Chicago Illinois 7 Day Itinerary

7-Day Chicago Itinerary: A Deep Dive into the Windy City

This itinerary balances iconic landmarks with off-the-beaten-path experiences for a truly immersive Chicago trip.

Accommodation:

  • Location: Consider staying in a centrally located neighborhood like:
    • The Loop: Great for first-time visitors, close to many attractions and the “downtown” experience.
    • River North: Lively area with art galleries, upscale dining, and nightlife.
    • Lincoln Park: Family-friendly neighborhood with parks, restaurants, and a charming atmosphere.

Day 1: Downtown Delights & Skyline Views

  • Morning: Arrive in Chicago and explore Millennium Park, home to Cloud Gate (“The Bean”), the Crown Fountain, and Jay Pritzker Pavilion.
    • Activity: Walk through the park, admire the iconic architecture, and visit the Art Institute of Chicago for a taste of world-class art.
    • Lunch: Grab a classic Chicago hot dog at Portillo’s Hot Dogs & Beefs. (Chicago hot dog: no ketchup!)
  • Afternoon: Visit the Willis Tower Skydeck for breathtaking panoramic views of the city.
  • Evening: Enjoy a delicious deep-dish pizza for dinner at Lou Malnati’s Pizzeria.

Day 2: History & Culture Immersion

  • Stay: Explore more of downtown, including:
    • Morning: Walk the Magnificent Mile, Chicago’s famed shopping and entertainment district.
    • Afternoon: Visit the Field Museum of Natural History or the Museum of Science and Industry for a deep dive into history and science.
    • Evening: Indulge in a Chicago-style dinner at Giordano’s.

Day 3: Art & Architecture Appreciation

  • Morning: Take a leisurely walk along the Chicago Riverwalk, enjoying the architecture and vibrant atmosphere.
  • Afternoon: Explore the diverse neighborhoods of Chicago, like the colorful murals of Pilsen or the trendy boutiques in Wicker Park.
  • Evening: Catch a live blues performance at Kingston Mines.

Day 4: A Taste of the Outdoors & Deep Dish Delight

  • Morning: Stroll through the beautiful Grant Park and enjoy its many attractions.

    • Things to do: Visit the Buckingham Fountain, the Art Institute’s Modern Wing, or the nearby Museum Campus for stunning views and outdoor activities.

  • Afternoon: Explore the city’s art scene with a walk along the lakefront in the afternoon. Enjoy the unique sculptures of the Chicago Cultural Center, wander through the Art Institute’s modern wing sculpture garden, or explore the vibrant street art in Wicker Park.

  • Evening:

Day 5: Exploring Lincoln Park

  • Morning: Visit Lincoln Park Zoo and enjoy the free admission and diverse animal exhibits.

  • Afternoon: Enjoy a picnic lunch overlooking the beautiful gardens of Millennium Park before heading to the zoo’s lush landscape for an afternoon stroll through the park’s serene paths.

  • Evening: Enjoy a delicious dinner at a popular Chicago pizza joint like Pequod’s Pizza or Pizano’s Pizza & Pasta.

Day 6: Taste of Chicago (and Beyond!)

  • Morning: Explore the Lincoln Park Conservatory and its stunning collection of plants.

  • Afternoon: Immerse yourself in the vibrant atmosphere of one of Chicago’s many museums, such as the Museum of Science and Industry, the Field Museum, or the Peggy Notebaert Nature Museum.

  • Evening: Enjoy a classic Chicago deep-dish pizza experience at Pizzeria Uno, Lou Malnati’s Pizza, or Gino’s East.

Day 7: Departure & Deep Dish Dreams

  • Morning: Stroll through the Lincoln Park Conservatory and enjoy the peaceful surroundings and beautiful flora.

Lunch: Grab some brunch at a local cafe like The Bongo Room or Summer House Santa Monica.

  • Departure: Depart from Chicago, taking with you memories of deep-dish pizza and the beauty of the city.

Things to Know:

  • Deep-Dish Pizza: A must-try in Chicago! Expect a thick crust with toppings layered in reverse order (cheese at the bottom, then toppings, then sauce on top).
  • Public Transportation: The CTA (Chicago Transit Authority) is excellent for getting around. Purchase a Ventra card for easy access to buses and trains.

Things to Do:

  • Millennium Park: Visit the iconic “Cloud Gate” sculpture (the Bean), enjoy a concert at the Jay Pritzker Pavilion, or stroll through the beautiful Lurie Garden.
  • Museum of Science and Industry: Explore this amazing museum with its interactive exhibits and diverse collection.
  • Navy Pier: A popular tourist destination with stunning views, restaurants, shops, and entertainment options.

