No products in the cart.
I’ve talked about how to do this before but this time, I’m totally going to break it down for you. People always ask how I travel with the whole family. This is everything I used to travel to Chicago – airfare and hotel. Besides my industry knowledge and credentials which really only work for 1 discount that is usually not much better than the best rate available, my main travel hacks include points and timing.
Just a Reminder…
You’ll find a lot of links to various resources on this site, some of these links are affiliate links that pay me a commission at no extra cost to you. If you make a purchase through these companies, this supports the photos and tips that are provided to inspire you in your own travels.
When I get an idea that I want to go somewhere, there are 2 resources that I check first. Sometimes, I get the idea from an email since my inbox fills up daily with travel deals. The lowest prices for airfare are usually found on Spirit, Frontier, Sunwing, and Allegiant Air. For various reasons, most people have strong feelings about some of these brands but if lowest price is your main concern then those are the ones that consistently serve up flight deals.
Don’t be dissuaded though, if you play your cards right, you can find the others at similar prices sometimes. The main complaint with the bargain flights is seat space, as they are a little smaller than some other carriers. I don’t snub them, especially on a short flight under 3 hours because the deals are sometimes worth it.Buy or gift Southwest Rapid Rewards Points
I showed you before how to use google to find hotels and the explore page for finding discounted flights. If you know where you want to go and when just head straight to https://www.google.com/travel/flights
Once you pull up flights, pay attention to the important things:
- Bags included?
- Time of day?
If you’re looking for an even cheaper price, head over to https://www.momondo.com/
You can search similarly to google flights and both will point out mix and match deals which might give you a $15 flight on Frontier and a $49 return flight on Southwest which was definitely worth it in my opinion. What’s great about this option? I can pack a medium bag inside a large bag for the flight going and pay for 1 bag. Then, I get to bring back 2 bags for free! Yes, I actually did it, it was stress free return packing and I will do it again.
So, for $64 roundtrip, you can see how affordable it might be to take the whole family.
- If you book a bargain carrier, they often offer a special which includes a carry-on, a checked bag, & seat assignment. You’re not saving if you add that because you will have to pay for it for each person. You’re better off booking 1-2 tickets separately and adding that package on then. We can usually get away with a backpack for each person and 1 – 2 checked bags. It makes life easier although you will have to live with only 1 or 2 pairs of shoes so choose wisely. For instance, a checked bag is $39 during booking. The special was $45. At check-in, adding a checked bag was $49! Just book someone separately and get the special.
- How do I ensure we all sit together? It’s a gamble but I haven’t lost yet. Always check-in at the 24 hour check-in time. Set an alarm to remember to do it for your return flight.
- If you don’t have a scale, get one. The last thing you want to do is go rummaging through your belongings in front of everyone because your bag is 2 pounds too heavy. We throw it in the carry-on so we can weigh our bags before we head to our return flight.
TSA Pre-check is a beautiful thing. $85 for 5 years of skip-the-line expedited security screening. We walked right through because no one was in the Pre-check line. CLEAR is even better with a completely touchless experience and if you have American Express, you may even be eligible for a $100 credit for CLEAR. It’s almost time for us to renew ours and believe me, I must have it. No shoes off, no taking out your computer. Best of all, kids under 12 automatically go through with you, no need to purchase it for them also. If you travel internationally, then you may want to look into Global Entry instead for $100. See all trusted traveler programs at Homeland Security.
8 Ways to get a Free Hotel Night
Most people agree that the ultimate travel perk is a free hotel night or “comp” (complimentary) room. How can you get a comp though?
- Complaining about something so horrendous that the hotel gives it to you. (Don’t just do this frivolously but if you have a real gripe that is truly egregious, then sure.)
- Take advantage of a free night promotion.
- Be a travel industry insider and participate in discounted/almost free promotions or sell enough to earn free nights.
- Be a travel blogger or influencer with a huge following and maybe certain hotels will work with you.
- Watch hotel rates and track to take advantage of best rate guarantees, file a claim and hope it gets approved.
- Get a credit card affiliated with a hotel chain that earns free nights/points.
- Join a hotel loyalty program, earn points by traveling and directing any other loyalty programs to that one in order to get enough points for a free night.
- My way – use a combination of loyalty programs and branded credit cards for maximum savings.
My Way to Free Hotel Stays
How did I stay at Londonhouse Chicago for 5 days with 2 rooms for free? The third room was a travel agent rate which I lucked out on, finding one that good is rare. So, let’s focus on the freebies. I used these 5 programs:
- Hilton Honors Loyalty Program
- Hilton Honors American Express Credit Card
- Hilton Family Pooling
- Hilton Points Bonus Promotion
- American Express Green Card Points Transfer
Breaking it Down
My husband is Diamond in the loyalty program and I am Gold. His is from traveling, mine is from paying bills. We earn points on the Hilton cards by paying monthly bills, grocery shopping, and eating out. It’s all money we’re spending anyway, this way we actually get something extra from it. We were just short of the amount needed for both rooms. But, I made a huge mistake.
- I booked the first room at 180,000 points for the 5 day stay. How? Each night might have a different amount, the lowest was 45,000 points and remember 5 nights booked on points comes with 1 night free. After our stay, he was credited a 10,000 point bonus plus an extra 1,000 point bonus bringing the total down to 169,000 points.
- He still had points left over which he transferred to me through the Family Pooling.
- We also transferred a few points from American Express which transfers at a 2:1 rate, plus there was a 40% bonus at the time too! 1000 points becomes 2800! These points transfer almost instantly.
- Here’s the mistake – I was waiting for the points to show, they took 24 hours and I forgot to book it. By the time I went back, 2 days later, the cost was now 247,000 points. I wanted to cry.
- I now had to buy points or pay $670! I got lucky again because there was a special going on for a matching points bonus! But I screwed up again and bought more than I needed due to a miscalculation. For $400 I bought the 40,000 points with an extra 40,000 points bonus and wound up with an extra 10,000 points. Oh well, I’ll spend it and this is still cheaper than the best nightly rate.
- If I had not made mistake #1, it would’ve been totally free. Always book it when you see it and know it’s a deal. Prices tend to go up usually instead of down. I watched for the next 2 weeks and the prices never got even close to what they were when I booked the first 2 rooms. (Besides, there are Best Rate Guarantees that can help you out if you see the price lower after you’ve booked.)
Flights = $64 * 7 = $448
Missing Hotel points = $400
Total = $848
(Not counting the 3rd room because 7 people could stay in 2 rooms.)
And guess what, I earned over 25,000 points on the travel agent rate room so I’m this much closer to my next free stay. I didn’t get any free upgrades but I kind of felt like I had already won. Besides, I never complain about an almost free stay, unless it’s horrendous.