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Chicago

5 day itinerary for Chicago

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Best food

Great food

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Itinerary

Here's a suggested itinerary for 5 days in Chicago, with a focus on the city's best and great food:

Day 1:

  • Start your day with breakfast at The Bongo Room, a popular brunch spot known for its creative pancakes and omelets.
  • After breakfast, head to the Art Institute of Chicago to explore one of the world's greatest art collections.
  • For lunch, grab a Chicago-style hot dog at Portillo's or a deep-dish pizza at Lou Malnati's.
  • Spend the afternoon exploring Millennium Park, home to the iconic Cloud Gate sculpture (also known as "The Bean") and the Crown Fountain.
  • For dinner, head to Girl & the Goat, a trendy restaurant known for its inventive small plates and cocktails.

Day 2:

  • Start your day with breakfast at Yolk, a popular breakfast spot with multiple locations throughout the city.
  • Spend the morning exploring the Magnificent Mile, a stretch of Michigan Avenue known for its high-end shopping and architecture.
  • For lunch, head to Eataly, a massive Italian marketplace with multiple restaurants and food counters.
  • In the afternoon, take a boat tour of the Chicago River to learn about the city's architecture and history.
  • For dinner, head to Alinea, one of the world's best restaurants known for its avant-garde cuisine and multi-course tasting menus.

Day 3:

  • Start your day with breakfast at Wildberry Pancakes and Cafe, a popular breakfast spot with a wide variety of pancakes and omelets.
  • Spend the morning exploring the Lincoln Park Zoo, a free zoo with a wide variety of animals.
  • For lunch, head to The Purple Pig, a popular restaurant known for its Mediterranean-inspired small plates.
  • In the afternoon, take a stroll along the Lakefront Trail, a scenic path that runs along Lake Michigan.
  • For dinner, head to Avec, a popular restaurant known for its Mediterranean-inspired small plates and communal seating.

Day 4:

  • Start your day with breakfast at Little Goat Diner, a popular breakfast spot with a wide variety of breakfast dishes and pastries.
  • Spend the morning exploring the Museum of Science and Industry, one of the largest science museums in the world.
  • For lunch, head to Fat Rice, a popular restaurant known for its Macanese cuisine.
  • In the afternoon, take a walk through the historic Hyde Park neighborhood, home to the University of Chicago and the Obama Presidential Center (opening in 2021).
  • For dinner, head to Spiaggia, a high-end Italian restaurant known for its pasta and wine selection.

Day 5:

  • Start your day with breakfast at Do-Rite Donuts, a popular donut shop with multiple locations throughout the city.
  • Spend the morning exploring the Chicago Cultural Center, a historic building with free art exhibits and events.
  • For lunch, head to Xoco, a popular restaurant known for its Mexican street food and hot chocolate.
  • In the afternoon, take a walk through the trendy Wicker Park neighborhood, known for its street art and independent boutiques.
  • For dinner, head to Monteverde, a popular Italian restaurant known for its pasta and cocktails.

I hope this itinerary gives you a good starting point for your trip to Chicago! Let me know if you have any other questions or if there's anything else I can help with.

Places of interest

The Bongo Room Chicago

The Bongo Room

The Bongo Room is a popular breakfast and brunch spot in Chicago known for their creative and indulgent dishes.

Art Institute of Chicago Chicago

Art Institute of Chicago

The Art Institute of Chicago is one of the oldest and largest art museums in the United States, featuring a vast collection of artworks from around the world.

Portillo's Chicago

Portillo's

Portillo's is a popular Chicago-based restaurant chain known for its hot dogs, Italian beef sandwiches, and chocolate cake shakes.

Lou Malnati's Chicago

Lou Malnati's

Lou Malnati's is a famous Chicago-style deep dish pizza restaurant that has been serving up delicious pies since 1971. Their signature buttery crust, tangy tomato sauce, and gooey cheese make for a mouthwatering experience.

Millennium Park Chicago

Millennium Park

Millennium Park is a public park located in the heart of downtown Chicago. It features iconic landmarks such as the Cloud Gate sculpture (also known as "The Bean"), the Jay Pritzker Pavilion, and the Crown Fountain.

Cloud Gate sculpture (The Bean) Chicago

Cloud Gate sculpture (The Bean)

Cloud Gate, also known as "The Bean," is a public sculpture located in Millennium Park in Chicago. Designed by artist Anish Kapoor, the sculpture is made of stainless steel and reflects the city's skyline and surrounding environment.

Crown Fountain Chicago

Crown Fountain

Crown Fountain is an interactive public art installation located in Millennium Park, Chicago. It consists of two 50-foot glass towers that project images of Chicago residents and spout water from their mouths.

