Why is it so hard to book connecting rooms? TPG compares the process at 4 hotel brands

"I can put in the request, but I can't guarantee it."

Any traveler who has ever tried to book connecting rooms in a hotel — no matter which brand or price point — will likely be familiar with that refrain.

Families with young children and larger groups traveling together often prefer to book adjoining rooms that share a connecting (lockable) door for privacy, convenience or just peace of mind.

With the surge in multigenerational travel that's expected to continue through the summer, the demand for room types that offer more flexible footprints has never been greater.

"Connecting rooms can extremely valuable in giving families the space they want — or need — on trips, but they are still often a royal pain to book and confirm," says Summer Hull, TPG's director of content.

Many travelers end up shelling out far more money (or points) to book suites as an alternative while others lean on luck that a connecting room will be available at check-in.

Unfortunately, trying to game the system to secure connecting rooms rarely works.

"I never know whether to check in online or not," said TPG reader Ben Blaney. "I don't want to fall foul of an automated system assigning rooms, but I also want to be first in line for allocation."

The seemingly random allotment of connecting rooms can be a frustration for travelers who wind up with a connecting room even when they don't want one. Some hotel guests flinch at the idea of sharing a door with a stranger who might be gearing up for a night on the town just as they are putting their toddler to bed.

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To figure out why it's so difficult to book connecting rooms (and find ways to improve the experience), we decided to play around with the system.

This adventure involved booking connecting rooms at four major hotel brands: IHG, Marriott, Hilton and Hyatt. Of these brands, Hilton is the only one that currently guarantees connecting rooms through its "Confirmed Connecting Rooms" website and app feature that launched in June 2021.

So, is one brand better than another when it comes to accommodating families? And is there anything you can do to improve your chances of getting a connecting room?

Here you'll find the answers to all those questions — and more.

IHG - Kimpton Cottonwood Hotel

Time outlay: 23 minutes.
Result: Adjacent rooms.
Lesson learned: Only the hotel (not the reservations agent) can guarantee connecting rooms.

The boutique Kimpton brand, which was acquired by IHG in 2017, is known for its whimsical decor, guest-centric service and thoughtful perks. You're guaranteed a complimentary bike rental, a yoga mat and free bones for your pooches — but what about connecting rooms?

The Kimpton Cottonwood is a stylish 1916 landmark property in Omaha's historic Blackstone district.

Hotel websites generally provide little or no information about how to book connecting rooms, so you'll need to call the central reservation line.

The call to IHG started off reasonably painless. After a short hold while the agent contacted the hotel's front desk, the agent confirmed that connecting rooms were not just available but "guaranteed."

We reserved two standard rooms during the 23-minute call (always expect reservations for more than one room to take a while as a lot of superfluous information is required, such as the names and ages of your children). You should also expect a litany of questions to confirm the data that was stored in the system when you joined the hotel's loyalty program.

For added confidence, I was given the name of the front desk agent who had confirmed the rooms, and they tossed in free valet parking.

Several hours later at check-in, I was told that "while every attempt had been made to honor my request, unfortunately, there were no connecting rooms available."

After the time I had invested on the phone and a pretty emphatic "guarantee," I was astounded. So what happened?

Connecting rooms, I learned, are allocated on a first-come, first-served basis. Their reasoning was that between my call at 10 a.m. and our arrival at 6 p.m., the rooms had been allocated to guests who booked several days before I did. Connecting room requests for same-day reservations will always be the most difficult to accommodate, according to Kimpton's front desk staff.

The friendly check-in staff worked hard to provide a solution. I was finally offered two rooms next to each other, or "adjacent" in hotel lingo.

As every parent knows, that's very different from connecting rooms.

Adjacent rooms aren't too much of a problem, especially if it's to provide extra space for tweens or teens who are reasonably independent. For families with younger children, it's much more comforting to have that interior door connecting the two rooms.

Marriott — The Westin Michigan Avenue Chicago

Time outlay: 35 minutes.
Result: Connecting rooms.
Lesson learned: Be tenacious; call the hotel after making your reservation and again on check-in day.

This Westin outpost in Chicago is a behemoth, with more than 420 rooms. It also boasts a prime location among the upscale stores on the glitzy Magnificent Mile. Before making a reservation, it seemed wise to do some research and figure out the odds of getting a connecting room on a blustery weekend in early April.

Unlike at the Kimpton, which has just 205 rooms, the scale and modernity of this Westin property would seem to work in my favor.

Bypassing the central reservation system, I called the hotel directly. The front desk agent gave cause for optimism, explaining they have a fair number of connecting rooms on each floor — plenty available for that evening, in fact — and assured me "it shouldn't be a problem."

As it was a same-day reservation, the front desk agent suggested I call central reservations again a couple of hours after I had booked my rooms to reiterate my request for connecting rooms.

If you are accustomed to just hitting enter on a website app, this constant back and forth will start to get a bit tedious. I spent around 35 minutes on the phone with the reservations agent confirming details that I was pretty sure were already saved in my Marriott Bonvoy account. Then, I set a timer on my watch for 2:30 p.m. to call the hotel directly and track my request. After some hold time on this second phone call, the agent told me I had been allocated two connecting rooms.

