Jim Dries of Sequim, Washington, has been a tour guide on Sports Travel and Tours’ Windy City Plus trip for several years. If you ask him, Chicago is one of the best cities to visit in the United States.
In terms of its baseball merits, Chicago is one of the few cities—along with New York and Los Angeles—that still has two major league baseball teams. While on the Windy City Plus trip, travelers are able to visit both Wrigley Field, home of the Cubs, and U.S. Cellular Field, home of the White Sox.

Wrigley Field
Jim stresses, though, that there is much more to see in the Windy City than ballgames. Travelers will tour the city as a whole, including Wrigleyville, the unique neighborhood surrounding Wrigley Field, and they’ll have the option to visit other attractions as well.
“They can take advantage of whatever they choose to do,” Jim says. “There are great museums, great theaters, great restaurants and sports bars, and wonderful boat tours on the Chicago River. The Chicago boat tours are some of the best I’ve ever been on.”
In addition to the overall city tour, travelers will get an insider look at Wrigley Field from perspectives like the press box, clubhouses, dugouts and possibly the field itself.
The Windy City Plus trip, which is scheduled for Friday, Aug. 7 to Wednesday, Aug. 12, will feature four games at four different ballparks. Although the focus is on Chicago, travelers will also watch games at Miller Park in Milwaukee and Busch Stadium in St. Louis.

Busch Stadium
This year, Jim won’t be able to lead the Windy City Plus trip. Instead, he will be a tour guide for Sports Travel and Tours’ Central Express trip, which has stops in Chicago, St. Louis, Milwaukee, Minneapolis and Kansas City.
Jim enjoys that Sports Travel and Tours plans out most aspects of its trips for the travelers, while also leaving them with free time to explore on their own. For example, depending on what time they choose to arrive at the Palmer House in Chicago, the hotel of choice for the Windy City trip, travelers have free time prior to the trip’s reception on Aug. 7.
“Even though it’s been modernized, it’s still a fantastic, classic hotel with great history and old portraits of entertainers who have performed there,” Jim says, noting visitors should explore the hotel itself.
There is additional leisure time scheduled for the following day, Aug. 8, in the morning and evening. Jim recommends trip participants visit Buddy Guy’s Legends, a house of blues that is just a couple of blocks from the Palmer House.
During last year’s trip, Jim remembers taking some travelers to lunch at Manny’s Coffee Shop & Deli. Some of the group’s members were Chicago natives who had moved to San Francisco. They remembered Manny’s from their childhood and, back in their hometown, they were showing their new San Franciscan friends around the city and enjoying the night life. Jim fondly dubbed the little group “The San Francisco Seven.”
“That was a great, fun group,” Jim says. “That’s what’s great about Sports Travel and Tours’ baseball trips. All the travelers have an interest in baseball, but each person has some other hidden dimension, like The San Francisco Seven. They were a bunch of fun-loving guys having a great time on the Windy City Plus trip.”
Learn more or register for Windy City Plus.

Tour Host Jim Dries and family