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'Wildcard' incentive trip to Chicago

Have you ever considered choosing a ‘wildcard’ destination for an incentive trip? Project Manager Amy-Jo Brown shares how a quirky destination like Chicago can be the ultimate trip for your delegates.


Chicago is a destination that not many clients consider as a first option as they don’t often understand the appeal it has once you get there, but it is an unforgettable experience.

For an incentive there are great centrally located luxury hotels to choose from and you can easily fill the days with energetic activities, sporting events, boat cruises, art, film location or architectural tours or simply free time shopping at leisure. 

Like a mini New York, Chicago is designed on a grid system making it easy to move from place to place and it feels safe wandering around and soaking up the café culture, or drinking and dining at the many restaurants and bars, where you can also experience the great American hospitality.

It is one of those destinations that you do fall in love with because of the different elements – tree lined sidewalks, fascinating architecture, beaches on Lake Michigan and spacious parks - all adding to the appeal, especially when the sun is shining.

Talking from experience

Last year, we used Chicago as part of a twin centre incentive. Guests arrived at O'Hare International Airport) and stayed two nights at the luxury Waldorf Astoria hotel on the first and final night of the trip.

The Waldorf Astoria Chicago is a fantastic five star hotel. The hotel is in a great location, is very elegant, has a stunning interior and is beautifully furnished. From my experience, on both occasions, the staff offered the best service, especially the concierge, all our guests felt like royalty.

The following day, guests were then taken to a five star Brush Creek Ranch in Wyoming for three nights. Before heading back home, we went back to Chicago, giving guests’ time of leisure to explore the city.

Lots to see and do

Chicago has so many leisure opportunities to offer. Everywhere you go there is something different giving those on an incentive plenty to do and see. I personally would love to go there again and would feel confident taking a group on an incentive again, as feedback from a prior incentive was very positive. 

We offered delegates the option to go out on an architectural boat tour of the city, Chicago baseball Wrigley Field tour, or visit the shopping outlets. A lot of the guests wanted to explore the city by visiting the shops and taking the boat tour.

Final Thought

I would pitch Chicago as a ‘wildcard’ incentive destination throughout the summer months, whether it is a twin centre incentive trip or a four night luxury stay. As it has the second busiest airport in the world, getting to Chicago is usually quite easy and it is only one hour further by air from the UK than New York. 

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