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14-Day Family Friendly Luxury Itinerary in Chicago

Viewed by 183 travelers

Day 1: Arrival and Exploration

Chicago, USA

9:00 AM

Breakfast at The Bongo Room

Start your luxury adventure with a sumptuous breakfast at The Bongo Room, famous for its decadent pancakes and brunch specialties.
Walk to the restaurant, 10 mins
USD 60, 1 hour

10:30 AM

Millennium Park

Stroll through Millennium Park, enjoying its iconic Cloud Gate sculpture and the beautiful landscaping that makes it a staple of the city.
5-minute walk from The Bongo Room
Free, 2 hours

1:00 PM

Lunch at Lou Malnati’s Pizzeria

Indulge in Chicago’s classic deep-dish pizza at Lou Malnati's, a perfect spot for families.
Taxi ride, 10 mins
USD 70, 1.5 hours

3:00 PM

The Art Institute of Chicago

Explore the diverse art collections of the Art Institute, with stunning artworks that appeal to visitors of all ages.
Short walk from Lou Malnati’s
USD 60, 2 hours

5:30 PM

Chicago Riverwalk

Take a leisurely walk along the Chicago Riverwalk, soaking in views of the city’s architecture.
5-minute walk
Free, 1 hour

7:00 PM

Dinner at The Signature Room

Enjoy a fine dining experience at The Signature Room with a breathtaking view of the city skyline as the backdrop.
Taxi ride, 15 mins
USD 250, 2 hours
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Day 2: Museum Day

Chicago, USA

8:00 AM

Breakfast at Beatrix

Fuel up with a wholesome breakfast at Beatrix featuring fresh, seasonal dishes.
Taxi ride, 10 mins
USD 50, 1 hour

9:30 AM

Field Museum

Visit the Field Museum and explore the ancient dinosaur exhibits and interactive displays that captivate young minds.
Taxi ride, 15 mins
USD 80, 3 hours

1:00 PM

Lunch at Portillo's

Savor Chicago's famous Italian beef sandwiches at Portillo's, a fun atmosphere for families.
Taxi ride, 10 mins
USD 60, 1 hour

2:30 PM

Shedd Aquarium

Dive into the wonders of the underwater world at Shedd Aquarium, home to fascinating sea life.
Short taxi ride, 10 mins
USD 80, 2.5 hours

5:00 PM

Navy Pier

Head to Navy Pier for family-friendly attractions including rides and games.
Taxi ride, 10 mins
Free (attractions extra), 2 hours

7:30 PM

Dinner at Riva Crab House

Dine at Riva Crab House on Navy Pier for seafood delicacies and stunning lake views.
Short walk at Navy Pier
USD 200, 1.5 hours
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Day 3: Cultural Adventures

Chicago, USA

8:30 AM

Breakfast at Wildberry Pancakes and Cafe

Start the day with delicious pancakes and breakfast options at Wildberry Pancakes.
Taxi ride, 10 mins
USD 50, 1 hour

10:00 AM

The Chicago Children's Museum

Explore the interactive displays at The Chicago Children's Museum, perfect for the little ones.
Taxi ride, 10 mins
USD 70, 2 hours

12:30 PM

Lunch at Shake Shack

Enjoy burgers and shakes at Shake Shack, a family-friendly spot with outdoor seating.
Walking distance
USD 50, 1 hour

1:30 PM

Lincoln Park Zoo

Visit Lincoln Park Zoo, where you can see animals up close in a beautiful park setting.
Taxi ride, 15 mins
Free, 2 hours

4:00 PM

The Lincoln Park Conservatory

Wander through the tropical gardens and vibrant floral displays at the Conservatory adjacent to the zoo.
Short walk
Free, 1 hour

5:30 PM

Dining at The Chopping Block

Join a family-friendly cooking class at The Chopping Block, where you’ll prepare and enjoy your own meal.
Taxi ride, 20 mins
USD 300 (includes meal), 3 hours
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Day 4: Fun Under the Sun

Chicago, USA

9:00 AM

Breakfast at Egg Harbor Café

Savor a hearty breakfast at Egg Harbor Café, known for its omelets and pancakes.
Taxi ride, 15 mins
USD 50, 1 hour

10:30 AM

Grant Park

Spend the morning enjoying the wide-open spaces of Grant Park, perfect for a family picnic.
Taxi ride, 10 mins
Free, 2 hours

1:00 PM

Lunch at The Halal Guys

Grab delicious street food at The Halal Guys, perfect for fueling your day.
Taxi ride, 10 mins
USD 50, 1 hour

2:30 PM

Skydeck Chicago

Experience breathtaking views of the city at Skydeck Chicago, standing on the Ledge for thrilling photos.
Taxi ride, 15 mins
USD 80, 2 hours

5:00 PM

Shopping at The Magnificent Mile

Stroll and shop along the famous Magnificent Mile with opportunities to find family souvenirs.
Walking distance
Varies, 1.5 hours

