TVH Traveler Trip: Sister Surprise Trip to Chicago - Using Miles & Points!


We love family vacations but we all know that planning them can be difficult when you're coming from different locations and can't decide where to go or what to do. This is exactly what our surprise trips are made for - and we really loved sending three lovely sisters on an amazing adventure to Chicago!

Chicago waterfront, navy pier

If you're reading our blog, you're probably already familiar with our surprise vacation packages, but did you know that we can also book a surprise trip using award miles and points? Yes! Our travelers used our trip planning service and working with their husbands, we were able to coordinate and book all three flights and a suite in downtown Chicago using award redemptions!

Over this past Labor Day weekend, we found directs flights for all three sisters on Southwest Airlines (one of our favorites for their generous baggage policies), and stayed 3 nights at the Renaissance Chicago Downtown Hotel, in a spacious "Riviere Suite" with a view of the Chicago River. With complimentary breakfast and club lounge access, this was Marriott points put to good use!

After landing and checking in, we almost always want to go get something to eat, so we made reservations for our traveling trio at The Gage, a classy restaurant just across the street from Millennium Park, where they could stop by after dinner to enjoy Chicago's annual Labor Day weekend Jazz Festival. 

The next day, Saturday, we recommended some artistic pursuits. Starting off the day, we suggested they head over to the Art Institute of Chicago to check out their newly opened Contemporary wing. The AIC contemporary collection is one of the most comprehensive in the world, and is housed in a beautiful new wing of the museum. One of the sisters had a special interest in architecture, and Chicago is famous for it's skyscrapers. One fantastic way to enjoy them, was to take an architecture cruise down the Chicago River with the Chicago Architecture Foundation. Not only is it a fun trip down the river, but you can take a load off your feet for a while and enjoy the day!

Chicago River Cruise

Sunday, we set up a fun day for our traveling sisters, starting off with brunch reservations at a cute cafe a few blocks from the hotel. Then, it was off to the northern end of town for a walking tour of the Lincoln Park neighborhood, themed around Chicago's history with prohibition-era gangsters and the Blues clubs they frequented. Lastly, they had to go get some deep-dish pizza. Chicagoians have passionate opinions on who has the best pizza, but Giordano's is a classic!

For their last day, we suggest some activities and let our travelers decide what to do with their free time. Would they rather shop along the Magnificent Mile, wander the waterfront and Navy Pier, or pursue whatever else had caught their imagination while out and about (we like seeing the view from the top of the John Hancock Center, ourselves)? They surprised us by deciding to stop at the University of Chicago to visit another iconic architectural landmark, Frank Lloyd Wright's Robie House. After that, it was back to the airport for their return flights home! 

If you'd like us to plan your next family get-together, start out by filling out our trip survey!