Live data — refreshed 12:46 AM CDT
Apartments in Old Town with a Rooftop
225 apartments available in Old Town with a Rooftop. Median rent $3,380. Live prices updated every few hours from the property's own leasing systems.
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.
225
Available
14
Buildings
$3,380
Median rent
$2,095
Cheapest
Available now (30 of 225)
$2,095
Studio · 609sf
Cobbler Square Lofts #D406
Old Town
$2,168
Studio · 515sf
North Vine #0814
Old Town
$2,172
Studio · 615sf
Cobbler Square Lofts #E403
Old Town
$2,283
2BR · 958sf
Schiller Place Apartments #203
Old Town
$2,283
2BR · 936sf
Schiller Place Apartments #202
Old Town
$2,291
Studio · 625sf
Cobbler Square Lofts #C100
Old Town
$2,345
Studio · 510sf
1250 LaSalle #0807
Old Town
$2,350
-0.5BR · 546sf
1225 Old Town #0424
Old Town
$2,355
1BR · 649sf
1250 LaSalle #0504
Old Town
$2,363
Studio · 565sf
North Vine #0608
Old Town
$2,395
1BR · 662sf
1250 LaSalle #0911
Old Town
$2,399
1BR · 630sf
1250 LaSalle #0506
Old Town
$2,412
-0.5BR · 546sf
1225 Old Town #0824
Old Town
$2,413
-0.5BR · 546sf
1225 Old Town #0724
Old Town
$2,415
Studio · 543sf
1225 Old Town #0812
Old Town
$2,415
Studio · 505sf
Old Town Park 3 #0704
Old Town
$2,418
Studio · 565sf
North Vine #0312
Old Town
$2,427
-0.5BR · 536sf
1225 Old Town #1023
Old Town
$2,433
Studio · 526sf
Xavier #1606
Old Town
$2,453
-0.5BR · 573sf
1225 Old Town #0711
Old Town
$2,453
-0.5BR · 546sf
1225 Old Town #0624
Old Town
$2,465
Studio · 589sf
Cobbler Square Lofts #D101
Old Town
$2,466
-0.5BR · 546sf
1225 Old Town #1024
Old Town
$2,468
-0.5BR · 579sf
1225 Old Town #0519
Old Town
$2,480
Studio · 569sf
Xavier #1510
Old Town
$2,485
Studio · 505sf
Old Town Park 3 #1604
Old Town
$2,497
Studio · 856sf
Cobbler Square Lofts #G314
Old Town
$2,508
Studio · 565sf
North Vine #1012
Old Town
$2,524
Studio · 560sf
Cobbler Square Lofts #D405
Old Town
$2,526
Studio · 550sf
Cobbler Square Lofts #D505
Old Town
Top buildings for this search
- Cobbler Square Lofts41 units · $2,095–$4,274
- Old Town Park 234 units · $2,555–$7,383
- Old Town Park 329 units · $2,415–$4,911
- 1225 Old Town26 units · $2,350–$6,191
- Old Town Park25 units · $2,610–$5,211
- North Vine19 units · $2,168–$4,983
- The Archer13 units · $2,767–$4,215
- Xavier10 units · $2,433–$4,055
Frequently asked
What's the cheapest in Old Town with a Rooftop right now?
Cobbler Square Lofts #D406 at $2,095/month, 609 square feet. Located at 1350 N Wells St.
How many apartments are available in Old Town with a Rooftop?
225 apartments are currently listed across 14 buildings in Old Town with a Rooftop. Median rent is $3,380.
Which buildings in Old Town offer apartments with a Rooftop?
Top buildings by current inventory: Cobbler Square Lofts, Old Town Park 2, Old Town Park 3, 1225 Old Town, Old Town Park.
Is the rooftop usable year-round?
Most rooftop decks in Old Town are partially open year-round, with covered seating and fire pits for cooler months. Pools and outdoor grills are typically May-September.
Compare Old Town to nearby neighborhoods
More in Old Town
Updated July 27, 2026 at 12:46 AM CDT. Prices, availability, and amenities are pulled from each property's own leasing system and refreshed every few hours. No paid placement.