7:00 PM

Dinner at Joe's Stone Crab

Indulge in a seafood feast at Joe's Stone Crab, a luxurious dining experience.
Taxi ride, 10 mins
USD 300, 2 hours
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Day 5: Outdoor Adventure

Chicago, USA

8:00 AM

Breakfast at Ann Sather

Enjoy a delightful breakfast at Ann Sather, known for its cinnamon rolls and Swedish specialties.
Taxi ride, 10 mins
USD 60, 1 hour

9:30 AM

Bike along the Lakefront Trail

Rent bikes and ride along the scenic Lakefront Trail, enjoying views of Lake Michigan.
Taxi ride, 10 mins to rental place
USD 50 (rental), 2.5 hours

12:00 PM

Lunch at The Dock at Montrose Beach

Unwind with a relaxed lunch at The Dock overlooking the beach.
Taxi ride, 10 mins
USD 70, 1.5 hours

1:30 PM

Montrose Beach

Spend the afternoon playing at Montrose Beach, enjoying the sand and surf with beach games.
Walking distance
Free, 3 hours

5:30 PM

Ice Cream at Jeni's Splendid Ice Creams

Cool off with delicious, artisanal ice cream from Jeni's, a family favorite.
Taxi ride, 15 mins
USD 40, 1 hour

7:00 PM

Dinner at FireLake Grill House

Conclude your day with a cozy meal at FireLake Grill House, focusing on local ingredients.
Taxi ride, 20 mins
USD 200, 2 hours
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Day 6: History and Heritage

Chicago, USA

8:30 AM

Breakfast at Fig & Olive

Kick off your day with Mediterranean-inspired dishes at Fig & Olive.
Taxi ride, 10 mins
USD 80, 1 hour

10:00 AM

Chicago History Museum

Dive into the city's past at the Chicago History Museum, where exhibits reveal the rich local heritage.
Taxi ride, 15 mins
USD 70, 2 hours

12:30 PM

Lunch at Frontera Grill

Enjoy vibrant Mexican cuisine at Frontera Grill, known for its flavorful dishes.
Taxi ride, 10 mins
USD 90, 1.5 hours

2:00 PM

Chicago River Architecture Cruise

Take a family-friendly architecture cruise on the Chicago River to learn about the city's stunning skyline.
Short walk to the dock
USD 120, 1.5 hours

4:00 PM

The Magnificent Mile

Spend free time exploring shops and attractions on The Magnificent Mile.
Taxi ride, 5 mins
Varies, 2 hours

6:30 PM

Dinner at The Grill on the Alley

Indulge in a robust dinner at The Grill on the Alley, a prime steakhouse in Chicago.
Taxi ride, 10 mins
USD 250, 2 hours
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Day 7: Theme Park Irony

Chicago, USA

8:00 AM

Breakfast at the hotel

Enjoy a relaxing breakfast at your hotel before a day filled with fun.
N/A
Included with stay, 1 hour

9:30 AM

Six Flags Great America

Spend the day at Six Flags Great America, an exciting amusement park with thrilling rides and entertainment for all ages.
Taxi ride, 1 hour
USD 300, 8 hours

5:30 PM

Dinner at the park

Enjoy a casual dining meal within the park, with various options available.
N/A
USD 100, 1 hour

7:00 PM

Return to Chicago

End the day with a peaceful return trip to the city after a fun-filled day.
Taxi ride, 1 hour
USD 60, 1 hour
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Day 8: Relax and Rejuvenate

Chicago, USA

9:00 AM

Breakfast at Cafe Ba Ba Reeba!

Enjoy a Spanish brunch with tapas at Cafe Ba Ba Reeba!, a fun dining experience for families.
Taxi ride, 15 mins
USD 70, 1 hour

10:30 AM

Spa day at The Peninsula

Indulge in a luxurious family spa day at The Peninsula, offering kid-friendly treatments.
Taxi ride, 10 mins
USD 500 (varies based on treatment), 3 hours

2:00 PM

Lunch at The Purple Pig

Savor Mediterranean-inspired dishes at The Purple Pig, known for delicious small plates.
Short taxi ride, 15 mins
USD 80, 1.5 hours

3:30 PM

Stroll and relax at the shoreline

Spend the afternoon strolling along the shoreline of Lake Michigan, taking in the scenic views.
Short taxi ride, 10 mins
Free, 2 hours

5:30 PM

Dinner at RPM Steak

Dine at RPM Steak for a modern take on classic steakhouse dining in an upscale atmosphere.
Taxi ride, 15 mins
USD 250, 2 hours
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Day 9: Sightseeing and Culture

Chicago, USA

9:00 AM

Breakfast at The Original Pancake House

Relish in delightful pancakes and warm syrup at The Original Pancake House.
Taxi ride, 10 mins
USD 50, 1 hour

10:30 AM

Museum of Science and Industry

Explore hands-on exhibits at the Museum of Science and Industry, often hailed as one of the greatest museums.
Taxi ride, 15 mins
USD 80, 3 hours

