26023 Milwaukee Brewers vs. Chicago Cubs
There's something timeless about summer, baseball, and a ballpark filled with cheers, hot dogs, and friendly rivalry. Join Windstar Travel for a two-day getaway to Milwaukee to watch the Cubs take on the Brewers at beautiful American Family Field.
View Dates & BookJune 26-27, 2026
There is something timeless about summer, baseball, and a ballpark filled with cheers, hot dogs, and friendly rivalry. Join Windstar Travel for a two day getaway to Milwaukee to watch the Chicago Cubs take on the Milwaukee Brewers at beautiful American Family Field. Add in a comfortable overnight stay, plenty of laughs with fellow travelers, and a stop at one of the most delightfully quirky museums in the country, and you have the perfect recipe for a classic Midwest road trip.
Tour Includes:
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Deluxe Roundtrip Motorcoach Transportation
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On-Board Friendly Host
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1 Night Hotel Accommodations
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1 Meal
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Cubs vs. Brewers at American Family Field
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National Bobblehead Hall of Fame & Museum
Tour Pricing:
$525 pp Double | $625 Single
Non-Members Add $30
Day 1
Day 1 june 26: Road Trip to the Rivalry
Your baseball adventure begins with convenienTheret pickups throughout Southeast Iowa as we make our way north toward Wisconsin. Along the way, we will enjoy a rest and refresh stop in Davenport and a relaxed lunch break in Rochelle, Illinois, giving everyone time to stretch, grab a bite, and settle into vacation mode.
By mid afternoon we arrive at our hotel, the Hampton Inn & Suites Milwaukee West, located near State Fair Park. After a short rest, we board the motorcoach once again and head to the main event.
As the sun begins to dip and the stadium lights glow, we arrive at American Family Field. Feel the energy build as fans pour through the gates wearing their team colors. Then it is time for the words every baseball fan loves to hear…PLAY BALL!
Watch the Cubs and Brewers battle it out in this storied rivalry while you enjoy the atmosphere, the food, and the unforgettable experience of Major League Baseball in person. Following the game, we return to the hotel for a relaxing evening.
Day 2
Day 2 june 27: Bobbleheads & The Road Home
After breakfast at the hotel, we load up and head into downtown Milwaukee for a stop that is guaranteed to make you smile.
We visit the National Bobblehead Hall of Fame and Museum, home to a collection numbering in the tens of thousands. This lighthearted, nostalgic stop is packed with sports history, pop culture, and plenty of photo opportunities.
Following our visit, we begin our journey home with a lunch break in New Berlin and a rest stop in Davenport before returning to each drop off location by early evening.
Activity Level 2: RELAXED
Expectations: This tour requires light physical activity combined with shorter travel days. Tour members should expect intermittent walking, with occasional slight inclines and stair climbs, including boarding the motorcoach. Activities may include an occasional city or nature walking tour, stopping along the way. Guests should be able to climb a set of stairs, walk up or down slight slopes and navigate some uneven terrain or cobblestone. Please be aware that on tours with flights and cruises you will be required to handle your own luggage and walk longer distances in airports and cruise terminals. In addition, you may need to handle your own luggage at hotels where luggage handling is not available.
Appropriate for: Travelers who are somewhat physically fit and comfortable with longer days of touring (both walking tours and coach time).
Deposit & Final Payment: A $75 deposit per person is required within one week of reservation. Must be paid in full by May 12, 2026.
No refunds will be issued after 5:00pm on May 12, 2026.
Payment Methods:
Cash, checks, credit/debit cards and money orders are accepted. Make checks payable to Windstar and mail to 3211 Division Street, Burlington, IA 52601. There is a $30 fee for insufficient funds or returned checks. Credit/debit card payments (Visa, Mastercard and Discover) are subject to a 3% processing fee.
Travel Protection:
We recommend that you purchase a travel protection plan to help protect you and your travel investment against the unexpected. Please call to inquire about travel protection options.
A final departure letter packet will be sent approximately 10 to 14 days prior to the departure date. This will contain the scheduled departure times and locations, as well as other important information in regards to your upcoming tour. If the tour involves overnight accommodations, luggage tags will be provided as well.
Windstar Travel, parking lot owners and shopping center management assume and accept no responsibility for the safety of your vehicle or its contents at the place of departure. If you choose to park and leave your vehicle there, you do so willingly and at your own risk. If you choose to leave your vehicle, please park only in the areas designated in your final tour information packet. Vehicles not parked in the indicated areas may be subject to towing and all expenses incurred are the responsibility of the owner.
Below is a list of pick-up points available on this tour.
Below is a list of pick-up points available on this tour.
| Name | Address |
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| Burlington, IA | Lowe's 3435 E Agency St. |
| Davenport, IA | Comfort Inn & Suites, 8300 Northwest Blvd |
| Ft. Madison, IA | Lee County Historical Society 814 10th St. |
| Mediapolis, IA | Mepo Foods 111 N. Wapello Rd. |
| Muscatine, IA | Wal-Mart 3003 US-61 |
| Wapello, IA | Family Dollar | Dollar Tree 503 US 61 |
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