Traveling Inspired > family > Travel hacking our recent Chicago Trip (and welcome friends from Million Mile Secrets!)

Travel hacking our recent Chicago Trip (and welcome friends from Million Mile Secrets!)

My blog has been lucky enough to be featured on Million Mile Secrets!  It’s part of their interview series on Big Travel with Small Money. So I might have some new readers checking out the blog today! Woo Hoo!

So if you are new to the blog start here. I typically post 3 times a week. If you like what you see then follow me on Twitter (@trvlinginspird) or Instagram (@trvlinginspird) or on Facebook (Traveling Inspired). When I’m actively traveling I’ll update via Instagram and Twitter. When I’m home and can coordinate my thoughts, the trip posts go up on the blog and a few of my favorites are linked to the Facebook page. Points and miles trips and tricks can be found by clicking on the loyalty button on my home page.



Exited for new readers  and saving money today!!!


Speaking of…I wanted to give everyone a rundown on how we used points and miles on our recent Chicago trip with our oldest teenager, Junior. So here’s the breakdown:

Flights: We are lucky enough to have the Southwest Companion Pass. This enables me to fly free as long as I am with Hubby. This holds true even if he is traveling on points as well. Therefore, we only needed enough Southwest points for Hubby and Junior, while I used the Companion Pass. We flew into Chicago on a Sunday night and flew out on Thurdsay morning. Estimated Cash Price for 3 people: $1,100. Points used: 35,462 plus $33.60 in 9/11 security fees. Total Flight Savings: $1,066.40 or 97%



Southwest Companion Pass…enough said.


Hotel Room: Booking award nights with hotels is definitely easier with more advanced notice. However, Junior took his time deciding on Chicago as his trip location. We didn’t want to rent a car, so a location on the Magnificent Mile (or damn close) was important to us. My only choices due to award availability were the Courtyard Marriott Magnificent Mile or the Holiday Inn Express Magnificent Mile. Both seemed be asking for a lot of points for the award night due to the hotels being a high category redemption. But with Hubby traveling a lot on business, we are not lacking in Marriott points. It might not be the most cost effective redemption if you just look at points per dollar. However, based on location, 50 feet from Michigan Avenue and two doors down from Garrett’s Popcorn, we picked the Courtyard Marriott. Estimated Cash Price for 4 nights in a double queen: $1200. Points used: 140,000. Total Hotel Savings: $1200 or 100%.


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Hotel location 2 doors down…yes please!


Sightseeing: Typically I would only include money saving tips on activities in trip reports. For example, the morning segway tour was only $45, but the afternoon tour was $75. So get up out of bed and save some money. I’d also advise checking out travelzoo or groupon for your destination city. But this time we used the Chicago City Pass. We were planning on visiting 4 out of the 5 attractions offered with the City Pass so the numbers made sense. Not to mention that it gives you a fast pass at all the attractions and I’m all about avoiding waiting lines. Chicago City Pass Cash Price for 3 people: $288. Combined fast pass prices without the Chicago City Pass for 3 people: $492. Total Sightseeing Savings: $204 or 41%.

Transportation: We typically hate to rent a car in big cities. Between public transportation, taxis, and Uber, we tend to do okay. Don’t forget to factor in the hotel parking fees, as those can sometimes make or break that decision for you. Our hotel had a great doorman, and it seemed that there were always several taxis waiting at the door. We politely declined and used Uber every time. Our Uber to the airport for our departure included bottled water and a lollipop. Our driver said the lollipops were usually taken by kids and drunk college kids. Ha! However due to regulations and our late arrival Sunday night, we took a taxi from the airport straight to the hotel. It helped for comparison purposes. Taxi ride from Midway Airport to Courtyard Marriot (Sunday night): $35 tip included. Uber ride from Courtyard Marriott to Midway Airport (early Thursday morning): $20.36 tip included. One example of transportation savings: $14.64 or 42%.

That’s about all the comparisons I could do that were apples to apples. Our trips are rarely done completely using points and miles. It’s usually a combination of loyalty programs and cold hard cash. While utilizing a points earning credit card, of course. Not one part of this trip was sponsored by anyone. The links I’ve provided are not affiliated links, they are just there for your convenience. My Uber link is a referral link, but that’s the only one. If you use my link, we both get a free ride (up to $20). Then make your spouse get Uber on their phone from your referral and you’ll each get another free ride.

Dining out is always a big expense while traveling and I didn’t include it in my cost analysis here. But don’t forget you have to eat at home too. We tend to take protein bars on trips and skip out on breakfast at a restaurant unless it comes as a perk at our hotel. I’ve also used reward programs like Open Table when we eat out at places that require a reservation. Alll this talk about food is making me hungry! Join me next week when I review all the places we ate with our teenager in Chicago!

Oh! And if you’re new to Traveling Inspired…thanks for visiting, come back often, and don’t forget to follow me on your favorite social media platform!





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