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Discovering Chicago in 5 Days

Viewed by 65 travelers

Day 1: City Center Exploration

Chicago, USA

8:00AM

Breakfast at Wildberry Pancakes and Cafe

Enjoy a delightful breakfast at Wildberry Pancakes and Cafe with their signature pancakes and fresh juices.
Walk 5 minutes from Sheraton Downtown Riverpark Hotel to the restaurant.
$15, 1 hour

10:00AM

Art Institute of Chicago

Explore world-class art collections at the Art Institute of Chicago, home to works by renowned artists.
Take a 10-minute walk from the restaurant to the museum.
$25, 2 hours

1:00PM

Lunch at Lou Malnati's Pizzeria

Indulge in Chicago's famous deep-dish pizza at Lou Malnati's Pizzeria for a classic Windy City dining experience.
Walk 15 minutes or take a short taxi ride to the pizzeria.
$20, 1.5 hours

3:00PM

Chicago Riverwalk

Stroll along the scenic Chicago Riverwalk and admire the city's architecture and bustling river traffic.
Walk 20 minutes from Lou Malnati's Pizzeria to the Riverwalk.
Free, 1 hour

6:00PM

Dinner at Girl & The Goat

Experience innovative cuisine at Girl & The Goat, a top-rated restaurant known for its creative dishes.
Take a 15-minute taxi ride or public transportation to the restaurant.
$50, 2 hours
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Day 2: Magnificent Mile Shopping

Chicago, USA

9:00AM

Breakfast at Beatrix

Indulge in a delicious breakfast at Beatrix before a day of shopping on The Magnificent Mile.
Walk 10 minutes from Sheraton Downtown Riverpark Hotel to the restaurant.
$20, 1 hour

11:00AM

Shop at The Magnificent Mile

Explore upscale shops and boutiques along The Magnificent Mile, Chicago's premier shopping destination.
Walk from Beatrix to The Magnificent Mile for a day of retail therapy.
Varies, 3 hours

2:00PM

Lunch at The Purple Pig

Enjoy a Mediterranean-inspired meal at The Purple Pig, known for its tasty charcuterie and wine selection.
Walk 5 minutes from The Magnificent Mile to the restaurant.
$30, 1.5 hours

4:00PM

360 Chicago Observation Deck

Take in panoramic city views from the 360 Chicago Observation Deck in the iconic John Hancock Building.
Take a 10-minute taxi ride or public transportation to the observation deck.
$25, 1.5 hours

7:00PM

Dinner at RPM Italian

Dine on modern Italian cuisine at RPM Italian, a stylish restaurant with a vibrant ambiance perfect for dinner.
Take a 15-minute taxi ride to RPM Italian.
$40, 2 hours
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Day 3: Navy Pier Adventure

Chicago, USA

8:30AM

Breakfast at Yolk

Savor a tasty breakfast at Yolk, known for its delicious omelets and pancakes to fuel your day.
Walk 5 minutes from Sheraton Downtown Riverpark Hotel to the restaurant.
$15, 1 hour

10:00AM

Explore Navy Pier

Discover attractions, dining, and entertainment at Navy Pier, including the famous Centennial Wheel and Shakespeare Theater.
Enjoy a scenic 20-minute walk along the lakefront to reach Navy Pier.
Varies, 3 hours

1:00PM

Lunch at Riva Crabhouse

Feast on seafood with stunning Lake Michigan views at Riva Crabhouse, a perfect lunch spot at Navy Pier.
Walk 10 minutes within Navy Pier to Riva Crabhouse.
$35, 1.5 hours

3:00PM

Chicago Children's Museum

Enjoy interactive exhibits and educational fun at the Chicago Children's Museum for a family-friendly experience.
Walk 5 minutes from Riva Crabhouse to the museum.
$15, 2 hours

6:00PM

Dinner at Harry Caray's Italian Steakhouse

Dine on classic Italian and steakhouse dishes at Harry Caray's Italian Steakhouse, a beloved Chicago dining spot.
Take a 15-minute taxi ride to the restaurant.
$45, 2 hours
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Day 4: Millennium Park Experience

Chicago, USA

9:00AM

Breakfast at Goddess and The Baker

Start your day with artisanal coffee and pastries at Goddess and The Baker near Millennium Park.
Walk 10 minutes from Sheraton Downtown Riverpark Hotel to the cafe.
$10, 1 hour

11:00AM

Visit Cloud Gate (The Bean)

Marvel at the iconic Cloud Gate sculpture, known as 'The Bean', in Millennium Park and take memorable photos.
Walk 15 minutes from Goddess and The Baker to Millennium Park.
Free, 1 hour

1:00PM

Lunch at Cindy's Rooftop

Dine with stunning views at Cindy's Rooftop in Millennium Park while enjoying the Chicago skyline.
Walk 5 minutes within Millennium Park to the rooftop restaurant.
$30, 1.5 hours

3:00PM

Art Installations in the Park

Explore art installations and green spaces in Millennium Park, including the popular Lurie Garden and Crown Fountain.
Stroll around the park at your leisure.
Free, 2 hours

6:00PM

Dinner at The Gage

Indulge in rustic and refined dishes at The Gage, a historic building near Millennium Park with a mix of flavors.
Take a 10-minute walk or a quick taxi ride to The Gage.
$40, 2 hours
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Day 5: Wicker Park Vibes

Chicago, USA

9:30AM

Breakfast at Big Star

Enjoy flavorful breakfast tacos and margaritas at Big Star to kickstart your day in the artsy neighborhood of Wicker Park.
Take a 15-minute taxi ride to Wicker Park.
$20, 1 hour

11:00AM

Explore Wicker Park

Discover the eclectic mix of boutiques, cafes, and street art in the vibrant Wicker Park neighborhood.
Stroll around Wicker Park at your own pace.
Varies, 3 hours

2:00PM

Lunch at Antique Taco

Savor creative tacos and Mexican-inspired dishes at Antique Taco, a culinary gem in Wicker Park.
Walk 10 minutes to the restaurant in Wicker Park.
$25, 1.5 hours

4:00PM

Museum of Contemporary Art Chicago

Immerse yourself in contemporary art at the Museum of Contemporary Art Chicago, featuring innovative works.
Take a 20-minute taxi ride or public transportation to the museum.
$15, 2 hours

7:00PM

Dinner at The Violet Hour

Conclude your day with craft cocktails at The Violet Hour, a speakeasy-style bar known for its intimate ambiance.
Take a short taxi ride to The Violet Hour in Wicker Park.
$50, 2 hours
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