Why Reddit is swooning over Chicago’s skyline
A thread on r/Lollapalooza turned into a quick love letter to Chicago this week, with festival fans calling the city’s skyline the prettiest in North America. The conversation centered on the classic combo of lakefront, river, and dense high-rises that make for dramatic daytime and nighttime views — and a perfect backdrop for festival photos.
- Lake Michigan framing the skyline for wide, postcard-ready shots.
- The Chicago River slicing through the city and reflecting the lights after dark.
- Iconic architecture—from Willis Tower to the John Hancock—packed close enough to read on the skyline.
- Nighttime lighting and bridges that give the city a cinematic feel during shows and afterparties.
Best skyline-viewing spots during Lollapalooza
- Grant Park — the festival site itself provides skyline glimpses between sets.
- The Chicago Riverwalk — great for golden-hour photos and easy to access from festival areas.
- Buckingham Fountain and surrounding plazas — classic daytime vistas.
- Adler Planetarium and the Museum Campus — a wide, unobstructed sweep of the city across the water.
- Observation decks like 360 Chicago or Skydeck for elevated, sweeping panoramas.
The thread had the usual festival-era bragging rights and a little friendly pushback — New York, Toronto and Vancouver came up as contenders — but for Lollapalooza-goers the skyline is more than an argument: it’s part of the weekend’s vibe. Whether you’re chasing sunsets between sets or picking the best backdrop for your festival photos, Chicago’s skyline remains one of the city’s biggest flexes.