Chicago Illinois 2 Day Itinerary

Chicago, Illinois Itinerary - 2 Day Guide

Day 1: Explore the City’s Iconic Attractions

Morning

  • 8:00 AM: Start your day with breakfast at Lou Mitchell’s, a classic Chicago diner serving up pancakes, eggs, and more since 1923.
  • 9:00 AM: Take a short walk to the Willis Tower (formerly Sears Tower), one of the tallest buildings in the world. Take in panoramic views of the city from the Skydeck on the 103rd floor.

Afternoon

  • 12:00 PM: Grab lunch at Portillo’s, a Chicago staple for hot dogs, Italian beef sandwiches, and more.
  • 1:30 PM: Visit the Art Institute of Chicago, one of the largest and most visited art museums in the country. Be sure to see famous works like American Gothic and Nighthawks.

Evening

  • 6:00 PM: Head to Millennium Park for a stroll along the Lurie Garden, a beautiful green space in the heart of the city.
  • 7:30 PM: Catch a show at the Chicago Theatre, a historic venue hosting various performances throughout the year.

Where to Stay

Day 2: Discover Chicago’s Hidden Gems

Morning

  • 9:00 AM: Start your day with breakfast at Wildberry Cafe, a cozy spot serving up pancakes, omelets, and more in the Gold Coast neighborhood.
  • 10:30 AM: Explore the Chicago Riverwalk, a scenic path along the Chicago River that offers stunning views of the city’s skyline.

Afternoon

  • 12:00 PM: Visit the Field Museum, home to Sue, the largest and most complete T-Rex skeleton ever found.
  • 2:30 PM: Grab lunch at Xoco, a casual spot from celebrity chef Rick Bayless serving up fresh Mexican cuisine.

Evening

  • 6:00 PM: Head to Wicker Park for dinner and drinks. Try Big Star, a retro-style taco joint with great food and a fun atmosphere.
  • 8:30 PM: Catch some live music at Schubas Tavern, a historic venue hosting various acts throughout the year.

Transportation

  • The ‘L’ (elevated train): A convenient way to get around the city, with multiple lines and stations.
  • Chicago Transit Authority (CTA) buses: A comprehensive network of buses covering all areas of the city.
  • Ride-hailing services: Uber and Lyft are widely available in Chicago.

Tips

  • Be prepared for crowds and long lines at popular attractions like Willis Tower and the Art Institute of Chicago.
  • Try to avoid traveling during rush hour (7-9 AM and 4-6 PM) if possible.
  • Don’t forget to bring a camera to capture stunning views and memories!
  • Enjoy the city’s vibrant food scene, which offers everything from deep-dish pizza to authentic Mexican cuisine.

Other Tips

  • Be mindful of your surroundings in crowded areas like Millennium Park and Wicker Park.
  • Keep an eye on your belongings at all times, especially in touristy areas.
  • Don’t be afraid to ask for directions or assistance from locals.
  • Try to avoid eating too much deep-dish pizza (it’s delicious, but it can be a lot of food!).

I hope you enjoy your time exploring Chicago!