Lakefront Trail South from Navy Pier to Northerly Island
From Navy Pier, take the Lakefront Trail or, better yet, access the Lake Shore Drive overpass near the pier, which will keep you slightly closer to the water's edge as you head south to Northerly Island and the Adler Planetarium. You'll score some of the best, exhaust-free views of the city here, and the crowds will start to thin out on the 91-acre manmade peninsula. It'll feel pleasantly secluded winding through fields of wildflowers and prairie grass, but killer skyline views will keep you connected to the city and you'll clock a good six miles round trip.
North Shore Channel Trail from River Park to Skokie
Everyone loves Chicago's Lakefront Trail, but it can get packed during marathon training season. The less-populated, paved North Shore Channel Trail, which runs along the east side of the Chicago River as you head the four miles north from the park at Argyle and Francisco to Skokie, is a runner's dream. The wooded path tames the wind and provides cooling shade on hot summer days as you cut through several local parks with plenty of water fountains. The River Park track is perfect for speed work, and adventurous runners can eventually connect to the Green Bay Trail for a longer journey up to the Botanical Gardens.