How difficult is it to get Uber/Lyft or a taxi with a booster seat in Chicago?
thank you.

You can try it out yourself on the uber/lyft app - select an example pick up and drop off location and you'll see what's available. A quick check from ORD to MDW and I see an UberX, but no Lyft car seat rides available at this moment. A taxi queue at the airport would would give you the chance to ask multiple drivers. Calling the dispatch phone # for a taxi company would let you talk to a real person and explain you need a booster seat. You could look up taxi dispatch phone #s online and give them a call to now....

Thank you