2025 Compare Cities Overview:
Winnetka, IL vs Annapolis, MD

Change Cities
Highlights
Are people in Annapolis older or younger than people in Winnetka?
- The Median Age in Annapolis is 5.1 years younger than in Winnetka.

Are housing costs cheaper in Annapolis or Winnetka?
- Annapolis housing costs are 59.0% less expensive than Winnetka housing costs.

Which city has a longer commute, Annapolis or Winnetka?
- The average commute for residents of Annapolis is 10.6 minutes shorter than it is for residents of Winnetka.

Things to do in Winnetka?
Winnetka, Illinois is a vibrant village located in the northern suburbs of Chicago. The area offers plenty of activities for all kinds of interests, from shopping and dining to sports and recreation. Winnetka residents also have access to excellent educational opportunities, with pre-Kindergarten through college prep courses available at top schools. Nature lovers can explore the Lake Michigan shoreline or numerous parks and forest preserves nearby. Winnetka is perfect for those looking for an urban lifestyle that still retains its small-town charm!

Things to do in Annapolis?
Annapolis, Maryland is situated in Anne Arundel County giving visitors leisure areas such as Quiet Waters Park while also having restaurants like The Boatyard Bar & Grill plus entertainment opportunities at Annapolis Towne Centre.

 Winnetka, ILAnnapolis, MDUnited States
 Population  Unlock40,581329,725,481
 Median Income$250,001  Unlock$69,021
 Median Age  Unlock37.538.4
 Avg. Home Price$1,348,300  Unlock$338,100
 Unemployment Rate  Unlock5.4%6.0%
 Avg. Commute Time37  Unlock26.38
Reviews for Winnetka    2 Reviews

Having had children attend both public and private schools. I would say the private schools are better. While the public schools are fine, there isn't any way to measure  More

   |    Reply

This idyllic, leafy, close-in suburb north of Chicago comes straight out of a Frank Capra (or John Hughes - see Home Alone for a view of the housing stock and  More

   |    Reply

Start Your Review of Winnetka

Reviews for Annapolis    31 Reviews

Annapolis has extremely charming areas (mostly old Annapolis neighborhood's)-- Those very old area near the water have Amazing charm. You can start with downtown West  More

   |    Reply

Well, I really would give living in Annapolis 3.5 stars. I moved here by myself several years ago. One of the highs of this place is that there are a lot of terrific  More

   |    Reply

When we were trying to decide where in the USA to relocate to, Annapolis had enough interest that it made our list. Ultimately, we found a different city that offered  More

   |    Reply

Start Your Review of Annapolis


Premium Subscription
Includes Cost of Living compares for child care, utilities, transportation, health, taxes, housing for home owners vs renters, weather, insurance premiums and so much more.


The premier source for comprehensive city data for over 30 years.

© Best Places. All rights reserved.