My daughter’s school marching band has been invited (accepted?) to play in the Thanksgiving Day Parade in Chicago this year. They are driving up during the week and returning back immediately after the parade.
Of course the travel hacker in me doesn’t want to bother DRIVING from Cincinnati to Chicago – that’s what I got all these points for! I am not allowed to fly her to Chicago – the package for the school says that they all have to go together on the bus. But once the parade is over, they are released to parents and then we’re free to do whatever we want.
Travel Hacking the school trip – hotels
First off, I immediately booked 2 nights at the Sheraton Grand Chicago, which is the hotel where everyone is staying at and is within a mile of the parade route.
One interesting thing I noticed is that when I search Hotels.com for my dates, the Sheraton Grand Chicago can be had for $160 / night (after taxes). There are also many other hotels nearby that are pretty cheap as well. Perhaps this is the opposite of Super Bowl hotel deals, where CASH is much better than points. So I’m wondering if I should use Arrival miles for that and save my 24,000 SPG points for another time.
Travel hacking the trip – flights
Then it was time to look for flights. Now that Southwest flies out of Cincinnati (with direct flights to Chicago Midway), that seemed like the obvious move. Now that Southwest has opened up their schedule through November, I took advantage of the recent Southwest fare sale and booked tickets.
Since there is an awesome Southwest cancellation policy, I knew I wouldn’t be out anything if I needed to cancel or change. The flight to Chicago was easy – there were a variety of flights there that got me to Chicago in time (I’ll certainly beat the bus there! :-D)
But the way back was trickier. Southwest has 2 afternoon flights
In an ideal world, I’d prefer the 1:15 flight, as that would get me back home perhaps even in time for Thanksgiving Dinner with (the rest of) my family! But I just wasn’t sure I could make it through the parade madness and back to Midway in time. So I booked the 3:50 p.m. flight (with points, of course)
Trying to book 2 Southwest flights at the same time
But last night I had the brainstorm that I should be able to book 2 Southwest flights now, and then just cancel the one I’m not going to use on Thursday itself. Since Southwest has an awesome cancellation policy, it’s super easy to cancel a Southwest flight.
I saw this thread on Flyertalk and it looked like this was pretty doable / prevalent for awhile, and then Southwest had started cracking down on it. One nice thing that I have here is that the 2 flights won’t be in the air at the same time.
Ever had experience trying to book 2 Southwest flights at the same time? Leave your experiences in the comments. Or, failing that, if you’ve got experience with the Chicago Thanksgiving Day parade, will I make the 1:15 pm flight?
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Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
They’ll definitely cancel the later flight you book. I even tried getting around this when booking from different airports in the same area but it was a no-go. In my case I was trying to book a day-trip to Disneyland and wasn’t sure if we’d be exhausted by 5pm or if we’d want to stay and watch the fireworks. I originally booked a 5pm SNA-SMF, and then booked a 10pm LAX-SMF. By the next morning I had a cancellation email for the LAX-SMF flight.
They will cancel one of them- and there is no telling which one.
i’d keep the 1550 one. 1755 landing is still plenty of time home for a family dinner.
If only the CVG airport wasn’t in Kentucky and my in-laws didn’t live in the far northern suburbs…. 🙂
Use a full first name for one flight and a shortened version for the other flight. Do not use the same credit card. Do not use your frequent flyer number on both. You can always add the FF # later or even at the gate. If one of your credit cards was at a different address that would help. Or use a “Jr” on one reservation. My husband and son have this problem all the time…. Same names, addresses, and my husbands credit cards…… Different People….
Or you could just try to do what’s right instead of trying to scam their system. It’s one reason every carrier overbooks.
I’ve found that if you have 2 flights booked the same day, SW randomly cancelled one of the 2. Two flights for the same person on back to back days has never been an issue for me but same day has!