
WELCOME TO CHICAGO
"WINDY CITY"
Get ready for an unforgettable adventure on our bus tour from Winnipeg to Chicago! Travel in comfort as we take you across the prairies and into the heart of the Windy City. Enjoy scenic views along the way while we handle all the driving—so you can sit back, relax, and enjoy the journey.
Once in Chicago, explore iconic landmarks like Millennium Park, the Magnificent Mile, and the Navy Pier. Indulge in world-class shopping, sample famous deep-dish pizza, or take in the stunning architecture along the Chicago River. The tour is designed for maximum fun and minimal stress, making it perfect for singles, families, or groups of friends.
Choose Group Pricing
4
Quad Occupancy
(PER ROOM)
June 18 - 22, 2026
(5 Days / 4 Nights)
Winnipeg, MB to Chicago, IL
Package Includes
Bus Transportation
On-Board Entertainment
Hotel Accommodations
Daily Breakfast
All Excursions
Pick-up / Drop-Off
Adult - $1223.43 PP+GST
(DEADLINE: ) MAY 1, 2026
3
Triple Occupancy
(PER ROOM)
June 18 - 22, 2026
(5 Days / 4 Nights)
Winnipeg, MB to Chicago, IL
Package Includes
Bus Transportation
On-Board Entertainment
Hotel Accommodations
Daily Breakfast
All Excursions
Pick-up / Drop-Off
Adult - $1368.43 PP+GST
(DEADLINE: ) MAY 1, 2026
2
Double Occupancy
(PER ROOM)
June 18 - 22, 2026
(5 Days / 4 Nights)
Winnipeg, MB to Chicago, IL
Package Includes
Bus Transportation
On-Board Entertainment
Hotel Accommodations
Daily Breakfast
All Excursions
Pick-up / Drop-Off
King Bed - $1583.43 PP+GST
2 Queen Bed - $1617.43 PP+GST
(DEADLINE: ) MAY 1, 2026
1
Single Occupancy
(PER ROOM)
June 18 - 22, 2026
(5 Days / 4 Nights)
Winnipeg, MB to Chicago, IL
Package Includes
Bus Transportation
On-Board Entertainment
Hotel Accommodations
Daily Breakfast
All Excursions
Pick-up / Drop-Off
King Bed - $2447.43 PP+GST
2 Queen Bed - $2484.43 PP+GST
(DEADLINE: ) MAY 1, 2026
K
Kids Rate
(Price will vary per age)
June 18 - 22, 2026
(5 Days / 4 Nights)
Winnipeg, MB to Chicago, IL
Package Includes
Bus Transportation
On-Board Entertainment
Hotel Accommodations
Daily Breakfast
All Excursions
Pick-up / Drop-Off
Starting - $717.93 PP+GST
(DEADLINE: ) MAY 1, 2026
HAMPTON INN & SUITES
Enjoy your stay with our partners
In the Illinois Medical District, just a 10-minute drive from downtown Chicago. Located across the street from Rush University and a mile from the United Center. The WNDR Museum is under two miles away. Enjoy the indoor pool, 24-hour fitness center, and a free hot breakfast during your stay.



















