That One Time I got PAID to fly to Chicago and have an Awesome Time

That One Time I got PAID to fly to Chicago and have an Awesome Time

Remember when I said I flew to Chicago for $1? This last trip, I managed to snag an even better deal. Last weekend, Mr. A and I flew to Chicago...and actually MADE money. This is in no way a sponsored post. Frontier Flights didn't pay me to give them a good review. A hotel didn't give us a complementary stay. The city of Chicago didn't track me down and promise me an all expenses paid vacation to drop a few good words about Chicago. How did we manage this?

Here's how it all went down...

Since I had such a fabulous time during my first trip to Chicago, I decided that Mr. A and I were in desperate need of a date night in a new city. Frontier Flights had just sent an email about another amazing flight sale, and I had already signed up to be a Den Member so I could have access to even better deals. I figured "why not, you only live once." I booked our $19 flights, and scoured the internet for hotel deals. Sadly, our Chicago date night just happened to coincide with one of the largest annual  convention. Downtown hotel rates were through the roof.  We ended up staying at a seedy hotel (not going to name names) near the airport, on the not so good part of town (internet photos can be so misleading).

The first night was awful. I have a thing about hotels. After watching that 60 minutes expose on bed bugs, I prefer to shell out a few extra dollars and stay in a better hotel. Still, regardless of where I stay, I ALWAYS lift the bed, check the mattress and remove the sheets. Just in case...

After arriving at the Hotel from Hell, we decided to spend as little time as possible in that room. My wonderful Mother-In-Law grew up in Chicago, and had recommended Giordanio's for pizza, so we figured we'd stuff our faces with pizza and have a few drinks to ease the pain of having to sleep in a "Bate-esque" Hotel. The restaurant was actually located about 4 miles away from the hotel, so we figured we could walk to it. 10 minutes later, we were caught in a rain storm, and the sidewalk had run out. We were left with two choices: walk on the side of the highway, or go down a seedy alley that looked like something straight out of every horror movie ever made.

We called a cab, which actually turned out to be a Town Car and Limousine Company. We figured we were losing daylight and since we were only a few miles away, how costly could it be?  $38 dollars later, we arrived at Giordanio's.

Giordanio's turned out to be an excellent choice. The pizza was just as amazing as my Mother-In-Law mentioned. The atmosphere, was relaxing and they have awesome beer. Still, factoring in cab fare, it was decidedly the most "expensive" pizza we've ever had.

The cab ride back to the hotel didn't go any better. The cabby who arrived claimed he didn't know where the hotel was located, and his GPS, just happened to stop working. Luckily we had our phones with us, and managed to give him directions back to the hotel, but not before he managed to take us on a few unnecessary loops around the parkway.

By the time we arrived back at our hotel, we were so exhausted, that we practically collapsed into bed. I actually ended up apologizing to Mr. A because I felt like I had destroyed his first "Chicagoan" experience.

The next day we were up, dressed and ready to hit the road by 6:00 a.m. We had a quick breakfast and checked out. Then we did something we should have done the night before, we used Uber. Our driver was there is less than 2 minutes, and the ride downtown was absolutely free! See the night before, we met an awesome women in the hotel lobby who was a flight attendant and part time Uber driver. She was kind enough to give us a promo code for $25 off our first Uber ride. Still, even if we didn't have the promo code, I realized that the Uber ride was MUCH cheaper than the regular cab rate. Our "4 mile" cab ride the night before ended up costing us $18.  Our 15 mile, 30 minute Uber ride into Downtown Chicago would have only cost $23 without the promo. Our Uber driver was friendly, knowledgeable about Chicago, and had a working GPS. Score! Needless to say, he got a BIG tip!

Once we arrived Downtown, we immediately went into tourist mode. We hit up some of the the "must see" tourist sites in Chicago:

Magnificent Mile
The Cloud Gate aka "The Bean"
Boeing Gallery
The Chicago Institute of Art
The Navy Pier

Needless to say, day two was AMAZING. We met some incredibly helpful people, one who walked us nearly a mile to the bus station, and helped us figure out how to get our all-day bus passes. In the rain...

We spent the afternoon exploring and tasting our way through the bustling streets of Chicago. Mr. A was beyond impressed at how gorgeous Chicago is. Day two quickly washed away the horrors from the night before.

Soon, it was time for us to head to the airport. This time we called Lyft (we had another promo for $10 off your first ride). As we headed to the airport, I started to check us into our fight. But then I realized our flight had been delayed for two hours. We were ecstatic. This meant we had a few more hours to kill. Luckily our Lyft driver knew Chicago like the back of his hand and recommended this awesome restaurant called Portillo's. We spent the next hour or so stuffing our faces with the most amazing hot dogs I've ever had the pleasure of eating (little did we know a few days later The Who would release a report saying that hot dogs are just as carcinogenic as cigarettes).

We arrived at the airport early and made it to our gate with time to spare. Since we still had time, and I'm a bit of a nervous flier, we decided to get our pre-flight drink on. After I paid a visit to Margarita, we spent time aimlessly wandering around the airport. We boarded shortly after and 1.5 hours later, we were back in Raleigh.

That's when I got the first email. Because our flight had been delayed for 2 hours, Frontier Fights sent us $100 a piece in travel credit. The next day I woke up to another email, we had been given an additional $50 a piece in travel credit as another apology for our delay. That means we spent $80 on a roundtrip flight for two to Chicago, and were given $300 in travel credit, meaning that we were basically paid to go to Chicago and have an insanely awesome date night.

The moral of the story is three-fold, one: Horrible reviews aside, Frontier Flights is one of the least expensive ways to fly!  The flights are pretty basic, and I can't always promise that you'll get travel credit for flight delays, but I appreciate their attempts to put the customers first. Two: Sometimes a flight delay isn't a bad thing (unless you have a fight connection). Make the best of the delay. Three: Be friendly and talk to people. Because we were so chatty and friendly, we met some amazing people on our journey. Overall, they saved us MAJOR dollars just by giving us free promo codes and helping us navigate the busy streets of Chicago.

Since we have $300 in flight credit, Mr. A and I are already planning our next free trip. Luckily we're only a few hours away from ATL, which of course has one of the largest airports in the country. Frontier Flights has flights out of Atlanta to Montego Bay Jamaica, Punta Cana and Cancun for as little as $115 one way. Needless to say I have a feeling we're going to be adding a few more stamps to our passports sometime soon!

What is your best travel story? What are some of your money saving travel tips? Sound off in the comment section below!

Next week I'll be sharing some awesome photos and tips on what do see, do and eat in the Windy City!

Until next time,

1 comment :

  1. I'm like you I'd rather pay more money for a nice hotel. But it's great that you were able to enjoy your trip despite a bad hotel room. It's really awesome that you guys now have free airfare to use for a future trip. The delay worked out perfectly :)


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