14-Day Family Friendly Itinerary in Chicago

Day 1: Exploring Downtown

Chicago, USA

9:00AM

Breakfast at Wildberry Pancakes and Cafe

Start your Chicago adventure with a hearty breakfast, enjoying their famous berry bliss pancakes.
Located in the Loop, easily accessible by public transport.
USD20, 1.5 hours

11:00AM

Visit Millennium Park

After breakfast, stroll through Millennium Park, home to the iconic Cloud Gate sculpture.
Short walk from the breakfast spot.
Free, 2 hours

1:00PM

Lunch at Giordano's

Indulge in Chicago's famous deep-dish pizza at Giordano's, a family favorite.
Another quick walk from Millennium Park.
USD60, 1.5 hours

3:00PM

Explore The Field Museum

Spend your afternoon at The Field Museum where kids will love the dinosaur exhibits.
Take the bus from Giordano's; it’s a short ride.
USD100, 3 hours

7:00PM

Dinner at Portillo's

Enjoy classic Chicago-style hot dogs and Italian beef sandwiches for dinner.
Take a short bus ride or a 20-minute walk from the museum.
USD50, 1.5 hours
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Day 2: Museum Day

Chicago, USA

8:30AM

Breakfast at Yolk

Fuel up with a delicious breakfast at Yolk, known for its innovative dishes.
Located in the South Loop, easily accessible by bus.
USD40, 1 hour

10:00AM

Visit the Shedd Aquarium

Explore the vibrant aquatic life at Shedd Aquarium, perfect for families.
Bus or train to Museum Campus, a short stroll to the aquarium.
USD80, 2.5 hours

12:30PM

Lunch at The Shake Shack

Grab a quick bite with fulfilling burgers and shakes just nearby.
Walking distance from Shedd Aquarium.
USD50, 1 hour

2:00PM

Visit the Adler Planetarium

Check out the planetarium's interactive exhibits that are great for all ages.
Walk to the planetarium from the shake shack.
USD70, 2 hours

5:00PM

Dinner at Pizzafari

Enjoy dinner at the family-friendly Pizzafari in Lincoln Park Zoo.
Take a bus or taxi to Lincoln Park.
USD60, 1.5 hours
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Day 3: Cultural Immersion

Chicago, USA

9:00AM

Breakfast at Lou Mitchell's

Start your day with a delicious meal at this iconic diner known for its breakfast choices.
Located near the entrance to Route 66, very central.
USD40, 1 hour

10:30AM

Visit the Art Institute of Chicago

Explore the vast art collections, suitable for art enthusiasts of all ages.
Short walk from Lou Mitchell's.
USD70, 2.5 hours

1:00PM

Lunch at the Art Institute Café

Enjoy a light lunch with beautiful views of the gardens outside.
Located inside the Art Institute.
USD50, 1 hour

2:30PM

Visit the Museum of Science and Industry

Dive into the interactive exhibits at one of the largest science museums in the world.
Take public transport from the Art Institute; approximately 30 minutes.
USD80, 3 hours

6:00PM

Dinner at The Cheesecake Factory

Enjoy a vast menu selection perfect for every family member's taste.
Close to the museum, take a quick taxi or ride-share.
USD70, 1.5 hours
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Day 4: Outdoor Adventures

Chicago, USA

8:00AM

Breakfast at Kismet Café

Savor a delicious breakfast in a cozy neighborhood café.
Located in Lincoln Park; drive or take public transport.
USD30, 1 hour

9:30AM

Visit Lincoln Park Zoo

Enjoy a free family-friendly zoo that’s perfect for a morning visit.
Short walk from Kismet Café.
Free, 2 hours

12:00PM

Lunch at Peckish Pig

Relax with a scrumptious lunch featuring great comfort food.
A quick bus ride from Lincoln Park Zoo.
USD60, 1.5 hours

1:30PM

Head to the Lakefront Trail

Enjoy a scenic bike or walk on Lakefront Trail admiring lake views.
Easily accessible from Peckish Pig.
Free if walking; USD15 to rent bikes., 2 hours

4:00PM

Picnic at North Avenue Beach

Pack snacks and have a delightful picnic at this beautiful beach.
Right at the end of the Lakefront Trail.
USD20 (snacks), 1.5 hours

6:00PM

Dinner at The Melting Pot

Enjoy a fun fondue meal; a unique dining experience the whole family will love.
Short drive or bus ride from the beach.
USD80, 2 hours
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Day 5: Chicago By Architecture

Chicago, USA

8:30AM

Breakfast at Meli Cafe

Enjoy a bright and cheerful breakfast spot for scrumptious pancakes.
Nearby in the West Loop; access via bus or taxi.
USD45, 1 hour

10:00AM

Take an Architectural River Cruise

Learn about the history and architecture of Chicago with a scenic river cruise.
Boarding is at Michigan Avenue; short walk after breakfast.
USD120, 1.5 hours

12:00PM

Lunch at Navy Pier's Harry Caray's Tavern

Have a great lunch with views of the lake at this family-dining restaurant.
Short walk from the river cruise end point.
USD70, 1.5 hours

2:00PM

Explore Navy Pier

Spend the afternoon with family rides and attractions at iconic Navy Pier.
Located right next to your lunch spot.
USD50, 3 hours

6:00PM

Dinner at Bubba Gump Shrimp Co.

