When your friend says “hey, let’s go to Chicago to eat some deep dish pizza!” it’s hard to say no. Well, that happened to me and it started a plan for a quick weekend guy’s trip. We left Raleigh on the first flight Saturday morning and returned on the first flight back on Sunday night. All in all, it was a great, quick trip and we did some pretty cool things, but it was also exhausting.

Chicago is a quick and easy flight from Raleigh. At about 1.5 hours, it’s nice because you get there about 30 minutes after the time you left, including the time change. Alex has never had deep dish pizza and it was one of his bucket list things to do. He opened a Chase Sapphire Preferred a couple of years ago with the intention of using the points to go to Chicago (isn’t it amazing what points can do?!) and we finally settled on a weekend.

I have been to Chicago quite a bit. Having lived in Columbus, OH for about 4 years, Chicago was a quick flight or shortish drive, so my wife, Vicki, and I would take short weekend trips and I’d go for conferences. Chicago is one of my favorite cities and Alex had never been, so I was excited to show him around.


Chicago Millennium Park

Typical touristy visit to Millennium Park on a rainy day.


This trip was a super inexpensive trip. I have written about points and miles and the beauty of using them to save money on travel. With the points that Alex had from opening up the Chase Sapphire Preferred and some Southwest points that I had, we were able to get flights for $11.20 each in taxes. I had some extra Hyatt points in my account, so I used those to book our hotel. Hotel rates were absurd this weekend, so we saved about $550 for the one night!


Save money on hotels in Chicago

Standard rates for the night were $549. We paid $0 with points.


I actually came out with some more savings because of my Chase Sapphire Reserve. Each year you get a $300 travel credit that can be used on any travel expense. I was able to get a refund for the taxes on my flights, the cab to the airport, and my “L” ticket. All-in, the weekend for me was the cost of pizza and beer. Or about the same as what I would pay in Raleigh.


Save money in Chicago on travel purchases

Saving money on travel purchases with my Chase Sapphire Reserve travel credits.


Pizza was at the forefront of this trip. And a beef sandwich. I let Alex pretty much decide what we were doing since he has never been. We ate dinner at Giordano’s and lunch at Al’s Beef . Both were really good, although Giordano’s was a bit touristy. I really enjoy Gino’s East in River North more than Giordano’s – it’s more of a brewery-type of place. But you have to get a deep dish pizza when you’re in Chicago. Al’s Beef is another staple of Chicago dining. Head here if you’re looking for an inexpensive, hearty sandwich.


Deep dish pizza at Giordano's in Chicago

Deep dish pizza at Giordano’s


We spent most of the day in Wrigleyville in anticipation of going to the Cubs and Brewers game, but unfortunately, it was rained out. That’s alright because we were able to spend most of the afternoon walking around Wrigleyville and taking in the bar scene. When life gives you lemons, make lemonade, right?

The place we spent the most time was Sluggers. This is not your typical sports bar. Or is it? Maybe it’s how all sports bars should be? This place is huge. 2 stories of bars, arcades, more bars and batting cages. Yes, batting cages. One could argue this isn’t a good idea mixed with alcohol, but it was fun nonetheless. It was also a great place for families to hang out. Since the weather was so bad, it was nice to have a place where parents could grab a drink and kids could play games or take some bp.


Sluggers bar in Chicago

Sluggers is more than just a bar. Arcade games, batting cages, you name it.


This was my first trip away from H and Vicki, so it was a little stressful. We all did great, although I would say that Vicki had the more difficult assignment. I’m glad that we only did one night. It was exhausting waking up at 5am on Saturday and 5am on Sunday. It was also relaxing having a guy’s weekend, so I can’t complain. Another Traveling Dad, Jeff, just posted on planning a guy’s weekend trip and why it’s important to do so. I’m new to this whole parenting thing. But I’ve learned that it isn’t easy. I’m learning new things every day. There is a ton of research on how to raise kids, but they don’t come with manuals. It’s important to try and keep some sanity and getting away with your friends is a good way to do so. Also, I learned that my rain jacket is not water resistant. Tough thing to learn on a 50 degree day.