Furthest Skyline View Visible In Street View?

[jakeroot]

You can just barely make out Downtown Seattle from the Point Defiance/Ruston area (basically Tacoma), about 22 miles south-southwest.

[Terry Shea]

You can also see the Toronto skyline coming down from the plateau into Hamilton on 403.

Hmm. I don't know, there's definitely a skyline, but something tells me it's not Toronto.

You need to be further back and higher up.  Here's several views from Hamilton.  https://www.google.com/search?q=view+of+toronto+skyline+from+hamilton+bridge&tbm=isch&source=iu&ictx=1&fir=mNFxIZCYegICaM%252C8OpoYqFOZEpcjM%252C_&vet=1&usg=AI4_-kROL6KmWwkaWUWeSYg0j4R1kbBxUg&sa=X&ved=2ahUKEwie6ND7_drrAhUVHM0KHfHvAZYQ9QF6BAgKEDM#imgrc=LkCA2Ll4eZFvcM

[TheHighwayMan3561]

Minneapolis, 15 miles out.

https://goo.gl/maps/KEjB1GGVs9tfwmh29

[webny99]

Minneapolis, 15 miles out.
https://goo.gl/maps/KEjB1GGVs9tfwmh29

Speaking of the Twin Cities, I've always liked this view of St. Paul, 6 miles down the Mighty Mississippi. This one, too.

[Henry]

I'll take a stab at Atlanta, GA, at the top of Stone Mountain, which is roughly 20 miles east of it:

https://www.google.com/maps/@33.8060197,-84.1460139,3a,15y,253.15h,95.58t/data=!3m8!1e1!3m6!1sAF1QipOiLY3-qXFa_tOdTzdL6EYymDY0cvT4UI9Bvn6r!2e10!3e11!6shttps:%2F%2Flh5.googleusercontent.com%2Fp%2FAF1QipOiLY3-qXFa_tOdTzdL6EYymDY0cvT4UI9Bvn6r%3Dw203-h100-k-no-pi0-ya295.65152-ro-0-fo100!7i8192!8i4096

[Roadgeekteen]

It's not on a street (but it's on street view) but I saw the Toronto skyline from Fort Niagra state park about 30 miles away

[CtrlAltDel]

It's pretty close to the The Adventures Club Bourbon Soceity (sic), which is located right at the center of the interchange, apparently.

I'm sure you will all be happy to know, not that anyone asked, that The Adventures Club Bourbon Soceity has been removed from Google Maps.

[hobsini2]

Chicago, on various roads:

I-55 northbound: https://goo.gl/maps/vaM4YeaSRdYgam4p7
Plainfield Road, Darien: https://goo.gl/maps/BzTUfv67HXqvvrth8
I-290 eastbound: https://goo.gl/maps/P1qMRbg7Qb33SRyW6
I-90/94 eastbound: https://goo.gl/maps/o3q4nrAF7mrU69CT7
I-57 northbound (I-94 westbound): https://goo.gl/maps/yNPxi42BPPPv7u2Y7
I-90 westbound: https://goo.gl/maps/fgSZXLpsweCN5gqH6
Indiana Dunes SP: https://goo.gl/maps/TwDgYHnMWaq2KbcC8 (The winner at over 30 miles out)

It's not the winner, but I've always enjoyed the view from here, above I-290, since it meant that I was almost home. I especially liked it at night.

It's pretty close to the The Adventures Club Bourbon Soceity (sic), which is located right at the center of the interchange, apparently.

Not sure I believe the Kankakee sighting of Chicago but I do indeed have one that's further than 290 & St Charles Rd.
On the exit ramp from 355 South to 55 North. Zoom in and to the right of 55, you can see the Sears Tower at the right (refuse to call it anything but), Hancock on the left and Trump Tower (my obligatory middle finger to that) in the middle clearly.
https://www.google.com/maps/@41.7036265,-88.0314126,3a,45.9y,54.35h,84.05t/data=!3m7!1e1!3m5!1s84sKOG4SqtN_Q7OWoSzjfA!2e0!6s%2F%2Fgeo0.ggpht.com%2Fcbk%3Fpanoid%3D84sKOG4SqtN_Q7OWoSzjfA%26output%3Dthumbnail%26cb_client%3Dmaps_sv.tactile.gps%26thumb%3D2%26w%3D203%26h%3D100%26yaw%3D348.20703%26pitch%3D0%26thumbfov%3D100!7i16384!8i8192?hl=en

That's 23.7 miles as the crow flies to the Sears.
24.5 to Trump.
25.0 to Hancock.

[US 89]

I'll take a stab at Atlanta, GA, at the top of Stone Mountain, which is roughly 20 miles east of it:

https://www.google.com/maps/@33.8060197,-84.1460139,3a,15y,253.15h,95.58t/data=!3m8!1e1!3m6!1sAF1QipOiLY3-qXFa_tOdTzdL6EYymDY0cvT4UI9Bvn6r!2e10!3e11!6shttps:%2F%2Flh5.googleusercontent.com%2Fp%2FAF1QipOiLY3-qXFa_tOdTzdL6EYymDY0cvT4UI9Bvn6r%3Dw203-h100-k-no-pi0-ya295.65152-ro-0-fo100!7i8192!8i4096

Nah, Stone Mountain is only 14-15 miles east of downtown Atlanta by straight-line distance.

