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2026 Giants Midwest Swing

Giants Signature Vacation

Join us in Milwaukee and Chicago!

June 2-8, 2026

Milwaukee / June 2-5, 2026 / 3 Nights / 2 Games 

Chicago / June 5-8, 2026 / 3 Nights / 3 Games 

Giants Vacations Signature Vacation Includes:

  Round trip group airfare between San Francisco (SFO) and Chicago O’Hare. Guests must travel on the group flights.*

  Deluxe motor coach transportation to Milwaukee

Three nights deluxe accommodations in Milwaukee at The Trade, including a $75 per person hotel food and beverage credit

Welcome Dinner and Watch Party in Milwaukee

Tickets to two games against the Milwaukee Brewers at American Family Field

Exclusive brunch with Giants personnel

  Milwaukee City Tour

Farewell to Milwaukee Dinner

  Deluxe motor coach transportation for “the swing” to Chicago

Three nights luxury accommodations in Chicago at Hotel Zachary, including daily breakfast

Tickets to three games at historic Wrigley Field against the Chicago Cubs

 Architectural River Cruise

Tour of Historic Wrigley Field

Farewell Pizza & Beer Party

 Giants Vacations Road Trip Merchandise Item

All taxes and fees

  Deluxe motor coach transportation from Hotel Zachary to Chicago O’Hare

All package components and personnel are subject to change.

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Join Giants Vacations on a Midwest Swing to Milwaukee and Chicago!

Your Giants Vacation begins when the group will travel together from San Francisco to Chicago. Upon landing, we’ll travel by deluxe coach to Milwaukee for the first of three nights deluxe accommodations at The Trade, located in Deer District, Milwaukee’s newest neighborhood and premier sports and entertainment district. You’ll be just steps away from many restaurants, shops and activities. Lead off this exciting vacation by joining fellow Giants fans for a Welcome Dinner and Watch Party. While in Milwaukee, you attend an exclusive brunch with select Giants personnel, take in two games against the Brewers at American Family Field, explore Milwaukee on a city tour, and say so long to Milwaukee at a farewell dinner.

On Friday morning, June 5th, we’ll swing to Chicago by deluxe motor coach where you’ll check-in for three nights at Hotel Zachary, daily breakfast included. While in Chicago you’ll attend three games against the Chicago Cubs, tour historic Wrigley Field, relax onboard an Architectural River Cruise, and wrap up your amazing vacation with a farewell pizza and beer party.

This travel package also includes escorted transportation throughout, a Giants Vacations Road Trip merchandise item, and all taxes and fees. Make your plans today to join Giants Vacations on the Midwest Swing to Milwaukee and Chicago!


Independent Travel Expectations

Trip hosts are present to help coordinate the group experience. Guests must be able to: keep up with the group and follow the daily schedule as planned, carry and manage their own luggage, and navigate accommodations, venues, and activity locations independently.

Please note that our trip hosts are not able to provide support with wheelchairs or other personal mobility devices. If you require this level of assistance, we kindly ask that you travel with a companion who can support your needs.


*If you are not interested in the group air, please call us for more information.

Level Active

This trip is designed for travelers who are comfortable with full days of activity and a faster-paced itinerary. Activities may include extended walking tours, climbing stairs, navigating hilly or uneven terrain, and standing for long periods at events or attractions. Travelers should be prepared for days with few breaks, multiple hours of movement, and walking up to 3 miles over the course of a day.

Departures