When I’ve traveled to Chicago in the past, whether it be for a family vacation or to visit college friends, I’ve crashed on a couch, split the costs on an Airbnb or signed up for a hotel block with a larger group.
For my first adult solo trip to Chicago, I wanted to up my game. I have elite status with IHG One Rewards, so to maximize my rewards I focused on midrange IHG properties.
Kimpton is one of the largest boutique brands in the U.S., with properties in 52 cities across the world and around 20 new properties slated to debut over the coming years. In my mind, it’s one of the best hospitality brands out there, with affordable rates and distinctive lifestyle properties that exude an artsy vibe.
Book this, not that: Get the most value from your hotel points in Chicago
Based on my budget and brand affinity, I narrowed it down to the two Kimpton properties in Chicago (the Kimpton Gray and the Kimpton Hotel Monaco). Due to amenities, design and central location, the winner was the Kimpton Gray.
Located in the ornate, 19th-century New York Life Insurance building in the heart of the vibrant Chicago Loop (the central business district), what distinguishes the Kimpton Gray is its historical design married with contemporary flair.
The lobby is lavishly appointed with the hotel’s namesake Georgian gray marble, and throughout the public spaces, gilded light fixtures, local artworks, blue velvet curtains and leather furnishings create a plush, decadent ambience that’s great for either lounging or working.
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I personally loved working from the softly illuminated communal oak table in one area of the lobby. Truth be told, I was more comfortable working there than in my room. There was always an upbeat mood, with groups of travelers meeting to plan their days and co-workers finalizing presentations before meeting clients.
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One thing I love about Chicago is the metro and iconic L transit system. Coming from New York City, it’s a big plus to be able to take public transit throughout the city (and even the suburbs, if you choose) and navigate it easily. You can also take the L to get to both O’Hare International Airport (ORD) and Midway International Airport (MDW).
I flew into Southwest Airlines‘ Midway hub and then walked about 15 minutes to the Orange Line train. From there it was about a 35-minute direct L train ride to the Quincy stop, just a five-minute walk to the front steps of the hotel. Total cost out of pocket, $2.50.
A cab or ride-hailing service would have taken about the same amount of time, but costs between $40 and $50, depending on the time of day.
I planned my stay during Kimpton’s annual spring flash sale in late March. Room discounts ranged from 10% to 20% when booking directly with IHG, depending on the property.
After applying the 25% discount, my two-night stay in an Essential Room with one queen bed cost just $628.71. Rates were similar for both a Thursday- and Friday-night stay. If you choose to redeem IHG points, standard rewards start at 26,000 points per night. Not surprisingly, rates in Chicago tend to be higher during the balmy summer.
The Kimpton Gray is the kind of property that’s popular for weekend weddings and large group events, especially during spring and summer.
While the property’s historic architecture is certainly compelling, it lacked the aura of timeless luxury that I was hoping for, and there are plenty of signs that the hotel has been on the block for a while.
The hotel’s location at the heart of the business district makes it popular with business travelers. With a communal vibe in the lobby and thoughtful amenities, it’s a great place to work, mingle and plan a day of sightseeing.
I was getting a little stir-crazy in my room one day so I decided to relocate to the lobby and work there. With a great Wi-Fi connection and a drinks cart (complimentary coffee and citrus water), it was much more enjoyable to set up my laptop on the long wooden table and feel more in tune with the city’s energy.
At 5 p.m., the lobby took on a lively, convivial mood for Kimpton’s signature happy hour, with groups of friends and business associates gathering to kick-start an evening on the town.
Things I loved
- The daily happy hour in the lobby was a great way to start the evening.
- Central downtown location; it’s easy to access the airport and world-class tourist attractions like The Art Institute of Chicago.
- Decent pricing for a weekend stay in Chicago; less than an average of $300 per night.
- Vol. 39 cocktail bar for creative gin cocktails in a library-themed bar.
- I was able to use the online app check-in to secure my upgrade as a Diamond status member.
- Gym equipment was showing its age, making it an uninspiring place to work out.
- Poor service in the Fillmore restaurant, where food was just average and the breakfast menu limited.
- Certain blocks of the Loop can become quiet at night, which is not ideal for night owls who like to bar hop.
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HANNAH STRECK/THE POINTS GUY
I have stayed in my fair share of Kimpton hotels and it’s by far my favorite boutique hotel chain.
Thanks to my IHG One Rewards Diamond Elite status, I was upgraded to a one-bedroom king suite, which at over 500 square feet was certainly bigger than my studio apartment back in New York City.
Overall, the room did not flow well, mostly due to the strange furniture placement, which left some areas feeling bare and empty. I did appreciate the abundant natural light, though, which flowed through multiple windows.
Several design elements fostered a little more comfort and character — the sliding barn doors, deep soaking tub and contemporary bathroom fixtures have now all been entered into my Zillow home-search filters. I also really appreciated the functional armoire, which had an eclectic flower motif, where I stored my luggage.
A long desk set up against a wall provided a workspace of sorts and I was able to set up my laptop right next to the in-room Nespresso machine and feed my caffeine needs all day long.
But, far and away the highlight was the bathroom with a walk-in shower, lots of black granite and large mirrors above dual vanities. I am a sucker for hotel bathtubs and I couldn’t resist spending one evening in my deep soaking tub, luxuriating with a bottle of wine and a bath bomb.
Food and drink
There are a few on-site options where you can have a cocktail or grab a quick bite. All venues are open to the public and there was definitely a local vibe.
