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Apartments in Old Town with a Rooftop
206 apartments available in Old Town with a Rooftop. Median rent $3,168. 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.
$3,168
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
$1,979
1BR · 676sf
Schiller Place Apartments #101
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
$2,163
Studio · 510sf
1250 LaSalle #1605
Old Town
$2,230
1BR · 649sf
1250 LaSalle #0504
Old Town
$2,250
1BR · 714sf
The Archer #704
Old Town
$2,275
Studio · 510sf
1250 LaSalle #0807
Old Town
$2,283
2BR · 936sf
Schiller Place Apartments #202
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
$2,362
1BR · 640sf
1250 LaSalle #0608
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
$2,435
1BR · 630sf
1250 LaSalle #1306
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
$2,475
1BR · 714sf
The Archer #404
Old Town
$2,483
Studio · 505sf
Old Town Park 3 #2705
Old Town
$2,488
Studio · 505sf
Old Town Park 3 #3104
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
- The Archer$2,250–$3,958
Frequently asked
What's the cheapest in Old Town with a Rooftop 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 Rooftop?
Apartments are currently listed in Old Town with a Rooftop. Median rent is $3,168.
Which buildings in Old Town offer apartments with a Rooftop?
Top buildings by current inventory: Cobbler Square Lofts, Old Town Park 3, Old Town Park 2, North Vine, Xavier.
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 September 20, 2026 at 5:18 PM CDT. No paid placement.