Chicago, USA-5-day-itinerary

Day 1: Explore Downtown Chicago

Morning

  • Start your day at Millennium Park, one of the city’s most iconic attractions. Take a stroll through the beautiful Lurie Garden and snap a photo in front of the “Cloud Gate” sculpture (also known as “The Bean”).
  • Grab breakfast at Lou Mitchell’s, a beloved institution serving up classic American fare.

Afternoon

  • Visit the Art Institute of Chicago, one of the top art museums in the country. Spend a few hours exploring the vast collections, including works by famous artists like Monet and Picasso.
  • Take a short walk to Navy Pier, a lakefront attraction that offers stunning views of Lake Michigan. Catch a ride on the Centennial Wheel for panoramic views of the city.

Evening

  • Head to The Loop (Chicago’s downtown area) for dinner at Girl & the Goat, a trendy restaurant from Top Chef winner Stephanie Izard.
  • End your night with a show or concert at The Chicago Theatre, a historic venue that hosts a range of performances.

Where to Stay

Hotel suggestions in the Loop:

  • The Langham, Chicago
  • Kimpton Hotel Monaco Chicago

Things to Know

  • Be prepared for crowds and long lines at popular attractions.
  • Take advantage of Chicago’s comprehensive public transportation system, including buses and trains (the “L”).

Transportation Tips

  • Buy a Ventra Card or use contactless payment for easy travel on buses and trains.
  • Consider purchasing a Chicago CityPASS, which grants discounted admission to several top attractions.

Day 2: Wicker Park and Bucktown

Morning

  • Start your day in the trendy neighborhoods of Wicker Park and Bucktown. Grab coffee at Intelligentsia Coffee and explore the boutique shops along North Avenue.
  • Visit the Wicker Park Farmers Market (seasonal) for a taste of local flavors.

Afternoon

  • Head to The 606, an elevated trail built on an old rail line, offering great views of the city. Access the trail at the California Avenue entrance.
  • Stop by Myopic Bookstore, a beloved used bookstore with an impressive selection.

Evening

  • Enjoy dinner at Big Star, a taco joint with a fun atmosphere and delicious eats.
  • Catch live music or comedy at The Empty Bottle, a popular venue in Ukrainian Village.

Where to Stay

Hotel suggestions in Wicker Park:

  • The Robey
  • Acme Hotel Company

Things to Know

  • Be prepared for a more laid-back, neighborhood vibe in Wicker Park and Bucktown.
  • Explore the street art scene in the area, with many vibrant murals adorning building walls.

Day 3: Lincoln Park and Lakeview

Morning

  • Spend the morning exploring Lincoln Park Zoo, a free zoo in the heart of the city. Visit the historic landmark, the Lincoln Park Conservatory.
  • Take a stroll along the lakefront path, offering beautiful views of Lake Michigan.

Afternoon

  • Head to Wrigley Field, the iconic home stadium of the Chicago Cubs baseball team. Even if there’s no game scheduled, take a guided tour of the historic park.
  • Grab lunch at Alinea, a Michelin three-star restaurant (reservations required) or try Gio’s Italian Deli for a casual bite.

Evening

  • Enjoy dinner at The Purple Pig, a Mediterranean-inspired restaurant with small plates and craft cocktails.
  • End your night with a show at The Vic Theatre, a historic venue hosting live music, comedy, and more.

Where to Stay

Hotel suggestions in Lincoln Park:

  • Hotel Lincoln
  • The Willows Hotel

Things to Know

  • Be prepared for crowds around Wrigley Field on game days.
  • Take advantage of the lakefront path for scenic jogging or biking opportunities.

Day 4: Hyde Park and Museum Campus

Morning

  • Spend the morning exploring the University of Chicago, including the stunning Rockefeller Chapel.
  • Visit the Oriental Institute Museum, featuring a vast collection of ancient Middle Eastern and Egyptian artifacts.

Afternoon

  • Head to the Museum Campus, home to several world-class museums, including the Field Museum (home to Sue, the largest T. rex skeleton) and the Shedd Aquarium.
  • Take a stroll along the lakefront path, offering beautiful views of Lake Michigan.

Evening

  • Enjoy dinner at A10, a modern American bistro with seasonal menus.
  • Catch a show or concert at The Promontory, a state-of-the-art music venue in Hyde Park.

Where to Stay

Hotel suggestions in Hyde Park:

  • Hyatt Place Chicago/South-University Medical Center
  • The Study at University of Chicago

Things to Know

  • Be prepared for a more academic, intellectual vibe in Hyde Park.
  • Take advantage of the lakefront path for scenic jogging or biking opportunities.

Day 5: Pilsen and Chinatown

Morning

  • Explore the vibrant neighborhood of Pilsen, known for its colorful street art, independent shops, and rich Latinx culture. Visit the National Museum of Mexican Art.
  • Grab coffee at La Casa del Toño, a beloved café with traditional Mexican pastries.

Afternoon

  • Head to Chinatown, one of the largest in the country, for lunch at Qing Xiang Yuan Dumplings or Lao Sze Chuan. Explore the vibrant streets and shops.
  • Visit the Chicago Chinese Cultural Center, featuring exhibits on Chinese art, history, and culture.

Evening

  • Enjoy dinner at Spiaggia, a luxurious Italian restaurant with beautiful views of the Chicago River.
  • Catch a show or concert at The Harris Theater, a premier performing arts venue in Millennium Park.

Where to Stay

Hotel suggestions near Pilsen and Chinatown:

  • Hyatt Place Chicago/Downtown-The Loop
  • JW Marriott Chicago

Things to Know

  • Be prepared for a more laid-back, neighborhood vibe in Pilsen.
  • Take advantage of the cultural attractions and events in Chinatown.

Additional Tips and Recommendations

Transportation

  • Consider purchasing a Chicago CityPASS, which grants discounted admission to several top attractions and includes transportation options.
  • Use ride-hailing services like Uber or Lyft, or take taxis for shorter trips.

Safety

  • As with any major city, be aware of your surroundings, especially at night. Stick to well-lit areas and avoid walking alone in isolated spots.

Weather

  • Chicago is known for its unpredictable weather. Pack layers, including warm clothing for winter and waterproof gear for spring showers.
  • Take advantage of indoor attractions on rainy or cold days.

Budgeting

  • Plan ahead and book accommodations, restaurants, and attractions in advance to ensure availability and avoid higher prices.
  • Consider budget-friendly options like street food, food trucks, or casual eateries.

Enjoy your trip to Chicago!