Chicago In A Weekend

Several years ago, I won a trip to Los Angeles to see Taylor Swift in concert. I took my daughter. I have felt that I owed a trip to my son. (I’m one of those moms that tries really hard to make both my kids even!) So as his 16th birthday approached – I learned that I had achieved Companion status on Southwest Airlines. So I invited him to pick a destination and we would go there for his birthday. (I work with HelmsBriscoe – so I believed that I had hotel taken care of).

He decided that he wanted to go to Chicago. He also said he didn’t want to go unless his sister could go with. So, I booked my flight. I got his for free (companion) and then used some points for her flight. We were on our own Southwest Vacation!

Our agenda:

Saturday: Arrival at Midway at approx 9:50. Get picked up by my friend, Jennifer (who works for Starwood). She took us to The Gwen where we would be treated to an amazing suite and adjoining room. Thanks to the Chicago CVB (Choose Chicago) we were treated to tickets to the famous Field Museum. So the kids and I set out to walk across the park(s) to the museum seeing “The Bean” (officially called Cloud Gate) along the way. We also made sure to stop by a hot dog cart and get a real Chicago Dog. We messed around in the museum and then walked “home” to The Gwen. We did go out in the rain/snow again and got dinner at Gino’s East. Gino’s took a really long time. Despite being warned that it would take a while – we stayed. I felt satisfied that I had made sure that my kids got the quintissential Chicago food (Hot Dog and Pizza).

Sunday: Sunday I let the kids sleep in a bit. Then we headed out to the Willis Tower. I asked the kids if they would like to get an Uber or if we wanted to walk. They said walk. While it was only a 1.5 mile walk. It sure seemed longer in the Chicago cold. The Willis Tower had a thing called The SkyDeck on the 103rd floor. Where you can literally step out on a glass box (jutting outside of the building) and be above the city. We were glad we went that day as it was much clearer than it had been the previous day. Then we went to the John Hancock Building off Michigan Avenue to Tilt! and 360 Chicago. Once again, we were treated to amazing views – and literally tilted out over the city. For lunch, we headed to Harry Caray’s 7th Inning Stretch. But I think more than the food – or even who Harry was my son really liked the interactive Chicago Sports Museum (the interactive exhibits were really fun) – and admission is free with a certain purchase amount at the restaurant.

We headed back to the hotel then grabbed an Uber to the Colorado Avalanche v. Chicago Blackhawks game at the United Center. The atmosphere in the center is amazing! And Chicago really does love their Blackhawks. We had great seats and enjoyed the game (even though we – the Avalanche – lost). We were a little worried being the only people in Avalanche gear that we would be heckled – but the guys who sat next to us said, “no, not in Chicago – we are a sports town and just really like a great competition.” They were right!


Monday morning: Sadly, we had to fly back to reality. Although I thought I was a bit funny – when my daughter noticed on the flight tracker that it said we had 3 hours left in the flight, despite us being about an hour into a two and a half hour flight. I said very calmly, maybe we got on the wrong plane and we’re not headed back to Denver. She kept looking out the window very nervously until touchdown at DIA. #HomeSweetHome.

I need to send out a special thank you to Starwood Hotels (Jennifer and Haley) – our hotel host; Choose Chicago (Dawn) – for tickets to Field Museum, Sky Deck, 360 Chicago, Tilt and BLACKHAWKS (Dawn at Chicago and Steve at Blackhawks); and of course Southwest Airlines for my companion pass and easy to redeem points.

We had a great time in Chicago and may have even inspired a future Chicago resident in my son.

Where would you take a Southwest Airlines weekend get away? What would you do when you are there? Do you look at the Southwest site to get ideas? (There are lots of great ideas/sales right now)

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