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Chicago Marathon

How I Traveled Cheap to the Chicago Marathon

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The Chicago Marathon has been on my bucket list for quite some time! Every year, 45,000 runners take on the Chicago Marathon with the motivation to cross the 26.2-mile marker in the beautiful Grant Park and be awarded a finisher medal. Sitting here writing about this amazing experience does not do it justice. Chicago is a fantastic city that holds a really special place in my heart. This is the city that Lisa and I first visited together as a couple and holds the moment that I knew I’d someday ask her to marry me. In life, all we have are moments. It’s important to never forget the ones that have propelled us to where we are today. On October 13th, I’ll be proud to reflect on and create some new memories while I take a 26.2 Mile stroll through Chicago!

November 2015. Our first trip together 2 weeks after meeting each other!

Flights for FREE

Buffalo, NY to Chicago, IL is always Easy Peezy when it comes to free flights. My go-to method is Southwest which offers 13 routes daily to the windy city. Of course, I’m not into layovers unless there is a new airport lounge I’d like to check so I opted for one of the three direct flights between Buffalo and Chicago. Since the flight routes pretty much remain the same; I waited for Southwest to open up their new flight schedule and booked right away. 5,056 Southwest points which I transferred over from my Chase Sapphire Credit Card for the flight over!

And for the flights back I repeated the process above given that it’s the same 13 routes back from Chicago to Buffalo. Only 6,290 Southwest Points back!

For an additional $5.60 each way, I could add Lisa as my companion using the Southwest Companion Pass (BOGO FLIGHTS!) but sadly she cannot make it down for this marathon 🙁 

30,000
bonus points
PLUS Companion Pass® good though 2/28/24 after spending $4,000 on purchases in the first 3 months

$69 Annual Fee

30,000
bonus points
PLUS Companion Pass® good though 2/28/24 after spending $4,000 on purchases in the first 3 months

$69 Annual Fee

For the record, I love Southwest Airlines and Southwest Points! They are easy to earn via any of the 3 personal and 2 Business Southwest Credit Cards. In addition, Chase Ultimate Rewards points can be transferred to Southwest instantly at a 1:1 ratio. My favorite Chase Ultimate Rewards Credit Cards are the Chase Sapphire Preferred and the Chase Ink Business Preferred.

Hotel For FREE

It’s kind of an interesting and perhaps long story on how I ended up with two free hotel rooms for the Chicago Marathon which you can read at another time. For this post, I’ll stick with the hotel that I actually chose. The beautiful JW Marriott in the heart of downtown Chicago less than half a mile from the start and finish line. I originally booked this hotel for three nights using 35,000 Marriott Bonvoy points for each night. However, due to a change in my plans, I ended up only needing two nights. The big win here for me is that I was able to apply an annual free night certificate that I earned from one of my Marriott Credit Cards to one of the nights that I had already reserved. That left me needing to only use 35,000 points total for my two-night stay! 

75,000
Marriott Bonvoy Bonus Points
after spending $3,000 on eligible purchases within the first 3 months from account opening.

$125 annual fee. (Rates & Fees)

75,000
Marriott Bonvoy Bonus Points
after spending $3,000 on eligible purchases within the first 3 months from account opening.

$125 annual fee. (Rates & Fees)

Race Entry for FREE

This one was actually the easiest strategy in that I earned a $300 cash bonus from my Capital One Savor Cash Rewards Credit Card after spending $3,000 in the first three months. I ended up applying that credit to the $205.00 entry fee which leaves me with $95.00 left to spend on DEEP DISH PIZZA! 🙂 

Unlimited 3%
cash back
on dining, entertainment, popular streaming services, and at grocery stores (excluding superstores like Walmart® and Target®), plus 1% on all other purchases

$0 Annual Fee

Unlimited 3%
cash back
on dining, entertainment, popular streaming services, and at grocery stores (excluding superstores like Walmart® and Target®), plus 1% on all other purchases

$0 Annual Fee

Basic Break Down

Running 26.2 Miles for a MEDAL + PIZZA = Priceless 

Interested in learning more about running marathons? Be sure to also check out the Abbot World Marathon Major Challenge that I am going for! With Chicago behind me, I am now at 2 out of 6 races!

New to Credit Card Rewards Points? Check out the BASICS Below!

Editorial Disclaimer: Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities.

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