Inside: Day 2 of our Chicago weekend trip. Join along as we check out the “Upgrading My Style” package at the Loews Chicago O’Hare.
For our second night of our Chicago weekend, we stayed at the Loews Chicago O’Hare and took advantage of their “Upgrade My Style” package. I was very pleasantly surprised – normally, “airport” hotels aren’t all that exciting. But the Loews Chicago O’Hare may just be one of my favorite hotels ever.
Missed Day 1 of our Chicago weekend trip? Check it out HERE
Chicago Weekend Trip: “Upgrading My Style” with Loews Chicago O’Hare
The entire space is beautiful. It honestly reminded me of an art gallery – it showcased gorgeous artwork by local Chicago artists everywhere you looked.

The Upgrade Your Style package includes:
- Overnight Accommodations
- Fashion Outlet Savings Pass
- $50 gift card
- Complimentary breakfast at The Ashburn
- Complimentary self parking for one vehicle
On day 2 of our Chicago weekend, we were pretty exhausted from a full day of exploring when we checked in to this hotel. And then we made the mistake of flopping onto the bed as soon as we arrived.
Big mistake, because the beds were SO comfy and soft and warm that there was no way we were leaving the room for the rest of the night.
Luckily there were some awesome movies on tv and a great selection of items on their room service menu.

I was pleasantly surprised at how many different options they had available, and how utterly reasonable the room service prices were.
Kids menu items started at $6 and regular portions started at $14.
Room service is notoriously expensive, so we usually opt to skip it, but not at the Loews Chicago O’Hare. With such reasonable options, it was a no brainer to just stay in bed and order in.
They also provide complimentary wifi for up to three devices, so while the little one snuggled in to watch some Elf and Harry Potter, my husband logged in to check on some work (one of the “perks” of owning your business is that you never really stop working) while I spent some time writing.
So basically, we ordered in, changed into jammies, watched movies, and spent some time catching up on work.
Sounds like a pretty perfect, relaxing Chicago weekend if you ask me. This was exactly what my family needed.
We all ended up going to bed early and getting a fabulous night’s sleep.
In the morning we woke up totally refreshed and ready for another fun day in Chicago. We had a few last minute gifts to pick up, and since we were walking distance to the Fashion Outlet AND our “Upgrade Your Style” package included a pack of coupons and discounts we decided to make a day of it.
But before we headed out, I took an extra long shower under the fun rainfall shower head.
I absolutely love rainfall shower heads and beg my husband to install one in our house every time we come across them.
They just feel so fancy and fun to me! The shower gel, shampoo and conditioner smelled amazing, too!
After my excessively long shower, we headed downstairs for breakfast at The Ashburn.
I’m not huge fan of buffets in general, and especially hotel buffets, but I was totally blown away. Breakfast is included in the “Upgrade Your Style” package and you have the option of ordering off the menu or choosing the buffet.
The buffet included coffee, along with made-to-order omelettes, a waffle bar, tons of fruit, pastries, breads, and a nice spread of hot buffet items. There were also a few specialities available like breakfast pizza, house-cured salmon, and eggs Benedict.





The only thing better than the fresh, tasty breakfast items was the warm and friendly service. Our server, Theresa was on top of fresh coffee refills, and my requests for additional jam and hot sauce.
In fact, I even (loudly) dropped my knife on the floor, and in the time it took me to reach down and grab it, another server was there offering me a fresh one.
I would absolutely recommend brunch at The Ashburn, even if you’re not staying in the hotel. It was so delicious! This is going on my list of must-do’s for the next time I’m in town.
After breakfast we checked out of the hotel, but they kindly held our bags so we could walk over to the Fashion Outlet for some shopping fun.

As it was the week before Christmas, it was understandably packed! The Fashion Outlet has a ton of higher end shops, like:
- Gucci
- Armani
- Prada
- Burberry
- Coach
But also plenty of familiar and less expensive options like:
- J. Crew
- Bath and Body Works
- The Children’s Place
We spent a few hours wandering through the outlet and shopping for our last minute gifts. When it was time to leave, we popped back to the hotel, grabbed our bags, and used the complimentary shuttle to head to the airport. We had a wonderful, relaxing Chicago weekend and I found a new hotel to add to my favorites list.
If you’re looking for a stylish hotel with an amazing restaurant and fantastic location for a fun Chicago weekend, you won’t be disappointed with the Loews Chicago O’Hare!
pin me!