Chicagoland Holiday Activities

Downtown - Christkindlmarket (18Nov-

The iconic German-inspired holiday market dominates Daley Plaza downtown with traditional handmade gifts, foods and drinks from Germany and other European countries. And with your Ride in Bliss charter you and your family or guests can be dropped off curbside to get the most enjoyment before fingers and toes inevitably start to chill and your driver picks you up again curbside and whisks you home or on to your next frosty adventure. Don’t forget to eat some piping hot Bratwurst, enjoy a glass of infamous Gluhwein and take home that perfect blown glass ornament for your own family tree.

Downtown - Ice Skating at Millennium Park, McCormick Tribune plaza or Wrigley Field! (Nov 19-

A few minutes drive east from ChristKindlmarket is Millennium park where your driver can drop you off curbside so your family and friends can enjoy the picture postcard experience of ice skating outside under the stars under the watchful eye of giant skyscrapers with twinkling tree lights and seasonal music. Busiest times are 2-6pm and you can rent skates for $13-$15, or bring your own. But if that seems a little too crowded why not try ice skating alternatives at McCormick Tribune plaza or outside Wrigley field at Gallagher Way where decorations abound and there are lots of family friendly activities now expanded INTO the ball park!

Downtown - Magnificent Mile & Macy’s Department Store

Shopping and the Holidays are synonymous and so whether you are treating yourself to a little something or buying for friends and family, what better atmosphere than the iconic stores of Michigan Avenue? Dubbed the Magnificent Mile for good reason this tree lined boulevard of beautiful store fronts, street performers and Holiday cheer will inspire you. Gaze in wonder like so many generations have into the fantasy filled window displays of Macy’s department store on State Street.

Downtown - Navy Pier Winter Wonderland (Nov26-

Light sculptures and gardens, another skating rink! Holiday beer garden, kiddie train and more are part of Navy Pier indoor Winter Wonderland

North Suburbs - Lighstcape at Chicago Botanic Garden (11Nov-

These municipal gardens are a delight in any season with gardens inspired by countries from around the world. As a special treat for the Holidays new light installations and hidden music speakers delight eye and ear with Festive sights and sounds as you explore scenic trails.

South West - Tree lights at Morton Arboretum (Nov19-Jan7)

50 acres of the arboretum lit up in spectacular fashion with accompanying music. You will walk a one mile paved route amid interactive lighting effects that highlight the beauty of the trees in winter. Reservations and advanced ticket purchase advised, $16-$27 for guests. Visit

West Central - Sparkle Lights Festival in Rosemont (Nov16-

Impact Field will be transformed into 5 illuminated light villages, with a Holiday train for the kids and 3D features.

Far West - Balmoral Restaurant in Campton Hills (year round-

The Scottish do Christmas and New Year well. Treat yourself to an authentic Scottish food experience and sample some whiskeys in a themed restaurant, named for the famous castle in Scotland. Blantyre chicken, Scotch Eggs, Rosyth Haggis Drambuie, Young Bonnie Prince Charlie’s Beef Wellington, Ben Nevis Chili and Honey Grilled Salmon and Ye Royal Beef Marrow Bone to name a few. Adult Entrees $34-$55, Child plates $8-$18, Desserts $9-$18

Holiday Travel


Ready to charter your own vehicle?

To contact us and reserve your charter vehicle call (847) 845 1151 or make reservation online.

Build your own Adventure

Know of a Holiday event not listed here? Create your own unique experience by linking several Chicagoland events or destinations for your unique group and let us drive you there in safety and comfort so you can enjoy all of the food and drinking while we take care of the driving.

Free Car Seats

All Ride in Bliss vehicles can come fitted with free child car seats so you can leave yours in your own vehicle and save you the trouble of transferring them for this one trip. All seats are properly sanitized after every use for your families peace of mind.