What does the Airbnb management market in Chicago look like?

This snapshot compares 303 Airbnb management companies managing 3,992 tracked listings in Chicago. The table above ranks them by the VRM Index and compares guest rating, Guest Favorite share, occupancy against the group median, ADR, size, and operating scale. Median market ADR is $163, median occupancy, the table benchmark, is 65%, and the top 5 operators manage 16% of tracked listings. Data note: These figures are estimates based on Airbtics' tracked Airbnb and short-term rental data. Actual occupancy, ADR, and revenue may differ from a company's internal PMS or owner reports. We have refined this methodology over 6 years and use our best effort to keep the data accurate and useful.

How can I correct a result on this page?

If you are an employee of any of the companies on this page and would like to correct the result, please submit the form via this link. We can't guarantee the timeline, but we do typically update this every quarter.

Who are the best Airbnb management companies in Chicago?

Of the 296 management companies we track in Chicago, Hanna And Mark leads on Guest Favorites: 100% of its 11 listings carry Airbnb's Guest Favorite badge, against a 14% median across the city. It runs a 4.9 guest rating at 44% occupancy. Guest Favorite share is the clearest single read on consistent guest experience, but the table above lets you weigh it against occupancy, daily rate, and operating scale.

Which Airbnb management companies in Chicago have the best guest reviews?

Serg (5.0), Caryl (5.0) and Will (5.0) hold the highest guest ratings among Chicago management companies with at least five active listings. Where ratings tie we rank by the share of listings holding Airbnb's Guest Favorite badge. Serg ranks first because 100% of its listings are Guest Favorites.

Which Airbnb management company in Chicago is the best one for me?

It depends on what you are optimising for. Blueground is the most established operator in Chicago with 289 listings, and Flexhome posts the strongest booking performance at 94% occupancy. Alexandra earns the most per listing at $175,170 a year, Zilllow positions highest on nightly rate at $970, and Joan has grown its portfolio fastest at +400% year on year. Treat these as starting points rather than a final recommendation: the VRM Index in the table above folds guest reviews, Guest Favorite share, occupancy and operating scale into a single score if you would rather compare on overall strength.

Best Airbnb Management Companies in Chicago, United States

Name: Top Airbnb Management Companies in Chicago, United States
Creator: Airbtics

Updated October, 2026

Based on data from Airbtics, this page lists leading Airbnb management companies ranked by the VRM Index, a score out of 100 combining guest reviews, Guest Favorite share, occupancy, and local operating experience. Verified operators with a public website include a link to their full profile.

Companies are ranked by the VRM Index, a score out of 100 based on guest satisfaction, occupancy and operating scale.

How the score works

Factor	Maximum points
Guest rating	30
Guest Favorite share	30
Occupancy	30
Operating scale	10

Guest ratings earn 0 points at 4.3 or below, increasing evenly to 30 points at 4.8 or above.

Guest Favorite share and occupancy each earn 0.3 points per percentage point. For example, 75% occupancy earns 22.5 points. The occupancy comparison against the median does not affect the score.

Operating scale

We add together the days each company’s listings were live in this market over the past 12 months, converted to listing-months (days / 30). For example, 10 listings live every day of the past year contribute 120 listing-months.

Small: fewer than 120 listing-months — 0 points.
Medium: 120–240 listing-months — 5 points.
Large: more than 240 listing-months — 10 points.

These labels reflect last-12-month portfolio activity, rather than the company’s age.

How to read the table

Occupancy and daily rate are listing-weighted averages for the company’s Airbnb listings in this market over the past 12 months.
Guest Favorites shows the percentage of its listings currently carrying Airbnb’s Guest Favorite badge.
The +/− occupancy figure shows the difference in percentage points from the median occupancy of the companies in this table.
Rating highlights identify scores of 4.8 or above as standouts and scores below 4.4 as low.

Which listings are included

We include listings in this market that have been listed for more than 90 days and received at least one booking in the past 12 months. These criteria mean our listing counts may differ from those on a company’s Airbnb host profile.

