1 Place to People-Watch with Cats
5260 N. Clark St.
Tabbies can haughtily stare down passersby from the wraparound street-side patio at Lady Gregory’s Irish Bar & Restaurant, one of the few eateries in the city that allow cats. (Dogs, too.) ladygregorys.com
2 Matchmaker Mecca
4923 N. Clark St.
Grindr for dogs hasn’t been invented yet, but gay pet owners can meet up on Saturdays at the SoFo Tap’s Doggy Days (animal treats and drink specials included). thesofotap.com
3 Postworkout Refreshment
200 W. Montrose Harbor Dr.
Exhausted hounds can dry off after frolicking at the dog beach while their owners enjoy a grownup beverage at the Dock at Montrose Beach. thedockatmontrosebeach.com
4 Bar for Dog Lovers
3931 N. Ashland Ave.
Despite the feline name, Ten Cat Tavern has a patio that turns into a mini pooch park during warm months. As for inside? It’s not unusual to see a mutt perched on a barstool. 773-935-5377
5 Travel Bathroom Break
O’Hare International Airport
The AstroTurf and small red fire hydrants in the rotunda in Terminal 3 help pets get over their shy bladders. Pop-up sprinklers keep things tidy. flychicago.com
6 Raw-Food Store
1658 N. Milwaukee Ave.
Trendy diets aren’t just for humans: Kriser’s Natural Pet sells only corn-, soy-, and wheat-free food and treats, including a huge raw selection (pheasant patties, anyone?). krisers.com
7 Off-Leash Spot Near the 606
1722 N. Ashland Ave.
Dogs must stay tethered on the actual trail but can roam unfettered at Walsh Playground Park, a crowd-free dog run at the 606’s easternmost entrance. chicagoparkdistrict.com
8 Unexpected Training Ground
1232 W. North Ave.
Distracting sounds? Heavy traffic? Home Depot has it all, which is why pet owners take to the aisles to (unofficially) school their pups. homedepot.com
9 Soap for Human or Pet
859 W. Armitage Ave.
Bring Spot the next time you need to stock up on toiletries. The staff at Lush will fawn over your pet, yes. But some fans of its fragrant bar shampoos swear by them as doggie detergent. lushusa.com
10 Downtown Pet Fix
800 N. Michigan Ave.
No, he’s not winking. The Park Hyatt’s new house pug—recently adopted from PAWS Chicago—only has one eye. chicago.park.hyatt.com
11 Secret Entrance to the 900 North Michigan Shops
900 N. Michigan Ave.
The main mall does not welcome pets—but Bloomingdale’s does, so in-the-know owners enter off Walton Street. bloomingdales.com
12 Special-Occasion Wear
1 E. Delaware Pl.
Tails in the City caters to doggie dandies in the market for Burberry-style coats, canine Snuggies, and pastel whole-grain doughnuts. tailsinthecity.com
13 Mag Mile Pit Stop
520 N. Michigan Ave.
The Shops at North Bridge (including Nordstrom!) offers pet stations with water bowls and poop bags. theshopsatnorthbridge.com
14 Place to Rent a Pet
225 N. Wabash Ave.
Hotel Monaco lends lonely travelers a goldfish—for free. monaco-chicago.com
15 Dog Park That’s Not a Dog Park
5200 S. Hyde Park Blvd.
Leash-free dog parks are rare on the South Side, but when drained in the off-season (late October to mid-May), the fenced-in Hyde Park Boat Pond serves as a great alternative. (Mutts also love splashing around during the weeklong filling process each spring.) chicagoparkdistrict.com
16 Treats for All
1550 E. 55th St.
Everyone wins at Bonjour Café Bakery: famously flaky croissants for people, free biscuits for pups. 773-241-5300
Food Truck for Dogs
Fido to Go, a mobile “gourmutt” (womp, womp) café, offers handcrafted gluten- and allergen-free pet cookies and frozen treats—and even caters canine parties. Check its daily itinerary on Twitter (@fidotogo). fidotogo.net
Chicago’s Best Dog Parks
(See: Pink numbers on the map)
1 Montrose Beach, Uptown
Lawrence Avenue and Simonds Drive
Best for: Hot dogs who aren’t afraid of some waves.
Highlight: A generous 3.83-acre fenced-in beach that’s meticulously maintained by a dedicated team of volunteers.
2 Jackson Bark, Jackson Park
6401 S. Stony Island Ave.
Best for: German shepherds who think regular dog parks are for basic bitches.
Highlight: An agility run created from traffic signs and construction materials.
3 Wiggly Field, Lincoln Park
2645 N. Sheffield Ave.
Best for: Owners who despise the pee-covered dust that rises from gravel parks.
Highlights: Doubles as a speed-dating site (Chicago once named it the best place to meet people). Small hills and double gates keep pets from fleeing.
4 Montgomery Ward Park, River North
630 N. Kingsbury St.
Best for: Wearing out mutts (in the run) and kids (on the playground).
Highlights: A prime position along the Chicago River, plus specially treated asphalt that’s more comfortable for pooches.
5 Fred Anderson Park, South Loop
1611 S. Wabash Ave.
Best for: Little dogs who don’t play well with big ones.
Highlights: The most pup-friendly amenities: water features, free waste bags, AstroTurf for sensitive tootsies, and designated spots for different sizes of hounds.