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4-Day Family-Friendly Relaxation Itinerary in Chicago
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4-Day Family-Friendly Relaxation Itinerary in Chicago
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Day 1: Arrival & Exploration
Chicago, USA
8:00AM
Arrival at O'Hare International Airport
Welcome to Chicago! After landing, collect your luggage and prepare for a day of adventure before your check-in.
Use the Airport Transit system to get to Rosemont station, then take the Blue Line to downtown Chicago.
0, 1 hour
9:30AM
Breakfast at Lou Mitchell’s
Indulge in a classic Chicago breakfast at Lou Mitchell’s, known for their pancakes and famous coffee to start your day off right.
Walk a few blocks from the Blue Line station to Lou Mitchell’s.
CURRENCY20, 1 hour
11:00AM
Millennium Park Visit
Stroll through Millennium Park and delight in the beauty of The Bean and the lovely surroundings perfect for family photos.
Take a quick Bus or a short walk to Millennium Park.
0, 1.5 hours
1:00PM
Lunch at Giordano’s
Enjoy a traditional Chicago deep-dish pizza at Giordano’s, great for the whole family to refuel after exploring.
Take a quick walk from Millennium Park to Giordano’s.
CURRENCY50, 1.5 hours
3:00PM
Lincoln Park Zoo
Head over to Lincoln Park Zoo where the kids can enjoy animal exhibits in a beautiful outdoor setting, all free of charge!
Take a taxi or rideshare from Giordano’s to Lincoln Park Zoo.
0, 2 hours
5:00PM
Check-in at Airbnb
Now it's time to head to your Airbnb for some needed relaxation following a busy day.
Utilize rideshare or public transit to reach your Airbnb.
0, 1 hour
7:00PM
Dinner at Portillo's
Savor Chicago favorites like the Italian beef sandwich at Portillo's while enjoying the energetic atmosphere.
Use a rideshare service to Portillo's.
CURRENCY60, 1.5 hours
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Day 2: Aquarium & Relaxation
Chicago, USA
8:00AM
Breakfast at Wildberry Pancakes and Cafe
Start your day with a delicious breakfast of pancakes or crepes before the excitement at the aquarium.
Head to Wildberry, which is a short walk from your Airbnb.
CURRENCY40, 1 hour
9:30AM
Travel to Shedd Aquarium
Head towards Shedd Aquarium for a morning full of aquatic wonders and interactive exhibits.
Take a rideshare to Shedd Aquarium.
CURRENCY20, 30 minutes
10:00AM
Visit Shedd Aquarium
Explore the diverse marine life, including the dolphin show and the new wild reef exhibit that the whole family will enjoy.
Follow the directions given at the entrance to navigate the exhibits.
CURRENCY120, 3 hours
1:00PM
Lunch at Shedd Aquarium Café
Grab a casual lunch at the aquarium café with family-friendly options to refuel before more adventures.
Lunch options available within the aquarium.
CURRENCY50, 1 hour
2:00PM
Relaxing Walk Along Lake Michigan
Take a serene walk along the shores of Lake Michigan and enjoy the lovely city views and fresh air.
Exit the aquarium and walk along the shoreline.
0, 1.5 hours
3:30PM
Navy Pier Exploration
Make your way to Navy Pier for rides, games, and fun activities to entertain the entire family.
Take a rideshare to Navy Pier from Lake Michigan.
CURRENCY30, 30 minutes
5:00PM
Dinner at Harry Caray’s Tavern
Enjoy dinner with a view at Harry Caray’s Tavern, known for its family-friendly vibe and delicious American classics.
Walk along Navy Pier to reach Harry Caray’s Tavern.
CURRENCY70, 1.5 hours
7:00PM
Return to Airbnb
After a fun-filled day, head back to your Airbnb and unwind.
Utilize rideshare services to return to your accommodation.
CURRENCY20, 30 minutes
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Day 3: Museum & Shopping
Chicago, USA
8:30AM
Breakfast at The Bongo Room
Have a spectacular breakfast at The Bongo Room, where creative dishes make for a delightful morning.
Walk or take public transit to The Bongo Room.
CURRENCY50, 1 hour
10:00AM
Visit the Field Museum
Explore the wonders of history and science at the Field Museum, including dinosaurs and ancient artifacts that will capture everyone’s imagination.
Take public transit to the Field Museum.
CURRENCY100, 3 hours
1:00PM
Lunch at The Field Bistro
Conveniently located within the museum, enjoy a family-friendly lunch filled with delicious options.
Lunch options are available within the Field Museum.
CURRENCY50, 1 hour
2:00PM
Shopping on Magnificent Mile
After lunch, take a stroll along the Magnificent Mile and enjoy shopping at family-friendly stores and boutiques.
Take public transit to Magnificent Mile.
0, 2 hours
4:30PM
Coffee Break at Intelligentsia Coffee
Take a break to enjoy some of the best coffee in town while the kids enjoy a sweet treat.
Walk to Intelligentsia Coffee.
CURRENCY15, 1 hour
5:30PM
Dinner at The Cheesecake Factory
End your day with dinner at The Cheesecake Factory, offering a wide array of choices that cater to all family members' preferences.
Walk from Intelligentsia Coffee to The Cheesecake Factory.
CURRENCY80, 1.5 hours
7:00PM
Return to Airbnb
Wind down after another exciting day as you travel back to your Airbnb.
Use rideshare services to get back.
CURRENCY20, 30 minutes
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Day 4: Nature & Departure
Chicago, USA
9:00AM
Breakfast at Beatrix
Start your final day with a wholesome breakfast at Beatrix, known for its healthy and delicious menu.
Walk or take public transit to Beatrix.
CURRENCY50, 1 hour
10:30AM
Visit the Chicago Botanic Garden
Explore the tranquility and beauty of the Chicago Botanic Garden, an incredibly peaceful way to spend the morning.
Take a taxi or rideshare to the Chicago Botanic Garden.
CURRENCY20, 30 minutes
11:00AM
Gardening and Nature Tour
Take a self-guided tour of the gardens and let the kids enjoy the space with activities throughout the garden.
Follow the paths and signage around the gardens.
0, 2 hours
1:00PM
Lunch at Cafe at the Garden
Enjoy a delightful lunch overlooking the gardens, perfect for unwinding before your departure.
Dine at the on-site café.
CURRENCY50, 1 hour
3:00PM
Travel to O'Hare International Airport
Start your journey back to the airport, allowing yourself plenty of time for any last-minute checking in.
Pre-arrange a rideshare or taxi to O'Hare.
CURRENCY40, 30 minutes
4:00PM
Departure from O'Hare International Airport
Safely board your flight, filled with cherished memories from your Chicago family trip.
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Itinerary created by
Plantrip Team
September 30, 2024
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