You've said the compile log has no errors, but post it anyway. Sometimes a 2nd pair of eyes spots a mistake that you overlooked.
** Executing...
** Command: "C:\Program Files (x86)\TravisStEaM\steamapps\common\Team Fortress 2\bin\vbsp.exe"
** Parameters: -game "C:\Program Files (x86)\TravisStEaM\steamapps\common\Team Fortress 2\tf" "C:\Program Files (x86)\TravisStEaM\steamapps\common\Team Fortress 2\sourcesdk_content\tf\mapsrc\chill_winter.vmf"
Valve Software - vbsp.exe (Mar 6 2018)
4 threads
materialPath: C:\Program Files (x86)\TravisStEaM\steamapps\common\Team Fortress 2\tf\materials
Loading C:\Program Files (x86)\TravisStEaM\steamapps\common\Team Fortress 2\sourcesdk_content\tf\mapsrc\chill_winter.vmf
ConVarRef mat_reduceparticles doesn't point to an existing ConVar
Patching WVT material: maps/chill_winter/pl_barnblitz/blendmetalroofsnow_02_wvt_patch
Patching WVT material: maps/chill_winter/nature/blendrockgroundwallsnow_wvt_patch
Patching WVT material: maps/chill_winter/nature/blendgrasstosnow001_wvt_patch
Patching WVT material: maps/chill_winter/dev/dev_blendmeasure2_wvt_patch
fixing up env_cubemap materials on brush sides...
ProcessBlock_Thread: 0...1...2...3...4...5...6...7...8...9...10 (0)
ProcessBlock_Thread: 0...1...2...3...4...5...6...7...8...9...10 (0)
Processing areas...done (0)
Building Faces...done (0)
Chop Details...done (0)
Find Visible Detail Sides...
Merged 96 detail faces...done (0)
Merging details...done (0)
FixTjuncs...
PruneNodes...
WriteBSP...
done (0)
writing C:\Program Files (x86)\TravisStEaM\steamapps\common\Team Fortress 2\sourcesdk_content\tf\mapsrc\chill_winter.prt...Building visibility clusters...
done (0)
*** Error: Skybox vtf files for skybox/sky_nightfall_01 weren't compiled with the same size texture and/or same flags!
Can't load skybox file skybox/sky_nightfall_01 to build the default cubemap!
*** Error: Skybox vtf files for skybox/sky_nightfall_01 weren't compiled with the same size texture and/or same flags!
Can't load skybox file skybox/sky_nightfall_01 to build the default cubemap!
Finding displacement neighbors...
Finding lightmap sample positions...
Displacement Alpha : 0...1...2...3...4...5...6...7...8...9...10
Building Physics collision data...
done (0) (176156 bytes)
Placing detail props : 0...1...2...3...4...5...6...7...8...9...10
Compacting texture/material tables...
Reduced 909 texinfos to 424
Reduced 60 texdatas to 47 (2246 bytes to 1771)
Writing C:\Program Files (x86)\TravisStEaM\steamapps\common\Team Fortress 2\sourcesdk_content\tf\mapsrc\chill_winter.bsp
Wrote ZIP buffer, estimated size 13235, actual size 9671
16 seconds elapsed
** Executing...
** Command: "C:\Program Files (x86)\TravisStEaM\steamapps\common\Team Fortress 2\bin\vvis.exe"
** Parameters: -game "C:\Program Files (x86)\TravisStEaM\steamapps\common\Team Fortress 2\tf" -fast "C:\Program Files (x86)\TravisStEaM\steamapps\common\Team Fortress 2\sourcesdk_content\tf\mapsrc\chill_winter"
Valve Software - vvis.exe (Mar 6 2018)
fastvis = true
4 threads
reading c:\program files (x86)\travissteam\steamapps\common\team fortress 2\sourcesdk_content\tf\mapsrc\chill_winter.bsp
reading c:\program files (x86)\travissteam\steamapps\common\team fortress 2\sourcesdk_content\tf\mapsrc\chill_winter.prt
405 portalclusters
1039 numportals
BasePortalVis: 0...1...2...3...4...5...6...7...8...9...10 (0)
Optimized: 1005 visible clusters (2.53%)
Total clusters visible: 39738
Average clusters visible: 98
Building PAS...
Average clusters audible: 185
visdatasize:23670 compressed from 45360
writing c:\program files (x86)\travissteam\steamapps\common\team fortress 2\sourcesdk_content\tf\mapsrc\chill_winter.bsp
