Dog-Friendly Chicago Adventure

Day 1: Exploring the Loop

Chicago, USA

9:00 AM

Breakfast at Wildberry Pancakes and Cafe

Start your day with a delicious breakfast at Wildberry Pancakes and Cafe known for its fluffy pancakes and pet-friendly outdoor seating.
Walk from your accommodation or take a short taxi ride.
$$, 1 hour

11:00 AM

Millennium Park

Visit Millennium Park, where your furry friend can roam around the Pritzker Pavilion and take a selfie at the iconic Cloud Gate sculpture.
Walk or take a short bus ride to the park.
Free, 2 hours

1:30 PM

Lunch at Shake Shack

Enjoy a pet-friendly lunch at Shake Shack in the Loop, offering tasty burgers and milkshakes.
Walk from Millennium Park.
$, 1 hour

3:00 PM

Art Institute of Chicago

Explore the Art Institute of Chicago's outdoor areas with your dog, admiring the architecture and views of the city.
Walk to the museum.
$$, 2 hours

6:00 PM

Dinner at The Gage

End your day with a dog-friendly dinner at The Gage, a gastropub offering a variety of dishes and craft beers.
Walk from the Art Institute.
$$, 1.5 hours
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Day 2: Lincoln Park Adventure

Chicago, USA

8:00 AM

Visit Montrose Dog Beach

Start your day early at Montrose Dog Beach, letting your furry companion play in the sand and water.
Take a taxi or rideshare to the beach.
Free, 2 hours

11:00 AM

Brunch at Batter & Berries

Head to Batter & Berries for a delicious brunch with your pup on their outdoor patio known for their unique French Toast Flight.
Walk or take a short taxi ride.
$$, 1 hour

1:00 PM

Lincoln Park Zoo

Explore the Lincoln Park Zoo, which is pet-friendly, and enjoy the beautiful greenery and wildlife.
Walk to the zoo.
Free, 2 hours

4:00 PM

Shopping at Tails in the City

Treat your pup to some shopping at Tails in the City, a luxury pet boutique in Lincoln Park.
Walk or take a short bus ride.
$$$, 1 hour

6:00 PM

Dinner at The Blanchard

End your day with a fine dining experience at The Blanchard's pet-friendly patio, offering French cuisine.
Walk or take a short taxi ride.
$$$, 2 hours
View Hotel Availability

Day 3: Wicker Park Exploration

Chicago, USA

9:00 AM

Breakfast at Dove's Luncheonette

Start your day with a hearty breakfast at Dove's Luncheonette, known for its Mexican-inspired dishes and pet-friendly outdoor seating.
Walk or take a short bus ride to the restaurant.
$$, 1 hour

11:00 AM

Wicker Park Dog Park

Visit Wicker Park Dog Park for some off-leash playtime and socialization for your furry friend.
Walk to the park.
Free, 1.5 hours

1:30 PM

Lunch at Big Star

Enjoy a casual lunch at Big Star's outdoor patio, known for its tacos and margaritas, with a pet-friendly atmosphere.
Walk from the dog park.
$, 1 hour

3:00 PM

Shop at Doggy Style Pet Shop

Explore Doggy Style Pet Shop in Wicker Park for unique pet accessories and treats.
Walk or take a short bus ride.
$$, 1 hour

5:00 PM

Relax at The Robey

Wind down at The Robey's rooftop bar, where pets are allowed, and enjoy the sunset views of the city.
Walk or take a short taxi ride.
$$, 2 hours
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Day 4: Pilsen Art & Culture

Chicago, USA

9:30 AM

Visit National Museum of Mexican Art

Start your day with a visit to the National Museum of Mexican Art, where leashed dogs are welcome to explore the vibrant exhibitions.
Take a short taxi ride or public transportation.
Free, 2 hours

12:00 PM

Lunch at Carnitas Uruapan

Enjoy authentic Mexican cuisine at Carnitas Uruapan's outdoor seating area, perfect for a pet-friendly meal.
Walk from the museum.
$, 1 hour

2:00 PM

Art Murals in Pilsen

Take a leisurely walk through the streets of Pilsen to admire the vibrant art murals and street art with your furry companion.
Explore on foot.
Free, 1.5 hours

4:00 PM

Pilsen Community Books

Visit Pilsen Community Books, a pet-friendly bookstore, and browse through their unique selection of titles.
Walk or take a short bus ride.
$$, 1 hour

6:00 PM

Dinner at S.K.Y.