Enjoy seafood themed around the movie Forest Gump, perfect for families!
Walking distance from Navy Pier.
USD75, 2 hours
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Day 6: Into the Wild

Chicago, USA

8:00AM

Breakfast at The Original Pancake House

Delight in an extensive menu of pancakes and waffles to fuel your day.
Located on Lincoln Avenue; taxi or drive.
USD40, 1 hour

9:30AM

Visit the Lincoln Park Conservatory

Discover a stunning collection of flowers and plants within a glasshouse.
Short drive or public transport from pancakes.
Free, 1.5 hours

11:00AM

Head to the Chicago Nature Museum

Enjoy the interactive exhibits displaying nature’s wonders.
Short walk or drive from the conservatory.
USD70, 2 hours

1:00PM

Lunch at The Park Grill

This casual eatery offers outdoor seating with views of Millennium Park.
Take a bus to Millennium Park area.
USD50, 1.5 hours

3:00PM

Explore Grant Park

Spend the afternoon playing in this beautiful park featuring gardens and sculptures.
Located next to The Park Grill.
Free, 2 hours

5:00PM

Dinner at Pullman’s Portland

Savor delicious Southern-inspired dishes with a local flair.
Short commute; consider taxi or rideshare.
USD65, 1.5 hours
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Day 7: History and Art

Chicago, USA

9:00AM

Breakfast at Cathy’s Corner

Enjoy a simple breakfast in a local family diner.
Located in the suburb area; drive is best.
USD25, 1 hour

10:30AM

Visit the Chicago History Museum

Walk through Chicago’s past with interactive exhibits and storytelling.
32 minutes via bus from Cathy's Corner.
USD75, 2 hours

1:00PM

Lunch at the Chicago History Museum Café

Enjoy a variety of casual fare in a cozy setting.
Dining is available on-site.
USD50, 1 hour

2:30PM

Visit the Museum of Contemporary Art

Explore modern art collections and intriguing exhibitions.
Less than a 10-minute bus ride from the museum.
USD60, 2 hours

5:00PM

Dinner at Uncle Julio's

Taste delicious Mexican food served in a festive environment.
Take public transport or a short taxi ride.
USD70, 1.5 hours
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Day 8: A Day at the Parks

Chicago, USA

8:00AM

Breakfast at Ann Sather

Famous for cinnamon rolls, start your day with a delicious pastry.
Easy access via public transport in Lakeview.
USD30, 1 hour

9:30AM

Visit Grant Park

Explore the beautiful landscaping and iconic fountains of Grant Park.
Short bus ride from Ann Sather.
Free, 2 hours

12:00PM

Lunch at The Mexican Museum

Stir your taste buds with authentic Mexican cuisine in an artful setting.
Nearby Grant Park; take a bus.
USD60, 1.5 hours

1:30PM

Explore Lincoln Park

Enjoy the sprawling green space and lovely gardens at Lincoln Park.
Bus ride from restaurant, only about 15 minutes.
Free, 2 hours

4:00PM

Picnic in the Park

Pack up your favorite snacks and enjoy a peaceful picnic within Lincoln Park.
Settle on a nice patch of grass at the park.
USD20 (snacks), 1.5 hours

6:00PM

Dinner at Maggiano's Little Italy

Indulge in Italian family-style dining in a cozy atmosphere.
A straightforward bus ride from the park.
USD75, 2 hours
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Day 9: Shopping and Sightseeing

Chicago, USA

9:00AM

Breakfast at Bongo Room

Delight in innovative breakfast dishes and delicious coffee.
Easily accessible via public transport.
USD35, 1 hour

10:30AM

Visit Macy's on State Street

Explore this historic department store and its beautiful Christmas decorations if it's the season.
Located right around the Loop area.
Free, 1.5 hours

12:00PM

Lunch at FoodCourt at Water Tower Place

Grab a quick bite at this diverse food court with various options.
A short walk from Macy's.
USD50, 1 hour

1:30PM

Explore Michigan Avenue's Magnificent Mile

Spend the afternoon shopping and sightseeing along Chicago’s famous avenue.
Just a short walk from the food court.
Free; shopping varies, 3 hours

5:00PM

Dinner at Ed Debevic's

Enjoy a fun, retro diner experience known for its quirky waitstaff.
Accessible by public transport from the Magnificent Mile area.
USD70, 1.5 hours
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Day 10: Fun and Entertainment

