Chicago Usa 2 Day Itinerary

November 16, 2024

Day 1: Exploring Downtown Chicago

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.

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.

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.

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.

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.

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

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.

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.

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.

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.

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.