Holiday Shopping in Chicago

  • Date

    December 3, 2020 | Thu – 1 Day

  • Location

    Chicago, Illinois


Chicago is a shopper’s paradise, no matter what time of the year. But the Windy City pulls out all the stops for the Christmas season as the city glitters with holiday decorations and tempting goodies. And holiday shopping in Chicago is easy when you leave the hassle of driving and parking to Ambassadair. Chat with your travel companions, watch a movie, read a book, plan your shopping route or just sit back and relax while we navigate the route. Then, spend the day enjoying the city’s holiday decorations, restaurants, shops and museums.

Arrive mid-morning at a drop off point near Water Tower Place. Begin your shopping day along North Michigan Avenue armed with shopping maps and discount coupons. Featuring four shopping centers, State Street and the Magnificent Mile are favorite destinations for those wanting to shop the large retailers, department stores and luxury labels such as Burberry, Louis Vuitton and Chanel.

For those who want another kind of holiday shopping experience, check out the Christkindlmarket at Daley Plaza. Modeled on the Nuremburg, Germany Christmas market, this free open-air Christmas festival features international vendors offering handcrafted gifts such as nutcrackers, cuckoo clocks, ornaments, toys, jewelry and clothes. German schnitzel, sausages, sauerkraut, pastries and drinks (including the traditional German holiday market hot spiced wine, gluhwein) will surely put you into the holiday spirit!

At the end of the day, return to Water Tower Place with all your packages and board the motorcoach for the relaxing ride back to Indianapolis.


  • Hassle-free transportation to downtown Chicago
  • Drop off/pick up near Water Tower Place
  • Shopping maps
  • Discount offers and savings coupons


  • Roundtrip motorcoach transportation from Indianapolis
  • Escorted
  • Driver gratuity


Trip is also offered on December 1 and 5


  • Complete Package
  • $99

* Subject to change due to fuel surcharge

Final Payment: Full payment due at time of booking

Cancellation Fee Per Person: Booking-41 days: $25; 40-0 Days: No Refund

Trip Insurance: Optional Cancellation Waiver per person: $25. To purchase, call your Ambassadair Travel Counselor.

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