KNOWLEDGE CENTER · SEARCH AND FIT

Does a Car Fit Your Streeterville Routine?

By Joe Ridler, COO, Highland Real Estate Partners · Updated September 18, 2026

Decide by counting the trips and tasks that genuinely need a car, then confirm where you would keep it at home. A car may support a weekly cargo routine, an irregular destination, or a schedule that makes alternatives difficult. It may be unnecessary if most trips have workable non-car options and parking questions remain unresolved. The right answer depends on your calendar, not on a neighborhood label.

List the week you actually drive

For two ordinary weeks, record every trip you would make and mark its purpose:

Then label each trip must drive, could use another mode, or not yet tested. “I like having a car” is a valid preference, but keep it separate from a trip that truly requires one. If you drive mainly for convenience, compare the convenience with the time, attention, and recurring cost of keeping the vehicle.

Separate the car decision from the parking decision

Even if a car fits your routine, the apartment must fit the car. For Sienna, confirmed property information identifies paid parking in the attached Moment-owned, SP+-managed garage with direct indoor access, EV charging, and nearby metered street parking. That tells you which questions to ask; it does not answer current availability, price, charger compatibility or cost, clearance, assigned status, guest use, accessible parking, or waitlist handling.

Use the verified SP+ parking destination for current parking information, and keep price questions within the existing parking cost guide. Ask leasing which details apply to the specific residence and your vehicle before treating a space as part of your plan. Do not assume that nearby metered parking is a reliable overnight, guest, or resident solution.

Covered building entrance marked 423 East Ohio Street, viewed from the sidewalk.

Street rules are a separate source of uncertainty. The City of Chicago’s residential parking permit page explains the city’s residential parking permit zones and application information. Check the current signs and official rules for the exact block; do not infer eligibility or availability from the fact that a street has meters.

Score the routine, not the image of the routine

Try a simple weekly comparison:

QuestionHow many trips truly require it?

Keep a car in the plan
Record the recurring destinations
Use a non-car or occasional-car plan
Record the trips that remain workable

QuestionWhat do you carry?

Keep a car in the plan
Note the weight, size, and frequency
Use a non-car or occasional-car plan
Note delivery, transit, walking, or rental alternatives

QuestionWhat happens at home?

Keep a car in the plan
Confirm a parking path and current terms
Use a non-car or occasional-car plan
Confirm how occasional driving would work

QuestionWhat is the disruption cost?

Keep a car in the plan
Include moving, parking, and maintenance tasks
Use a non-car or occasional-car plan
Include waiting, transfers, or planning effort

QuestionWhat is still unknown?

Keep a car in the plan
Ask before signing
Use a non-car or occasional-car plan
Ask before abandoning the option

This is not a financial calculation unless you add your real figures. It is a way to expose the tradeoff. A car that is used once a month should be evaluated differently from one that carries equipment every day.

Test one representative day

Choose a day that includes the most demanding realistic task: a large grocery run, an appointment outside your usual route, or a trip with passengers. Plan it from the exact Sienna address using map and directions, and compare it with the non-car option. If the non-car plan fails because of a specific need, write that need down; it is more useful than a general feeling that the car is “easier.”

Before a tour, bring your vehicle’s dimensions and a list of questions. A tour or leasing conversation can resolve building-specific points, but only current written information should close a decision. If the car remains a conditional choice, write the condition: “I will keep it if the current space, vehicle fit, and terms are confirmed.”