Chicago in September

Chicago in September offers cooler weather and a respite from the busy crowds of the summer months after Labor Day Weekend. Despite the cooldown and fewer tourists, there are many activities and events to attend during this month.

This article was written by our Chicago resident!

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Below, you’ll find our unique guide on everything from what to pack to events to attend so you can fully enjoy the Windy City.

We cover everything you should know before visiting Chicago in September:

  • Weather details and temperatures
  • What to wear and outfit tips
  • The best tours, visits, and things to do
  • September Events

Make sure to read our 5 Chicago Must-Know September Tips at the end of this article!

💡 Read our Chicago in October tips if you are planning to visit later.

Activity Tips and Tours

When you visit Chicago in September, we highly recommend a river cruise, the Navy Pier Centennial Wheel, and visiting the Willis Tower Skydeck.

Chicago Tours >> Cheap Tickets

Tip: Get your tickets for the cruise in advance, if possible. Although September ist not that busy anymore, these tickets still sell out quickly. However, you are free to try buying your tickets later, of course.

Find more things to do (including free ones) at the bottom of this article.


The temperatures in September are mostly pleasant.

Chicago weather in September is generally warm with occasional fall-like days. With an average high temperature of 76°F, you’ll be able to enjoy outdoor activities without getting too hot or too cold. It rains on 9 days on average and it’s often unpredictable.

Average Temperature

The beginning of the month is winding down from the summer heat with an average high of 79°F. As the month continues, the average slips down to 69°F, indicating that fall has arrived.

Average high temperatures in September:

  • Early September: 79°F (26°C)
  • Mid-September: 76°F (24°C)
  • Late September: 69°F(20°C)

Mornings are relatively warm at the beginning of the month, with averages in the low 70s. As the month continues, mornings become chilly, with averages in the 50s.

Typical temperature progression during a day in September:

  • Morning: 69°F (20°C)
  • Afternoon: 76°F (24°C)
  • Late Evening: 72°F (22°C)

From the middle to the end of the month, you’ll want to wear a jacket for early morning activities. Avoid the chillier temps by leaving for activities after 9 am when the temperatures are generally over 69°F.


Chicago has an average rainfall of 8-10 rainy days in September. As the month continues, the chance of rain decreases from 30% to 26%. The rain can be pretty unpredictable; some days have stormy, wet weather all day. Other days have an hour or two of rain that becomes a pleasant, sunny day.

Local Opinions

While this article was written by our Chicago resident, we thought it’s still a good idea to provide you with some opinions from other locals:

❗ September has many warm days and cool nights. Earlier in the month, flower beds are still beautiful, but not so much anymore towards the end of the month. Many residents, me included, think September is the best month of the year in Chicago. Plus the fall entertainment season begins.

❗ September is the favorite month for many visitors. Make sure to come after our labor day weekend as kids are back in school and hotel prices come down.

❗ September is one of the top months to visit Chicago. You get the warmth of summer throughout the day and the crispness of autumn in the evening. The city is easily accessible by public transit, and walking along Lake Michigan is amazing. There are numerous iconic locations to visit, which are fantastic in September

Beach Weather | Swimming

September is still a great month to spend some time at the beaches of Chicago, especially when the weather is warm. However, Lake Michigan beaches are officially closed after Labor Day. That means there are no lifeguards on duty, and swimming is not permitted.

Technically, the beach season runs from Memorial Day until Labor Day in Chicago. Regardless, you can still go to the beach anytime in September and swim at your own risk without lifeguards. Usually, the water is still comfortable enough. Just be aware that you might have to pay a fine.

While the beaches are still crowded on Labor Day, they became a lot quieter after the first weekend.

What to Wear

It can get cooler, especially in the mornings and evenings in the second half of September.

Chicago is well-known for its unpredictable weather, making it challenging to pick an outfit for the day (we know first-hand!). We provide you with tips for the best outfit options:

During September in Chicago, you wear light jackets, t-shirts or long-sleeved shirts, breathable pants, and comfortable sneakers. Bring multiple layers for cooler mornings, rainy weather, and warmer daytime temps. Additionally, bring a raincoat and, when visiting in late September, a medium jacket.


When visiting at the beginning of the month, a light jacket is sufficient for the weather you’ll encounter in the mornings and evenings. As the month continues, you’ll want to bring a heavier jacket to help you stay warm, especially in the mornings.

A waterproof jacket is a great investment, as the mornings and evenings can be drizzly during this month. If you get stuck in the rain during an excursion without a jacket, the temperatures can feel much lower than they are. Bringing or buying an umbrella is a great option if more compact choices are available.


