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  • Location
    Chicago, IL
  • Date
    May 11-16, 2020
  • Price
    See Pricing
OverviewItineraryPricingDeparturesHotelBefore You Go




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8:00 am We depart from the Kingston Shrine Club (3260 Princess Street at Collins Bay Road) , travelling westward to our overnight accommodation in Jackson, Michigan at the Holiday Inn Express (517) 788-6400
  After your deluxe continental breakfast this morning, we depart for the Windy City! A stop will be made for lunch on our way.  Upon arriving in Chicago we’ll start with a guided city tour to see the best and most important sights in Chicago. Experience the city’s breathtaking skyline, architectural treasures, Magnificent Mile, theater and financial districts, and Millennium Park. This tour is a must for first-time visitors or anyone who would like a brief introduction to Chicago past and present. (Please note that our guide will try to cover as much as possible during the tour; however, due to traffic, parades, marathons, mayoral motorcades, and/or time constraint one or two items may be missed.)  Afterwards we’ll check into the Hampton Inn downtown, 1 block from the Chicago River and newly developed River Walk and a 10 minute walk to Navy Pier or Millenium Park and The Bean!  (312) 419-9014. A hot breakfast buffet is included every morning.  Your room includes a mini fridge and there is free tea and coffee in the lobby 24/7. Unpack, relax and freshen up before a lovely included welcome dinner.  After dinner, enjoy time on your own to wander the streets or enjoy a relaxing evening in our hotel. There is included high speed internet access in the hotel so you can keep in touch with friends and family.
  After breakfast, we will enjoy a visit to the Sears Sky Deck where you will experience the unbeatable views from one of the world’s tallest buildings! This has been featured on the History Channel’s Modern Marvel Presentation. From here our adventure continues as we depart for the corner of Millennium Park and Michigan South where we will tour Jewelry Row/Macy’s/State Street.  Lunch will be on your own.

Baseball Fans:

12:00 am: Transfer to Wrigley Field.

1:20 pm BATTER UP: Cubs vs Brewers

The motor coach will transfer those not attending the ball game back to the hotel so you can rest or explore more of the city on their own. The rest of the afternoon/evening is on your own to enjoy Millennium and Grant Park. In Grant Park, you can catch the spectacular show of Buckingham Fountain.  One of the largest fountains in the world, the Buckingham Fountain has an hourly 20 minute water display. The animation is best seen at dusk – after 8 pm – when it is accompanied with music and beautifully animated with a computerized choreography of color spotlights.

Tonight our entire group will enjoy a Chicago Themed dinner together!  Afterwards, we’ll make our way back to the hotel and you are at your leisure to enjoy the remainder of the evening as you please.

  Today, after a full American buffet breakfast, our day will begin with a wonderful treat – a Chicago Gangster tour!  The fascination with Chicago gangsters continues today despite the height of the gangster culture having taken place even before World War II. In this tour, Chicago’s Gangster past comes alive! Learn about Al Capone, John Dillinger, and other mob bosses, and see the scenes of their crimes. We’ll go to the John Hancock Skyscraper, Water Tower Place and Chicago’s Magnificent Mile to shop, have lunch and explore! This afternoon is free time to do as you please. The short walk to Navy Pier is the perfect way to spend a beautiful day in Chicago! This world famous area has something for everyone so enjoy!

Baseball Fans:

5:00 pm; Transfer to the stadium. Gates open at 5:40 pm

7:10 pm: Blue Jays vs Chicago White Sox * NOTE: It’s free t-shirt day today!

After this great game, we’ll transfer back to our hotel after which the evening is yours to enjoy on your own.

