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The Hunt

With a Grandchild on the Way, Chicago Beckoned. What Could They Get for Less Than $400,000?

A couple of longtime Floridians searched the Windy City for a good location (preferably on Lake Michigan), ample bedrooms and minimal stairs. Here’s what they found.

Alison and Harold Issen with their 5-month-old granddaughter near their new apartment. The couple moved to the Chicago area from Orlando, Fla., hoping to find a place near Lake Michigan where they could entertain family.
Taylor Glascock for The New York Times

When it came time to leave Florida, Harold and Alison Issen put together a list of their preferred destinations. The couple, who grew up on Long Island but didn’t meet until they were living in the Sunshine State, had raised their family in Orlando. As the years went by and their son and daughter grew up, they felt they had outgrown Florida.

“More and more every year, in some ways,” Ms. Issen said.

Houston, Denver and especially Asheville, N.C, were high on their list. They took their first stab at buying in Asheville last year, but arrived a little too late, just as prices there were soaring. On their way back, they learned that their son and daughter-in-law, who live in Chicago, were expecting their first child.

“That just shot Chicago to the top of the list,” Ms. Issen said. “They’re renting, and we’re like, ‘OK, it’s a little risky, but they love it.’”

Mr. Issen, 65, works as a research psychologist for the Navy, and Ms. Issen, 66, is a semiretired mental-health professional. The two set a budget of $350,000, but raised it to $400,000 after their financial advisor emphasized the advantages of getting a mortgage rather than buying in cash.

[Did you recently buy a home? We want to hear from you. Email: thehunt@nytimes.com]

The couple hoped to find something on the north side of Chicago, on or near Lake Michigan, or just north in suburban Evanston. They made their first trip to the area last December, and then another in February.

“It was very intense, and our poor Realtor was fantastic,” Ms. Issen said. “She doesn’t like to show more than three or four homes a day because they all start to blend together, and we’re like, ‘We need to see eight to 10,’ and she did it.”

The ability to be hands-on grandparents wasn’t the only draw. The couple were fans of “The Bob Newhart Show,” the 1970s sitcom set in Chicago. “Newhart would always come home to this nice condo overlooking Lake Michigan,” Mr. Issen said.

In addition to being close to the lake, they wanted a place with at least two bedrooms. Ms. Issen was willing to consider a single-family house, but her husband didn’t want to do yardwork. He did, however, want a place to store his tubas. They also wanted to avoid climbing a lot of stairs, which narrowed their options.

As for the Newhart fantasy, the couple found that many lakeside apartments in their price range were very small and lacked closet space and parking. “So living in a glass-front condo on the lakefront wasn’t the highest priority after all,” Mr. Issen said.

But a few blocks from the water, they could find three- and four-bedroom apartments, their broker, Tedi Smola of @Properties, in Evanston, advised them.

Among their options:

No. 1

Needs Work in Evanston

Taylor Glascock for The New York Times

This three-bedroom, two-bathroom apartment was in an eight-story co-op building in downtown Evanston. It was about 1,800 square feet, with a foyer, sunny living space and en suite primary bedroom. There was a decorative fireplace, and the dining room had sliders to a small balcony, but the apartment needed updating. Laundry facilities were in the basement, and there was a private parking space in a covered garage. The asking price was $344,900, with a monthly fee of $1,855.

No. 2

Chicago Duplex With Exposed Brick

Taylor Glascock for The New York Times

This four-bedroom, three-bathroom duplex condominium was in the lakeside Rogers Park neighborhood of Chicago. It was 2,700 square feet, with a spacious eat-in kitchen, gas fireplace, in-unit laundry and a deck. Each level had two bedrooms and extra spaces for an office or sunroom. The three-story brick building was two blocks from a cemetery to the north, and one block from a rail yard to the west. The asking price was $392,000, with a monthly fee of $340 and about $6,500 in annual taxes.

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No. 3

Quirky Layout in Evanston

Taylor Glascock for The New York Times

This four-bedroom, two-bathroom apartment in a large Evanston co-op complex was originally the home of the building’s architect, and its quirky layout included angular rooms and pass-throughs. It was about 2,200 square feet and had been fully updated, with a wood-burning fireplace, built-in shelving and two balconies. The building offered laundry facilities in the basement, a waiting list for a parking space and a pretty communal garden. The asking price was $400,000, with monthly fees of $2,170.

Find out what happened next by answering these two questions:

Which Would You Choose?

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Needs Work in Evanston

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Chicago Duplex With Exposed Brick

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Quirky Layout in Evanston

Which Did They Buy?

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Needs Work in Evanston

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Chicago Duplex With Exposed Brick

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Quirky Layout in Evanston