2026 Compare Cities Overview:
Middletown, NY vs Chicago, IL

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Highlights
Are people in Chicago older or younger than people in Middletown?
- The Median Age in Chicago is 2.7 years younger than in Middletown.

Are housing costs cheaper in Chicago or Middletown?
- Chicago housing costs are 13.5% less expensive than Middletown housing costs.

Which city has a longer commute, Chicago or Middletown?
- The average commute for residents of Chicago is 4.1 minutes longer than it is for residents of Middletown.

Things to do in Middletown?
Middletown is a city located in Orange County New York Its population was estimated at 28 800 as of 2019 It offers residents access to plenty of local amenities such as schools parks museums libraries recreational centers religious institutions sports clubs movie theatres galleries farmers markets entertainment venues restaurants etc

Things to do in Chicago?
Chicago, Illinois is an American icon. Located along the beautiful shores of Lake Michigan, it's a vibrant city with an energy like no other. It's renowned for its world-class museums and galleries, rich history and stunning architecture. With hundreds of parks and beaches to explore, amazing restaurants to sample, and a bustling nightlife scene - Chicago has something for everyone! It's the home of diverse cultures and international events, making it one of the most unique cities in the US.

 Middletown, NYChicago, ILUnited States
 Population  Unlock2,742,119329,725,481
 Median Income$59,755  Unlock$69,021
 Median Age  Unlock35.138.4
 Avg. Home Price$328,600  Unlock$338,100
 Unemployment Rate  Unlock9.0%6.0%
 Avg. Commute Time30.5  Unlock26.38
Reviews for Middletown    5 Reviews

I am a senior looking to move in a nice area in orange county. Thank you kindly for your help.   More

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Having lived in Middletown for the last 12 years, I have seen enormous changes. I can only imagine what natives have noted. Firstly, by Manhattan standards apartment  More

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Well first off let me say I like, but not love middletown. I am originally from the city. I have been here for one year and my mom has been here for a few. Im a young  More

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Reviews for Chicago    270 Reviews

I've lived in Chicago city and later moved to suburbs when family size increased. Absolutely love this city. This is the cleanest and most beautiful among the major  More

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Chicago is probably the best value in a major city that you can find and my personal favorite city. It will become increasingly important as climate change makes the  More

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I've live on north side and south side, UIC medical center. Don't move here go to the north side. No good amenities, if you get bored with one there is no other choices.  More

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