Chicago, USA-2-day-itinerary

Chicago 2-Day Itinerary

Day 1: Explore Downtown Chicago

Morning

  • 9:00 AM: Start the day at Millennium Park, a iconic downtown park featuring famous landmarks like the “Cloud Gate” sculpture (also known as “The Bean”) and the Jay Pritzker Pavilion.
  • 10:00 AM: Take a stroll through The Magnificent Mile, a 13-block stretch of Michigan Avenue lined with upscale shops, restaurants, and theaters.

Afternoon

  • 12:30 PM: Grab lunch at Portillo’s, a Chicago institution serving up classic hot dogs, Italian beef sandwiches, and more.
  • 2:00 PM: Visit the Art Institute of Chicago, one of the top art museums in the country, featuring a diverse collection of Impressionist, Post-Impressionist, and American art.

Evening

Day 2: Explore Millennium Park and Lake Michigan

Morning

Afternoon

  • 12:30 PM: Grab lunch at The Berghoff, a historic German restaurant in the Loop serving up classic sausages and sides.
  • 2:00 PM: Explore the Field Museum, one of the largest natural history museums in the world, featuring Sue, the largest T-Rex skeleton.

Evening

  • 7:00 PM: Enjoy dinner at Girl & the Goat, a trendy restaurant from Top Chef winner Stephanie Izard.
  • 9:00 PM: End the night with a scenic sunset view of Lake Michigan at the Navy Pier lakefront.

Accommodations

Luxury

  • The Langham, Chicago (4-star) - Located in the Gold Coast neighborhood, this luxury hotel offers stylish rooms and excellent service.
  • The Four Seasons Hotel Chicago (5-star) - This upscale hotel is situated on the Magnificent Mile and features elegant rooms with lake views.

Mid-range

  • Hyatt Place Chicago/Downtown (3-star) - A modern hotel in the Loop area, offering clean and comfortable rooms at an affordable price.
  • The Kimpton Hotel Monaco Chicago (4-star) - This boutique hotel is located in the Gold Coast neighborhood and features stylish rooms with a touch of elegance.

Transportation

By Air

  • Chicago O’Hare International Airport (ORD) - The main airport serving Chicago, located about 17 miles northwest of downtown.
  • Chicago Midway International Airport (MDW) - A smaller airport located on the city’s Southwest Side.

By Public Transit

  • CTA (‘L’) Trains - An efficient and affordable way to get around the city, with multiple lines that connect major neighborhoods.
  • Bus System - A comprehensive network of buses serving all areas of Chicago.

Tips

Weather

  • Summer (June-August): Expect hot and humid weather, with temperatures often reaching the 90s.
  • Winter (December-February): Be prepared for cold temperatures, snow, and freezing rain.
  • Spring (March-May) and Autumn (September-November): Mild temperatures and fewer crowds make these seasons ideal times to visit.

Safety

  • Be aware of pickpocketing in crowded areas like the Magnificent Mile and tourist hotspots.
  • Avoid walking alone at night, especially in unfamiliar neighborhoods.
  • Respect local customs when visiting museums, galleries, or other cultural institutions.

Other Recommendations

Visit a Museum

  • The Art Institute of Chicago (Day 1)
  • Field Museum (Day 2)

Try Local Cuisine

  • Deep-dish pizza at Lou Malnati’s (Day 1)
  • Girl & the Goat restaurant (Day 2)

Enjoy Live Music or Comedy

  • Second City comedy club (Day 1)
  • Live music at Navy Pier (Day 2)