By Liam 
This is the third installment of the $150 Getaway Challenge. For the uninitiated, my goal is to book weekend trips from a bunch of different cities for under $150 per person. I’m going to continue to run through the list of the biggest metropolitan areas in the USA for the foreseeable future. Feel free to request origin cities in the comments section. So far I’ve been able to book trips from NYC to Cincinnati for $136 and LA to Vegas for $121, both per person.
All of the trips I book have to conform to the following guidelines.
RULES:
- Flights + Accommodation must add up to under $150 for 2 people ($300 total)
- Must be at least a 2 night stay
- Accommodation must be at least a private room
- Travel dates must be within the next two months and fall between Thursday-Monday
- Basic Economy Tickets will be assumed whenever possible
So, Chicago is next on the list and had a few more options which conformed to these criteria than LA and New York did. If there’s a time to get out of Chicago, it’s most definitely in the Winter. Here’s the list of destination cities I had to choose from:
- Dallas
- Houston
- Phoenix
- Denver
- Jacksonville
- Tampa
- Fort Myers.
I thought about this practically and figured I would narrow the list down with a few criteria. The least amount of time during the workweek missed, the better. Price is obviously important and the desirability of each destination comes into play as well. Denver, Fort Myers, and Phoenix were enticing but I had to sacrifice on quality of the accommodation to make up for the price of the flights. Jacksonville was a surprise dark horse candidate.
However, one location managed to stand out from the pack and I was able to come in $64 under budget.
Best Itinerary from Chicago (ORD, MDW)
Destination: Tampa/St. Petersburg
Dates: 1/12-1/14
Flights: $133(!) (Frontier from ORD)
Airbnb: $103
Total: $236
Per Person: $118 (an early new record)
This location was Tampa/St. Pete area and it serves as a sunny break from the treacherous Chicago winter. Even though I’m not considering rental cars as part of the budget, adding one would only put you at $157 per person, which is pretty incredible.
The one downside about this itinerary is that you would return from your 2 night trip on a Monday night. Well worth it for a sunny vacation, an Airbnb minutes from the beach, and the ability to drive wherever you please.
An underappreciated arts and culture scene
Florida, apart from Miami, has a reputation of lacking in the culture department. This is an unfair depiction, as the Tampa Bay area has some great cultural attractions. It’s a metro area of three million people, so it’d be surprising if it didn’t. Then again, you could just spend your vacation lounging on the beach and choose to not see much of what it has to offer.
The Duncan McClellan Gallery in St. Petersburg gets stellar reviews, there’s good local theatres, a Holocaust museum, and a Salvador Dali museum. These just scratch the surface of what the area offers culturally.
Now that we’ve addressed that misconception, the Tampa area also has 3 pro sports teams, gorgeous gulf coast beaches (you knew that), a decent number of local breweries, both high end and bohemian shopping, nature preserves, Busch Gardens, a Thai Buddhist Temple, and a tropical fruit winery. You’ll hardly run out of things to do, especially in two days.
There’s also no shortage of cheap eats. There’s a surprising concentration of diners, maybe due to all of the transplants from the NY/NJ area. Along with that, there’s good Cuban, Thai, and Mexican food scattered around the area.
This concludes part three of the $150 Getaway Challenge. Next up will be a trip from Dallas. I’m expecting some interesting options and I’m definitely looking forward to it. If you like these posts, you can subscribe to my newsletter below to be notified when they come out.