Live data — refreshed 12:45 AM CDT
Apartments in Wicker Park with a Rooftop
19 apartments available in Wicker Park with a Rooftop. Median rent $2,495. Live prices updated every few hours from the property's own leasing systems.
About Wicker Park: Indie-music and creative-class neighborhood at the intersection of Milwaukee, Damen, and North avenues. Murals, dive bars, vintage shops, and brick walk-ups. Loud at night, walkable everywhere.
19
Available
5
Buildings
$2,495
Median rent
$2,057
Cheapest
Available now (19 of 19)
$2,057
Studio · 542sf
The Weyland #602
Wicker Park
$2,157
Studio · 558sf
The Weyland #405
Wicker Park
$2,225
Studio · 463sf
Wicker Park Connection #0711-H
Wicker Park
$2,243
Studio · 648sf
The Weyland #206
Wicker Park
$2,275
Studio · 463sf
Wicker Park Connection #1408-H
Wicker Park
$2,329
1BR · 604sf
The Weyland #707
Wicker Park
$2,329
1BR · 604sf
The Weyland #507
Wicker Park
$2,445
1BR · 603sf
The Weyland #407
Wicker Park
$2,445
-0.5BR · 548sf
1611 West Division #1011
Wicker Park
$2,495
1BR · 657sf
The Weyland #309
Wicker Park
$2,575
0.5BR · 570sf
Wicker Park Connection #0410-M
Wicker Park
$2,650
0.5BR · 572sf
Wicker Park Connection #0307-M
Wicker Park
$2,850
1BR · 637sf
Wicker Park Connection #0707-H
Wicker Park
$3,033
2BR · 940sf
The Weyland #716
Wicker Park
$3,195
2BR · 821sf
1611 West Division #1104
Wicker Park
$3,196
1BR · 797sf
1819 Lofts #308
Wicker Park
$3,210
1BR · 957sf
1241 N Milwaukee #401
Wicker Park
$3,297
2BR · 993sf
The Weyland #614
Wicker Park
$3,495
2BR · 1115sf
The Weyland #208
Wicker Park
Top buildings for this search
- The Weyland10 units · $2,057–$3,495
- Wicker Park Connection5 units · $2,225–$2,850
- 1611 West Division2 units · $2,445–$3,195
- 1819 Lofts1 unit · $3,196–$3,196
- 1241 N Milwaukee1 unit · $3,210–$3,210
Frequently asked
What's the cheapest in Wicker Park with a Rooftop right now?
The Weyland #602 at $2,057/month, 542 square feet. Located at 1980 N Milwaukee Ave.
How many apartments are available in Wicker Park with a Rooftop?
19 apartments are currently listed across 5 buildings in Wicker Park with a Rooftop. Median rent is $2,495.
Which buildings in Wicker Park offer apartments with a Rooftop?
Top buildings by current inventory: The Weyland, Wicker Park Connection, 1611 West Division, 1819 Lofts, 1241 N Milwaukee.
Is the rooftop usable year-round?
Most rooftop decks in Wicker Park are partially open year-round, with covered seating and fire pits for cooler months. Pools and outdoor grills are typically May-September.
Compare Wicker Park to nearby neighborhoods
More in Wicker Park
Updated July 27, 2026 at 12:45 AM CDT. Prices, availability, and amenities are pulled from each property's own leasing system and refreshed every few hours. No paid placement.