Chicago, USA

9:00AM

Breakfast at Bittersweet Pastry Shop

Start your day with great pastries and coffees in this charming bakery.
Take a bus from downtown for easy access.
USD25, 1 hour

10:30AM

Visit the Chicago Children's Museum

Explore interactive and playful exhibits designed specifically for kids.
Located at Navy Pier; accessible via a short bus ride.
USD80, 2 hours

1:00PM

Lunch at the Pier's Outdoor Food Court

Enjoy a casual lunch in a lively atmosphere by the waterfront.
Located right on Navy Pier.
USD50, 1 hour

2:30PM

Enjoy rides at Navy Pier's Amusement Park

Have some fun with thrilling rides and games for the family.
Staying at Navy Pier; just walk over.
USD70 (rides vary), 2.5 hours

5:00PM

Dinner at Pequod's Pizzeria

End your day with a delicious caramelized crust pizza that is a city favorite.
Bus or taxi back to Lincoln Park for easy access.
USD70, 1.5 hours
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Day 11: Family Fun Sports Day

Chicago, USA

8:00AM

Breakfast at Corner Bakery Café

Start with fresh coffee and baked goods at this delightful café.
Easily accessible in various parts of the city.
USD30, 1 hour

9:30AM

Visit Wrigley Field

Take a behind-the-scenes tour of this historic baseball stadium.
Take the train or taxi to Wrigley Field.
USD50 per person for the tour., 2.5 hours

12:00PM

Lunch at Wrigley Rooftops

Enjoy lunch while watching the game from one of the famous rooftop venues.
Located directly across the street from Wrigley Field.
USD80, 2 hours

2:30PM

Attend a Chicago Cubs Game

Catch a thrilling Cubs game and cheer for the home team in this iconic ballpark.
At Wrigley Field; part of the same location!
USD200 (depending on seats), 3 hours

6:00PM

Dinner at Hackney's on Lake

Enjoy a delightful dining experience after an exciting sports day.
Short walk from Wrigley Field.
USD75, 1.5 hours
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Day 12: Shopping and Relaxation

Chicago, USA

9:00AM

Breakfast at Frontera Grill

Enjoy a Latin-inspired breakfast at this popular dining spot.
Located in the River North area; take a taxi.
USD45, 1 hour

10:30AM

Visit the Chicago Botanic Garden

Immerse yourself in the beauty of nature and landscapes at this stunning garden.
Take a train to Glencoe, a short ride from downtown.
USD20 per family ticket, 2.5 hours

1:00PM

Lunch at The Grille at Aaron's

Enjoy delicious American fare overlooking the beautiful gardens.
On-site at the Botanic Garden!
USD60, 1.5 hours

2:30PM

Relax and Explore the Gardens

Take some time to wander and enjoy the carefully curated landscapes.
Free access after lunch.
Free, 2 hours

5:00PM

Dinner at Rosebud Italian Kitchen

End your day with fine Italian dinner in a warm environment.
Take a car back towards downtown area.
USD80, 2 hours
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Day 13: Final Adventures

Chicago, USA

9:00AM

Breakfast at Baker & Nosh

Enjoy a delightful breakfast experience at this renowned spot.
Easy access via public transportation.
USD35, 1 hour

10:30AM

Visit the Chicago Cultural Center

Explore the stunning architecture and art installations at this historic building.
Located in downtown; short walk from breakfast.
Free, 1.5 hours

12:00PM

Lunch at The Gage

Savor delicious contemporary American cuisine in this lively pub.
Just a few minutes walking distance.
USD70, 1.5 hours

1:30PM

Take a skyline tour with the Chicago Architecture Center

Get a fresh perspective on Chicago's architecture with a boat tour.
Walk from The Gage to the starting point of the tour.
USD140, 2 hours

4:00PM

Special Farewell Dinner at The Signature Room

Enjoy a memorable dinner with breathtaking views of the city atop the John Hancock Center.
Take a taxi or rideshare; it's centrally located.
USD200, 2.5 hours
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Day 14: Relax and Depart

Chicago, USA

9:00AM

Breakfast at The Breakfast House

Delight in a comforting breakfast at this cozy eatery.
Short taxi ride gets you there smoothly.
USD30, 1 hour

10:30AM

Last-minute Shopping at State Street

Pick up souvenirs and gifts for friends and family back home.
Take a bus downtown; very straightforward.
Varies, 2 hours

1:00PM

Lunch at Uno Pizzeria & Grill

End your trip with the original deep-dish pizza for lunch.
Take the bus back to the area for Uno's.
USD60, 1.5 hours

3:00PM

Pack and Depart

Head back to your accommodation to pack up and prepare for departure.
Travel back to your hotel; plan according to flight time.
Free, 1 hour
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