  With wonderful memories of Chicago, we begin our journey home and overnight at the Drury Inn, Troy, Michigan. (248) 528-3330. Upon arrival you’ll enjoy the included “Kick back” welcome of beverages from the bar and pub style food. The perfect way to wind up the day.
  After a deluxe continental breakfast, we will continue our travels home.  We will make a brief stop at the Duty Free before we cross back into Canada. We expect a mid afternoon arrival back home with plenty of fun and happy memories of our tour to the ‘Windy City’.
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  • 5 Nights accommodation as listed 
  • Round Trip luggage handling (ONE bag per person) 
  • 5 Breakfasts
  • 2 Dinners
  • Guided City Tour with a local guide
  • Visits to the Chicago Cultural Centre
  • The Magnificent Mile
  • Chicago Gangster Tour
  • Admission to the Sears Sky Deck
  • All taxes and gratuities except for your Tour Director & Driver

Baseball Package Add On: Cubs vs Brewers at Wrigley Field, Jays vs White Sox (Additional Fee)









Baseball Package: $200 CAD Incl. Hst

• A deposit of $100 is required at the time of booking

• The balance is due 60 days prior to departure
• Refunds are not available within 45 days of travel
• For the comfort of fellow travelers, kindly refrain from using scented products
• Must have valid passport to travel across the border
• Tipping for driver and tour director is voluntary
• Please note that cancellation and travel insurance is not covered in your package but is strongly recommended for out of province travel

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9:00 am Depart Belleville Maple Leaf Office at 81 Millennium Parkway (parking)
8:30 am Depart Napanee Flying J Northeast Corner of the Parking Lot
8:00 am Depart Kingston Shrine Club 3260 Princess Street (parking)
7:30 am Depart from Ganonoque Hwy 2 Carpool 
7:00 am Depart Brockville from Food Basics Jefferson Dr.
6:30 am Depart Kemptville Stinson Gas bar Hwy 42 
6:00 am Depart Ottawa: All Saints Lutheran Church 1061 Pinecrest Rd. (Parking) 
5:30 am Depart Ottawa: Robbie Italian Restaurant 1531 St. Laurent Blvd ( Parking)

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Holiday Inn ExpressSarnia Holiday Inn Entrance

All conveniently located near the newly renovated Holiday Inn Express and Suites of Jackson! We are happy to have you stay with us during your visit to the Jackson area. Several area golf courses are nearby, Grande Golf Club, Hickory Hills and Arbor Hills just to name a few. The area is home to many Historical Museums, Ella Sharp Museum, Cell Block 7 Prison Museum and the Coe House Museum are all just a short drive from the hotel. Jackson Crossing Mall and Westwood Mall are within 5 miles. We are just a short drive from these well-known Jackson restaurants; Klavon’s Pizzaria, Bella Knotte, AKA Sushi and Chillangos. Olive Garden, and Cracker Barrell Restaurant are all within walking distance. The area hosts many local wineries and brew pubs, we are located near Sandhill Crane Vineyards, Lone Oak Vineyard Estate, Grand River Marketplace.


The Hampton Inn Downtown Chicago

Popular attractions are under a mile away, including the theater district, Magnificent Mile, Millennium Park, and Navy Pier. A Ruth’s Chris Steak House is right in our hotel, and dozens of restaurants are in every direction. Take the Red Line nearby to Shedd Aquarium, the Field Museum, and McCormick Place. Enjoy our terrace and indoor pool. Hot breakfast and WiFi are on us.


Las Cruces Drury HotelDrury Inn, Troy Michigan 

The Drury Inn & Suites Detroit Troy is 20 miles north of Detroit off I-75: a convenient hotel close to the Canadian border and Lake St. Clair. Upscale shopping at Somerset Collection is two miles away. Guests enjoy Drury’s clean and comfortable rooms, waking up to a free hot breakfast and relaxing with free evening beverages at our 5:30 Kickback®.


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Cancellation & Medical Insurance is strongly recommended for overnight tours and out of country travel. Travel Insurance is available for purchase through Maple Leaf Tours.
  • Portage of 1 large suite case per person, you may also bring 1 carry-on per person
  • Please keep all medication with your person not in luggage
  • Cancellation and Medical insurance is not covered in your package but is strongly recommended for out of province travel
  •  Insurance is available through Maple Leaf, please call to inquire today!
  • There are regular stops made for comfort breaks
  • Tipping for tour director and driver is voluntary depending on quality of service
Tico Reg # 50023381

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