Check-in was seamless. There was no manic tapping on the computer to find an alternative or an empty apology. Within minutes, we were handed key cards for our connecting rooms.

Whether it was a credit to Marriott's customer service, sheer luck or dogged tenacity, for a few minutes it felt like we had been handed every parent's hotel world holy grail.

Hilton Chicago/Magnificent Mile Suites

Time invested: Five minutes.
Result: Connecting rooms.
Lesson learned: Booking connecting rooms on Hilton's website is quick, easy and stress-free.

In June 2021, when Hilton launched "Confirmed Connecting Rooms by Hilton," it promised to be a game changer.

In my experience, the ability to confirm connecting rooms online rather than on a lengthy phone call with plenty of hold time is a win.

We had heard mixed reviews from TPG staffers and readers about the new feature, so I was keen to test it out. On Hilton's website (you can also book using the app), I tried to book two connecting rooms at this Chicago property (right around the corner from the Westin) for two adults and two children. From signing into my Hilton Honors account to receiving my confirmation, the whole process took less than five minutes.

Once you enter your destination and travel dates, you have the option to add a second room. You can then allocate the adults and children to each room, and add their ages.

After selecting your hotel and clicking "View rates," you can choose the "Connecting Rooms" option. The caveat here is that you must book your rooms at least three days in advance to qualify for the connecting rooms guarantee.

You can browse the different room types and rates available, then make your selections for each room. You'll then proceed to the payment and confirmation pages.

For my Chicago stay, I had multiple room options and rates to choose from, even though my lead time was pretty short — just three days before my stay. I scanned room availability for the peak summer season, when family and group bookings surge, and there were still plenty of connecting rooms available across all types, rate categories and configurations. However, the prices for July and August were double what I paid in April.

Booking the rooms on the website (whether as a guest or as a Hilton Honors member) was, for the most part, simple and intuitive. Most importantly, I didn't have to follow up or figure out a backup plan in case the connecting rooms were not available at check-in. In my experience, Hilton took the hassle and uncertainty out of booking connecting rooms.

Hyatt Centric Chicago Magnificent Mile

Time invested: 18 minutes.
Result: Rooms allocated on opposite sides of the hotel.
Lesson learned: Calling reservations may avail a great family discount, but no guarantee of connecting rooms.

The Hyatt Centric is another downtown Chicago property with 419 rooms. There's no wow factor in terms of style, decor or lifestyle experience, but the location, amenities (including a decent-size pool and gym) and efficient service make it popular among business travelers and families.

Since there's no online booking option for connecting rooms, nor information on the Hyatt website, I called the central reservations line. Reminiscent of the Kimpton playbook, the reservations agent placed me on hold to call the property directly to confirm the availability and configuration of connecting rooms for that evening.

They had every iteration, it seemed: kings that connect to kings, queens that connect to doubles, even king suites that connect to standard kings. However, they "couldn't confirm or guarantee anything until check-in."

It turned into another lengthy process (18 minutes), but I made a request for a king room connecting to a double. I also called the hotel again in midafternoon to apply the lessons learned from my win at the Westin. In this particular instance, my call resulted in a significant discount that I was not aware existed and cannot be booked on the website.

We were offered a 50% "family plan" discount for booking a second room for children 18 years and under — a very worthy 18-minute time investment. This discount isn't available across the board, but it does happen. It's always worth asking if there is a family discount on the second room.

On the call, the front desk agent, who was initially rather vague and noncommittal, eventually said I had been allocated two connecting rooms as requested: a corner king that connected to a double.

A few hours later at check-in, the front desk agent told me that I did indeed have the connecting rooms. Just when I thought I was all set, the agent realized the double room I had booked was actually occupied by other guests. The agent assured me my second room was located "nearby" on the same floor. Since there was a long line forming behind me, I took the keys and went up to the rooms to check out what that arrangement looked like.

The second room was on the same floor, but not nearby. It was, in fact, on the opposite side of the hotel. This doesn't seem all that unusual.

"We have had some rooms that didn't end up as connecting so the family got split down the hall, which isn't nearly as convenient as that means each parent gets split into different rooms," recalls Hull.

For families like me with tweens and teens, that's generally not a problem. For families with younger children, the only option would be for parents to divide and conquer, or to request a refund and pile the whole family in one room.

Bottom line

Trying to reserve connecting rooms can add a layer of stress and uncertainty for families with young children who need and value a larger, more flexible hotel setup. Planning ahead and booking well in advance will certainly help improve your chances of securing an adjoining room. In my experience, calling the hotel front desk directly a couple of hours after making the reservation and again on the day of check-in made all the difference.

Large, modern hotels are more likely to have connecting rooms than historic, boutique hotels that prioritize charm, style and ambience over functionality.

Booking connecting rooms on Hilton's website was, indeed, a game changer. It was quick, easy and, most importantly, it eliminated the uncertainty that clouds busy travel days. Whenever I need connecting rooms in the future (unless there is a compelling reason to stay at another brand) I will be checking out all Hilton hotel options first.