Chicago Usa 2 Day Itinerary
Day 1: Exploring Downtown Chicago
Morning
- Start at Millennium Park: Begin your day at this iconic park in the heart of downtown Chicago. Take a stroll through the beautiful Lurie Garden, snap a photo in front of the “Cloud Gate” sculpture (also known as “The Bean”), and catch a free outdoor concert or event if scheduled.
- Walk to the nearby Art Institute of Chicago: Spend a few hours exploring one of the top art museums in the country. The museum’s collection includes works by famous artists like Monet, Picasso, and Warhol.
Lunch
- Grab a slice at Lou Malnati’s Pizzeria: This classic Chicago pizzeria has been serving up deep-dish pies since 1975. Try the spinach and sausage or the classic cheese.
Afternoon
- Take an Architecture River Cruise: Learn about Chicago’s rich architectural history on this guided boat tour along the Chicago River.
- Explore The Magnificent Mile: This famous stretch of Michigan Avenue is lined with high-end boutiques, art galleries, and iconic landmarks like the Tribune Tower and Water Tower Place.
Evening
- Dine at Girl & the Goat: Top Chef winner Stephanie Izard’s Mediterranean-inspired restaurant offers a lively atmosphere and creative dishes like wood-fired lamb ribs and seafood paella.
- Catch a show at the Chicago Theatre: This historic venue hosts a variety of performances, from comedy acts to concerts and plays.
Where to Stay
- The Wit Hotel: This stylish boutique hotel in the River North neighborhood offers comfortable rooms, a rooftop bar, and easy access to downtown attractions.
Things to Know
- Be prepared for variable Midwestern weather: pack layers and waterproof gear.
- Take advantage of Chicago’s comprehensive public transportation system, including buses and trains ( Ventra app).
- Tip your servers and bartenders 15-20% in restaurants and bars.
Transportation
- From O’Hare International Airport: Take the Blue Line train ($3) to downtown Chicago or book a shuttle/Uber/Lyft.
- Get around the city: Use public transportation, hail a taxi, or ride-share with services like Uber or Lyft.
Tips
- Buy a Chicago CityPASS for discounted admission to top attractions.
- Be mindful of pedestrian and bike traffic in busy areas.
- Don’t forget to try some classic Chicago-style hot dogs at Portillo’s or Alinea!
Day 2: Exploring Neighborhoods
Morning
- Breakfast in Wicker Park: Head to this trendy neighborhood and grab coffee and a pastry at La Colombe or breakfast at Big Star.
- Explore the 606 Elevated Trail: This former rail line turned park offers great city views and a unique perspective on Chicago’s neighborhoods.
Lunch
- Try a classic Chicago-style hot dog at Portillo’s: This casual spot in Wicker Park serves up some of the city’s best dogs, complete with relish, onions, tomatoes, sport peppers, and celery salt.
- Visit the Ukrainian Institute of Modern Art: This small museum showcases contemporary Ukrainian art and offers a unique cultural perspective.
Afternoon
- Walk through Lincoln Park: This sprawling green space is home to the Lincoln Park Zoo, the Peggy Notebaert Nature Museum, and plenty of walking trails and picnic areas.
- Shop along Armitage Avenue: This charming street in Lincoln Park is lined with independent boutiques, antique shops, and art galleries.
Evening
- Dine at Alinea: For a truly unique dining experience, head to this Michelin three-star restaurant, known for its avant-garde, experimental cuisine.
- Catch live music at the Green Mill Jazz Club: This historic club in Uptown has hosted some of jazz’s biggest names and offers an intimate setting for music lovers.
Where to Stay
- The Robey: This stylish hotel in Wicker Park offers comfortable rooms, a rooftop lounge, and easy access to neighborhood attractions.
Things to Know
- Be prepared for crowds and long lines at popular attractions.
- Don’t skip trying some of Chicago’s famous Italian beef sandwiches!
- Take time to explore the city’s many neighborhoods, each with its own unique character.