Chicago vs New York: Is Chicago a Steal? 1555 N. Dearborn Parkway in the Gold Coast

This corner 1-bedroom in the Constellation at 1555 N. Dearborn Parkway in the Gold Coast came on the market in April 2025.

Built in 1967, it has 90 units and valet on-site parking. It has door staff and an exercise room.

This unit has floor-to-ceiling windows with three exposures: north, east and south views.

There’s even a floor-to-ceiling window in the galley kitchen with white cabinets, gray quartz countertops, and “top of the line” stainless steel appliances, including a dishwasher.

There are cherry hardwood floors throughout and a foyer.

On the fourth floor, it has tree top views of Lincoln Park.

The unit has some of the features Chicago buyers look for including central air and valet parking on-site, but it doesn’t have in-unit washer/dryer. There’s a laundry room in the building.

The building is located on Lincoln Park, near the Chicago History Museum, North Street Beach and the shops and restaurants of Old Town and East Lincoln Park.

Listed at $275,000, that’s $24,000 higher than the 2018 sales price of $251,000.

Sophia Klopas and Jason Stratton at Jameson Sotheby’s have the listing. See the 21 pictures and the floor plan here.

Unit #4A: 1 bedroom, 1 bath, no square footage listed

  • Sold in April 2003 for $235,000
  • Sold in May 2006 for $252,000
  • Sold in May 2009 for $194,000 (was bank owned)
  • Sold in June 2018 for $251,000
  • Currently listed at $275,000
  • Assessments of $1064 a month (includes gas, doorman, cable, exercise room, exterior maintenance, scavenger, snow removal, Internet)
  • Taxes of $5551
  • Central Air
  • No in-unit washer/dryer but laundry room in the building
  • On-site valet parking available
  • Bedroom: 13×13
  • Living/dining combo: 21×16
  • Foyer: 6×13
  • Kitchen: 9×7

At the same time that Redfin showed me this unit in Chicago, it also gave me a 1-bedroom in New York City’s West Chelsea neighborhood at 420 W. 23rd.

This building was built in 1984 and is 12 stories with just 39 units. It has door staff and a common garden.

There’s no parking or exercise room.

This New York City unit is a 700 square foot unit, which also has a balcony. Subtract the balcony and it’s 654 square feet.

It also has a galley kitchen that the listing says is “recently refurbished” with stainless steel appliances including a dishwasher and a microwave range hood. It also has “ample” counter space.

There’s no window in the galley kitchen.

The listing says the bedroom could do a king bed.

The living room has reddish wood looking floors, but the listing doesn’t say if they are hardwoods.

It has some of the features a buyer might want including a 2 zone HVAC.

There’s no washer/dryer in the unit either, but it is not as common in NYC as in Chicago. There is a laundry room in the building (not all buildings have a laundry room so this is considered an amenity.)

The listing says it has views of London Terrace and historical Chelsea. From the balcony, you can even see a sliver of the river.

The building is near the shops and restaurants of Chelsea, public transportation and is just one block from High Line.

It was listed in 2022 for $1.1 million and then reduced but was withdrawn in 2023. It was listed for rent at $4600 a month in 2023.

But it has come back on the market in April 2025 for $999,000.

Is Chicago real estate a steal compared to other major cities like New York?

Laurie Lewis and Charlie Miller Miller at Corcoran Group have the listing. See the 7 pictures here. Sorry, no floor plan.

420 W. 23rd St Unit #9B: 1 bedroom, 1 bath, 700 square feet

  • No prior price on Zillow going back to 2014
  • Listed in October 2022 for $1.1 million
  • Reduced
  • Was listed for rent in February 2023 for $4600
  • Currently listed for $999,000
  • Assessments of $1077 a month (includes maintenance and door staff)
  • Taxes of $13,824
  • 2 zone HVAC
  • No in-unit washer/dryer but laundry room in the building
  • No parking
  • West Chelsea location
  • No room sizes listed
  • 1 Bedroom
  • Living room
  • Kitchen
  • Balcony

 

3 Responses to “Chicago vs New York: Is Chicago a Steal? 1555 N. Dearborn Parkway in the Gold Coast”

  1. It’s interesting to see what gets emphasis in NYC listings versus Chicago’s.

    In Chicago it is still parking, the flooring and the kitchen countertops.

    In NYC it is laundry in the building and whether or not you even HAVE kitchen countertops.

    Lol.

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  2. Also, the rent on the NYC unit doesn’t match the sales price. Maybe it hasn’t sold for 3 years because it doesn’t make any sense to buy it. Prices for 1-bedrooms have gotten too high, with 7% mortgage rates, to make it make sense even with $5,000 a month rental costs for 1-bedrooms.

    In Chicago, in some cases, it’s cheaper to buy than to rent but probably not in this unit given the $1000 HOA payment.

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  3. “probably not in this unit given the $1000 HOA payment”

    *definitely* not if $4600 is still the asking rent.

    Even using a 5 cap (too low), and rounding down both the HOA and taxes to $1k/month, the rent-indicated value is $624k.

    Use the 7 cap that rates indicate, and it’s $445k.

    Rent would need to be well over $6k to even get close to being “worth” the ask, based on rent.

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