Trail Run
Des Plaines River Trail
This 55-miler meanders alongside the through forested open spaces and the heart of the northern burbs.
Work Out
East Bank Club
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
Road Bike/Run
Lakefront Trail
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.
Explore
Chicago River
Rent a kayak and glide through a canyon of skyscrapers. rents by the hour and leads evening tours. From $20.
Swim
Portage Park and Lake Michigan
On the northwest side of town, has an Olympic-size outdoor pool (one-month pass, $25), but we prefer Lake Michigan at Ohio Street Beach, a triathlete favorite.
Stay
TheWit
This 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.
Gear Up
Nike Chicago
Located on the city’s Magnificent Mile, the has Thursday night training runs with multiple distances and provides free gear storage.
Bobby’s Bike Hike
You can rent a for $7 a day. But for, say, a GTR Carbon Elite with Shimano 105 components, reserve online with (from $65 per day).