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I Stayed in a 5 Star Hotel in Chicago for $93/Night – Here’s How

I Stayed in a 5 Star Hotel in Chicago for $93/Night – Here’s How
Annette Miller May 14, 2018
Want to Earn Some Extra Money?

In the world of frugal travel, scoring a deal on a fabulously luxurious hotel can be the penultimate thrill of planning a trip. might seem past its prime, making it an app you be overlooking when planning a trip to a huge destination like the Windy City.

With dozens of hotels in dense downtown areas like you’ll find in Chicago, deals are waiting around every corner.

Read on to learn how to hack the Name Your Own Price bidding system and, with a little bit of luck and detective work, discover which specific hotels are listed blind in their virtual clearance aisle called “Express Deals”.

You Can Do This, Too!    

Before we begin, let’s get something out of the way.

  1. You might be asking yourself something like, “Is this one of those situations where once every five years one genius can score a room at the Four Seasons for under $100 a night if the moon and Venus are properly aligned? I hate those articles!”

    Answer:  The steps described in this article are very repeatable and reliable, not the exception to the rule.
  2. You might also be wondering, “When the title says ‘Chicago,’ do they really mean a far-flung suburb that would require an hour on the train to get anywhere fun?”

    Answer:  We are talking about downtown, city center hotels in Chicago.

In 2014, I first learned about how the site works (and how to use it to my advantage!). Since then, nearly every time I have visited a major city, I have investigated options.

That strategy has paid off handsomely in both savings and free upgrades at check-in.

Having booked over 20 high-end hotel rooms in nearly a dozen cities, I am speaking from direct personal experience. Of those reservations, 5 were in downtown Chicago.  

This is just a well-kept secret among frugal travelers, as best I can tell!

Frugal Travelers Do Stay in Fancy Hotels

Could I stay somewhere cheaper than I typically do (whether using to book my lodging or not)? Yes.  Could you? Sure, of course.

In fact, I could easily half half my spending versus the $93 hotel I booked in Chicago and still be in a decent location at a respectable hotel chain.  

With that said, Candace here at Frugal for Less recently broke down the difference between frugal and cheap behavior.  

Spoiler alert!  One involves making savvy decisions to enjoy your life more. The other is a justification for being a grinch and existing, rather than thriving, on the sidelines.  

I love that staying somewhere I normally could not afford feels like beating the system. It’s like a “how much luxury can I get for my budget?” game.

Luxury and relaxation for a stupidly great price? If there are two things I’m known for among friends, its random knowledge about frugal hacks and fancy things at not-fancy prices. (Ask my friends.)

As a bonus, I usually do have an idea of which hotel I’m booking although it is not officially confirmed until after bids are accepted. 101: Clues Everywhere

Which hotel will I get?

You’ll notice throughout the site that subtly suggests the hotel you might end up at if you Name Your Own P (NYOP) rice is a mystery.

Their messaging on this is sort of like, “Be flexible, we’ll deal with the rest!” This is a smidge of misdirection. I get why they do it, but the reality is a little different.

In fact, a bit of detective legwork often means you can narrow down which hotel you’re bidding on.

As a savvy frugal traveler, you’re likely familiar with the concepts and tools uses. What’s unique about the site are the small hints hidden in plain site on every page.

And these little clues are what you’ll need to exploit put together to save up to 60% on a hotel’s retail rate.

→ Caveat:  Not every single hotel will always be listed as some hotels may have sold out or may only be taking reservations through NYOP. Thus, it is possible you will be bidding on a hotel which is not listed anywhere on the site at the time you are doing research and bidding.  

The Must-Know Lingo

There are a few terms you’ll need to know to successfully navigate the site. Some of these words probably seem obvious, but the way the site uniquely uses some phrases matters:  

  • Bid – Amount you are offering to pay pre-tax and pre-fees for a hotel room per night
  • Deal AssistantA bot programmed to help you navigate Name Your Own Price
  • Express Deal Listing of hotels without their names, but which includes their location and star level

→ Pro Tip: Express Deals are coded with the same information used in the NYOP bidding system. You can use the clues to eliminate hotels in the area and star level you’re looking to stay to narrow down which hotels you might see in the Express Deals list.

  • Guest rating – Bracketed rating system which reflects how guests reviewed the hotel
  • Hotel AmenitiesFeatures of a hotel, such as a gym, restaurant, business center, and so on
  • Member DealsDiscount applicable to members with a login
  • Name Your Own Price (NYOP) System for bidding for your preferred hotel star level and location
  • StarsThe unique rating assigned to a hotel by

→ NOTE: This does not necessarily correspond to traditional hotel star ratings

  • Zone – Neighborhood areas within a city, used when bidding on areas you’d like to stay

Bid Hacking Prep

Make Sherlock Holmes Proud

You can get to NYOP from a few ways, including the homepage of 

While bidding, you’ll want to have two windows open:  one with the NYOP bidding system and one with the list of hotels in the city you’re bidding in.