Girl & the Goat Chicago

Girl & the Goat

Girl & the Goat is a trendy restaurant in Chicago that serves creative small plates with global flavors, using locally sourced ingredients.

Yolk Chicago

Yolk

Yolk Chicago is a popular breakfast and brunch spot known for its creative menu items and generous portions.

Magnificent Mile Chicago

Magnificent Mile

Magnificent Mile is a prestigious shopping district in Chicago, known for its upscale stores, restaurants, and hotels. It stretches along Michigan Avenue from the Chicago River to Oak Street.

Eataly Chicago

Eataly

Eataly Chicago is a vibrant Italian marketplace that offers a variety of high-quality food and drink options, including fresh produce, artisanal cheeses, handmade pasta, and more.

Chicago River boat tour Chicago

Chicago River boat tour

Enjoy a scenic boat tour of the Chicago River and learn about the city's architecture and history.

Alinea Chicago

Alinea

Alinea is a three-Michelin-starred restaurant in Chicago that offers a unique and innovative dining experience with its multi-course tasting menu.

Wildberry Pancakes and Cafe Chicago

Wildberry Pancakes and Cafe

Wildberry Pancakes and Cafe Chicago is a popular breakfast spot known for their delicious pancakes, waffles, and other breakfast dishes.

Lincoln Park Zoo Chicago

Lincoln Park Zoo

Lincoln Park Zoo is a free 35-acre zoo located in Chicago, Illinois. It is home to over 1,000 animals from around the world and offers a variety of exhibits and attractions for visitors of all ages.

The Purple Pig Chicago

The Purple Pig

The Purple Pig is a popular restaurant in Chicago that offers Mediterranean-inspired small plates and a wide selection of wine.

Lakefront Trail Chicago

Lakefront Trail

The Lakefront Trail in Chicago is an 18-mile long path that runs along the shore of Lake Michigan, offering stunning views of the city skyline and the lake. It is a popular spot for walking, running, biking, and rollerblading.

Avec Chicago

Avec

Avec Chicago is a Mediterranean-inspired restaurant located in the West Loop neighborhood of Chicago. The menu features small plates meant for sharing, wood-fired dishes, and an extensive wine list.

Little Goat Diner Chicago

Little Goat Diner

Little Goat Diner is a popular restaurant in Chicago that serves up creative twists on classic diner fare, along with a variety of cocktails and craft beers.

Museum of Science and Industry Chicago

Museum of Science and Industry

The Museum of Science and Industry in Chicago is one of the largest science museums in the world, featuring interactive exhibits and hands-on experiences for visitors of all ages.

Fat Rice Chicago

Fat Rice

Fat Rice Chicago is a restaurant that serves Macanese cuisine, which is a blend of Chinese and Portuguese flavors. They offer unique dishes such as arroz gordo (a rice dish with various meats and seafood) and egg tarts for dessert.

Hyde Park neighborhood Chicago

Hyde Park neighborhood

Hyde Park is a historic neighborhood located on the South Side of Chicago, known for its beautiful architecture, cultural landmarks, and proximity to Lake Michigan. It is home to the University of Chicago and boasts a diverse community with a rich history.

Obama Presidential Center Chicago

Obama Presidential Center

The Obama Presidential Center in Chicago is a museum and library dedicated to the legacy of former President Barack Obama. It features exhibits, archives, and programs that highlight his life and presidency.

Spiaggia Chicago

Spiaggia

Spiaggia Chicago is an upscale Italian restaurant located in the Gold Coast neighborhood, offering contemporary cuisine and stunning views of Lake Michigan.

Do-Rite Donuts Chicago

Do-Rite Donuts

Do-Rite Donuts Chicago is a popular donut shop located in the heart of the city. They offer a variety of delicious and unique donut flavors, as well as coffee and other beverages.

Chicago Cultural Center Chicago

Chicago Cultural Center

The Chicago Cultural Center is a historic landmark building that serves as a cultural hub for the city, offering free art exhibitions, performances, and events throughout the year.

Xoco Chicago

Xoco

Xoco Chicago is a Mexican restaurant that serves delicious street food and traditional dishes.

Wicker Park neighborhood Chicago

Wicker Park neighborhood

Wicker Park is a trendy neighborhood in Chicago known for its vibrant nightlife, unique boutiques, and diverse dining options. It's also home to numerous art galleries and music venues.

Monteverde Chicago

Monteverde

Monteverde is a modern Italian restaurant in Chicago's West Loop neighborhood, offering handmade pasta and other Italian dishes with a contemporary twist.

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