This Reader Redemption Story is from our friend and fellow teacher, Nicole. She and her husband visited Chicago during Christmastime to celebrate their wedding anniversary!

I have always wanted to visit a big city during the holidays. This December, my wish came true when my husband and I traveled to Chicago to celebrate our 15th anniversary. We picked the perfect time to visit. The streets and store windows were decked out with holiday decor, and the cloudy, crisp weather was the perfect backdrop for our tour of Chicago.

Flights / Transportation: We flew round trip from Kansas City (MCI) to Chicago Midway (MDW) using our Southwest Companion Pass and Southwest points. Our total cost for flights was just $22.40 in fees.

Once we arrived in Chicago, we used Lyft for easy transportation to and from the airport. With our Chase Sapphire Preferred card, we earned 5X points on all our rides. When we were in the city, we walked everywhere with ease.

Stay: While in Chicago, we stayed at Thompson Chicago. We wanted something a little more upscale since we were celebrating our anniversary, and this chic hotel with a midcentury modern feel did the trick. Our stay was made possible by using points we had earned using our Chase Freedom Flex card.

Fun: We loved the ease of walking everywhere! Our hotel was just blocks from Michigan Avenue so we could walk the Magnificent Mile. We stopped in many shops, admired the architecture, watched ice skating at Millenium Park, and popped into some fun pubs to warm up.

One of our highlights was taking a Lyft to Wrigleyville for Winterland at Gallagher Way. We could shop at Christkindl Market and walk onto Wrigley Field, which was transformed into a winter wonderland. A great experience for my husband, a lifelong Cubs fan.

Eat: One of the things we looked forward to most was deciding where to eat in Chicago. Wildberry Cafe was a favorite breakfast spot, with two locations for us to choose from. How can one stay in Chicago and not eat pizza? We opted to try Giordano’s at the Navy Pier, and it did not disappoint! 

Final Thoughts: Our trip to Chicago was everything we hoped it would be! We got to see so much at the pace we desired and loved the beautiful holiday decorations around the city. We enjoyed it so much we have already planned a return trip this summer and are bringing our children. 

We look forward to exploring more museums, parks, and restaurants with our family. A Cubs game is on the agenda as well as another pizza place! Thanks to Companion Passes and points, we can do and see so much more.

We truly appreciate you sharing your points and miles experiences, Nicole! It is so much fun and informative to hear about how other people travel with points and miles.

Cards that made this trip possible

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