Chicago to Milwaukee: How we decided to relocate our family

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We love Chicago

My husband and I were both born and raised in the Chicago area. We both found our way back and committed to staying after college. We loved living in Chicago: Always something going on. So many neighborhoods to explore. Friends and family nearby or happy to visit us. We knew we would never leave! After my daughter was born, we loved raising her as a “city kid.” Riding the El, exploring neighborhood parks, trying new foods at world-class restaurants… we were relishing our life and the experiences we were sharing with her!

Outgrowing our family home

But, through a series of events, my father-in-law joined our family. We decided that it would be best for everyone if he lived with us or very nearby. We explored senior apartments in our area, and learned of the 5+ year wait lists. There was no way we could all live together in our 2 bedroom condo so we put our condo on the market and started looking for multi-family housing.

Looking for a Chicago 2-flat

Although our condo sold quickly, our home search didn’t go quite as well. Most homes that would meet our needs were at the top of our price range. We were stretching our budget for homes that weren’t quite right– compromises included school districts we didn’t feel comfortable with, homes that needed significant repairs, or neighorhoods that didn’t have the conveniences (such as walkable grocery stores or “L” access) that we were used to. But we persisted.

The home search expands

The closing date for our condo came and went but we continued our search. We moved our things into storage and our family into my father-in-laws home in the suburbs. We briefly considered renovating that home to meet our needs or looking for something suitable nearby. But, my husband and I missed city living too much. We did not feel at home in sprawling suburbia. Realizing that we’d be making significant compromises to live in Chicago, we decided to expand our search. We set up online home searches in Cincinnati, Nashville, Indianapolis, Minneapolis and began road tripping to explore Midwestern cities. One afternoon I chatted with a friend who had moved to the Milwaukee area a few years prior and a light bulb went off. That evening, I proposed exploring Milwaukee to my husband.

Schools, neighborhoods, quality of life

We began exploring Milwaukee and found walkable, lovely neighborhoods where we could imagine spending time. We explored the schools and were excited about the options available to us. And, we looked at home prices and realized that we could find a home within our budget without the types of difficult compromises we’d encountered in Chicago – if we found a home that needed work, we could afford to update, homes in the school districts we liked were within our budget, while public transportation focused on buses rather than the “L” the city overall was much more compact making bike and car commuting much more palatable.

It seemed almost too good to be true but the more we looked the more sure we were that we had found our home. With each visit we were more sure that Milwaukee would meet the needs of all of our family members.

Making Milwaukee Home  

Before long, we found a home that met our needs perfectly. We moved the whole family in, my daughter started school, and we began exploring and acclimating to Milwaukee. After 1 year, I feel confident in saying that we made the right choice. We’ll always love Chicago, but Milwaukee is now our home.

Chicago to Milwaukee: How we decided to relocate our family