Kennesaw Mountain is a bit farther at about 19 miles, and there are a few more hills a bit farther out from which you can probably see the downtown skyline.

[ChiMilNet]

Not really a street view, but I have seen the Sears Tower from Illinois Beach State Park... that's about 40-45 miles as a crow flies (I tried looking for Milwaukee as well, since it's about midway in between, but I couldn't spot it unfortunately). Also, a spot I remember seeing it as a kid was from the I-80/US45(LaGrange Rd) interchange when crossing over I-80. I don't know if development over there has changed that, but that's gotta be a good 25 or so miles. Also, not a street view again, but Swallow Cliff Woods has a really cool view of the Sears Tower on the trail.

[stevashe]

Here's an interesting one: TWO skylines are visible from Somerset Boulevard SE, Seattle (~8 miles) and Bellevue (~4 miles).

[fillup420]

Not much of a skyline, but there is a spot on I-40 east coming into Asheville NC, at the top of a grade where the Biltmore House is very prominent off in the distance. I would have to drive the route again to note the exact spot, but its somewhere between MM 30-40.

[jakeroot]

Here's an interesting one: TWO skylines are visible from Somerset Boulevard SE, Seattle (~8 miles) and Bellevue (~4 miles).

I remember "running into" that view a couple years ago just driving around. Absolutely gorgeous view.

[tallfull]

The Renaissance Center in downtown Detroit can also be seen in the Street View of the ramp from southbound Mound Rd. to eastbound I-696, a distance of 11 miles. The Ren Cen continues to be visible from Mound Rd. as you travel south from there.

https://www.google.com/maps/@42.4863634,-83.0454662,3a,15y,176.47h,90.46t/data=!3m7!1e1!3m5!1s8vwTzjuaGHgaCDGlLrXRzg!2e0!6s%2F%2Fgeo3.ggpht.com%2Fcbk%3Fpanoid%3D8vwTzjuaGHgaCDGlLrXRzg%26output%3Dthumbnail%26cb_client%3Dmaps_sv.tactile.gps%26thumb%3D2%26w%3D203%26h%3D100%26yaw%3D181.8725%26pitch%3D0%26thumbfov%3D100!7i16384!8i8192!5m1!1e1?hl=en

Grand River Avenue between Evergreen and Outer Drive you can make out the Ren Cen about 11 miles away.

https://www.google.com/maps/@42.4078313,-83.2361583,3a,15y,116.35h,91.82t/data=!3m6!1e1!3m4!1sAzf1osuAwirQW2wusuXoqQ!2e0!7i16384!8i8192!5m1!1e1?hl=en

[tallfull]

Also in person you can see Detroit's skyline from the hill at Stony Creek Metro Park about 26 miles from Downtown Detroit. You can also see Downtown Detroit in person from Metro Beach at the end of 16 Mile Road which is about 20 miles from Downtown Detroit.

Stony Creek is due north of Downtown Detroit with nothing in the way of the view from the top of the hill.

The view of Detroit's skyline from Lake St. Clair Metropark (formerly and still commonly known as Metro Beach) is visible in Street View, from the circle at the end of Train Rd., 21 miles away.

https://www.google.com/maps/@42.5642693,-82.7842012,3a,15y,219.08h,93.45t/data=!3m6!1e1!3m4!1sRVtXYJj1UshBQzOM2tNy1Q!2e0!7i13312!8i6656

[Occidental Tourist]

From Colt Road in Rancho Palos Verdes, you can see Downtown LA in Google Maps.  Distance is 20 miles.

From Ridge Park Road in Newport Beach, you can just barely make out the outline of Downtown LA.  Distance is 39 miles.

[jdbx]

From westbound US-50 between El Dorado Hills and Folsom, you can see Sacramento at a distance of about 25 miles.  I seem to recall that a similar view is also available on I-80 from around Loomis.

[ozarkman417]

Not necessarily a whole skyline, but Springfield MO's tallest building (the Hammons Tower) can be see from Highlandville, MO on US 160/MO 13, a distance of 18 1/4 miles.

[MikieTimT]

The furthest I've spotted a metropolitan area was back in '93 when a buddy of mine and I road tripped from Charleston, AR to Las Vegas, NV, nonstop.  It was nighttime after turning off I-40 in Kingman, AZ onto US-93, and as soon as we got out of the light pollution of Kingman, we saw the light pollution of Las Vegas on a clear night, 100+ miles away.

[jmd41280]

The US Steel Tower in Pittsburgh can be spotted from this vantage point 15 miles away along McDowell Road in Canonsburg. It is just to the left of the light post in the middle of this photo.

The US Steel and BNY Mellon Towers in Pittsburgh can also be spotted from this vantage point (also 15 miles away) along Williamsport Road in Monongahela.

There are many points further out that one can spot the US Steel and BNY Mellon Towers, however they are not accessible (or visible) via Street View.