Switch market

Rank	VRM Indexout of 100	VRM Name	Review Score	Guest Favorites	Occupancyvs median 65%	Average Daily Rate	Number of Listings	Operating scale	Portfolio analytics
#1	88	Nicole And Matt	4.9 👑	90%	86% +21	$365	21	Medium	View portfolio →
#2	87	Laura T	4.9 👑	81%	91% +26	$181	16	Medium	View portfolio →
#3	86	David	4.9 👑	83%	87% +22	$219	29	Medium	View portfolio →
#4	86	The Walton Residence	5 👑	100%	86% +21	$491	5	Small	View portfolio →
#5	86	Victor	4.9 👑	100%	85% +20	$129	5	Small	View portfolio →
#6	85	Anthony	4.9 👑	100%	83% +18	$289	6	Small	View portfolio →
#7	84	Chicago Hospitality Club	4.8 👑	65%	81% +16	$499	39	Large	View portfolio →
#8	83	Ari	4.9 👑	100%	78% +13	$142	5	Small	View portfolio →
#9	83	Josh	4.9 👑	100%	77% +12	$453	7	Small	View portfolio →
#10	82	Caryl	5 👑	100%	75% +10	$253	6	Small	View portfolio →
#11	82	Peter	5 👑	100%	75% +10	$322	5	Small	View portfolio →
#12	82	Hubbard Holdings	4.9 👑	53%	87% +22	$678	45	Large	View portfolio →
#13	82	Joan	4.9 👑	100%	73% +8	$218	10	Small	View portfolio →
#14	81	Trove	4.8 👑	70%	83% +18	$304	23	Medium	View portfolio →
#15	80	Stephanie	4.8 👑	52%	83% +18	$253	34	Large	View portfolio →
#16	80	Aaron	4.9 👑	80%	88% +23	$207	5	Small	View portfolio →
#17	79	Ensavi	4.8 👑	67%	97% +32	$107	6	Small	View portfolio →
#18	78	Victor	4.9 👑	85%	76% +11	$58	14	Small	View portfolio →
#19	78	Afsha	4.9 👑	83%	78% +13	$181	6	Small	View portfolio →
#20	78	Will	5 👑	100%	59% -6	$490	5	Small	View portfolio →

Data Seen By

BiggerPockets

Compare all 296 companies with full metrics

Occupancy, daily rate, reviews, and listing-level history for every manager in Chicago in the Airbtics app.

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All 296 Airbnb management companies tracked in Chicago

Ranked by the VRM Index, continuing from the table above.

Chicago Airbnb Investor Guide

Chicago Airbnb management company FAQs

What does the Airbnb management market in Chicago look like?

This snapshot compares 303 Airbnb management companies managing 3,992 tracked listings in Chicago. The table above ranks them by the VRM Index and compares guest rating, Guest Favorite share, occupancy against the group median, ADR, size, and operating scale. Median market ADR is $163, median occupancy, the table benchmark, is 65%, and the top 5 operators manage 16% of tracked listings.

Data note: These figures are estimates based on Airbtics' tracked Airbnb and short-term rental data. Actual occupancy, ADR, and revenue may differ from a company's internal PMS or owner reports. We have refined this methodology over 6 years and use our best effort to keep the data accurate and useful.
How can I correct a result on this page?

If you are an employee of any of the companies on this page and would like to correct the result, please submit the form via this link. We can’t guarantee the timeline, but we do typically update this every quarter.
Who are the best Airbnb management companies in Chicago?
Of the 296 management companies we track in Chicago, Hanna And Mark leads on Guest Favorites: 100% of its 11 listings carry Airbnb's Guest Favorite badge, against a 14% median across the city. It runs a 4.9 guest rating at 44% occupancy. Guest Favorite share is the clearest single read on consistent guest experience, but the table above lets you weigh it against occupancy, daily rate, and operating scale.
Which Airbnb management companies in Chicago have the best guest reviews?
Serg (5.0), Caryl (5.0) and Will (5.0) hold the highest guest ratings among Chicago management companies with at least five active listings. Where ratings tie we rank by the share of listings holding Airbnb's Guest Favorite badge. Serg ranks first because 100% of its listings are Guest Favorites.
Which Airbnb management company in Chicago is the best one for me?
It depends on what you are optimising for. Blueground is the most established operator in Chicago with 289 listings, and Flexhome posts the strongest booking performance at 94% occupancy. Alexandra earns the most per listing at $175,170 a year, Zilllow positions highest on nightly rate at $970, and Joan has grown its portfolio fastest at +400% year on year. Treat these as starting points rather than a final recommendation: the VRM Index in the table above folds guest reviews, Guest Favorite share, occupancy and operating scale into a single score if you would rather compare on overall strength.

Explore vacation rental manager analytics on Airbtics

You can access detailed analytics on vacation rental managers, including their KPIs and their listings’ historical performance, on the Airbtics platform. Top operators use this data for benchmarking and to stay ahead of the market.

Airbnb property manager host insights dashboard in the Airbtics app, showing listings, average rating, revenue, occupancy, daily rate, inventory growth, and a map of managed listings

Explore managers in the app →