Virgin Hotel or Stay Pineapple?

Question

I'm planning a trip to Chicago this fall for my husband and I. This will be the first real time either of us has had to explore Chicago. I've only ever been there for work conferences. I was thinking September 21 - 25 (Sun - Thur) as it's our anniversary, and that feels like a fine excuse to take a vacation. That woud give us 3 full days and nights in the city, with a travel day on either end.

We're planning on doing a lot of the touristy things and will be taking public transportation, so I was looking in the downtown/loop area. Two hotels in particular seem like a really good combination of price and location - Virgin Hotel and Stay Pineapple. Has anyone stayed at either one? They seem to be on par with each other on price and ammenities.

Answer

Both Virgin Hotel and Stay Pineapple are excellent options for your anniversary trip to Chicago, and each has its own unique appeal. Here’s a breakdown of both to help you decide which one might suit your needs best:

Virgin Hotel:
The Virgin Hotel Chicago is known for its modern, sleek design and vibrant atmosphere. It’s a bit more luxurious in terms of decor and amenities, with a trendy, upscale vibe. The hotel is located in the River North area, which is ideal for access to many of Chicago’s popular spots. It’s a short walk to the Loop, Millennium Park, and the Magnificent Mile. Guests rave about the spacious rooms, which are designed with comfort and functionality in mind, including a “lifestyle” layout with separate work areas and a cozy lounge area.

The Virgin Hotel also offers several on-site dining options, including a rooftop bar with great city views and a chic restaurant. If you’re looking for a more cosmopolitan, trendy vibe, this might be a great fit for your anniversary trip.
Stay Pineapple:
Stay Pineapple is a more quirky and playful option compared to Virgin Hotel. Located near the Chicago Loop, it’s also within walking distance of key attractions like Millennium Park, the Art Institute of Chicago, and the Magnificent Mile. The hotel has a fun, vibrant atmosphere with a distinct style—expect lots of bright colors and whimsical touches throughout the property. It’s a bit more budget-friendly compared to Virgin Hotel but still offers great amenities, like free coffee, snacks, and the signature pineapple-themed touches (you’ll find pineapple everywhere!).

The rooms are cozy and well-appointed, but they don’t have the same sleek design or luxury vibe as Virgin Hotel. If you’re looking for something less formal but still comfortable and conveniently located, Stay Pineapple might be the more relaxed choice.

Both hotels are very well-situated for tourists, with easy access to public transportation and the major attractions in Chicago. Here are a few additional things to consider:

Virgin Hotel: More upscale, ideal for those who prefer a chic, trendy hotel with amenities like a rooftop bar and high-end dining. It’s perfect if you want a more luxurious, cosmopolitan experience.
Stay Pineapple: More casual and budget-friendly, with a fun, playful vibe. It’s great if you prefer something more relaxed but still very comfortable with great service.

Both hotels offer a unique experience, and your choice ultimately depends on whether you’re in the mood for a slightly more upscale stay (Virgin) or a fun, relaxed environment (Stay Pineapple). Either way, you’ll be in a great location to explore the best of Chicago! Happy anniversary and enjoy your trip!