DISCLAIMER: These rates are subject to change based on availability. Prices reflected here were taken from averages collected by www.theoutsidesalesrep.com

The Windy City. Ah what a wonderful visit. The beautiful blue Lake Michigan, vibrant green parks around every corner, and the seemingly infinite number of people always walking their dogs in the middle of the work day. The only downsides of working out of Chicago are the traffic (check our podcast guide to make this less worse), the winter weather and the cost. But hey, that’s why we’re here!

Over the years, we have compiled expense-worthy hotels that still showcase a 5-Diamond experience.

The LondonHouse Chicago Downtown, Hilton – $138

LondonHouse recently replaced The Drake on here, after a few stays it was clear that LH Chicago was a step above. It starts with the welcoming. The lobby at LondonHouse is absolutely stunning and is graced with immaculate black stone walls. The concierge at the front is always available and the view leading up to the hotel is unparalleled when it comes to hotel location.

The room was the second thing we noticed a huge increase in class and style compared to other Chicago hotels. The sheets are pristine, silky white and the down comforter is heavenly. The room is large and accompanied with a high class bathroom that you cannot get anywhere else for this price. Your normal Keurig?
Yea right, each room has an espresso machine capable of making normal coffee as well.

The restaurants, yes plural, here are fantastic. There is a rooftop view here that finds itself on every person’s Chicago bucket list when they visit. The bar is a little pricey and the wait time can be a turn off but for the most part, it is worth it. I highly recommend the House Old Fashioned.


Palmer House, a Hilton Hotel – $133

This one has always been one of my favorites. I love hotels that have a unique, open lobby. The Palmer is the belle of the ball on presentation. They host weddings in their lobby it is so pretty. It looks like a medieval castle hallway with large grand stairs and the bar down there is an inexpensive wraparound bar, so you’re rarely underserved.

The food here is very good, though not as good as The Drake and they provide convenient table service with new waiting technology so you know when your food is coming. This comes in handy when you’re considering another glass of wine before your salad (read how to stay fit while on the road here). The rooms are slightly smaller than I prefer and the set up is not the most intuitive. But hey! The place was started back in 1873! Location is A+ here and parking is around $55 valet.

Our Winner


Renaissance Chicago Downtown Hotel – $155

Now I know this goes slightly higher than our budget, but we love this hotel so much that we made an exception. It’s worth the extra $5. From the moment you walk in off of Wacker you are greeted with social ambiance. Most nights, and all weekends, there is a band playing or someone singing in the bar foyer. You can always find me lounging on the padded concert seating area right in front of the speakers with a Weller/Ginger Ale in my hand. (Below)


The event space is perfect for weddings and conferences, I have had a holiday party for work here before as well. You have all the amenities of Downtown Chicago right outside your door, plus the view of the river at night is amazing. The rooftop bar is awesome during the summer especially when you get a light, no wind evening. I highly recommend this hotel for its rooms and food, but the social aspect is bar-none for hotels in Chicago.


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