1:30 PM

Lunch at Café for the Museum of Science and Industry

Enjoy lunch at the museum's café with kid-friendly options.
N/A
USD 60, 1 hour

3:00 PM

Rebuild Foundation

Discover local art and culture at the Rebuild Foundation, engaging with the community through artistic initiatives.
Taxi ride, 15 mins
Free, 2 hours

6:00 PM

Dinner at The Duck Duck Goat

Experience Asian-inspired dishes and family-style meals at The Duck Duck Goat.
Taxi ride, 15 mins
USD 150, 2 hours
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Day 10: Urban Exploration

Chicago, USA

8:30 AM

Breakfast at The Little Goat Diner

Enjoy a creative breakfast with a twist at The Little Goat Diner, a local favorite.
Taxi ride, 15 mins
USD 70, 1 hour

10:00 AM

Chinatown Adventure

Explore the vibrant neighborhood of Chinatown, filled with unique shops and cultural experiences.
Taxi ride, 20 mins
Free, 2.5 hours

12:30 PM

Lunch at MingHin Cuisine

Delight in dim sum and authentic Chinese dishes at MingHin Cuisine.
Walking distance within Chinatown
USD 80, 1.5 hours

2:00 PM

Brookfield Zoo

Visit Brookfield Zoo, an expansive facility with various exhibits and activities for all ages.
Taxi ride, 30 mins
USD 120, 3 hours

5:30 PM

Dinner at Wildfire

Conclude your day with a meal at Wildfire, featuring wood-fired dishes and an inviting ambiance.
Taxi ride, 30 mins
USD 200, 2 hours
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Day 11: Shopping and Revelry

Chicago, USA

9:00 AM

Breakfast at The Hotel at Midtown

Start the day with a lovely breakfast spread at your hotel.
N/A
Included with stay, 1 hour

10:30 AM

Shopping on the Magnificent Mile

Take a family shopping trip along the famous Magnificent Mile, seeking out the best stores.
Walking distance
Varies, 3 hours

1:30 PM

Lunch at Eataly

Explore Italian marketplaces and indulge in delicious meals at Eataly.
Walking distance
USD 75, 1.5 hours

3:00 PM

Chicago Magic Lounge

Visit the Chicago Magic Lounge for an interactive magic show that captivates guests of all ages.
Taxi ride, 15 mins
USD 100, 2 hours

5:30 PM

Dinner at RPM Italian

Savor Italian cuisine at the trendy RPM Italian with its delightful menu.
Taxi ride, 15 mins
USD 200, 2 hours
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Day 12: Relax and Reflect

Chicago, USA

9:00 AM

Breakfast at The Goddess and Grocer

Enjoy a casual but delightful breakfast with health-conscious options.
Taxi ride, 15 mins
USD 60, 1 hour

10:30 AM

Explore the Chicago Botanic Garden

Discover the beauty of nature at the Chicago Botanic Garden, offering a peaceful retreat.
Taxi ride, 30 mins
Free, 2 hours

1:00 PM

Lunch at The Bistro in the Garden

Dine at The Bistro overlooking the gardens with fresh seasonal dishes.
N/A
USD 100, 1.5 hours

3:00 PM

Return to Chicago

Head back to the city and enjoy leisurely activities or shopping.
Taxi ride, 30 mins
USD 50, 1 hour

5:30 PM

Dinner at Hugo's Frog Bar & Fish House

Indulge in a delicious seafood dinner at Hugo's, a Chicago staple.
Taxi ride, 15 mins
USD 200, 2 hours
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Day 13: Last Adventures

Chicago, USA

9:00 AM

Breakfast at The Kitchen

Start your final day with locally sourced ingredients at The Kitchen, a farm-to-table experience.
Taxi ride, 15 mins
USD 70, 1 hour

10:30 AM

Wrigley Field Tour

Take a tour of the iconic Wrigley Field, a staple of baseball history.
Taxi ride, 15 mins
USD 40, 1.5 hours

12:30 PM

Lunch at The Brick Yard

Refuel with a casual lunch at The Brick Yard, featuring classic American fare.
Short taxi ride, 15 mins
USD 70, 1 hour

2:00 PM

The Chicago Cultural Center

Visit the Chicago Cultural Center for free exhibits and architectural beauty.
Taxi ride, 10 mins
Free, 1.5 hours

4:00 PM

Explore the Chicago Union Station

Take in the historical grandeur of Chicago's Union Station and some last-minute shopping.
Taxi ride, 10 mins
Free, 1 hour

5:30 PM

Farewell Dinner at Alinea

Celebrate your adventure with a farewell dinner at the renowned Michelin-starred Alinea.
Taxi ride, 15 mins
USD 600, 3 hours
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Day 14: Departure

Chicago, USA

8:00 AM

Breakfast at the hotel

Enjoy one last breakfast at the hotel before preparing for your journey home.
N/A
Included with stay, 1 hour

10:00 AM

Check-out and Departure

Check-out of the hotel and prepare for your journey home, taking cherished memories with you.
Taxi to airport
USD 50, 1 hour
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