How To: Whisk Her Away On A Surprise Vacation!

Sounds like a cool idea that would never be doable, right? Surprising your significant other with a spontaneous trip... Too expensive, logistically impossible. Or is it? I'll share with you how I once threw together a surprise romantic weekend trip for less than $500.

So I was living in Vegas at the time, which might have helped in terms of finding cheap flights, but hear me out. We were supposed to go see Celine Dion one night and Celine caught the flu or a cold or something and the show was cancelled, so I threw together an amazing Chicago trip in a day! I started with Google Flights to see where I could get a cheap flight. Chicago is a MAJOR hub and Frontier had a great deal on like $59 flights. Since it was essentially a 36 hour trip, we only needed a backpack full of clothes and one actual night in a hotel.

Need a cheap hotel? Find hotels that are trying to fill up for that night by using the Hotel Tonight app. Last minute hotel deals are a real thing! We spent something around $75 and ended up in a pretty nice hotel in Downtown Chicago.

So we flew overnight Friday into Saturday morning, got into Chicago Saturday morning and got some breakfast and found our hotel. We couldn't actually check in until 3pm but they let us hang in the lobby for a bit to charge our phones and they happily took our bags when we went exploring. Luckily, we had lots to do in our abbreviated surprise weekend trip thanks to CityPASS. Pretty much every major city has a discount deal with CityPASS where you can see all the major museums, landmarks and tourist attractions. So in Chicago, for like $108 per person, we got to do the Shedd Aquarium, the Chicago Skydeck, The Field Museum, the Planetarium and the John Hancock Tower. AND a lot of these things came with skip the line passes. We tried to eat at all the Famous Chicago eateries and soak up as much of Chicago as we could on our "surprise" weekend trip. Before we knew it we were on our Sunday evening flight back home with an awesome weekend of memories to take with us.

I could get into the nitty gritty about how I surprised her with this trip, but I just wanted to show you how someone on a budget could whisk someone away on a romantic weekend trip.

If you'd like to hear our Chicago story in more detail, we talked about it on Moug & Carly in the morning, here it is: