CHICAGO -- The snow was falling sideways outside, blown by a bone-chilling, 40-mph Chicago wind, but that didn’t stop the 8,000 amped-up fans who filled the Allstate Arena Saturday (March 9) for Kenny Chesney’s “No Shoes, No Shirt, No Problems” tour.

More than a month into his first tour as a headliner, Chesney acts like he’s comfortable at the top of the bill. Silhouetted against an opaque screen at the back of the stage, the Tennessee native let the suspense build for a few bars before emerging to the thunderous applause and shrieks that would continue throughout the night.

“Last year with Tim [McGraw], the crowds were incredible, and this year they’ve just kinda gone up a couple of notches,” Chesney told CMT.com backstage. “It means a lot when you know they’ve paid to come see you, and your name is on the ticket.”

He learned a thing or two about headlining his own tour by opening shows for top draws like George Strait and his buddy, McGraw, Chesney said.

“We’ve toured with a lot of people, some of them treated us great, and some of them didn’t treat us so well,” he said. “George and Tim were great to me, so I wanted to treat [my opening acts] the way I wanted to be treated back then. Touring at that kind of level for the past three or four years, we got to see what it really takes and what you have to do to make a tour work -- and it is work.”

Another thing he learned from McGraw was to hit ‘em early and hit ‘em hard. Opening the nearly two-hour set with his latest sing-along hit, “Young,” Chesney fired off up-tempo favorites “Don’t Happen Twice,” “She’s Got It All” and “Fall in Love” in rapid succession, with very little talk between tunes. That set the pace for the night –- the fans rarely settled into their seats.

To maintain the frenzied pitch, Chesney reduced the hit ballads “Me and You,” “You Had Me From Hello” and “That’s Why I’m Here” to an abbreviated medley –- the only disappointing moment of the show.

He used the extra time for covers of Conway Twitty’s “Lay You Down” and rockers such as ZZ Top’s “Tush” and John Mellencamp’s “Jack and Diane.” Although he pulled them off, it would have been better to hear Chesney sing his own hits in full, especially the powerful “That’s Why I’m Here.”

Opening acts Carolyn Dawn Johnson, Phil Vassar and Sara Evans held their own and received enthusiastic receptions during their short sets. Johnson, who kicked things off with a 20-minute performance, has brought her own band on the road for the first time. Vassar ran onto the stage, spinning atop his piano and turning the hall into a huge sing-along on tunes including “Six Pack Summer” and “Just Another Day in Paradise.” Evans opened her set with “I Keep Looking,” the latest release from the platinum-selling Born to Fly. Her 2½ -year-old son, Avery, watched from the side of the stage, jamming out as his mom worked.

“He really doesn’t know anything else,” Evans told CMT.com. “Avery thinks every kid’s mom rides a tour bus and sings every night.”

The four acts on the bill have ties to each other. Evans and Johnson got acquainted last summer on Reba McEntire’s “Girls Night Out Tour,” and old friends Evans and Chesney worked some dates together with Vassar late last year. Johnson worked as a waitress at Vassar’s bar in Nashville when both were trying to land a record deal. The “six degrees of Kenny Chesney” has made for genuine camaraderie on the tour. The artists play basketball on warm days and hang in Chesney’s “positive vibe room” after the show. (The “positive vibe room” is a dressing room at the venue transformed by wall tapestries, lava lamps, incense and good music where all the acts, their bands and even a few lucky fans can relax before moving on to the next stop).

“Carolyn, Phil and Sara bring more to the show than just their hit records,” Chesney explained. “They bring a good attitude and that’s why it’s so much fun out here.”

No Shoes, No Shirt, No Problems is also the name of Chesney’s new album, due April 23. The title reflects his love of the islands, where Chesney says he can “flush out his mind” and get back to focusing on music. With the lost-youth anthem “Young” as the first release, the singer admits that the new album is a bit reflective -- both of good times and bad.

“Maybe it’s just the mood I’m in,” Chesney said. “I would say there are probably six songs that have that kind of theme. I didn’t realize it until it was all done, mixed and mastered and we had the album sequenced and I was sitting listening to it one night, and it hit me that a lot of the songs are looking back.”

The CMT-sponsored “No Shoes, No Shirt, No Problems” tour continues through August. Chesney will tape a CMT concert special in Daytona Beach, Fla., Tuesday (March 12). It airs in April. He’ll make an appearance on CMT’s Top Twenty Countdown on Friday (March 15), and he’ll share his favorite videos in an upcoming special, Stranded: Desert Island Videos.

Complete tour schedule