First up, the Fillmore. This is an Asian fusion restaurant where guests can also grab breakfast in the morning. I ate at this restaurant every day during my stay. I ordered a different dish each morning, ranging from eggs Benedict to apple French toast. Overall, the food was satisfying but rather predictable.
There was a small snafu. The restaurant did charge me for breakfast, even after I had presented my free hotel breakfast voucher, but the front desk took care of that upon checkout.
The service, though, was not up to the standard of previous Kimpton properties where I have stayed. It was clear it was very understaffed, with just one server working 10-plus tables. It took a while for my food to appear after ordering, and trying to get a refill on coffee, or any other beverage, was difficult.
Next up, Boleo. This massive rooftop restaurant and lounge is located on the 15th floor. There was an infectious party vibe for sure, and it’s great for catching a summer breeze, but don’t expect grand city views.
The creative menu draws inspiration from Peruvian and Argentine street food. A friend joined me for dinner and we ordered pan con chicharron sliders (mini pork belly burgers, $14), anticuchos de hongos (a mushroom dish, $12), yuca fries ($12) and arroz zambito (a rice pudding dessert, $9). The flavors were authentic and the service (unlike at Fillmore) was on point.
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HANNAH STRECK/THE POINTS GUY
Saving the best for last, Vol. 39 is a sophisticated cocktail bar. Appointed with plush leather chairs and couches surrounded by bookshelves lined with literary classics, the ambience lends itself to both solo and business travelers stopping by to unwind with a quick drink as well as couples enjoying a date night.
Instead of choosing from the cocktail menu, which features classic and Chicago-inspired libations, I asked the bartender to whip up a cocktail based on my favorite liquor and ingredients. I wasn’t disappointed.
Amenities and service
The check-in staff was incredibly warm and welcoming, reaching out on a daily basis to see if I had everything I needed and always on hand to point me in the right direction.
I had high expectations for the on-site spa. Being a solo trip and all, I had decided it was a good time to treat myself and indulge. But the “spa” wasn’t quite the luxe sanctuary I’d hoped for. It felt like an afterthought, a multipurpose room that the property had decided to transform into a spa. I still got a massage — a great massage, in fact — but in what felt like a supply closet in its former life. If you want a true spa experience, there are undoubtedly better options outside the hotel.
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HANNAH STRECK/THE POINTS GUY
The gym is a few steps from the spa and has a large selection of equipment, ranging from free weights to elliptical machines and yoga mats. Everything was kept in good condition, but it did feel like it was time that the gym was upgraded. The windows also looked right out into an alleyway. When I was on the treadmill, my view was of delivery vans and noisy garbage trucks.
Out and about
This was my first time back in Chicago since the onset of the COVID-19 pandemic, and honestly, I was a bit shocked. With many Chicagoans working remotely, the downtown area does feel sleepy after 6 p.m., with little foot traffic. But many of Chicago’s iconic attractions (and the city’s stunning lakefront) are located less than a 15-minute walk away. It’s also easy to access the trendy restaurants of River North, Fulton Market and the West Loop, all just a short cab ride away (or 20-to-40-minute walk).
If you are an architecture aficionado, the Kimpton is surrounded by many of Chicago’s iconic skyscrapers, like the Willis Tower (about an eight-minute walk from the hotel) and the Rookery. Other tourist attractions such as Millennium Park, Chicago’s renowned Art Institute and the Riverwalk are all less than a 20-minute walk away.
The hotel’s main entrance and lobby were accessible and wheelchair-friendly. The hotel has two entrances and they are both on the ground floor and connect directly to a hall of elevators that will take you to the lobby or your hotel room.
Travelers can book any of the five accessible room types, ranging from Essential Rooms to one-bedroom suites. All the rooms, except the queen bed Essential Rooms, have bathrooms retrofitted with roll-in showers. Rooms with queen-size beds have bathrooms that come with shower-tub combinations with grab bars.
All guest rooms have accessible communication features such as:
- Telephone ring signaler
- Visual alarm clock
- Bed shaker
- Telephone in-line amplifier
- Door knock alert
Diamond Elite status
My stay at the Kimpton Gray was my third experience with my newly acquired Diamond Elite status. As a newbie, I checked in by using the app, anticipating that I could go directly to my room upon arrival, but instead, I found that I had not been given my complimentary room upgrade — a perk of elite status. Luckily, the front desk team was able to honor my upgrade from an Essential Room to a one-bedroom suite.
Another perk of my status is free daily breakfast, one of the most coveted amenities of high-level loyalty status. While it’s great that I was able to save money on this solo trip, the Fillmore restaurant (which is not owned and operated by the property) was subpar at best.
My late-checkout perk also alleviated a lot of stress on my final day. With a late flight out of Chicago and needing to catch up on some work, it was extremely convenient to be able to stay in my room till 2 p.m.
I had secured a round-trip flight to Chicago using the last of my stash of 11,000 Southwest points during one of the airline’s seasonal spring sales. Combined with booking my room during Kimpton’s “Beginning of Summer” sale, I spent a grand total of around $651 for all hotel and transportation expenses.
By making the most of my Diamond status perks, and redeeming Southwest points, the total price was something I could swallow for a solo trip. Without my perks, points or taking advantage of seasonal sales, I would have paid more than $900 for my hotel and transportation.
But would I check back in to the Kimpton Gray? I would say, probably not. While it was a convenient, central, lively and functional place to spend a weekend, there was nothing special or memorable about the property that would make me want to return. Long story short: Thanks to being just a little bit points and miles savvy, I got my money’s worth.