Things to Consider:

  • Time of Year: Chicago has distinct seasons. Be prepared for cold winters (pack warm clothes!) and hot summers.

  • Neighborhoods: Chicago is known for its vibrant neighborhoods. Consider:

    • The Loop: Downtown Chicago, home to many museums and attractions.

  • Deep-Dish Pizza: This is a big one! Deep-dish pizza is traditionally deep, with the cheese first and toppings (often chunky) piled on top of it. Be prepared for a hearty meal.

  • Chicago Cubs Game: For baseball fans, catching a game at Wrigley Field is a must-do.

Where to Stay: Consider staying in hotels near the following locations:

  • Downtown/The Loop: The Palmer House Hilton, Hyatt Regency Chicago

  • Wicker Park: The Robey, Hotel Lincoln

Where to Eat: For an authentic deep-dish pizza experience, try:

  • Deep-Dish Pizza:
    • Lou Malnati’s Pizzeria (multiple locations)
    • Pequod’s Pizza (known for its caramelized crust)
    • Giordano’s Pizzeria & Restaurant (multiple locations)

Where to Eat:

  • Deep Dish Pizza: This Chicago staple is known for its unique deep, buttery crust.

  • Chicago Riverwalk: Enjoy the scenic beauty of the city along the water.

  • The Magnificent Mile: Shop at a variety of upscale stores and restaurants on this iconic stretch.

Things to do:

  • Enjoy the views from the Skydeck:

    • A classic Chicago tourist experience, the Skydeck offers breathtaking panoramic views.

  • Explore Chicago’s vibrant cultural scene: Visit one of the many “deep dish” pizza places (like Lou Malnati’s) and try a slice with a deep-dish crust, cheese first, and sauce on top!

  • Enjoy a leisurely stroll: Take in the sights and sounds of the city while enjoying a delicious meal.

  • Magnificent Mile: Explore the bustling shopping district and its many attractions like the Art Institute of Chicago, Water Tower Place, and the Museum of Contemporary Art Chicago.

Things to consider:

  • Reservations: For popular restaurants or attractions on the Magnificent Mile, reservations are highly recommended.

  • Budget: Prices on the Magnificent Mile can be high, so factor that into your dining choices.

  • Deep Dish Pizza Preferences:

    • Do you like thin crust or deep dish? Chicago has it all!

  • Dining Options:

    • Explore the diverse culinary scene of Chicago:

For a thicker, “deep-dish” pizza experience:

  • Pequod’s: (Known for its deep-dish) This is a great place to try a deep dish pizza.

  • Giordano’s: (A local favorite) *

  • Lou Malnati’s: (Authentic deep-dish, Chicago style) Enjoy a slice with a variety of toppings, and experience the “Chicago way” of pizza making.

  • Deep-Dish Pizza: Try a deep dish pizza with classic toppings like sausage, pepperoni, or mushrooms.

Enjoy the experience:

  • Enjoy the delicious and unique flavors of Chicago’s iconic food scene.

  • Enjoy a slice of deep-dish pizza!

  • Budget: Remember that deep-dish pizza is a rich meal and can be expensive.

  • Pizza Styles: Consider trying different styles of deep dish (deep-dish, stuffed crust, pan pizza) to find your favorite.

Things to consider for deep dish pizza:

  • Ingredients:
    • Do you want your pizza “stuffed” or “deep-dish”?
  • Cheese: Deep-dish pizzas are typically known for their abundance of cheese (often a blend of mozzarella, cheddar, and provolone), so be sure to consider your own tolerance for cheesy goodness.

Cheese Choices:

  • Do you want traditional deep-dish pizza with a crust covered in cheese?

“Deep Dish Pizza”:

  • Deep Dish Pizza: This is the real deal!

  • Thin Crust: Think about what kind of sauce and toppings you’d like to enjoy.

  • Chicago Style: For “deep dish” pizza, consider a classic deep-dish pie from Lou Malnati’s Pizzeria & Restaurant.

  • Pizza Size:

  • Deep-Dish Pizzas are usually bigger than other pizzas.

  • Start with a smaller slice to get a sense of the size and richness.

  • Enjoyment: Enjoy your pizza!

Remember: “Deep Dish” Pizza is a Chicago institution, so don’t be afraid to try different variations and toppings until you find your perfect slice.