Chicago, Illinois-3-day-itinerary

August 5, 2024

Day 1: Wednesday

Breakfast: Start your day at Wildberry Cafe, a popular spot for breakfast and brunch. Try their signature pancakes or omelette.
Millennium Park: Head to Millennium Park, one of Chicago’s most iconic spots. Take a stroll through the beautiful Lurie Garden and snap a photo in front of the famous “Cloud Gate” sculpture (also known as “The Bean”).
Willis Tower (formerly Sears Tower): From Millennium Park, take a short walk to the Willis Tower, which offers breathtaking views of the city from its Skydeck on the 103rd floor.

Lunch: Grab some lunch at Lou Malnati’s Pizzeria, a Chicago institution for deep-dish pizza.
The Art Institute of Chicago: Spend the afternoon exploring the world-class art collection at The Art Institute of Chicago. Be sure to see famous works like “American Gothic” and “Nighthawks.”
Shopping: End your day with some shopping along the Magnificent Mile, which features high-end retailers and souvenir shops.

Dinner: Enjoy dinner at Girl & the Goat, a Mediterranean-inspired restaurant from Top Chef winner Stephanie Izard.
Live Music: Catch a live music performance or comedy show at one of Chicago’s many venues, such as The Vic Theatre or The Second City.

Consider staying in the downtown area or near Millennium Park for easy access to public transportation and attractions.

Hotel: Book a room at The Langham Chicago for upscale accommodations and a prime location.
Airbnb: Alternatively, rent an apartment through Airbnb and enjoy more space and amenities like a kitchen or living area.

CTA (Chicago Transit Authority): Use the CTA’s efficient public transportation system to get around the city. You can purchase a Ventra card for easy travel.
Ride-hailing: Alternatively, use ride-hailing services like Uber or Lyft to get where you need to go.

Day 2: Thursday

Breakfast: Start your day with breakfast at The Original Pancake House, a popular spot for pancakes and waffles.
Navy Pier: Head to Navy Pier, a lakefront attraction that offers stunning views of Lake Michigan. Take a boat tour or rent a bike and explore the pier.

Lunch: Grab some lunch at Portillo’s, a Chicago institution for hot dogs and Italian beef sandwiches.
The Field Museum: Spend the afternoon exploring The Field Museum, home to Sue, the largest and most complete T. rex skeleton ever found.

Dinner: Enjoy dinner at Alinea, a Michelin-starred restaurant known for its avant-garde and experimental cuisine.
Nightlife: End your night with some nightlife in Wicker Park, a trendy neighborhood with bars, clubs, and live music venues.

Weather: Chicago weather can be unpredictable. Be sure to pack layers and check the forecast before heading out.
Tipping: In Chicago, it’s customary to tip 15-20% at restaurants and bars.
Safety: As with any major city, take necessary precautions to stay safe in Chicago.

Day 3: Friday

Breakfast: Start your day with breakfast at The Bagel Restaurant, a popular spot for bagels and coffee.
Chicago Riverwalk: Head to the Chicago Riverwalk, a scenic pedestrian path along the river. Take a stroll and enjoy the views of the city.

Lunch: Grab some lunch at Xoco, a casual spot for Mexican-inspired street food.
The 606: Spend the afternoon exploring The 606, an elevated park built on a former rail line. Take in the views of the city and enjoy the public art installations.

Dinner: Enjoy dinner at Blackbird, a Michelin-starred restaurant known for its seasonal American cuisine.
Farewell: End your trip with a final farewell to Chicago. Take some last-minute photos and memories before heading home.

Tips

Explore neighborhoods: Don’t just stick to the tourist areas. Explore other neighborhoods like Wicker Park, Logan Square, or Pilsen for unique shops, restaurants, and experiences.
Try local breweries: Chicago has a thriving craft beer scene. Try visiting some of the many local breweries for a behind-the-scenes look at the brewing process.
Be prepared for crowds: Some popular attractions can get crowded quickly. Plan ahead and consider visiting during off-peak hours or on weekdays.

Other Things to Do

Take a food tour: Explore Chicago’s culinary scene with a guided food tour that takes you to some of the city’s best restaurants and eateries.
Visit a museum: Chicago has many world-class museums, including The Museum of Science and Industry, the National Museum of Mexican Art, or the DuSable Museum of African American History.
Go shopping: In addition to the Magnificent Mile, consider visiting other shopping districts like State Street, Michigan Avenue, or the Wicker Park/Bucktown area for unique boutiques and shops.