Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

14-Day Family-Friendly & Dog-Friendly Midwest Adventure

Viewed by 116 travelers

Day 1: Explore Chicago

Chicago, Illinois

8:00AM

Breakfast at Lou Mitchell's

Start your day with a hearty breakfast at this iconic diner known for its delicious pancakes and welcoming atmosphere.
Located in the West Loop area, Lou Mitchell's is easy to get to from downtown.
USD20, 1.5 hours

10:00AM

Millennium Park and Cloud Gate

Take a leisurely stroll around Millennium Park and admire the famous 'Bean' sculpture, perfect for family photos.
The park is a short 15-minute walk from Lou Mitchell's.
Free, 1.5 hours

12:00PM

Lunch at Portillo's

Enjoy a Chicago-style hot dog and Italian beef sandwich at this beloved fast-casual restaurant.
About a 10-minute drive from Millennium Park.
USD30, 1 hour

1:00PM

Visit the Shedd Aquarium

Explore the incredible aquatic life at the Shedd Aquarium, a fantastic experience for families of all ages.
Located approximately 20 minutes from Portillo's by car.
USD39.95, 2 hours

3:30PM

Relax at North Avenue Beach

Let your dog run at the pet-friendly area and enjoy the stunning views of Lake Michigan.
A 15-minute drive from the aquarium.
Free, 2 hours

6:00PM

Dinner at Giordano's

Indulge in some world-famous Chicago deep-dish pizza at Giordano's, a family favorite.
Located about 20 minutes from North Avenue Beach.
USD60, 1.5 hours
Find Hotels in Chicago

Day 2: More Chicago Adventures

Chicago, Illinois

8:00AM

Breakfast at Wildberry Pancakes and Cafe

Dig into a delicious breakfast with a variety of options, from fluffy pancakes to hearty omelets.
Situated near Millennium Park, easy to reach.
USD25, 1.5 hours

10:00AM

Lincoln Park Zoo

Explore the free Lincoln Park Zoo, which is welcoming to dogs as long as they’re on a leash.
A 15-minute drive from the cafe.
Free, 2 hours

12:30PM

Lunch at The Purple Pig

Savor Mediterranean-inspired dishes in a rustic atmosphere. They have outdoor seating for dogs.
A 10-minute drive from the zoo.
USD50, 1.5 hours

2:00PM

Explore the Art Institute of Chicago

If time allows, take the family to the Art Institute to see rich exhibitions of art, an essential Chicago experience.
15-minute drive from The Purple Pig.
USD25, 2 hours

4:30PM

Stroll along the Chicago Riverwalk

Enjoy a scenic walk along the river while your dog gets some exercise before dinner.
About 10 minutes from the Art Institute.
Free, 1.5 hours

6:00PM

Dinner at Real Urban Barbecue

Feast on authentic Chicago barbecue with dog-friendly outdoor seating.
A short 10-minute drive from the Riverwalk.
USD50, 1.5 hours
Find Hotels in Chicago

Day 3: Milwaukee Bound

Milwaukee, Wisconsin

8:00AM

Breakfast at Cafe Hollander

Enjoy a Dutch-inspired breakfast at this cozy cafe with a pet-friendly patio.
Located in Milwaukee on your way out of the city.
USD20, 1.5 hours

10:00AM

Visit the Milwaukee Art Museum

Don't miss this iconic architectural wonder and its collection of modern and contemporary art.
Just a 10-minute drive from the cafe.
USD19, 2.5 hours

1:00PM

Lunch at Milwaukee Public Market

Explore a variety of food vendors at this vibrant market while enjoying a casual lunch.
A short 5-minute drive from the museum.
USD40, 2 hours

3:00PM

Stroll around Lakefront Park

Take your dog for a walk around this scenic park known for its beautiful lake views.
Only 10 minutes away by car.
Free, 1.5 hours

5:00PM

Visit Miller Park

Catch a Milwaukee Brewers game if they're in season, or enjoy a guided tour of the stadium.
20-minute drive from Lakefront Park.
USD25, 2 hours

7:00PM

Dinner at AJ Bombers

Relax at this fun burger spot known for its artsy atmosphere and outdoor seating for dogs.
A short 10-minute drive from the stadium.
USD50, 1.5 hours
Find Hotels in Milwaukee

Day 4: More Milwaukee Fun

Milwaukee, Wisconsin

8:00AM

Breakfast at Blue's Egg

Savor inventive twists on breakfast classics at this popular local spot.
Located about 15 minutes from your hotel.
USD25, 1.5 hours

10:00AM

Discover the Harley-Davidson Museum

Dive into the rich history of Harley-Davidson bikes, a fun experience for the whole family.
Only 10 minutes away from the breakfast spot.
USD22, 2 hours

