For this itinerary, it's time to escape downtown completely and spend the day on the North Side of the city. You'll start out in Lincoln Park, which is both an actual park and the name of a popular residential neighborhood, where singles and young families can be seen strolling or jogging along the lakefront paths during nice weather. You'll also visit two major cultural institutions, both suitable for kids, and then head into a residential neighborhood for some shopping.
Start: Bus no. 151 or 156 to North Cannon Drive and Fullerton Parkway.
1. Lincoln Park Zoo
A beloved local institution, this zoo won't dazzle you a la San Diego, but it does a good job of covering all the bases, with a mix of indoor habitats and naturalistic outdoor environments (plus, did I mention it's free?). Don't miss the Regenstein African Journey exhibit (which re-creates both a tropical jungle and a dusty African savanna) and the internationally renowned Great Ape House. If you have kids, stop at the Children's Zoo, where a unique climbing structure gives little ones 2 and older a chance to release some energy.
Just south of the zoo, this re-creation of a working farm gets children in touch (literally) with animals. The highlight for many little ones is the giant John Deere tractor; you'll usually find a line of kids waiting for their turn to sit behind the massive steering wheel (along with parents waiting to snap a picture).
3. Bird's Eye Bar & Grill
This cafe, located on the roof of the zoo's gift shop, has outdoor seating and panoramic views over the zoo. You can order the usual hot dogs and fries, but there's also a selection of more health-conscious wraps.
4. North Avenue Beach
Come summer, this is Lincoln Park's prime playground — a place to jog, play volleyball, build sandcastles, or simply pose. Even in August, the water is usually icy, but if you want to at least dip your feet in Lake Michigan, this wide stretch of sand is the place to do it. Just south of the beach, a grassy stretch of park offers picture-perfect views of downtown.
Take a taxi to the corner of Halsted Street and Armitage Avenue.
5. Armitage Avenue
To call this the city's chicest shopping strip isn't meant as a put-down to Michigan Avenue; while the Mag Mile goes for big and showy, the boutiques along Armitage tend to be smaller and more personal (most are independently owned rather than chain stores). You'll find an especially appealing selection of home decor stores and gift shops with eclectic selections of well-designed merchandise. Wander the surrounding side streets to see the neighborhood's eclectic mix of historic homes and modern mansions.
If you're ready to wind down, you'll find plenty of restaurants nearby or in adjacent Old Town. But if you'd like to explore one more neighborhood, take a taxi to the corner of North Avenue and Damen Avenue, then walk north along Damen.
If you're not shopped out yet, finish up the day with a walk through Bucktown, home to the city's highest concentration of edgy clothing boutiques. It feels grittier than Armitage Avenue, and that's part of the appeal for the cool kids who live here.
7. Northside Bar
Bucktown's unofficial neighborhood hangout, this low-key cafe is a sandwich spot by day and a bustling bar by night. When the weather's nice, grab a seat on the outdoor patio and people-watch with everyone else.
8. Improv and Sketch Comedy
Although it's best known for Second City, Chicago is home to a number of excellent improv and sketch comedy troupes. You can catch rising stars before they land their own sitcom deals. Second City is the big man on campus, while iO is the slightly scrappier and more creative bunch. If you're here with older kids or teens, catch the family-friendly ComedySportz.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.