Des Plaines River Trail
This 55-miler meanders alongside the Des Plaines River through forested open spaces and the heart of the northern burbs.
East Bank Club
This gym is massive and has exercise classes—from yoga to indoor track cycling—every 30 minutes during peak morning and evening periods. Bonus: the outdoor pool deck has a bar. From $25 per day
The 18-mile paved path goes through downtown along the edge of Lake Michigan. To up the distance, continue north for six miles to Northwestern University’s campus.
Rent a kayak and glide through a canyon of skyscrapers. Wateriders rents by the hour and leads evening tours. From $20.
Portage Park and Lake Michigan
On the northwest side of town, Portage Park has an Olympic-size outdoor pool (one-month pass, $25), but we prefer Lake Michigan at Ohio Street Beach, a triathlete favorite.
This 310-room hotel is in the heart of downtown, just a few blocks from Millenium Park’s running trails. Its open-air rooftop bar draws a crowd of locals on warm nights. From $269.
Located on the city’s Magnificent Mile, the megastore has Thursday night training runs with multiple distances and provides free gear storage.
Bobby’s Bike Hike