As the temperatures are warmer during the day, you can wear short-sleeved shirts, shorts, sneakers, or a dress. Sneakers are recommended, even with a dress, as you’ll be walking a fair amount in the city.

At the end of the month, the ideal outfit switches to pants or jeans, longer-sleeved shirts, and light to medium jackets. Sneakers or comfortable walking shoes are still excellent during the end of the month.

What to Wear List
  • Raincoat or light waterproof jacket (necessary for rainy days/unpredictable weather)
  • Medium jacket (for those visiting toward the end of September)
  • Light, breathable shirts
  • Light shorts/pants
  • Long-sleeved shirts (for chillier temperatures)
  • Caps or hats (during sunny days)
  • Water-resistant shoes/comfortable shoes
  • Multiple pairs of socks (necessary when rain is present)
  • Sunscreen
  • Compact umbrella

Crowds and Rates

As September generally offers pleasant weather, you can expect a medium amount of crowds. However, this number will still be much fewer than June through August.

💡 Labor Day weekend is an exception. Especially when the weather is pleasant, beaches and other outdoor spots will be quite busy this Saturday, Sunday, and Monday.

On some occasions, you may even be able to see popular attractions without a long wait. September is the best month for outdoor activities like water cruises as the crowds are more manageable.

You’ll start to see a decrease in hotel rates and flight rates this month. While they won’t be much lower than in the summer months, you’ll still find them slightly more affordable.


Some of the best events occur in September in Chicago, including multiple music festivals and food festivals. While the crowd numbers may be lower, the number of September events remains high.

Here are a few great options to choose from when visiting Chicago.

Chicago Jazz Festival

While most music festivals in Chicago require the purchase of a ticket, the annual jazz festival surprisingly does not. This festival intends to encourage people to listen to and appreciate jazz.

You’ll be able to enjoy music from Chicago musicians and international artists. This is a first-come, first-serve free event, so you’ll want to arrive as early as possible for the best seats. This is an excellent event for families, couples, and solo travelers.

  • When: September 1-4
  • Where: Millennium Park, 201 E. Randolph St., Chicago, IL 60601
  • Price: Free
Bike the Drive

This event is beloved by locals and tourists alike. Lake Shore Drive shuts down each year to allow thousands of people to bike ride along the waterfront.

You will need to register for this event ahead of time. You can easily rent a bike for the event if you’re visiting. Or, enjoy from the sidelines as you watch the bikers zoom past.

  • When: September 4
  • Where: DuSable Lake Shore Drive
  • Price: $70 per adult, $18 per biker under 17 years old
Sundays on State

Sundays on State is a fun event from July to September each year. Each Sunday, specific streets are shut down to allow shopping, activities, and art to be enjoyed.

You can expect everything from live music like hip hop to free workout classes, karaoke, and more. The best part about this event is that it’s free and open to everyone.

  • When: Sundays July – September
  • Where: State Street, between Lake and Madison
  • Price: Free
Sam Adams Lakeview Taco Fest

This taco festival is a fun event that offers taco and beer pairings for adults and fun activities for kids. Multiple bands play live music, and there are even Mexican wrestlers that you can watch.

Multiple vendors set up around the festival, cooking up fresh tacos to purchase. Enjoy tacos with various fillings ranging from mushrooms to steak and seafood.

  • When: September 17-18
  • Where: 3500 N. Southport Ave., Chicago IL
  • Price: Free, suggested $10 donation (food + drinks not included)


Things to Do

September is one of the best months for enjoying activities and events due to fewer crowds, especially after Labor Day weekend. During this month, you can enjoy the best of both worlds – warmer weather and shorter lines. Whether you attend a music festival on Milwaukee Ave. or head to the Lincoln Park Zoo, you’ll find plenty of things to do this month.

Here are a few fantastic activities to choose from when visiting Chicago in September.

Architecture River Cruise

Chicago River architecture tours are a must-do activity. Especially in September, when the weather is mostly pleasant.  You’ll experience awesome views and learn about the most famous skyscrapers like the Willis Tower (previously the Sears Tower).

IMPORTANT: We highly recommend making a reservation in advance as the cruises are very popular. However, you are free to try getting a ticket on short notice of course.

  • When: Year-round | Best in the summer
  • Where: Corner of Michigan (DuSable) Bridge
  • Price: about $40 per person

Book Tickets in Advance

Navy Pier Centennial Wheel

The Centennial Wheel is one of the most iconic activities in Chicago and a must-do in September. This 200-foot Ferris wheel offers spectacular panoramic views of the Chicago skyline, Lake Michigan, and Navy Pier. Each car is temperature-controlled so that you can ride at the end of September as well.

