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One of the best ways that I have met new moms was through playgroups and storytimes. Our church hosts a playgroup during the colder months while our local library branch holds a storytime mostly year round (and score that both options are free!).
Otherwise I know there is something called the Neighborhood Parents Network that also hosts playgroups, etc though the membership costs money. And you can always just take your LO to a play space (like the Sod Room in South Loop) or any playground and potentially strike up a conversation there with someone. Sometimes the park district also has Mom-n-Tot, etc classes so that may be worth looking into as well. Hope that helps!