbs. Instead of meeting in the same location each month, we gather at different Chicago area restaurants for dinner and good conversation – guests included. 

If you’ve no one to ski or bike or travel with, you’re sure to enjoy Club 50’s welcoming style. The membership is an interesting mix of singles and couples, all busy staying active, making new friends and sharing activities.

*Due to COVID-19, some of the events and activities of Chicagoland Club 50 have been cancelled or postponed.  Check the calendar to see what's currently going on with Club 50.


Western Ski Trips

Club 50 travels to American and Canadian resorts such as Snowmass, Big Sky, Park City and Lake Louise. Whether you cruise greens and blues or explore expert terrain, there will be a place for you. The group likes to get an early start and at day’s end the group relaxes together at its nightly pre-dinner wine and cheese gatherings.


We choose destinations that offer skiing for a wide range of abilities and select lodgings that are close to the slopes.  This year Club 50's trip to Park City, UT has been cancelled due to COVID–19.  The Club still hopes to join CMSC at Mammoth Mountain, CA.

Midwest Ski Trips

This year we have trips planned to Crystal Mountain in Michigan and to Chestnut Mountain in Illinois. Due to COVID–19, please check with the trip leader to learn the latest.

Flash Ski Trips 

Good snow conditions in Wisconsin allow for last minute, day-long ski excursions. If you’d like to check us out on one of these trips, contact to get on our flash email list and to spend a day skiing with us.


Monthly Dinner Meetings

One Sunday each month, Club 50 gathers for dinner and conversation. Members plan and host dinners at their favorite restaurants around the Chicagoland area. Guests are welcome to attend. 



Bowlers gather once a month at Pinstripes in South Barrington where we enjoy an afternoon of bowling and lunch. All abilities are welcome. We cheer for everybody!


Baseball Games
While the group is committed to participating in sports, we also enjoy baseball games, picnics and outdoor concerts.

During the sailing season in Chicago Captain David hosts groups on his sailboat, Phriendship II, out of Waukegan Harbor. 


Other Club Activities



Cross Country Skiing


And whatever our members think of next!
To find out what events are coming up, check out our calendar.


As an all-volunteer organization we rely on members for leadership. There are many opportunities to participate including:

  • Sponsoring a monthly dinner
  • Recommending and coordinating an activity
  • Leading a ski trip
  • Serving as an advisor or a member of the board


To get on our Events email list, contact Come to a dinner or an event and check us out! You may participate in two events, other than ski trips, without joining. 

Use the attached membership application to join Club 50.