1:00PM

Lunch at The Honest Loose Meat Company

Enjoy classic loose meat sandwiches in a quirky setting.
A quick 10-minute drive from the museum.
USD30, 1 hour

2:15PM

Explore Milwaukee County Zoo

Spend the afternoon visiting various animals at this family-friendly zoo that's fun for all ages.
About 20 minutes away by car.
USD16, 3 hours

5:30PM

Relax at the Kettle Moraine State Forest

Take your dog for a scenic walk in the woods before dinner, surrounded by nature.
About a 30-minute drive from the zoo.
Free, 1.5 hours

7:30PM

Dinner at Zaffiro's

Conclude the day with delicious pizza at this local favorite with family-style dining available.
20-minute drive back to Milwaukee.
USD45, 1.5 hours
Find Hotels in Milwaukee

Day 5: Travel to Madison

Madison, Wisconsin

8:00AM

Breakfast at Michel's Family Restaurant

Start your day at this welcoming diner with a diverse selection of breakfast options.
A 15-minute drive from your hotel in Milwaukee.
USD20, 1.5 hours

10:00AM

Drive to Madison

Take a scenic drive to Madison, enjoying the picturesque countryside.
The journey will take approximately 1.5 hours.
Free, 1.5 hours

11:30AM

Visit the Wisconsin State Capitol

Explore the majestic State Capitol building and its beautiful architecture.
Located in the heart of downtown Madison.
Free, 1.5 hours

1:00PM

Lunch at The Old Fashioned

Taste some classic Wisconsin fare at this cozy restaurant.
A 5-minute walk from the Capitol.
USD40, 1.5 hours

2:30PM

Explore the University of Wisconsin-Madison Campus

Wander around the university's beautiful campus and the picturesque Lake Mendota.
A 10-minute walk from the restaurant.
Free, 2 hours

4:30PM

Relax at Olbrich Botanical Gardens

Enjoy the beauty of nature at these stunning gardens that are pet-friendly.
About a 15-minute drive from the university.
Free, 1.5 hours

6:15PM

Dinner at Graze

Enjoy a farm-to-table dining experience with stunning views of the Capitol.
Only a 10-minute drive from the gardens.
USD50, 1.5 hours
Find Hotels in Madison

Day 6: Madison Adventures

Madison, Wisconsin

8:00AM

Breakfast at Marigold Kitchen

Start your day with a farm-fresh breakfast in a charming setting.
About 10 minutes from your hotel.
USD20, 1.5 hours

9:30AM

Visit the Madison Children’s Museum

Enjoy hands-on exhibits and outdoor activities that are fun for all ages.
A short drive away from breakfast.
USD10, 2 hours

12:00PM

Lunch at The Dane

Savor locally sourced dishes at this family-friendly restaurant with outdoor seating.
Just 10 minutes from the museum.
USD40, 1.5 hours

1:30PM

Explore the Henry Vilas Zoo

Visit this free zoo that features a variety of animals and a petting zoo area.
About 10 minutes from the lunch venue.
Free, 2.5 hours

4:00PM

Relax at Warner Park

Unwind with your furry friend in this spacious pet-friendly park.
A quick 15-minute drive from the zoo.
Free, 2 hours

6:15PM

Dinner at The Great Dane Pub & Brewing Co.

Enjoy a delicious dinner with craft beers in a vibrant atmosphere.
Located about 15 minutes from Warner Park.
USD50, 1.5 hours
Find Hotels in Madison

Day 7: Minneapolis Arrival

Minneapolis, Minnesota

8:00AM

Breakfast at The Good Day Café

Start your day with wholesome breakfast options in a relaxed setting.
Located near your hotel in Madison.
USD20, 1.5 hours

9:30AM

Depart for Minneapolis

Enjoy the scenic two-hour drive to the vibrant city of Minneapolis.
The drive is straightforward; just follow the main highways.
Free, 2 hours

11:30AM

Visit the Walker Art Center

Explore modern art exhibitions in a stunning venue, a must-see for art lovers.
A short drive from downtown Minneapolis.
USD15, 2 hours

1:30PM

Lunch at The Bachelor Farmer

Enjoy a meal influenced by the Nordic cuisine in a cozy atmosphere.
Only 10 minutes away from the Walker Art Center by car.
USD50, 1.5 hours

3:00PM

Explore the Minneapolis Sculpture Garden

Take a stroll through this beautiful park featuring an impressive collection of outdoor sculptures.
Just a 5-minute drive from the restaurant.
Free, 1.5 hours

