All Real Estate Services are offered through Chalet Realty (DBA of Mahalla Realty LLC).
Texas Real Estate Commission Consumer Protection NoticeTexas Real Estate Commission Information About Brokerage ServicesTREC DisclaimerChalet (“GetChalet Inc.”) provides general educational content and tools for real-estate investors. Chalet is not a law firm, CPA firm, or investment adviser, and does not provide tax, legal, or accounting advice. Nothing on this site creates a CPA-client, attorney-client, or fiduciary relationship. Tax laws change, and state rules may differ from federal rules (e.g., California decouples from federal bonus depreciation). Always consult your own qualified tax and legal professionals about your specific situation.
The term 'Airbnb' is used on our site in a colloquial sense, akin to saying 'I am going to Airbnb it.' This usage is intended to refer broadly to the concept of short-term rentals and not specifically to the Airbnb platform or services. Airbnb, Inc. is not affiliated with Chalet, nor does it endorse or sponsor our services. We use the term in this generalized manner to easily convey the idea of participating in short-term rental activities, recognizing 'Airbnb' as a term familiar to many in this context.
Affiliate & Referral Disclosure. Chalet may receive referral fees or other consideration when you engage with featured agents, lenders, cost-seg providers, or other partners referenced on this site. These relationships may influence which partners we present. We follow the FTC Endorsement Guides and aim to disclose material connections clearly and conspicuously.
Chalet (DBA of GetChalet Inc.) is not affiliated, associated, authorized, endorsed by, or in any way officially connected with Airbnb, Airbnb.com, or any of its subsidiaries or its affiliates. The official Airbnb website can be found at http://www.airbnb.com. The name "Airbnb" as well as related names, marks, emblems and images are registered trademarks of Airbnb, Inc.
602 N May St unit 65, Chicago, IL, USA
Covers its debt with margin to spare at the current price.
Investment potential
Your scenario · adjust the levers below or open advanced settings to see how returns change
$99,429
$8,286/mo · at 63% occupancy & $536/night
$40,115
$3,343/mo after costs & mortgage
Cap rate
14%
Cash-on-cash
26.7%
DSCR
2.34
Confidence
Your assumptions
Revenue
$99,429/yr
Market avg: $99,429/yr · 63% occ · $536 ADR
Financing
$29,939/yr
Operating costs
$29,376/yr
How this property compares to similar short-term rentals nearby.
Comparable set · 50 properties
$218–$701
Median $537
39%–86%
Median 63%
$45.5K–$163.5K
Median $98.5K
207–365
Median 316
This property · $99.4K
Comparable properties (50)
Cash flow potential High · Appreciation potential Medium
341 days available · 281 days booked ·
304 days available · 227 days booked ·
356 days available · 288 days booked ·
321 days available · 203 days booked ·
300 days available · 217 days booked ·
332 days available · 189 days booked ·
320 days available · 238 days booked ·
324 days available · 208 days booked ·
353 days available · 220 days booked ·
325 days available · 268 days booked ·
365 days available · 273 days booked ·
319 days available · 197 days booked ·
314 days available · 160 days booked ·
365 days available · 161 days booked ·
284 days available · 208 days booked ·
296 days available · 223 days booked ·
256 days available · 185 days booked ·
285 days available · 199 days booked ·
274 days available · 177 days booked ·
306 days available · 178 days booked ·
282 days available · 213 days booked ·
272 days available · 157 days booked ·
330 days available · 191 days booked ·
331 days available · 206 days booked ·
298 days available · 193 days booked ·
365 days available · 241 days booked ·
243 days available · 156 days booked ·
317 days available · 174 days booked ·
329 days available · 161 days booked ·
337 days available · 191 days booked ·
269 days available · 172 days booked ·
336 days available · 260 days booked ·
365 days available · 211 days booked ·
207 days available · 127 days booked ·
365 days available · 199 days booked ·
306 days available · 201 days booked ·
298 days available · 154 days booked ·
365 days available · 177 days booked ·
243 days available · 149 days booked ·
365 days available · 218 days booked ·
275 days available · 136 days booked ·
343 days available · 176 days booked ·
226 days available · 113 days booked ·
326 days available · 273 days booked ·
288 days available · 111 days booked ·
365 days available · 174 days booked ·
240 days available · 160 days booked ·
211 days available · 156 days booked ·
233 days available · 94 days booked ·
295 days available · 134 days booked ·
Revenue and occupancy reflect Chalet's modeled estimates from observed booking activity for comparable active listings. Individual results vary with management, seasonality, and pricing.
Who this property is for
The same property is a great buy for one investor and a trap for another. Here's the honest read.
1031 / high-equity buyer
~$123.5K
Year-1 tax shield
Buying with cash or low leverage removes the debt-coverage problem entirely, so the thesis rests on appreciation plus a large first-year write-off. At roughly 25% of purchase price, the shield is substantial enough to carry the deal on its own.
DSCR cash-flow buyer
2.34
DSCR at asking
At asking price the property clears the 1.20 DSCR most lenders require, so it should qualify for DSCR financing and cover its own debt service from day one. This is the buyer this deal is built for.
Price-disciplined buyer
—
Break-even purchase price
Even a deep discount doesn't get this deal to break even within a realistic range, so there's no price anchor to negotiate toward. A price-disciplined buyer should pass unless the revenue assumptions change.