The standard tickets are great for times when there are fewer crowds, like rainy days. We suggest purchasing the express tickets to jump to the front of the line.

  • When: Year-round
  • Where: 600 E. Grand Avenue, Chicago, Illinois 60611
  • Price: $19.62 per person for standard entry, $30.52 per person for express entry

Book Tickets in Advance

Art Institute Tour

If you’ve never experienced the Art Institute in Chicago, we highly recommend visiting this location in September. You’ll be able to recognize this famous building by the green lions that “guard” the exterior, which is also the meeting point for the tour.

Inside, you’ll be guided through sections of the museum that are filled with paintings, sculptures, and other mediums by the likes of Picasso and Rembrandt. Purchase skip-the-line tickets (highly recommended) and find additional details here: Art Institute Tour.

  • When: Year-round
  • Where: 111 S Michigan Ave, Chicago, IL 60603
  • Price: $115.54 per person
Walking by Lake Michigan

Lake Michigan is stunning to see, but nothing beats walking along the lake nearby Navy Pier on a pleasant day in September. This route allows you to view the famous Ferris wheel with the skyline of Chicago in the background.

We love this route as it will take you alongside the beach. You can walk, jog, or bike ride on this path.

  • When: Year-round
  • Where: Lakefront trail off Fullerton Avenue
  • Price: Free
The Chicago Theatre Marquee Tour
  • When: Year-round, great in April
  • Where: 175 N State St, Chicago, IL 60601
  • Price: $18 per person

This tour of the Chicago Theatre Marquee is a perfect activity to try on a rainy day in September. You will love this tour which takes about 60 minutes.

Purchase tickets and find additional information here: The Chicago Theatre Marquee Tour.

The Magic Parlour
  • When: Fridays + Saturdays year-round
  • Where: 17 E Monroe Street, Chicago IL 60603
  • Price: $79 per person

Take your family (12+ years old) to view a show at The Magic Parlour in Chicago in September. They offer incredible magic shows! Very comfortable as only 50 people are allowed.

There is a dress code for the shows, which is noted as cocktail attire. Expect to be called up on stage at any point during the show. The magician (Dennis Watkins) has been featured on larger TV channels like FOX, ABC, and WGN.

Find more information and purchase tickets here: The Magic Parlour Chicago.

Museum of Science and Industry

  • When: Year-round | Great in April
  • Where: 213 W Institute Pl, Chicago, IL 60610
  • Price: $10 entry fee

The Museum of Science and Industry in Chicago is fun to explore. With so many interactive exhibits and unforgettable experiences, discovering everything might take more than one day. So, it will definitely keep you entertained and educated on one or more unpleasant September days.

Field Museum of Natural History
  • When: Year-round | Great in April
  • Where: 1400 S Lake Shore Dr, Chicago, IL 60605
  • Price: $26 ticket

The Field Museum of Natural History is worth visiting year-round, but particularly in September if it rains. It holds over 35 world-renowned natural history exhibitions. Explore the subterranean life in the Underground Adventure exhibit. Experience the gemstones in the Hall of Gems and one of the largest collections of Chinese jade in North America in the Hall of Jades.  Check out the Ice Age mammoth hunters and the temples of the Aztecs. Finally, visit the Dinosaur Hall Evolving Planet exhibit. Your kids will love it!

360 Observation Deck
  • When: Tours available throughout the year
  • Where: 875 N. Michigan Avenue, Chicago, IL 60611
  • Price: $30 per person

If you spend only a few days in Chicago in September, the 360 Observation Deck is a must-visit. Soaring 1,000 feet over Chicago’s legendary Michigan Avenue, 360 is one of Chicago’s most impressive attractions.

Tickets to skip the line (recommended) for a faster entry: 360 Observation Deck – Skip the Ticket Desk.

5 September Must-Know Tips and Facts

  1. The weather is pleasant and the temperatures are usually warm enough to explore outdoors, at least until mid-September. Choose one of the numerous walking or Segway tours (highly recommended!)
  2. A river architecture cruise is one of the best things you can do on a pleasant day in September
  3. Hotel prices drop after Labor day due to the end of the tourism season.
  4. There is a slim chance of flight delays or cancelations if a storm comes through in September.
  5. After Labor Day weekend, the beaches are technically closed until Memorial Day next year. If the police catch you swimming or wandering in off-limits areas you may be subject to a fine.

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