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Romantic Honeymoon Getaway in Chicago
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Romantic Honeymoon Getaway in Chicago
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Day 1: Explore City Landmarks
Chicago, Illinois
8:00AM
Breakfast at Wildberry Pancakes and Cafe
Start your day with a delectable breakfast at Wildberry Pancakes and Cafe, known for their delicious pancakes and cozy ambiance.
Head to Millennium Park by taking the 'L' train to the Millennium Station.
$20, 1.5 hours
10:00AM
Millennium Park
Take a romantic stroll through Millennium Park and capture a photo of the iconic Cloud Gate sculpture, also known as 'The Bean'.
Walk south towards the beautiful Chicago Riverwalk.
Free, 2 hours
12:00PM
Lunch at City Winery Chicago Riverwalk
Enjoy a lovely lunch with stunning river views at City Winery Chicago Riverwalk, offering a selection of wine and delicious dishes.
Walk along the Riverwalk towards Navy Pier.
$40, 1.5 hours
2:00PM
Navy Pier
Explore Navy Pier, a waterfront destination with attractions, shops, and stunning views of Lake Michigan. Enjoy a ride on the iconic Centennial Wheel.
Take a taxi or walk towards the Art Institute of Chicago.
$25, 2 hours
4:00PM
Dinner at The Signature Room at the 95th
Indulge in a romantic dinner at The Signature Room at the 95th, located on the 95th floor with breathtaking panoramic views of the cityscape.
Head back to your accommodation for a restful evening.
$100, 2 hours
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Day 2: Cultural and Wildlife Experience
Chicago, Illinois
9:00AM
Breakfast at Beatrix
Start your day with a delicious breakfast at Beatrix, known for their healthy and flavorful options to fuel your day of exploration.
Make your way to the Art Institute of Chicago, either by walking or taking public transportation.
$25, 1.5 hours
11:00AM
Art Institute of Chicago
Explore the renowned Art Institute of Chicago, home to a vast collection of art including masterpieces by famous artists. Immerse yourselves in art and culture.
Walk towards Lincoln Park Zoo for a nature-filled experience.
$30, 2 hours
1:00PM
Lunch at Cafe Brauer
Enjoy a charming lunch amidst nature at Cafe Brauer in Lincoln Park, offering a tranquil setting near the zoo and the pond.
Take a leisurely stroll through Lincoln Park towards the Magnificent Mile.
$35, 1.5 hours
3:00PM
Lincoln Park Zoo
Visit the Lincoln Park Zoo, a free and beautiful zoo showcasing a variety of animals. Take a romantic walk hand in hand through the zoo.
Head to the Magnificent Mile for a shopping and dining experience.
Free, 2 hours
5:00PM
Shopping at the Magnificent Mile
Explore the upscale shops and boutiques along the Magnificent Mile, a shopper's paradise with a plethora of options for gifts and souvenirs.
End your day with a romantic dinner at The Purple Pig.
$80, 2 hours
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Itinerary created by
Plantrip Team
July 12, 2024
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