Is there any way to force Chrome to try HTTPS first before HTTP when I only type
stackoverflow.com in the address bar?
You could try this HTTPS Everywhere Chrome extension.
Force HTTPS in Chrome
Google is one of the more aggressive companies pushing to make this happen. Here are several ways you can force HTTPS in Chrome to ensure your browsing is as safe as possible.
Startup Chrome with HTTPS
Chrome support typing chrome://net-internals/ into your address bar, and then include HSTS menu item. HSTS is HTTPS Strict Transport Security: a way for sites to elect to always use HTTPS. HSTS is supported in Google Chrome, Using this setting you can now force HTTPS for any domain you want, and even “pin” that domain so that only a more trusted subset of CAs are permitted to identify that domain. The downside is that if you force a domain that does not have SSL at all you won’t be able to get to the site.
Force HTTPS with KB SSL Enforcer extension
This extension will force HTTPS in Chrome for websites that support, It is not completely secure against the infamous Firesheep, but it does minimize the risk greatly. Due to Chrome limitations KB SSL Enforcer redirects the page while it is loading. You get a quick flicker of the unencrypted page, but it redirects you as fast as possible.
HTTP extension to Force HTTPS in Chrome
Use HTTP will forces defined sites to use HTTPS instead of HTTP. It comes preloaded with two defined sites: Facebook and Twitter. Like the previous extension the initial request is sent to site not using HTTPS.