5:00PM

Visit the Mall of America

Spend the evening exploring one of the largest malls in the country, pet-friendly areas included.
Located about 20 minutes away from the garden.
Free (shopping at your own discretion), 2.5 hours

7:30PM

Dinner at Crave

Enjoy contemporary dining with a diverse menu in a lively atmosphere.
Within the Mall of America.
USD50, 1.5 hours
Find Hotels in Minneapolis

Day 8: Minneapolis Highlights

Minneapolis, Minnesota

8:00AM

Breakfast at The Lowry

Savor a range of hearty breakfast options in a welcoming neighborhood cafe.
Located near downtown Minneapolis.
USD25, 1.5 hours

9:30AM

Visit the Guthrie Theater

Take a tour of the iconic theater with stunning views of the Mississippi River.
A quick 10-minute drive away.
USD10 (tour), 1.5 hours

11:00AM

Explore Minnehaha Park

Discover beautiful waterfall vistas and lovely trails in this expansive park.
Located about a 15-minute drive from the Guthrie.
Free, 2 hours

1:00PM

Lunch at Sea Salt Eatery

Enjoy fresh seafood dishes with an outdoor patio that's dog-friendly.
Only a 5-minute drive from the park.
USD35, 1.5 hours

3:00PM

Visit the Mill City Museum

Learn about the city's milling history and enjoy interactive exhibits suitable for all ages.
A 15-minute drive from lunch.
USD12, 2 hours

5:00PM

Stroll along the Stone Arch Bridge

Walk across this historic bridge and take in the stunning views of the skyline.
Only a 10-minute drive from the museum.
Free, 1.5 hours

7:00PM

Dinner at Pizzeria Lola

Indulge in delicious wood-fired pizzas with a fun atmosphere for all ages.
Located about 20 minutes from the bridge.
USD45, 1.5 hours
Find Hotels in Minneapolis

Day 9: St. Paul Discovery

St. Paul, Minnesota

8:00AM

Breakfast at Waffle Bar

Start with delicious custom waffles in a casual setting.
Located just across the river near St. Paul.
USD15, 1.5 hours

10:00AM

Visit the Science Museum of Minnesota

Explore interactive science exhibits and watch an IMAX movie together as a family.
A 15-minute drive from the breakfast spot.
USD20, 2.5 hours

12:30PM

Lunch at Mickey's Diner

Enjoy classic diner fare at this charming and historic eatery.
Only a 10-minute drive away.
USD30, 1.5 hours

2:00PM

Stroll through the Como Park Zoo and Conservatory

Visit this beautiful zoo and conservatory with free admission.
A quick 10-minute drive from the diner.
Free, 2.5 hours

5:00PM

Explore the Minnesota State Capitol

Discover the stunning architecture of this historic building in downtown St. Paul.
About 10 minutes away.
Free, 1.5 hours

7:00PM

Dinner at The Happy Gnome

Enjoy a fantastic selection of craft beers and a diverse menu in a cozy atmosphere.
Only a 5-minute drive from the Capitol.
USD50, 1.5 hours
Find Hotels in St. Paul

Day 10: Return to Chicago

Chicago, Illinois

8:00AM

Breakfast at The Buttered Biscuit

Enjoy delicious biscuits and gravy in this delightful cafe.
Located just over the border in Illinois.
USD20, 1.5 hours

10:00AM

Depart for Chicago

Take a scenic drive back, reflecting on our adventures.
The drive will take around 30 minutes.
Free, 30 minutes

10:30AM

Explore the Art Institute of Chicago (Round 2)

For returning visitors, enjoy more exhibitions at this iconic museum.
Same as before.
USD25, 2 hours

1:00PM

Lunch at The Smith

Savor a delightful lunch with modern American fare in a vibrant setting.
Located near the art institute.
USD40, 1.5 hours

2:30PM

Visit the Field Museum

Explore this intriguing natural history museum, perfect for families.
About a 10-minute drive from the lunch spot.
USD26, 2.5 hours

5:00PM

Relax at Grant Park

Unwind in this expansive park, enjoying the sights and sounds of the city.
Only a short drive from the museum.
Free, 1.5 hours

7:00PM

Dinner at the Chicago Chop House

Cap off the day with a classic steak dinner at this upscale restaurant.
Located about 10 minutes from Grant Park.
USD70, 2 hours
Find Hotels in Chicago

Day 11: Indianapolis Exploration

Indianapolis, Indiana

8:00AM

Breakfast at Milktooth

Start your day with inventive brunch options at this trendy eatery.
Located in Indianapolis, Indiana.
USD25, 1.5 hours

9:30AM

Visit the Indianapolis Zoo

Spend the day exploring the zoo and its beautiful gardens.
A short drive from Milktooth.
USD28, 3 hours

