Top 10 Dog-Friendly Date Ideas in Chicago, IL

Introduction

With lakeshore walks, award-winning bars and restaurants, and plenty of sights to see, the Windy City is a wonderful place for romance. And don’t worry if Spot’s got a special place in your heart -- Chicago boasts plenty of pup-inclusive options to prevent you or your date having to leave your fur-balls at home. We’ve put together a list of ten options to suit almost all interests and budgets, whether you’re just getting to know a new interest or celebrating a long-term relationship.

And if your date balks at spending the evening with your buddy, it might just be best to stay home solo!

Wander around Navy Pier

Make no bones about it, a  walk around Navy Pier can make for a memorable date. One of Chicago’s true gems, the pier boasts wonderful views of the city skyline, plenty of interesting public art, and oodles of bars and restaurants. Unfortunately, your pupper won’t be allowed in any indoor areas or on the Ferris wheel, but there’s still plenty to see and do outside.

Take a walk on the Chicago Lakefront Bike Path

A great choice for either a daytime date or an after-dinner stroll, the Chicago Lakefront Bike Path hugs the shores of Lake Michigan for over 18 miles, passing through pristine parkland (ideal for picnics) and offering gorgeous views of the city itself. Take the trailhead from Navy Pier or access the path from one of the 13 neighborhoods on the route. Remember to bring waste bags!

Skip along Lake Michigan with Seadog Cruises

Seadog Cruises are very happy to welcome your buddy aboard! Leaving from Navy Pier, this speedboat tour zips across Lake Michigan, taking in the sights of the city along the way. However, if you three are in no hurry (or you have a special architecture, design or urban planning nerd in your life), the longer River and Lake Architecture Tour might be a better option.
Need a hand? Let a dog walker from Wag! help out!

Brave the cold on Montrose Beach

A beach date in February? Don’t knock it ‘til you’ve tried it! You, your date, and your doggo will need to wrap up warm, but even inclement weather can’t spoil the view. Plus, your furry friend can run free on Montrose Dog Beach, though it’s probably best to keep them out of the water. Remember, pups aren’t allowed on the people side of the beach.

Treat yourselves at Margie's Candy Montrose

Why not grab some sweets with your sweetie after your walk on the beach? The second location of a 90-year-old Chicago institution, Margie’s Candies Montrose serves up the best in all sorts of delicious candy and homemade ice cream. Unfortunately, though, the Fido-friendly outdoor seating isn’t heated -- if you and your date want to split a sundae, you might have to do so quickly.

Grab a beer at Bucktown Pub

While plenty of Chicago eateries welcome wagging tails outside, there’s no getting around the fact that February is cold. Fortunately, there are some establishments out there that cater to canines indoors, including the furrific Bucktown Pub. The pizza specials are ideal for a laid-back, casual, or budget-friendly date, and the bar boasts a serious selection of craft beers. They also have free popcorn!

Find a spark at Fireside

Annual Valentine’s specials and a pup-friendly patio? You’d be barking mad not to check out Fireside, a reasonably priced restaurant with a decent cocktail selection. According to local legend, Fireside may be haunted, but whether that’s a plus or a minus is up to you. You might find yourself watched by spirits from the local cemetery, but the crabcakes are still pretty good.

Sit inside at SoFo Taphouse

Chicago’s LGBT community might know SoFo Taphouse as a better place to get a date than bring one, but this bar is pawesomely pup-friendly. Providing the place isn’t crowded, doggos are welcome inside, and you and your date can bond over a game of darts. You can also check out the local, independent art on the walls, with a different artist featured every two months.

Keep it low-key at Ten Cat Tavern

Don’t let the name fool you -- Ten Cat Tavern is definitely geared more towards canines than felines. Another watering hole that allows pooches indoors, the atmosphere at Ten Cat is decidedly unpretentious, with beer costing as low as $3. Like SoFo, you’ll also find some fascinating local art hanging inside, as well as a pool table, a jukebox, and a room with a charming fireplace.

Get set to impress at Nellcote

If you’re looking to pull out all the stops, Nellcote is the paw-fect place for you! Between the gleaming marble, chandeliers, and delicious Italian food, your date is guaranteed to be impressed, and the restaurant caters to canines outside. Be sure to stay for dessert -- the marscapone cheesecake is an experience you won’t forget. Nellcote is pretty paw-pular, so reserving in advance is absolutely essential.