End your day with a dinner at S.K.Y., known for its contemporary American cuisine and pet-friendly outdoor seating.
Walk or take a short taxi ride.
$$$, 2 hours
View Hotel Availability

Day 5: Lakefront Trail Adventure

Chicago, USA

8:00 AM

Morning Walk at Lakefront Trail

Start your day with a refreshing morning walk along the Lakefront Trail, a pet-friendly path with stunning views of Lake Michigan.
Take a taxi or rideshare to the trail.
Free, 2 hours

10:30 AM

Navy Pier

Explore Navy Pier with your furry friend, taking in the sights and sounds of this iconic Chicago attraction.
Walk or take a short bus ride.
Free, 2 hours

1:00 PM

Lunch at Riva Crab House

Enjoy lunch at Riva Crab House's pet-friendly outdoor patio, offering seafood dishes with a view of the lake.
Walk from Navy Pier.
$$$, 1 hour

3:00 PM

Dog-Friendly Boat Tour

Embark on a dog-friendly boat tour from Navy Pier, cruising along the Chicago River and Lake Michigan with your pup.
Walk to the boat tour departure point.
$$$, 1.5 hours

5:00 PM

Relax at Ohio Street Beach

Unwind at Ohio Street Beach, a pet-friendly beach where your dog can dip their paws in the water and play in the sand.
Walk from the boat tour.
Free, 1.5 hours
View Hotel Availability

Day 6: Hyde Park Discovery

Chicago, USA

9:00 AM

Breakfast at Valois Restaurant

Start your day with a classic breakfast at Valois Restaurant, a dog-friendly diner known for its hearty meals and diverse menu.
Take a taxi or rideshare to Hyde Park.
$, 1 hour

11:00 AM

Explore Promontory Point

Visit Promontory Point, a pet-friendly park offering panoramic views of the lake and city skyline, perfect for a leisurely stroll with your pup.
Walk to the park.
Free, 1.5 hours

1:30 PM

Lunch at Medici on 57th

Enjoy lunch at Medici on 57th's outdoor patio, a Hyde Park institution known for its diverse menu and pet-friendly atmosphere.
Walk from Promontory Point.
$$, 1 hour

3:00 PM

Visit Museum of Science and Industry

Explore the Museum of Science and Industry's outdoor areas with your furry companion, marveling at the exhibits and interactive displays.
Walk to the museum.
$$, 2 hours

6:00 PM

Dinner at Virtue Restaurant

End your day with a soulful dinner at Virtue Restaurant's pet-friendly patio, offering Southern-inspired dishes and hospitality.
Walk or take a short taxi ride.
$$$, 2 hours
View Hotel Availability

Day 7: West Loop Culinary Delights

Chicago, USA

8:30 AM

Breakfast at Little Goat Diner

Start your day with a delightful breakfast at Little Goat Diner, a pet-friendly spot with a diverse menu and cozy atmosphere.
Walk or take a short bus ride to the restaurant.
$$, 1 hour

10:00 AM

Visit Skinner Park

Explore Skinner Park with your furry friend, offering green spaces and walking paths for a relaxing morning stroll.
Walk to the park.
Free, 1 hour

12:00 PM

Lunch at Publican Quality Meats

Indulge in a gourmet lunch at Publican Quality Meats' outdoor patio, known for its sandwiches and charcuterie boards, with a pet-friendly vibe.
Walk from Skinner Park.
$$, 1 hour

2:00 PM

Shopping at Randolph Street Market

Browse through the unique finds at Randolph Street Market, a pet-friendly shopping destination with antiques, vintage items, and artisan goods.
Walk or take a short bus ride.
$, 1.5 hours

4:00 PM

Coffee at Sawada Coffee

Enjoy a coffee break at Sawada Coffee's outdoor seating area, known for its matcha latte and pet-friendly ambiance.
Walk to the coffee shop.
$, 1 hour

6:00 PM

Dinner at Girl & the Goat

End your Chicago adventure with a dinner at Girl & the Goat, a pet-friendly restaurant offering innovative dishes and a lively atmosphere.
Walk or take a short taxi ride.
$$$, 2 hours
View Hotel Availability