12:30PM

Lunch at The Eagle

Enjoy fried chicken and southern comfort food at this family-friendly joint.
Only 10 minutes from the zoo.
USD45, 1.5 hours

2:00PM

Explore White River State Park

Take a walk or have a family picnic at this beautiful park with great views.
A quick 10-minute drive from lunch.
Free, 1.5 hours

3:30PM

Visit the Children's Museum of Indianapolis

Explore the largest children's museum in the world, packed with fun for the family.
Only a 5-minute drive from the park.
USD22, 2.5 hours

6:00PM

Dinner at St. Elmo Steak House

Indulge in a classic Indianapolis steak dinner at this renowned establishment.
Located about 10 minutes from the museum.
USD80, 2 hours
Find Hotels in Indianapolis

Day 12: Indianapolis Discovery Day

Indianapolis, Indiana

8:00AM

Breakfast at The Cake Bake Shop

Delight in delicious pastries and sweet treats at this charming cafe.
Located near downtown.
USD20, 1.5 hours

9:30AM

Visit the Indiana State Museum

Explore Indiana's natural and cultural history through engaging exhibitions.
A short drive from the cafe.
USD18, 2 hours

11:30AM

Lunch at The Slippery Noodle Inn

Enjoy a meal at Indiana's oldest bar, with a wide variety of comfort foods.
Only 10 minutes away.
USD30, 1.5 hours

1:00PM

Explore the Indianapolis Museum of Art

Discover inspiring artworks and stroll through the beautiful grounds.
About a 15-minute drive from lunch.
Free, 2.5 hours

3:30PM

Visit the Indianapolis Motor Speedway

Check out the iconic racetrack and learn about its rich racing heritage.
A 20-minute drive away.
USD10, 2 hours

6:00PM

Dinner at The Oceanaire Seafood Room

Enjoy fresh seafood in a sophisticated environment.
A 10-minute drive from the racetrack.
USD70, 2 hours
Find Hotels in Indianapolis

Day 13: Columbus Adventure

Columbus, Ohio

8:00AM

Breakfast at Kittie's Cafe

Enjoy pancakes and a wonderful breakfast experience at this cozy cafe.
Located during your drive to Columbus.
USD25, 1.5 hours

10:00AM

Travel to Columbus, Ohio

Make your way to Columbus, enjoying the scenic drive.
The drive will take approximately 3 hours.
Free, 3 hours

1:00PM

Lunch at North Market

Savor eclectic offerings from numerous vendors in this bustling market.
Located in downtown Columbus.
USD30, 1.5 hours

2:30PM

Discover the Columbus Museum of Art

Explore the museum's impressive collection and vibrant exhibits.
A 15-minute walk or 5-minute drive away.
USD18, 2 hours

5:00PM

Relax at Franklin Park Conservatory

Stroll through the beautiful park and enjoy the stunning plant collections.
A quick 10-minute drive from the museum.
USD10, 1.5 hours

7:00PM

Dinner at The Barn at Rocky Fork.

Cap off your day with delicious farm-to-table dishes in a charming atmosphere.
About 20 minutes away.
USD50, 1.5 hours
Find Hotels in Columbus

Day 14: Columbus Farewell

Columbus, Ohio

8:00AM

Breakfast at The Breakfast at Tiffany's

Indulge in a memorable breakfast experience with unique options.
Situated in Columbus.
USD20, 1.5 hours

10:00AM

Visit the Topiary Park

Walk through this beautiful park filled with topiary sculptures depicting famous paintings.
Only a 15-minute drive away.
Free, 1.5 hours

11:30AM

Relax at Goodale Park

Enjoy the green space and lovely trails in this serene park that welcomes dogs.
A quick drive from the Topiary Park.
Free, 1 hour

1:00PM

Lunch at The Pearl

Savor a unique lunch experience with tasty seafood and craft cocktails.
Located about 10 minutes away.
USD40, 1.5 hours

3:00PM

Explore the COSI Science Center

Spend the afternoon engaging with interactive science exhibits, perfect for families.
About 10 minutes from the restaurant.
USD25, 2 hours

5:30PM

Wrap Up at the Scioto Mile

Enjoy scenic views of the riverfront before heading back.
A quick 10-minute drive away.
Free, 1.5 hours

7:00PM

Dinner at Lindey's

End your trip with a memorable dining experience offering upscale American cuisine.
Located about 10 minutes from the Scioto Mile.
USD70, 2 hours
Find Hotels in Columbus
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version
Itinerary created by AI-assisted, human-reviewed

Plan Your midwest Trip

Cost Estimator
Estimate your trip budget
Packing List
Get a custom checklist
Weather Expert
Check weather & best time to go