6 Dog-Friendly Weekend Getaways From Chicago

Pupper would agree, the Midwest is best. But the Midwest isn’t just Chicago and our cool breweries, thicc pizza, or lake views. Adventure is out there, and there are sniffs to be sniffed in our neighboring cities and towns! Pack your bags, get ready for wags, and make a break for one of these awesome dog-friendly weekend getaways from Chicago.

1. Indiana Dunes

Chicago is known for improv and the rule of “Yes, and.” But the Indiana Dunes is where you’ll be saying, “Yes, SAND!” Just 35 miles out of the city, it’s the perfect dog-friendly day trip from Chicago. You and your dune doggy will love exploring the park trails, lakeshore, and beaches.

There are lots of pet-friendly accommodations, stores, and restaurants around town. The Taltree Arboretum and European market are also worth a sniff. Check out the official guide to Spot-friendly Indiana Dunes spots here.

2. Starved Rock 

Don’t go chasing waterfalls. Please stick to the Rovers and the licks that you’re used to. Just kidding–do chase the waterfalls (after heavy rains) at this gorgeous (and free) State Park! Less than 100 miles outside Chicago, Starved Rock boasts 18 canyons, picturesque sandstone bluffs, fun local wineries and breweries with dog-friendly patios, and a rich cultural history. Fall is paws down the best for high-tailing it to the trails for drool-worthy views.

3. Amish Country 

From locally-owned shops to beautiful parks and trails, there are so many pet-friendly things to do in northern Indiana’s Amish Country. Try the Shipshewana Trading Place, where leashed pups are welcome to peruse the Midwest’s largest flea market by your side. Just a warning: after a weekend learning about the Amish way of life, you may find it hard to scoot back to the hustle and bustle of the city.

4. Lake Geneva 

Wisconsin is the perfect place to take lots of “cheesy” vacay photos with your dog! Most restaurants allow dogs on their patios, and many adorable bed and breakfasts welcome them as well. This resort town pampers pups as much as humans, so the two of you can relax and rejuvenate together. If you’re feeling less R&R and more outdoorsy, take a hike on Big Foot Beach State Park right next to Geneva Lake.

5. Milwaukee

Pupper is here for the beer, and there’s no place better than Milwaukee. Exceptionally pet-friendly, you may have a hard time convincing Fido to come back to Chicago with you. Stay a while at one of their many pet-friendly hotels, but the boutique Kimpton Journeyman sounds barkin’ awesome–gorgeous views of the river, no extra pet fees, and loaners to make him comfortable.

Take a stroll along the dog-friendly Riverwalk to learn about Milwaukee history and see rotating art. And of course, you need to get a beer. Check out the Black Husky Brewing Company that’s B.Y.O.F. for Bring Your Own Fido (or food, whatever you need). 

6. Indianapolis

About a 3-hour drive from Chicago, Indianapolis is home to many dog-friendly breweries, shops, and restaurant patios. A personal Sidewalk Dog favorite, Metazoa Brewing Co., boasts a dog park, and donates 5% of their profits back to animal and wildlife organizations. Sip a Puppy Slumber Party or Ruh Roh Ale, then go check out Three Dog Bakery on Mass Ave. to pick out some pup-approved treats.

Dog’ll ruv walking on the Cultural Trail, which connects Mass Ave. to Indy’s five other Cultural Districts. When you make it to Broad Ripple, sniff out their dog park before dining on the patio at Broad Ripple Brewpub, an English-style pub with a giant patio and delicious vegan fare.

Cap your visit with a stay at the Bottleworks Hotel, a luxury hotel within a former Coca-Cola bottling plant that has a storied history.

What are your pupper’s favorite places for a weekend getaway? Do tell in the comments below! And don’t forget to tag us with #SidewalkDog in you and your pup’s weekend getaway!

Featured photo by James Barker

Sidewalk Dog’s mission is to help dog parents spend more time with their puppers by discovering and sharing activities they can do and places they can go—together! Sniff out our award-winning newsletter and Instagram, and join our Dog-Friendly Chicago Facebook Group.

More reads you’ll ruv:

Your email address will not be published. Required fields are marked *

The internet’s most dog-friendly website. Sidewalk Dog is your go-to resource for all things dog. Trusted by more than 250,000 dog people around the world.

Join the Pack