Grab a pen and paper or open a Google Sheet, then get ready to take some note while you do some detective work!

How Bidding (And the Biggest Hack) Works

The basic rules of how bidding works in NYOP are simple. There are two steps. This is two-step process is one of the things that’s unique to and a key hacking opportunity:

  • In Step 1, you pick Zone preference.
  • In Step 2, you pick Star level.

Bidding begins with selecting one Zone and one Star level. If an initial bid is unsuccessful, you are allowed to add another Zone, Star level, or adjust date preferences.

→ Pro tip: “Free Bids” are the biggest secret to hacking the NYOP bidding system. This refers to bidding on a star level in an area where no hotels have that star level.

Free bids come into play when adding Zones or Star levels with phantom matches.

In other words, if you are bidding for 5-star hotels (Step 1) but include a Zone without any 5-star hotels, you are allowed to bid because you technically have added a zone, thus followed the algorithmic rules of the bidding system.

Determine Desired Location/Zones  

To book a room in Chicago, the first thing is deciding where is ideal to stay. For the purpose of my trip, anywhere near the Loop would be perfect.

I just compared the location of the conference on Google Maps with the Zones in the NYOP bidding tool.

From the NYOP page, you can see Zones 2, 3, 4, 5, and 6 are all within an acceptable distance. That’s 100% a personal preference, by the way.

You might be fine with a slightly different radius, so Zone 11 (Linkin Park) might work well for you.  In this way, picking your target location is like any other booking scenario.

Assuming it would work with my budget ($99/night), any four to five star hotel in Zones 2-6 will be my target for securing a room.  

→ Pro Tip: Use a discount parking app when you’re in a big city like Chicago. I’m a huge fan of SpotHero because there are always plenty of nearby spaces and I can usually find a spot for about half of what the hotel would charge for self-park or valet.

Decide on Desired Star Level  

Before I can start bidding, the next step is taking an “inventory” of Zones with hotels in my desired star level.  To do this, click on each zone one at a time.

→ Pro Tip:  If you highlight multiple zones at once, you cannot accurately determine which Zones do not have hotels in your desired star level.   

When I click on “Millennial Loop” (Zone 2), I can see that under Step 2 I could pick any star level between 1 star and 5 stars. That means there are hotels in all star levels in this particular Zone.  

By comparison, if I picked “Mount Prospect” (Zone 16), the star levels from 3.5 and up are grey; this means no hotels above three stars are available in that area.  

Your Battle (Bidding) Strategy  

Here’s where my love of spreadsheets comes in.

There are a few things you need to be crystal clear on before you start bidding or else you’ll waste time, bids, and possibly wind up in a part of town you’ll dread! (Uhg, trust me. )   

  1. First, note the highest hotel star level available in each Zone using process from the last step.
  2. Next, mark or highlight your desired zones.
  3. Then, sort by highest star level.
  4. Fill in YES or NO for bidding in each Zone

When to Bid in a Zone

YES   NO  
In a target zone (area you want to stay) In non-target zone with hotels of desired star level (inconvenient location)
In non-target zone without hotels in desired star level (“free bid”)

Altogether, there are 12 Zones ideal for bidding and 4 which I must avoid to avoid the risk of booking a hotel that’s completely inconvenient (see:  Midway Airport, Zones 9 and 10, or out by O’Hare in Zones 7 and 8).

Room Rates

Pay close attention to dollar amounts and percentage discounts marked across the site. For example, this room is marked down 17% from the original retail rate, making it $186 now.

You can also see the room was originally $224.  

This specific pattern (looking at discounting percentage) is most useful for reverse-engineering which hotels have Express Deals.

But, this is also an important clue about which hotels might be discounting and willing to take a low-ball offer.  

Before bidding, I recommend browsing the list to see which hotels are most discounted in the zones and star levels you want to stay.

This will give you an idea of which hotels might be willing to take a rock-bottom price in NYOP.

Bid Amounts

Let’s do some review and basic math to determine what to bid for the best possible rate.

→ Pro Tip:  When investigating what to bid, check out what recent users have paid. This social information can be found all over their site. Note this person paid $177/night but the room retails for $199/night and I got it for $93/night.

  1. The max budget I set was $99/night (before taxes and fees).
  2. I have 12 Zones for bidding, thus 12 bids available.   
  3. I need to determine my starting bid. So what is the lowest amount I should start with?  The cheapest room I’ll be bidding on is a 4 star room. Based on research in my last step, the lowest those rooms retail for is $139/night. If 60% off is the max people can save in NYOP, the lowest rate on the cheapest room would be about $83/night.
  4. Subtracting $83 from $99, my range is $16.

Based on all of this, it makes sense to go ahead and round up my starting bid to $87/night.

With each new bid I can add $1 to my offer and inch my way from what is realistically the least I could expect to pay if I got the least upscale room up toward my max budget of $99 for the most upscale room.

Begin Bidding!  

