Skylar Diggins in a black Chicago Sky uniform pointing
May 27, 2026; Chicago, Illinois, USA; Chicago Sky guard Skylar Diggins (4) reacts against the Toronto Tempo during the first half at Wintrust Arena. Mandatory Credit: Kamil Krzaczynski-Imagn Images

CHICAGO โ€” Early in the Chicago Skyโ€™s season, Jacy Sheldon sported light-blue nails, matching her new teamโ€™s colors. Getting her nails done before the team headed out on a road trip was tough, as she had barely been in Chicago for a month when she had to find a spot for a fresh set.

โ€œHonestly, itโ€™s hard!โ€ Sheldon said to IX Sports. โ€œThe girls help. I’m lucky enough to know some people from Chicago, so figuring out where everyone goes, getting some recommendations, and it’s kind of a trial and error process.โ€

For jobs outside of professional sports, relocation can take months. WNBA players donโ€™t have that kind of luxury, and it can make the every day work of getting to know a new home difficult.

The shortened free agency period this year meant players had a quick turnaround between signing and reporting in Chicago for media obligations and the start of training camp. Then, the Sky started the season on a four-game, 10-day road trip.

Players didnโ€™t have the time to run errands familiar to anyone who has relocated for a job. For a mom like Skylar Diggins, her first concern was how to make sure her two children were quickly situated.

โ€œIt’s not just a one-time thing,โ€ Diggins said. โ€œWe play in the spring and summers. My kids are homeschooled, and so it’s setting up all the resources for them, their activities. They travel on the road with us, so just trying to like cherry pick activities for them to do when we get there, and things like that. It’s more so just set it up for my family to run efficiently. You rely on the local resources, be it a team or former players and friends that you met that have been through organizations.โ€

The Skyโ€™s front office also wants to make the transition seamless so their players can focus on basketball, and enjoy their lives in Chicago. They have help ready from when players first get to town.

โ€œWith things that we know are immediate needs: dog walkers, house cleaners, dry cleaners, and then restaurants that would deliver to their apartment. We took those, and we put that on the fridge [of the team-supplied apartments],โ€ said Ann Crosby, the vice-president of basketball operations and one of the teamโ€™s longest-tenured employees.

Beyond the more urgent needs, the Sky staff create both a written manual and an app giving A-to-Z recommendations from longtime Chicago residents. The team moved its housing from the north suburbs to downtown Chicago this year, so they needed to update recommendations.

โ€œWe have a lot of people who work for us that live in the city, so we just all collaborated,โ€ Crosby said. โ€œI like to ask a lot of people a lot of different questions, and get everybody’s feedback, just so that you know we have a variety, whether it’s like this manicure place does dip, this place does not, this place doesn’t do feet, or this place is really good at feet! We just literally like we just asked, and then I Yelp, TikTok, Instagram, Google it all together.โ€

Gabriela Jaquez, the Skyโ€™s first-round draft pick and the youngest person on the team, turned to social media for ideas of which restaurants to check out.

โ€œThe new thing with the Gen Zers is using TikTok as a search engine,โ€ Jaquez said. โ€œIโ€™ve looked up places to see in Chicago on TikTok. I’ve gotten great recommendations, and I can go where TikTok says. I’ve also had teammates or people that I meet recommend things, which has been great.โ€

Both Jaquez and Diggins โ€” and Digginsโ€™ kids โ€” have enjoyed exploring what Chicago has to offer, particularly in the summer.

โ€œI’m so lucky to live in a beautiful city like Chicago. I mean, [Lake Michigan] is beautiful. I can’t get over it,โ€ Jaquez said. โ€œI just went on a walk on the lake yesterday, and I was just like, this is crazy, it looks like an ocean, and so having a big body of water is comforting. I got to go to a farmer’s market that was super cool, and I think it’s just super cool just to see the community all outside and just enjoying the sun.โ€

Diggins said her kids are busier than she is in taking in all Chicago has to offer.

โ€œThe thing about it is in Chicago, it’s not hard to find something new, especially around this time. It’s probably the most entertaining city,โ€ she said. โ€œThere’s nothing like summertime Chicago, so be it swim lessons or gymnastics, from the museums to the Shedd Aquarium to the Color Factory Museum, my kids are out and about. It’s fun being in a city that has so much to do. It keeps them busy, and I love that, because then they take naps and go to bed early.โ€


Rep The IX Sports at your next game!

Shop the logo collection or special “Womenโ€™s Sports are Front Page News” collection now on Shopify.


Leave a comment

Your email address will not be published. Required fields are marked *