1) Lakefront Trail Bike, jog or walk this popular 18.5-mile paved route that skirts Lake Michigan and runs through parks and along beachfronts. It’s part of the city’s 200 miles of designated bike paths and on-street bike lanes. bikechicago.com/suggestedrides/
2) Bobby’s Bike Hike Blend exercise with insights into Chicago’s history and architecture on the relaxed, three-hour Lakefront Neighborhoods Tour or City Lights at Night Tour. The company leads other biking and walking tours and has bike rentals by the hour, half day or full day. (312) 915-0995; bobbysbikehike.com
3) Northerly Island Cast a fishing line from the grassy shore or leisurely stroll the wildflower-strewn, paved paths of Northerly Island, which was once an airstrip. A top photo spot to capture skyline views, the tranquil 91 acres of lakefront also serves as a summer concert venue, bird-watching haven, and winter snowshoe and cross-country ski destination. The park hosts sled dog demonstrations during the free Polar Adventure Days. (312) 745-2910; chicagoparkdistrict.com/parks/northerly-island-park/
4) Kayak Chicago Paddle the Chicago River and Lake Michigan as you learn about the city’s beginnings as a waterfront trading post and admire today’s skyscrapers. Guided tours run 2.5 hours May through October. You can also rent kayaks and stand-up paddleboards for exploring on your own. (312) 852-9258; kayakchicago.com
5) Golf Get your game in at links near the Loop. Chicago Park District runs eight courses and driving ranges, including nine-hole South Shore Golf Course and Sydney R. Marovitz and 18-hole Jackson Park Golf Course and driving range. Play mini golf with the kids or hit practice balls year-round at the Diversey Range’s covered and heated stalls (club rental available). Head to windswept Harborside International Golf Center for a challenging links experience.
6) Montrose Point Bird Sanctuary Bird watchers might spot rare or seldom-seen species along the well-marked paths of this sanctuary, one of the Midwest’s top rest stops for birds winging along the U.S. Central Flyway (chicagoparkdistrict.com/facilities/birding-areas/). Killdeer, piping plovers, whimbrels and Nelson’s sparrows have been reported within the 15-acres of woodlands, dunes and beach jutting into Lake Michigan. During spring and fall migrations, bird watchers flock to the Magic Hedge, a former Cold War Nike missile site camouflaged by perfect-for-perching thick shrubs. The Chicago Audubon Society conducts free bird-watching walks at Montrose Point (5 miles north of the Loop) and other Chicago-area bird sanctuaries.
7) Chicago Botanic Garden You could ramble for hours through this free, stunning, 385-acre outdoor museum of 26 display gardens in north suburban Glencoe (self-guided tour maps available). The English Walled Garden showcases centuries of Brit design. Graceful, arched stone bridges connect Malott Japanese Garden’s three serene islands. Bike or walk the new North Branch Trail section. Open year-round; garden entrance is a 1-mile walk from Braeside Metra train station. (847) 835-5440; chicagobotanic.org
8) Chicago Architecture Foundation Tours Dozens of tour options let you easily customize your experience: Choose a mode of transportation (walking, bike, Segway, boat, L train, bus/trolley), a length (one to three-plus hours), a location and an interest to explore Chicago’s architecture in the Loop, city neighborhoods and suburbs. (312) 922-3432; architecture.org
9) Segway Tours You cover a lot of ground wheeling around town on these simple-to-operate, battery-powered vehicles. Chicago Segway Tours features 10 themed itineraries along the lakefront, Michigan Avenue and Chicago River. Safety-conscious guides share city history and stop for photos during two-hour tours operated year-round. Join Haunted Halloween and Holiday Lights seasonal spins. (312) 552-5100; chicagosegways.com