"Related Midwest's lakefront rental — 500 units, 47 floors, and some of the best lake views in Chicago."
Ratings Breakdown
Upper Level's exclusive rating for Chicago winter survivability — indoor parking, pedway access, CTA proximity, and wind exposure.
The Rundown
500 Lake Shore Drive is one of Related Midwest's flagship Chicago rental properties — 47 floors, 500 units, and a location right on Lake Shore Drive that delivers some of the best lake views available in a rental building.
The building was completed in 2014 and has been well-maintained since. Related Midwest is one of the most professional residential management companies in Chicago, and it shows — the building is clean, well-staffed, and responsive. The amenity package is excellent: two pools (indoor and outdoor), a large fitness center, yoga studio, rooftop terrace, and 24/7 doorman.
The views are the main event. East-facing units have direct lake views that are genuinely spectacular. The building's position on Lake Shore Drive means you're watching the lake from your window, not from a distant rooftop. Upper-floor east-facing units are among the best rental views in Chicago.
The trade-off is price — 500 LSD is not cheap. You're paying for the location, the views, and the Related Midwest management quality. But for renters who prioritize lake views and professional management, it's one of the best options in Streeterville.
Who Lives Here
Affluent professionals and couples who prioritize lake views. Some empty nesters who want a rental rather than ownership. A mix of long-term residents and shorter-term renters attracted by the location.
The Neighborhood
Lake Shore Drive in Streeterville — the lakefront path is literally across the street. Navy Pier is a short walk. The Mag Mile is close. This is one of the most desirable addresses in Chicago for lake proximity.
What You Get
Elevator Experience
Upper Level Intel
East-Facing Units Only
If you're paying 500 LSD prices, you should be in an east-facing unit with lake views. West-facing units are significantly less compelling at the same price point. Be specific about unit orientation when leasing.
Lake Shore Drive in Winter
The building's position on Lake Shore Drive means you're exposed to lake wind in winter. The building itself is well-sealed, but the walk to the CTA or parking can be brutal on cold, windy days. Budget for more Ubers in January and February.
The Good & The Not-So-Good
Wins
- ✓Direct lake views from east-facing units — among the best in any rental building
- ✓Two pools (indoor and outdoor)
- ✓Related Midwest management is best-in-class
- ✓Lakefront path directly across the street
- ✓Excellent amenity package
Watch Out
- ✗Lake Shore Drive traffic noise on lower floors
- ✗No pedway access
- ✗Premium pricing — you pay for the views
- ✗West-facing units don't have lake views and are harder to justify at the price
The Verdict
500 Lake Shore Drive is the best lake-view rental in Streeterville. Related Midwest management, excellent amenities, and direct lake views make it worth the premium — if you're in an east-facing unit.
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