Valentine's Day at Oak Brook Hills Resort Chicago

Tips for planning the best Valentine’s Day date 

Valentine’s Day should be a joyous, fun, celebration of love. Far too often what it creates instead is stress for those tasked with organizing their Valentine’s Day date. Will their significant other like the things they have planned? What gift does the person want? Didn’t we just get done with the gift-giving season in December?  

The first thing to do is take a deep breath. Here at the Hilton Chicago Oak Brook Hills Resort, we have been helping people create the perfect Valentine’s Day date, or even a weekend, for decades and we understand what will make you look good. So, let’s look at some key steps and tips you should consider when planning your Valentine’s Day date.   

Of course, if you just want to book your Valentine’s Day stay at Oak Brook Hills right now, you can do that, too, by visiting our website.  

Understand what your Valentine wants 

Romantic dinner at Oak Brook Hills Resort.

Yes, it comes down to communication. This can be a challenge if you are new to the relationship, but what does your Valentine want? Is a nice dinner an option? What about gifts or flowers? If your idea is to do something elaborate, will your significant other like that? It takes planning to make a good Valentine’s Day. Trying to put something together, on your own, last minute, can be a challenge. If a home cooked meal is something your significant other would want, do you have skills for that?  

Start planning early  

Calendar for planning Valentine's Day dinner

The fact is, to get the best results from your Valentine’s plans takes time and careful design. If you didn’t start planning for Valentine’s Day right after Christmas or just after the first of the year, you might find yourself struggling. Getting a reservation at just the right restaurant can be a challenge because those seats fill up fast. Valentine’s Day is also a busy time for jewelers, florists and other romantic gift creators. Plus, a hastily-put-together Valentine’s Day can be spotted pretty easily and you could end up paying for it the rest of the year.   

Planning early can extend to the days right before the holiday. For example, to make sure the flowers get to your loved one’s place of employment means discussing with the florist and even making sure the place where you Valentine works will accept flowers delivered that morning. Make sure your loved one is at least somewhat aware of the plans you’re making because there’s a good chance they’re also making plans and you don’t want them to be at cross purposes. Trying to surprise each other can be risky, so make sure preparations have been made.  

Another nice touch is to get a Valentine’s Day card, but put in in the mail days before the actual holiday. Your significant other checking the mail and finding your card can be a nice surprise. Or maybe you can mail it to their work place? Think a little outside the box even with the simple things and it can go a long way toward making the day special.  

Book in advance  

This goes hand-in-hand with the planning early and communication portions of the holiday plans. However, if there’s a favorite restaurant you want to visit, make sure to book the table early so you aren’t scrambling the day-of finding an alternative. In fact, consider several potential alternatives and start making phone calls. Have a few different places in mind. There may be other out there making their plans early and tables book up fast. 

The same holds true if you want to travel for Valentine’ Day. Tickets should be purchased well in advance, cars rented, hotel rooms booked.  Trying to surprise someone with travel can be a trick in its own right and could lead to disaster for the one you love, if you aren’t prepared.   

Remember simple can work  

Valentine's Day candy and flower for holiday planning

Of course, strategy is still involved, but there is the temptation to create a Valentine’s Day experience that outdoes everyone else. Remember that a simple dinner, getting the right Valentine’s Day card or visiting a place you both love and remember can be enough. Planning ahead to ensure the cards get there ahead of time, or the flowers arrive at the right time and at the right place can be the perfect way to impress your loved one without having to get too crazy about the day. Remember, this should be a fun, happy, holiday and not one that raises your blood pressure to unhealthy levels.  

How Oak Brook Hills Resort can help you with Valentine’s Day  

The Hilton Chicago Oak Brook Hills Resort and Conference Center

Doing all the above can be a lot of work and we know it can take weeks of planning. There’s another solution, too. You can just book a stay at the Hilton Chicago Oak Brook Hills Resort for Valentine’s Day and let us take care of most of the details. Of course, you should book your stay now, while there are still rooms available, but here’s what our Valentine’s Day stay provides:  

  • Rates staring at $129.  
  • Sparkling wine or cider upon check-in  
  • Romantic dinners available at our B. Restaurant with great views and romantic atmosphere. (check out our Valentine’s dinner menu here).  
  • Early check-in or late check out so you don’t have to rush or worry about time  
  • Breakfast for two served in your room  

Plus, if you stay with us, you get full use of all the resort has to offer such as the spa, indoor pool, fitness center, etc.   

All you need to do is make the reservation, pack your bags, and get to Oak Brook Hills. We’ll help with the rest of it. You get to appear the hero. Book your stay now