[JREwing78]

It's not going to win any points for distance (6.5 miles), but this view of Wisconsin's capital from US-14 south of Madison always makes me smile. https://goo.gl/maps/mQVVZRQ7H1wcMG3C6

[23skidoo]

The Renaissance Center in downtown Detroit can also be seen in the Street View of the ramp from southbound Mound Rd. to eastbound I-696, a distance of 11 miles. The Ren Cen continues to be visible from Mound Rd. as you travel south from there.

You can also see downtown Detroit from the rural outskirts of Windsor. Here's a glimpse of the RenCen from Lakeshore Rd 107 in Lakeshore, Ontario, 13 miles southeast of downtown: https://www.google.com/maps/@42.2689235,-82.8026249,3a,15y,288.42h,89.45t/data=!3m7!1e1!3m5!1sfok1Gg8jy_oKe8mWgILaoQ!2e0!5s20120701T000000!7i13312!8i6656

I've also been able to see downtown Detroit at I-696 and Woodward. You can just barely see the downtown skyline from 11 miles north: https://www.google.com/maps/@42.4748509,-83.1446859,3a,15y,153.59h,89.69t/data=!3m7!1e1!3m5!1sD8PARHuQhvzIZ0MxQd3HKA!2e0!5s20150801T000000!7i13312!8i6656

Anecdotally, I've been able to see what I thought was downtown Detroit from as far away as M-14 while going eastbound over the bridge at Sheldon (22 miles!), but I can't seem to see it on StreetView.

[hobsini2]

It's not going to win any points for distance (6.5 miles), but this view of Wisconsin's capital from US-14 south of Madison always makes me smile. https://goo.gl/maps/mQVVZRQ7H1wcMG3C6

I have always been a fan of the view straight down E Washington Ave on US 151 by I-39/90/94. Zoom in and just right of the road.
https://www.google.com/maps/@43.1352999,-89.2982984,3a,15y,227.52h,89.87t/data=!3m6!1e1!3m4!1sgM6JLlsZihqlvg8Zk4U5-w!2e0!7i16384!8i8192?hl=en

[ET21]

Chicago, on various roads:

I-55 northbound: https://goo.gl/maps/vaM4YeaSRdYgam4p7
Plainfield Road, Darien: https://goo.gl/maps/BzTUfv67HXqvvrth8
I-290 eastbound: https://goo.gl/maps/P1qMRbg7Qb33SRyW6
I-90/94 eastbound: https://goo.gl/maps/o3q4nrAF7mrU69CT7
I-57 northbound (I-94 westbound): https://goo.gl/maps/yNPxi42BPPPv7u2Y7
I-90 westbound: https://goo.gl/maps/fgSZXLpsweCN5gqH6
Indiana Dunes SP: https://goo.gl/maps/TwDgYHnMWaq2KbcC8 (The winner at over 30 miles out)

Adding another to the list
I-355 southbound ramp to I-55 northbound: https://www.google.com/maps/@41.7033323,-88.0292162,3a,15y,61.64h,88.96t/data=!3m7!1e1!3m5!1s08YgB6feNbUWMM_WQm9B4g!2e0!6s%2F%2Fgeo2.ggpht.com%2Fcbk%3Fpanoid%3D08YgB6feNbUWMM_WQm9B4g%26output%3Dthumbnail%26cb_client%3Dmaps_sv.tactile.gps%26thumb%3D2%26w%3D203%26h%3D100%26yaw%3D16.638187%26pitch%3D0%26thumbfov%3D100!7i16384!8i8192

Google Streetview doesn't show a good look but if you are traveling eastbound on either 79th or 87th streets in Bridgeview the skyline popped up briefly at your 10 o'clock. However, trees have since grown it looks like since the last time I was on those bridges 
https://www.google.com/maps/@41.7333889,-87.8088946,17.69z

[cbeach40]

You can also see the Toronto skyline coming down from the plateau into Hamilton on 403.

Hmm. I don't know, there's definitely a skyline, but something tells me it's not Toronto.

Yeah Hamilton is right there, but on a clear day you can see Toronto from the top of the escarpment there with the naked eye, usually at a bearing of about 10-11 o'clock. Doesn't look like the weather was favourable anytime that GSV has gone through though.

You can make the Toronto skyline out from the Burlington Skyway here, distance of 50.55 km (31.41 mi).
https://goo.gl/maps/MNYt6UM7mJ4gAXXT7
Or a little clearer here from Niagara-On-The-Lake, 48.59 km (30.19) from the CN Tower
https://goo.gl/maps/JPAHEsQL1jkEhuXd6

Also in person you can see Detroit's skyline from the hill at Stony Creek Metro Park about 26 miles from Downtown Detroit. You can also see Downtown Detroit in person from Metro Beach at the end of 16 Mile Road which is about 20 miles from Downtown Detroit.

Stony Creek is due north of Downtown Detroit with nothing in the way of the view from the top of the hill.

If on a boat you can see the Renaissance Center and the rest of the skyline clearly from the mouth of the St. Clair River, also about 26 miles from downtown.