For my trip, the biggest discounts were in the Magnificent Mile zone, which also happens to be where the highest star level was (five).

As you can see above, suggests the retail rate average for the type of room on which you are bidding.

This is like them saying, “You realize you’re bidding on a luxury hotel at a flea motel rate, right? Our hotel clients probably won’t accept that.”

Ignore that.   

→ Pro Tip:  Start bidding in the highest star level and work your way down, pairing it with your lowest bid.

The idea behind this strategy is to bid the lowest possible amount for the best possible room. I mean, that’s the frugal traveler’s dream, right?

Amenities as Clues

As you begin bidding, you’ll be able to see:

  • Guest Rating bracket (e.g., 8-star, 9-star)  
  • Hotel Amenities  

These can be compared to the Amenities listed for the main page listing to narrow down which hotels you may be bidding on. Often, the Guest Rating is most helpful for process of elimination.

From the above information, I was able to narrow down what I thought I was bidding on to two hotels.

If you go back to the list of hotels, you’ll notice hotels like this Hyatt Centric Chicago Magnificent Mile.

In this example, you can see the list of specific amenities offered; it includes free internet, a swimming pool, pets allowed, and more.

By clicking on the link, the entire list of amenities becomes visible. This is the sort of thing I’d put into an Excel column, personally (and I do).

As I added more bids and zones, I did see a slight change in the guest score rating they guaranteed.

My 5 Star Hotel Experience  

In the end, I ended up with a phenomenal reservation at The Intercontinental on Michigan Avenue.  

Based on my winning rate of $93, you can surmise it took me 7 rounds of bidding in order to secure a confirmation. From start to finish, I needed to add 6 Zones of bidding.

So worth it!

At check-in, I was basically treated like royalty. I asked if they could do anything for me about a room with a city view.

They were happy to oblige. In many places and on many days, that would warrant an upgrade fee but  there were admittedly at least two things working in my favor.

  1. The weather. Chicago was getting Lake Effect blizzard-like conditions that day. It was not a fully booked day in the hotel, that much was clear. Large hotels have vacancies frequently, so while you can’t expect the penthouse, it isn’t unreasonable to ask if they have something with a corner view. (No need to fib and say you’re on your honeymoon.)  
  2. I asked respectfully and kindly.

The Chicago trip was hardly the only hotel I’ve gotten free upgrades on an already ridiculously reduced room rate.

In July 2014 while traveling along the coast in Maine, I got a similar upgrade just for asking. That was during their peak travel season.

Got a gorgeous view of the bay on Portland. In Washington state last fall, a huge wave of cancellations due to hurricane conditions in Atlanta grounding most of Delta’s fleet nationwide led to the best free travel upgrade hookup of my life.

My boyfriend and I got bumped from a $200/night room at a four and a half star hotel to a $750/night room.

In fact, the hotel honored that free upgrade both nights we were there. The tub filled from the ceiling. There was champagne at check-in. It. Was. Extra.

→ Pro Tip:  Hospitality professionals like to feel helpful. All humans like to feel appreciated. Especially when greeted with respect and genuine curiosity (“Could you do me the small kindness of checking if it would be possible to have a room with a city view as a complimentary upgrade?”), my experience has been that professionals in hospitality are often inclined to say yes.   

Whirlwind Recap

  • Name Your Own Price on is a legitimate way to snag a great deal on a great room in a great city. You can do this! What you need to master the art of NYOP bid hacking is all here.
  • You can probably even guess which hotel you’re bidding on.  
  • Free bids are the key to NYOP.  
  • Parking in huge cities can be a bummer, but discount parking is a thing! Check out SpotHero.
  • Think of yourself as a mad scientist. Don’t be afraid to take a formulaic approach to bidding! There’s so much info to help you get the best deal (especially what recent users have paid).
  • The goal is to get the best possible room for the least possible rate.  
  • Hospitality professionals like to feel helpful. All humans like to feel appreciated. Free upgrades come to those who are antithetical to jerkish behavior.

Final Thoughts

There can be a bit of leg work involved to get the best deal via NYOP on It may or may not be for you! But if I’m being completely honest, I find the game-like experience fun.  

I have stayed in hotels across across the country where that’s the case using the process, clues, and pro tips described above.

Specifically, I have had great success stretching my budget with Name Your Own Price in:

  • Seattle, WA
  • Atlanta, GA
  • Boston, MA
  • Chicago, IL
  • Louisville and Lexington, KY
  • Portland, Maine  

→ Pro Tip:  Major cities are easiest to get the best deals in, but these steps can also work in smaller markets.  

Frugality is mindfulness about your financial habits and, yes, a little effort.  It can be the difference between squeezing the most memories out of a trip, like savoring complimentary champagne at check-in.

What other bidding secrets do you want to know? What can I clarify? Are you interested in learning more about Express Deals? Tweet me your follow-up questions @millerannette for an FAQ Part II article.   

Annette Miller

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