Chicago Rd, Oswego, IL Property Records

Kendall County property records for 53 addresses on Chicago Rd, Oswego, IL · Last verified August 2026

Chicago Rd Highlights

Properties 53
Median Sale Price $290,000
Deeds and Mortgages on File 79
Median Price per Sqft $130
Owner Occupied 53%
Median Annual Tax Bill $6,853
Median Year Built 1960
Median Ownership Tenure 10 years

Properties on Chicago Rd

Owner names and prior sale amounts shown locked below are available instantly with a free trial.

55 Chicago Rd

3,360 sqft · 0.546 acres

Last Sale Tax Bill Prior Sale Owner Records
$270,000Jan 1998 $9,2422024 2 Names on Record AssessorUpdated Jun 2026

58 Chicago Rd

3,510 sqft · Built 1940 · 0.322 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$560Jan 2008 $6,1712024 Amount on Record Aug 1996 1 Name on Record Assessor + 1 DocumentUpdated Jun 2026

67-69 Chicago Rd

5 bd · 2 ba · 2,410 sqft · 0.2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$65,000Jan 2013 $6,8532024 —Oct 2011 1 Name on Record AssessorUpdated Jun 2026

82 Chicago Rd

1 ba · 976 sqft · 0.202 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$112,000Nov 2015 $5,9612024 Amount on Record Mar 1994 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

105 Chicago Rd

1 ba · 2,500 sqft · 0.308 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$450,000Sep 2025 $7,9212024 Amount on Record Oct 1998 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

108 Chicago Rd

5 bd · 2.5 ba · 2,508 sqft · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$56,000Sep 2010 $2,0692025 Amount on Record Aug 2010 1 Name on Record AssessorUpdated Jul 2026

112 Chicago Rd

3 ba · 2,694 sqft · 0.386 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$194,000Jun 2019 $9,9302024 Amount on Record May 1993 2 Names on Record Assessor + 1 DocumentUpdated Jun 2026

116 Chicago Rd

1 ba · 1,584 sqft · 0.285 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$113,000Jan 2014 $6,6552024 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

117-119 Chicago Rd

6 bd · 3 ba · 2,940 sqft · 0.201 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$305,000Aug 2022 $10,3252024 —Jan 2015 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

120 Chicago Rd

1.5 ba · 1,392 sqft · 0.19 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$5,7462024 —Aug 2010 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

124 Chicago Rd

4 bd · 2 ba · 1,650 sqft · 0.789 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$205,000Jul 2026 $4,5542025 2 Names on Record Assessor + 1 DocumentUpdated Aug 2026

125 Chicago Rd

3 bd · 1 ba · 1,622 sqft · 0.189 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$196,000Sep 2014 $6,9302024 Amount on Record Aug 1991 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

155 Chicago Rd

4 bd · 2 ba · 2,209 sqft · 0.277 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Sep 2024 $7,2082024 Amount on Record Mar 1999 1 Name on Record Assessor + 3 DocumentsUpdated Aug 2026

156 Chicago Rd

3 bd · 2 ba · 1,904 sqft · 0.6 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$40,000Dec 2022 $5,8692024 —Dec 2022 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

163-165 Chicago Rd

6 bd · 3 ba · 2,892 sqft · 0.274 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$317,500Dec 2020 $10,8942024 Amount on Record Oct 2001 2 Names on Record Assessor + 4 DocumentsUpdated Aug 2026

170 Chicago Rd

3 bd · 1 ba · 1,014 sqft · 0.6 acres

Last Sale Tax Bill Prior Sale Owner Records
$32,000Feb 2021 $2,0692025 Amount on Record Sep 2014 2 Names on Record Assessor + 4 DocumentsUpdated Aug 2026

175 Chicago Rd

4 bd · 2 ba · 2,678 sqft · 0.539 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$350,000Apr 2022 $8,2022024 Amount on Record Nov 2012 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

204 Chicago Rd

2 bd · 2 ba · 1,535 sqft · 0.5 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$155,000Feb 2019 Amount on Record Sep 2000 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jun 2026

207 Chicago Rd

3 bd · 1.5 ba · 2,378 sqft · 0.301 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$80,000Nov 1987 $3,3552024 1 Name on Record Assessor + 1 DocumentUpdated Jun 2026

212 Chicago Rd

3 bd · 2 ba · 1,744 sqft · 0.5 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$173,000May 2016 $7,0202024 Amount on Record Aug 2014 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

217 Chicago Rd

2 bd · 1 ba · 1,036 sqft · 0.286 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,3692024 1 Name on Record AssessorUpdated Jun 2026

224 Chicago Rd

4 bd · 1.5 ba · 1,976 sqft · 0.559 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$278,000Jun 2018 $7,2142024 Amount on Record Mar 2017 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

238 Chicago Rd

3 bd · 1 ba · 1,144 sqft · 0.93 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$270,000Sep 2023 $6,8112024 Amount on Record May 1986 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

256 Chicago Rd

4 bd · 1.5 ba · 2,700 sqft · 0.7 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$460,000Apr 2025 $7,8112024 Amount on Record Oct 2020 2 Names on Record Assessor + 5 DocumentsUpdated Aug 2026

263 Chicago Rd, #265

4 bd · 2 ba · 1,614 sqft · 0.242 acres

Last Sale Tax Bill Prior Sale Owner Records
$184,000Nov 2016 $6,1582024 Amount on Record Jul 2009 2 Names on Record Assessor + 4 DocumentsUpdated Jun 2026

