September 30–October 3, 2027
4 days / 3 nights
$1,199 CAD
Travel from Toronto & the GTA—or meet us directly at the hotel.
See Chicago. Bring Home the Stories.
Stand beneath remarkable skyscrapers, stroll along the lakefront and discover the character behind Chicago’s famous skyline. With guided sightseeing, three hotel nights and round-trip coach travel from Toronto arranged, there’s room to enjoy both the landmarks and your own discoveries. Come with a friend, a partner or on your own—we look forward to welcoming you aboard Chicago: Skylines & Stories.
Pickup Times & Joining Instructions
Join our coach at one of our convenient pickup locations across the GTA and along the tour route—or meet us directly at the hotel.
Travelling from elsewhere? Make your own way to Chicago and meet us at the hotel for the same three-night stay, daily breakfasts and guided experiences with the group. Airfare is not included.
Pickup Locations & Times
Mississauga | 6:30 AM
Location: Just south of Hwy 401 at Hurontario St (Exit 342)
Address: 25 Watline Ave, Mississauga, ON L4Z 1P3
Etobicoke | 6:50 AM
Location: In front of Tim Hortons
Address: 415 The Westway, Etobicoke, ON M9R 1H5
North York | 7:15 AM
Location: Passenger Pickup & Drop-Off Zone adjacent to York Mills Subway Station, south of the gas station
Address: 4015 Yonge St, North York, ON M2P 1N6
Scarborough | 7:35 AM
Location: Kennedy Commons — in front of Metro
Address: 20 William Kitchen Rd, Scarborough, ON M1P 5B7
Just off Hwy 401 at the Kennedy Rd exit.
Pickering | 8:00 AM
Location: SmartCentres Pickering — Home Depot Contractor Entrance
Address: 1105 Kingston Rd, Pickering, ON L1V 1B5
Cobourg | 9:00 AM
Location: Best Western Plus Cobourg Inn & Convention Centre
Address: 930 Burnham St, Cobourg, ON K9A 2X9
Colborne | 9:30 AM
Location: The Big Apple
Address: 262 Orchard Rd, Colborne, ON K0K 1S0
Brighton | 10:15 AM
Location: Brighton Car Park, 15336 Telephone Road, Brighton, ON K0K 1H0 Directions: Hwy 401 Exit 509 at County Road 30
Landmark: Directly across from McDonald’s and Shell
Parking: Availability and rules vary by pickup location. Guests leaving a vehicle do so at their own discretion. We recommend arranging a drop-off, using a rideshare service, or confirming parking directly with the property.
Timing Reminder for All Bus Tour Pickups
Please arrive at least 15 minutes early. Pickup times are estimates and may vary due to traffic, road conditions, or weather. Our vehicle departs promptly to keep the tour on schedule.
Before You Book
Deposit & Final Payment
A non-refundable deposit per person is required to secure your reservation. The remaining balance is due 45 days before departure. Please review the cancellation terms and consider travel insurance before booking.
Travel Insurance
Travel insurance is not included. We strongly recommend purchasing coverage for trip cancellation, delays, and medical emergencies.
Is This Tour Right for You?
Our tours are designed for independent, active travellers. Guests should be able to walk comfortably for 20–30 minutes at a time.
Not suitable for wheelchairs, walkers, scooters, or guests requiring continuous assistance.
What to Pack
Please bring:
* Government-issued photo ID
* Comfortable walking shoes
* Layered clothing
* Daily medications
* Small day bag, reusable water bottle, and weather-appropriate items
Luggage
We recommend one checked suitcase and one personal item per guest. Please label your suitcase with your name, phone number, and tour name.
A colourful ribbon or luggage tag is helpful for easy identification.
On the Coach
Our full-size coaches include an onboard washroom, with comfort stops approximately every 2–2.5 hours. Seats are assigned before departure.
You are welcome to bring snacks, drinks, books, headphones, and a travel pillow.
Timing & Etiquette
Please arrive at least 15 minutes before departure. Coaches depart on schedule and cannot wait for late arrivals.
Please respect quiet hours, use headphones for personal entertainment, and keep aisles clear.
Daily Schedule
Your Tour Manager will review the next day’s schedule each evening, including departure times, meeting points, and special instructions.
Optional activities, meals, or schedule updates will be clearly communicated in advance.
Stay Connected
Please keep your phone charged and check your email before departure for important reminders and final tour information.
Emergency contact details will be provided before your trip.
Guest Courtesy
We ask all guests to be respectful of fellow travellers, guides, drivers, hotel staff, and local communities.
Disruptive or abusive behaviour may result in removal from the tour without refund.
Our Goal
We want every guest to enjoy a smooth, comfortable, and memorable travel experience.
Frequently Asked Questions
Is this tour suitable for seniors?
Yes, for active seniors who can participate independently. This tour welcomes adults who are comfortable walking, navigating stairs and boarding the coach without assistance. Personal care, mobility and lifting assistance are not provided.
What is the activity level and how much walking is involved?
This tour has a
moderate activity level, with walking tours, photo stops and free time to explore. Guests should be comfortable walking for 20–30 minutes at a time and managing stairs and uneven surfaces. Comfortable, supportive walking shoes are recommended.
What is the typical group size?
Group size varies by departure. Travellers joining directly at the hotel participate in the same sightseeing program as those travelling with us from Toronto.
Which hotel will we stay at?
The tour includes
three nights at a Chicago-area hotel, with breakfast each morning. Accommodation is outside downtown Chicago, with coach transportation provided for scheduled sightseeing. Please refer to the accommodation details for this departure.
What happens if I need to cancel my booking?
Deposits are non-refundable. If you cancel at least 45 days before departure and have not paid your final balance, you may transfer your deposit once as a credit toward another tour within 12 months, subject to our booking terms. Once paid in full, bookings are 100% non-refundable. We strongly recommend travel insurance covering cancellation, interruption and emergency medical expenses.
What happens if CosmoVista Tours cancels the tour?
If we cancel your tour, you will receive a full refund of all tour payments made to CosmoVista Tours. We will notify you as early as possible.