0 seconds elapsed
** Executing...
** Command: "C:\Program Files (x86)\TravisStEaM\steamapps\common\Team Fortress 2\bin\vrad.exe"
** Parameters: -game "C:\Program Files (x86)\TravisStEaM\steamapps\common\Team Fortress 2\tf" -noextra "C:\Program Files (x86)\TravisStEaM\steamapps\common\Team Fortress 2\sourcesdk_content\tf\mapsrc\chill_winter"
Valve Software - vrad.exe SSE (Mar 6 2018)
Valve Radiosity Simulator
4 threads
[Reading texlights from 'lights.rad']
unknown light specifier type - lights
[56 texlights parsed from 'lights.rad']
Loading c:\program files (x86)\travissteam\steamapps\common\team fortress 2\sourcesdk_content\tf\mapsrc\chill_winter.bsp
Setting up ray-trace acceleration structure... Done (5.63 seconds)
2309 faces
1889786 square feet [272129216.00 square inches]
150 Displacements
410684 Square Feet [59138524.00 Square Inches]
2309 patches before subdivision
67143 patches after subdivision
sun extent from map=0.173648
116 direct lights
BuildFacelights: 0...1...2...3...4...5...6...7...8...9...10 (29)
BuildVisLeafs: 0...1...2...3...4...5...6...7...8...9...10 (13)
transfers 4448535, max 486
transfer lists: 33.9 megs
GatherLight: 0...1...2...3...4...5...6...7...8...9...10 (0)
Bounce #1 added RGB(126867, 80922, 47805)
GatherLight: 0...1...2...3...4...5...6...7...8...9...10 (0)
Bounce #2 added RGB(21760, 8003, 4085)
GatherLight: 0...1...2...3...4...5...6...7...8...9...10 (0)
Bounce #3 added RGB(5144, 1240, 472)
GatherLight: 0...1...2...3...4...5...6...7...8...9...10 (0)
Bounce #4 added RGB(1020, 148, 48)
GatherLight: 0...1...2...3...4...5...6...7...8...9...10 (0)
Bounce #5 added RGB(231, 22, 6)
GatherLight: 0...1...2...3...4...5...6...7...8...9...10 (0)
Bounce #6 added RGB(49, 3, 1)
GatherLight: 0...1...2...3...4...5...6...7...8...9...10 (0)
Bounce #7 added RGB(11, 0, 0)
GatherLight: 0...1...2...3...4...5...6...7...8...9...10 (0)
Bounce #8 added RGB(2, 0, 0)
GatherLight: 0...1...2...3...4...5...6...7...8...9...10 (0)
Bounce #9 added RGB(1, 0, 0)
Build Patch/Sample Hash Table(s).....Done<0.0701 sec>
FinalLightFace: 0...1...2...3...4...5...6...7...8...9...10 (7)
FinalLightFace Done
0 of 0 (0% of) surface lights went in leaf ambient cubes.
ThreadComputeLeafAmbient: 0...1...2...3...4...5...6...7...8...9...10 (9)
Writing leaf ambient...done
Ready to Finish
Object names Objects/Maxobjs Memory / Maxmem Fullness
------------ --------------- --------------- --------
models 52/1024 2496/49152 ( 5.1%)
brushes 530/8192 6360/98304 ( 6.5%)
brushsides 3875/65536 31000/524288 ( 5.9%)
planes 3116/65536 62320/1310720 ( 4.8%)
vertexes 4076/65536 48912/786432 ( 6.2%)
nodes 1402/65536 44864/2097152 ( 2.1%)
texinfos 424/12288 30528/884736 ( 3.5%)
texdata 47/2048 1504/65536 ( 2.3%)
dispinfos 150/0 26400/0 ( 0.0%)
disp_verts 11030/0 220600/0 ( 0.0%)
disp_tris 17280/0 34560/0 ( 0.0%)
disp_lmsamples 989636/0 989636/0 ( 0.0%)
faces 2309/65536 129304/3670016 ( 3.5%)
hdr faces 0/65536 0/3670016 ( 0.0%)
origfaces 1367/65536 76552/3670016 ( 2.1%)
leaves 1455/65536 46560/2097152 ( 2.2%)
leaffaces 2543/65536 5086/131072 ( 3.9%)
leafbrushes 1546/65536 3092/131072 ( 2.4%)
areas 11/256 88/2048 ( 4.3%)
surfedges 16445/512000 65780/2048000 ( 3.2%)
edges 9545/256000 38180/1024000 ( 3.7%)
LDR worldlights 116/8192 10208/720896 ( 1.4%)
HDR worldlights 0/8192 0/720896 ( 0.0%)
leafwaterdata 0/32768 0/393216 ( 0.0%)
waterstrips 239/32768 2390/327680 ( 0.7%)
waterverts 0/65536 0/786432 ( 0.0%)
waterindices 4332/65536 8664/131072 ( 6.6%)
cubemapsamples 25/1024 400/16384 ( 2.4%)
overlays 12/512 4224/180224 ( 2.3%)
LDR lightdata [variable] 5445996/0 ( 0.0%)
HDR lightdata [variable] 0/0 ( 0.0%)
visdata [variable] 23670/16777216 ( 0.1%)
entdata [variable] 192483/393216 (49.0%)
LDR ambient table 1455/65536 5820/262144 ( 2.2%)
HDR ambient table 1455/65536 5820/262144 ( 2.2%)
LDR leaf ambient 3165/65536 88620/1835008 ( 4.8%)
HDR leaf ambient 1455/65536 40740/1835008 ( 2.2%)
occluders 0/0 0/0 ( 0.0%)
occluder polygons 0/0 0/0 ( 0.0%)
occluder vert ind 0/0 0/0 ( 0.0%)
detail props [variable] 1/12 ( 8.3%)
static props [variable] 1/54916 ( 0.0%)
pakfile [variable] 9671/0 ( 0.0%)
physics [variable] 176156/4194304 ( 4.2%)
physics terrain [variable] 45206/1048576 ( 4.3%)
Level flags = 0
Total triangle count: 6314
Writing c:\program files (x86)\travissteam\steamapps\common\team fortress 2\sourcesdk_content\tf\mapsrc\chill_winter.bsp
1 minute, 6 seconds elapsed
** Executing...
** Command: Copy File
** Parameters: "C:\Program Files (x86)\TravisStEaM\steamapps\common\Team Fortress 2\sourcesdk_content\tf\mapsrc\chill_winter.bsp" "C:\Program Files (x86)\TravisStEaM\steamapps\common\Team Fortress 2\tf\maps\chill_winter.bsp"
** Executing...
** Command: "C:\Program Files (x86)\TravisStEaM\steamapps\common\Team Fortress 2\hl2.exe"
** Parameters: -game "C:\Program Files (x86)\TravisStEaM\steamapps\common\Team Fortress 2\tf" -novid +map "chill_winter" -steam