I'm a huge lover of long weekends. I've found that they're just the antidote for that extra boost of energy we need to keep us going. One of the main reasons that I love long, holiday weekends is that they're the perfect excuse for a mini getaway. Planning a full on vacation is a lot of work, and even more so - a lot of money. Taking a trip over a long weekend is a more affordable way to get out of town and see somewhere new.
Read on for tips + my top 5 recommendations for a long weekend trip.
For a little bit of background, I'm basing my preferences on places that have been easy for me to visit from Chicago. Prices to fly from different cities may vary. I suggest downloading "Hopper" onto your phone and entering dates and locations where you'd like to fly. They'll send you notifications when a flight is a really good deal. Sometimes, they'll even take note of the type of location your looking for and send you other suggestions that are really good deals.
Another tip I have is not to fear discount airlines such as Frontier or Spirit. Long weekends aren't the time for long haul flights. If you're going to fly on a discount airlines, the time to do it is when you won't be on the plane for too long. That being said, discount airlines are not always the cheapest. Southwest and United often have amazing deals!
Finally, I try to choose cities that I feel I'd feel satisfied only spending a few days in. The "small city/big city" vibe is perfect for a couple day trip.
Without further adieu, here are my top 5 recommendations for a long weekend:
1). Charleston, South Carolina.
I can't recommend a visit to this place enough. Some of the most beautiful historic preservation you can find in the United States is here in this city. We visited a historic plantation (as seen below), walked through the pastel colored historic homes, ate the best fried chicken we've ever had, took a Civil War tour, took a ghost tour, sat by the ocean, and bought ourselves preppy pastel outfits to fit in with the locals. There is great shopping and a cool bar scene. You can save money by staying in the suburbs right outside of the city.
2). Philadelphia, Pennsylvania
Another historic city, Philadelphia has a ton to do. Center City is where you'll find Independence Hall, the Liberty Bell, and several other spots key to American History. It is totally worth taking a guided tour where you'll learn about tons of hidden historical gems located all over the city. You can't miss the art museum (the famous Rocky stairs are here) or the Franklin Science Institute (it is one of the best I've ever visited). Finally, don't miss the neighborhoods here - Rittenhouse Square and Fishtown are both fabulous for dining and night life. We used AirBNB here so that we could afford to stay in some of the cooler neighborhoods.
3). Las Vegas, Nevada
My mom and I once spent a week in Vegas. Three years later and I think I am still recovering. You only need a few days here to have a great time. I took a long weekend here with my best friend. We had the time of our live, and we hardly spent any money. Seriously. Do yourself a favor and book a spontaneous trip here. It is a city that is dedicated to relaxation, and you can do it on a budget. My biggest tip? Stay at the Flamingo in an updated "Fab" room. The updated rooms here are BEAUTIFUL and incredibly inexpensive. You'll be in the middle of the Strip and have walking access to anything you need. Splurge on a buffet and a nice meal, then opt for cheaper options the rest of the time. Buy your own booze, set a gambling limit, and HAVE FUN.
4). Washington, D.C.
If you're a museum nerd, this is your paradise. I happen to love visiting museums. All of the museums here are free! Air and Space is my favorite, but the Portrait Museum and Natural History Museum are my other top favorites. Georgetown is trendy and adorable along with several other cool neighborhoods surrounding the city. You could come here over and over again, yet you'd still be able to find a ton of stuff to do. At the same time, you'll feel satisfied only spending a few days here.
5). Pittsburg, Pennsylvania
Pittsburg is definitely a "small city/big city" vibe. Fun fact - it has more bridges than any other city in the world! The downtown definitely is worth checking out. We explored the "Strip District" which had a ton of great food and artisan crafts and the "South Side" neighborhood which is great for nightlife and dining.
Bonus - Chicago!
I didn't add it to the list since I live here, but check out my Chicago page for a list of my absolute favorite spots in the city! It is an AMAZING place well worth at least a long weekend.
Places that are next on my list? Well, there are many... Austin, Nashville, Portland, Toronto, and Seattle are all on my watchlist! Where are you hoping to visit on your next long weekend?
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