Live data — refreshed 5:18 PM CDT
Apartments in Old Town with a Pool
173 apartments available in Old Town with a Pool. Median rent $3,200. Live prices and availability.
About Old Town: Triangle of late-1800s graystones and brick three-flats between LaSalle and Wells, anchored by Second City and the Old Town School of Folk Music. Tree-lined streets, walkable to Lincoln Park or the lake.
$3,200
Median rent
$1,947
Cheapest
Available now
$1,947
Studio · 603sf
Cobbler Square Lofts #C300
Old Town
$1,956
Studio · 570sf
Cobbler Square Lofts #E201
Old Town
$2,091
Studio · 646sf
Cobbler Square Lofts #D311
Old Town
$2,092
Studio · 646sf
Cobbler Square Lofts #D308
Old Town
$2,095
Studio · 609sf
Cobbler Square Lofts #D406
Old Town
$2,291
Studio · 625sf
Cobbler Square Lofts #C100
Old Town
$2,297
Studio · 855sf
Cobbler Square Lofts #A308
Old Town
$2,350
Studio · 515sf
North Vine #0814
Old Town
$2,379
-0.5BR · 573sf
1225 Old Town #0711
Old Town
$2,380
Studio · 543sf
1225 Old Town #0812
Old Town
$2,395
Studio · 627sf
Cobbler Square Lofts #D103
Old Town
$2,425
Studio · 505sf
Old Town Park 3 #0702
Old Town
$2,425
Studio · 505sf
Old Town Park 3 #1905
Old Town
$2,446
-0.5BR · 595sf
1225 Old Town #0817
Old Town
$2,448
Studio · 565sf
Old Town Park 2 #0802
Old Town
$2,463
Studio · 565sf
Old Town Park 2 #1502
Old Town
$2,465
Studio · 589sf
Cobbler Square Lofts #D101
Old Town
$2,469
Studio · 569sf
Xavier #1510
Old Town
$2,473
Studio · 547sf
Xavier #1013
Old Town
$2,483
Studio · 505sf
Old Town Park 3 #2705
Old Town
$2,488
Studio · 505sf
Old Town Park 3 #3104
Old Town
$2,491
Studio · 554sf
Cobbler Square Lofts #D404
Old Town
$2,523
Studio · 505sf
Old Town Park 3 #3304
Old Town
$2,524
Studio · 560sf
Cobbler Square Lofts #D405
Old Town
$2,526
-0.5BR · 595sf
1225 Old Town #0917
Old Town
$2,526
Studio · 550sf
Cobbler Square Lofts #D505
Old Town
$2,542
Studio · 608sf
Cobbler Square Lofts #D502
Old Town
$2,543
Studio · 565sf
Old Town Park #1913
Old Town
$2,553
Studio · 505sf
Old Town Park 3 #3402
Old Town
$2,576
Studio · 736sf
Cobbler Square Lofts #F202
Old Town
Top buildings for this search
- Cobbler Square Lofts$1,947–$4,187
- Old Town Park 3$2,425–$23,177
- Old Town Park 2$2,448–$7,780
- North Vine$2,350–$7,432
- Xavier$2,469–$4,363
- Old Town Park$2,543–$4,879
- 1225 Old Town$2,379–$6,076
- 1325 N Wells$3,290–$4,300
Frequently asked
What's the cheapest in Old Town with a Pool right now?
Cobbler Square Lofts #C300 at $1,947/month, 603 square feet. Located at 1350 N Wells St.
How many apartments are available in Old Town with a Pool?
Apartments are currently listed in Old Town with a Pool. Median rent is $3,200.
Which buildings in Old Town offer apartments with a Pool?
Top buildings by current inventory: Cobbler Square Lofts, Old Town Park 3, Old Town Park 2, North Vine, Xavier.
Which Old Town buildings have a pool?
The buildings matching this search all feature a pool — most are rooftop pools open seasonally (typically May through September). Top buildings: Cobbler Square Lofts, Old Town Park 3, Old Town Park 2, North Vine.
Compare Old Town to nearby neighborhoods
More in Old Town
Updated September 20, 2026 at 5:18 PM CDT. No paid placement.