267 Chicago Rd

3 bd · 1.5 ba · 1,196 sqft · 0.179 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$142,000May 2017 $6,2892024 Amount on Record Apr 2017 1 Name on Record Assessor + 3 DocumentsUpdated Jun 2026

268 Chicago Rd, #270

4 bd · 3 ba · 2,224 sqft · 0.839 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$87,900Mar 1985 $9,1342024 1 Name on Record Assessor + 2 DocumentsUpdated Jun 2026

278 Chicago Rd

4 bd · 3 ba · 2,224 sqft · 1.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$265,000Oct 2019 $8,2162024 —Jun 2019 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated Jun 2026

280 Chicago Rd

3,376 sqft · Built 1968 · 0.354 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,4622024 2 Names on Record AssessorUpdated Jun 2026

281 Chicago Rd

3 bd · 1 ba · 988 sqft · 0.46 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$290,000Aug 2025 $6,1412024 Amount on Record Feb 2019 1 Name on Record Assessor + 4 DocumentsUpdated Jun 2026

305 Chicago Rd

3 bd · 1.5 ba · 1,104 sqft · 0.44 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$119,000Sep 2012 $6,2082024 —May 2012 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

308 Chicago Rd

4 bd · 2 ba · 2,336 sqft · 0.451 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,0732024 2 Names on Record AssessorUpdated Jun 2026

309 Chicago Rd

3 bd · 1 ba · 1,008 sqft · 0.23 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$138,000Jun 2004 $5,7012024 Amount on Record Apr 1984 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

311 Chicago Rd

3 bd · 2 ba · 977 sqft · 0.23 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$80,500Dec 1987 $5,4822024 Amount on Record Sep 1986 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

312 Chicago Rd

3 bd · 1.5 ba · 1,001 sqft · 0.451 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$46,500Jun 1976 $7,5452024 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

313 Chicago Rd

4 bd · 3 ba · 1,689 sqft · 0.23 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$137,000Mar 1994 $5,1042024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

314 Chicago Rd

3 bd · 4 ba · 1,562 sqft · 0.903 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$180,000Jul 2013 $7,1462024 Amount on Record Jan 2006 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

315 Chicago Rd

3 bd · 1.5 ba · 1,028 sqft · 0.23 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$127,000Feb 2016 $5,7142024 Amount on Record Oct 2003 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

316 Chicago Rd

4 bd · 3 ba · 2,958 sqft · 2.91 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$275,000Aug 1989 $15,0222024 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

317 Chicago Rd

5 bd · 2.5 ba · 1,056 sqft · 0.23 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$180,000Nov 2017 $7,1842024 Amount on Record Oct 2008 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

318 Chicago Rd

0.787 acres

Last Sale Tax Bill Prior Sale Owner Records
$70,000Aug 2020 $2,4262024 —Dec 2002 2 Names on Record Assessor + 1 DocumentUpdated Jun 2026

319 Chicago Rd

4 bd · 1.5 ba · 1,122 sqft · 0.23 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$152,500Jul 2016 $7,4802024 —Jan 1998 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

320 Chicago Rd

4 bd · 2.5 ba · 2,632 sqft · 0.903 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$193,700Feb 1993 $12,2372024 Amount on Record Jan 1989 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

321 Chicago Rd

3 bd · 1.5 ba · 864 sqft · 0.23 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$6,6262024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

323 Chicago Rd

4 bd · 2.5 ba · 2,280 sqft · 0.23 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$315,000Mar 2026 $8,7132024 Amount on Record Jan 2026 2 Names on Record Assessor + 2 DocumentsUpdated Jun 2026

324 Chicago Rd

0.634 acres

Last Sale Tax Bill Prior Sale Owner Records
$39,000Oct 2005 $1,5062024 Amount on Record Jan 1989 1 Name on Record Assessor + 1 DocumentUpdated Jun 2026

325 Chicago Rd

3 bd · 1.5 ba · 1,158 sqft · 0.231 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$201,000Aug 2004 $7,3492024 Amount on Record Sep 1995 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

326 Chicago Rd

4 bd · 2.5 ba · 2,506 sqft · 0.732 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$155,000Mar 2021 $10,4692024 Amount on Record Aug 2011 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

356 Chicago Rd

1,716 sqft · Built 1920 · 0.608 acres

Last Sale Tax Bill Prior Sale Owner Records
$170,000Dec 2017 $5,5732024 Amount on Record Dec 1997 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

401 Chicago Rd

0.393 acres

Last Sale Tax Bill Prior Sale Owner Records
1 Name on Record Owner Occupied AssessorUpdated Jun 2026

405 Chicago Rd

2,392 sqft · Built 1993 · 0.669 acres

Last Sale Tax Bill Prior Sale Owner Records
$550,000Jul 2004 $6,8342024 Amount on Record Nov 1992 1 Name on Record AssessorUpdated Jun 2026

410 Chicago Rd

29,918 sqft · Built 2000 · 2.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,600,000Dec 2018 $44,0982024 Amount on Record Dec 2000 1 Name on Record Assessor + 3 DocumentsUpdated Jun 2026

411 Chicago Rd

1,421 sqft · Built 2004 · 0.789 acres

Last Sale Tax Bill Prior Sale Owner Records
$542,000Sep 2011 $7,0152024 Amount on Record Aug 2001 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

Property Records in Nearby Streets