What Clothes to Pack for a Trip to Chicago during September to November

What clothes to pack for a trip to Chicago How to plan a trip to Chicago?

Award-winning architecture, world-class museums, rocking music festivals and out-of-this-world cuisine, Chicago has all the offerings you’d expect from a major city. Mad about sport with a pro team for every season, watching a game is a local rite of passage, while the city’s 24 beaches and 580 parks offer a different form of relaxation. Architecture-fundis will delight in the awe-inspiring structures, from the spectacular glass-floored Willis Tower to Frank Lloyd Wright’s famous Robie House, foodies will swoon over the myriad choices of outstanding and world cuisine, and music-lovers will rock to their heart’s content with the city’s music festival offerings. The Windy City has something for everyone.

Weather in Chicago during September, October and November

The best time to travel to Chicago is during the spring, summer and autumn – winter can be brutal with freezing temperatures, snow, sleet, and of course, the wind! Head to the city during the autumn months of September and October to experience the city at its best. Days are sunny and bright, and temperatures are slightly cooler than the hot summer months, hovering in the 60s and 70s during the day and dropping into the 40s at night, so while summer clothing is fine for the day, be sure to pack warm clothes for the evenings.

The beginning of the school year boasts fewer crowds and plenty of accommodation at lower rates. Late October into November could see the temperature drop considerably and some attractions close for the winter season.

What clothes to pack for Chicago in September, October and November


  • Shorts, dresses, skirts (thicker fabric than summer dresses)
  • T-shirts, long casual tops, light cardigans
  • Casual Capri pants, long slacks
  • A lightweight jacket
  • A windbreaker / waterproof rain jacket
  • Footwear: Comfortable walking shoes, trainers, boots
  • Scarf, pashmina, warm hat/hoodie


  • T-shirts, short-sleeve shirts for day wear
  • Long sleeve shirts, long tops, jerseys for evening wear
  • Jeans, chinos, slacks
  • Lightweight jacket for evening wear
  • Windbreaker / waterproof jacket
  • Footwear: Comfortable walking shoes, trainers, boots
  • Scarf, warm hat/hoodie


  • Dresses, skirts, T-shirts (girls), shorts, T-shirts, casual shirts (boys)
  • Jeans, pants, track suits
  • A windbreaker / waterproof jacket
  • Footwear: trainers, comfortable walking shoes, sandals

Things to see and do in Chicago

Chicago has something for everyone from impressive architecture and beautiful urban spaces to outstanding museums, art galleries and institutes and superb shopping and dining. Here are the top 10 things to see and do in the Windy City.

Top Ten Attractions:

1. Millennium Park- Home to the famous Crown Fountain and Cloud Gate, better known as “The Bean”, Millennium Park rests in the Loop, a 24.5-acre space used to showcase cutting-edge art, architecture and landscaping.

2. Wills Tower Skydeck- The 110-story Willis Tower Skydeck boasts breathtaking views of the city – particularly from The Ledge, a platform that extends outwards over the city made entirely of glass.

3. Grant Park and Buckingham Fountain- Grant Park is a vast green space bordering the eastern edge of the Loop and packed with several of Chicago’s most popular attractions. The Buckingham Fountain rests at the center of the park and is one of the largest fountains in the world, featuring 134 jets used to shoot water as high as 150 feet into the air during the 20-minute choreographed displays.

4. The Field Museum- Occupying a large section of Grant Park’s Museum Campus, this extensive natural history museum houses superb exhibits showcasing artefacts that span history and the globe, and is home to Sue, the largest, most complete Tyrannosaurus rex ever discovered, who is 42 feet long from nose to tail, and boasts 58 terrifying teeth!

5. Wrigley Field- Home to Chicago’s Major League Baseball team, the Cubs, catching a game or touring the famous field is a must on a visit to Chicago.

6. Art Institute of Chicago- This world-class institute is home to one of the country’s most impressive collection of Impressionist and Post-Impressionist art and features more than 300,000 works from all over the world.

7. Chicago Architecture Cruise- Take in the city’s magnificent array of architecture on this unrivaled architecture tour, which showcases some of the world’s most famous buildings and structures.

8. The Magnificent Mile- Shop until you drop on the Magnificent Mile, which is home to big brand-name stores like Macy’s, Saks Fifth Avenue, and Neiman Marcus, as well several top-notch restaurants and luxury hotels.

9. 360 Chicago- One of the best places to experience Chicago’s world-famous skyline is from the 360 CHICAGO observation deck, which towers 1,000 feet over the Magnificent Mile from its location on the 94th floor of the John Hancock Center.

10. Navy Pier- Extending out into Lake Michigan, Navy Pier offers a variety of family-friendly entertainment in the way of a towering Ferris wheel, swing-seat rides and a carousel.