Everyone Knows It's Windy

Okay, so the snow should finally be done now, and it’s time to add Chicago back in to your potential vacation sites. May is a particularly good time to go, because it’s still shoulder season, the weather is usually cool and energizing, and you can score a decent deal on some of the city’s most interesting hotels. Not to mention a great airfare.

I found a roundtrip fare there from New Orleans on United.com for $127 on the long weekend starting May 12 using the site’s flexible dates tool. And that’s a nonstop on an airline where you can still bring a carryon for free. Travelzoo.com has some great ideas for scoring reasonably priced rooms at some of the city’s coolest hotels. Look for “destinations” on the left-hand side of the home page. Among the myriad offerings by the tourism promotion folks in Chicago is the Chicago Greeter program—free tours of the city conducted by local volunteers.