Chicago 5-Day City Experiences, Foodie, Nature, Relaxation Itinerary

Day 1: City Exploration

Chicago, USA

8:00AM

Breakfast at Yolk

Start your day with a delicious breakfast at Yolk, known for its tasty omelets and pancakes.
Yolk is located in the South Loop. You can take a short walk or a quick ride from your accommodation.
$15, 1 hour

10:00AM

Millennium Park

Visit Millennium Park to see the famous Cloud Gate sculpture, also known as 'The Bean'. Enjoy the beautiful gardens and art installations.
Millennium Park is a short walk from Yolk.
Free, 2 hours

12:30PM

Lunch at Lou Malnati's Pizzeria

Indulge in Chicago's famous deep-dish pizza at Lou Malnati's. Don't miss out on this iconic food experience.
Lou Malnati's has multiple locations in Chicago. You can take a short ride to the nearest one.
$20, 1.5 hours

3:00PM

Art Institute of Chicago

Explore one of the oldest and largest art museums in the United States. Admire famous artworks from around the world.
The Art Institute is within walking distance from Lou Malnati's.
$25, 2 hours

6:00PM

Dinner at Girl & the Goat

Experience innovative and flavorful dishes at Girl & the Goat, a top-rated restaurant in Chicago.
Girl & the Goat is located in the West Loop. You can take a short ride from the Art Institute.
$50, 2 hours
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Day 2: Foodie Delight

Chicago, USA

9:00AM

Brunch at Beatrix

Start your day with a delicious and healthy brunch at Beatrix, known for its fresh ingredients and vibrant atmosphere.
Beatrix is located in River North. You can take a short walk or a rideshare from your accommodation.
$30, 1.5 hours

11:00AM

Chicago Food Planet Food Tour

Embark on a food tour with Chicago Food Planet to sample a variety of local dishes and learn about the city's culinary scene.
The tour starting point is in the Loop. You can take a short ride or public transportation to get there.
$75, 3 hours

3:00PM

Navy Pier

Explore Navy Pier, a popular tourist attraction offering shopping, dining, and entertainment options. Enjoy the views of Lake Michigan.
Navy Pier is easily accessible by public transportation or rideshare from the Loop.
Free, 2 hours

6:00PM

Dinner at Alinea

Indulge in a world-class dining experience at Alinea, known for its innovative and artistic dishes.
Alinea is located in Lincoln Park. You can take a rideshare or public transportation from Navy Pier.
$300, 3 hours
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Day 3: Nature Escape

Chicago, USA

9:00AM

Breakfast at Wildberry Pancakes & Cafe

Enjoy a delicious breakfast at Wildberry Pancakes & Cafe, known for its mouthwatering pancakes and omelets.
Wildberry Pancakes & Cafe is located in Streeterville. You can take a short walk from your accommodation.
$20, 1 hour

10:30AM

Chicago Botanic Garden

Explore the beautiful landscapes and diverse plant collections at the Chicago Botanic Garden. Take a relaxing stroll in nature.
The Garden is located in Glencoe, a short drive or public transportation ride from Streeterville.
$25, 2 hours

1:00PM

Lunch at The Hampton Social

Enjoy a coastal-inspired dining experience at The Hampton Social, known for its seafood dishes and beachy vibes.
The Hampton Social has a location in Streeterville, where you can walk or take a short ride back.
$40, 1.5 hours

3:00PM

Lakefront Trail Biking

Rent a bike and cycle along the scenic Lakefront Trail, offering stunning views of Lake Michigan and the city skyline.
You can rent bikes at various locations along the trail. Start from Streeterville for a leisurely ride.
$15, 2 hours

6:00PM

Dinner at The Signature Room

Dine at The Signature Room on the 95th floor of the John Hancock Center. Enjoy panoramic views of Chicago while savoring gourmet cuisine.
The Signature Room is a short ride or walk from the Lakefront Trail.
$70, 2 hours
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Day 4: Relaxation Day

Chicago, USA

9:00AM

Morning Yoga at Maggie Daley Park

Start your day with a rejuvenating yoga session at Maggie Daley Park, surrounded by greenery and peaceful vibes.
Maggie Daley Park is located in the Loop, a short walk or ride from your accommodation.
Free, 1 hour

10:30AM

Spa Day at The Peninsula Chicago

Indulge in a luxurious spa day at The Peninsula Chicago. Treat yourself to massages, facials, and relaxation in a serene setting.
The Peninsula Chicago is located in the Magnificent Mile area, easily accessible by public transportation or rideshare.
$200, 3 hours

2:00PM

Lunch at Cindy's Rooftop

Enjoy a rooftop dining experience at Cindy's with scenic views of Millennium Park and the city skyline.
Cindy's Rooftop is located in the Loop, a short walk or ride from The Peninsula.
$35, 1.5 hours

4:00PM

Shopping on Magnificent Mile

Explore the upscale shops and boutiques on the Magnificent Mile. Shop for luxury brands and unique finds.
The Magnificent Mile is within walking distance from Cindy's Rooftop.
Varies, 2 hours

7:00PM

Dinner at RPM Italian

Savor modern Italian cuisine at RPM Italian, known for its delicious pasta dishes and trendy ambiance.
RPM Italian is located in River North, a short ride or walk from the Magnificent Mile.
$45, 2 hours
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Day 5: Cultural Immersion

Chicago, USA

10:00AM

Breakfast at Mindy's Hot Chocolate

Start your day with a cozy breakfast at Mindy's Hot Chocolate, known for its decadent hot chocolate and comfort food.
Mindy's Hot Chocolate is located in Wicker Park. You can take a short ride or public transportation from your accommodation.
$25, 1.5 hours

12:00PM

Visit The Field Museum

Explore The Field Museum, home to a fascinating collection of natural history exhibits, including Sue the T-Rex.
The Field Museum is located in Museum Campus, easily accessible by public transportation or rideshare from Wicker Park.
$30, 3 hours

3:30PM

Chicago River Architecture Tour

Embark on an architectural boat tour along the Chicago River. Learn about the city's iconic buildings and skyline.
The tour departs from various points along the river. You can catch a tour from the Museum Campus area.
$40, 2 hours

6:00PM

Dinner at Frontera Grill

Enjoy authentic Mexican cuisine at Frontera Grill, a renowned restaurant by Chef Rick Bayless.
Frontera Grill is located in River North. You can take a short ride or public transportation from the river tour.
$40, 2 hours
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