For a buyer who materially participates and qualifies for the STR tax treatment.
$123.5K
Estimated first-year deduction · range $102.5K–$140.8K
Why this matters here
At a marginal bracket, this deduction can be worth $37.9K–$52.1K in estimated federal tax saved.
This only applies if you meet the IRS material-participation tests for short-term rentals and are not using a full-service property manager.
Estimate, subject to CPA review. Cost-segregation percentages shown here are illustrative and depend on an actual study of the property.
Some states do not conform to federal bonus depreciation, so your state may not allow the same first-year treatment shown above.
Chalet can introduce a cost-segregation partner — this is not tax, legal, or financial advice.
How cash-on-cash return moves with purchase price. The marked line is break-even (1.0 DSCR).
At this price: cash-on-cash +26.7%, DSCR 2.34, cash flow $40,115/yr
| Price vs asking | Price | Cash-on-cash | DSCR | Band |
|---|---|---|---|---|
| -25% | $375,000 | 40.5% | 3.12 | Positive |
| -22% | $390,000 | 38.5% | 3.00 | Positive |
| -15% | $425,000 | 34.2% | 2.75 | Positive |
| -8% | $460,000 | 30.5% | 2.54 | Positive |
| Asking | $500,000 | 26.7% | 2.34 | Positive |
| +8% | $540,000 | 23.5% | 2.17 | Positive |
| +15% | $575,000 | 21.0% | 2.03 | Positive |
Break-even price
Out of range
This deal does not reach break-even within ±25% of asking.
Discount needed
—
The gap between asking and the price a cash-flow buyer can underwrite.
If refi to 5.5% in 24 mo
+$4,388/yr
Illustrative cash-flow improvement at asking price if rates fall. Planning figure, not a forecast.
Annual avg $8,286 · peaks at $11,114 in May
Annual avg 62% · peaks at 74% in Jun
$3,343/mo after all expenses
Cash to close
Down payment, closing costs, and furnishing
$145,000
Return on cash:44.9%
You qualify for STR financing
Your DSCR is 2.34 · lenders typically require 1.0+.
Get matched with 2–3 vetted STR lenders, free.
What the deal returns over the hold — including the tax shield, which is the whole point for an appreciation buyer.
Levered IRR
46.4%
over 5-yr hold, with tax shield
Equity multiple
3.5×
total proceeds vs. $145,000 invested
Projected value at exit
$638,141
year 5 · 5.0% annual appreciation
Tax shield contribution
+10.4 pts
of IRR comes from year-1 depreciation
| Year | Equity | Appreciation | Cumulative cash flow | Total value |
|---|---|---|---|---|
| Year 1 | $128,809 | $25,000 | $85,810 | $239,619 |
| Year 2 | $132,894 | $51,250 | $127,416 | $311,560 |
| Year 3 | $137,274 | $78,813 | $170,537 | $386,623 |
| Year 4 | $141,970 | $107,753 | $215,193 | $464,917 |
| Year 5 | $147,007 | $138,141 | $261,410 | $546,557 |
Projection, not a promise.
Assumes 5.0% annual appreciation, 1.5% rent growth (operating costs held flat), and that the property qualifies for short-term-rental tax treatment. The year-1 depreciation shield depends on a real cost-segregation study and your tax situation — consult a CPA.
Appreciation is the dominant driver of this return. When cash flow is negative, the deal depends on the property gaining value — it is not paying for itself from income.
Appreciation, rent growth, and financing rates are editable under Edit financials.
STR deals turn on local rules and demand that a generalist agent misses. Chalet matches you with a vetted Chicago agent who knows which properties actually cash flow — and which to avoid.
© 2026 Chalet. All rights reserved.
This analysis is generated by Chalet's Airbnb Calculator
Visit getchalet.com for more tools
Real Estate Investment Analysis & Market Insights
Disclaimer. This page and the data presented are for informational purposes only. The information provided should not be construed as financial, legal, or investment advice. Market conditions can change rapidly, and past performance does not guarantee future results. Always consult with qualified professionals before making investment decisions.
1220 W Hubbard St, Chicago, IL 60642, USA
4 bed 2 bath 10 guests
Revenue
$77,563/yr
Daily Rate
$501
Occupancy
0.5%
1340 W Hubbard St, Chicago, IL 60642, USA
2 bed 3 bath 6 guests
Revenue
$69,809/yr
1945 N Howe St, Chicago, IL 60614, USA
2 bed 2 bath 6 guests
Revenue
$58,680/yr
610 W Kemper Pl, Chicago, IL 60614, USA
3 bed 2 bath 8 guests
Revenue
$64,360/yr
560 W Fullerton Pkwy, Chicago, IL 60614, USA
2 bed 1 bath 6 guests
Revenue
$42,464/yr
2425 West Lyndale Street, Chicago, IL, USA
3 bed 1 bath 8 guests
Revenue
$43,540/yr
Daily Rate
$394
Occupancy
0.7%
Daily Rate
$349
Occupancy
0.7%
Daily Rate
$447
Occupancy
0.6%
Daily Rate
$269
Occupancy
0.6%
Daily Rate
$268
Occupancy
0.6%