Chicago in September – Travel Guide

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.

In this guide about Chicago in September, you will learn about

• 5 Must-Know Tips for September
• The Weather in September
• What to wear in September| Outfits | Packing List
• Crowds and Rates
• The Best Things to Do
• Events in September
• 5 Top Food Spots (at the end of this article 💡)

This article was written by our Chicago resident!

All of the links above open in a new tab. They are incredibly useful for your Chicago summer visit.ll of the links above open in a new tab. They are incredibly useful for your Chicago trip.

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

Must-Do Activity in September: River Cruise

If you’re visiting Chicago this September, a river cruise is an absolute must-do, the highlight of the city’s attractions.

💡 It’s a breathtaking journey where the vibrant landscapes and the architecture along the riverbanks come to life. Among all the amazing experiences in Chicago, cruising the river during this season stands out as a truly unique adventure, offering unparalleled views of the city’s iconic views.

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.

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.

Weather

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.

Rainfall

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 | Packing Tips | Outfits

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, 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 light raincoat or a poncho and, when visiting in late September, a medium jacket.

Essential: Light Rain Poncho

Morning/Evening

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.

Daytime

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.

These are the must-have clothing items, including tips and explanations, for an unforgettable fall in the city:

Essential Clothing Items

Denim Jeans

Denim jeans are my top choice for fall outfits in Chicago. They offer versatility and comfort in fluctuating temperatures. Combine them with a long-sleeve shirt for a classic and stylish look, perfect for visiting a museum or enjoying a river cruise.

Buy Jeans on Amazon | Outfit Deals

Jacket/Coat

In September, coats like trenches, leather jackets, and light-down jackets are perfect for the city.  These coats are great because you can wear them with t-shirts when it’s not too cold or sweaters when it’s chillier to stay warm.

Buy Fall Jackets on Amazon | Outfit Deals

Tops

The tops you pack depend on the usual temperature. It’s good to bring some t-shirts to go with a leather jacket or trench coat. Also, pack some sweaters, which can be worn even without a coat or jacket, based on the weather. Jeans and a sweater always make a great outfit.

Dresses and Skirts

Fall is a good time to pack dresses and skirts. You can wear them with tights and a jacket. Depending on the weather, you might need thermal tights. Remember to check the weather app to see what it’s going to be like.

Sweaters

Sweaters are a staple for your fall outfits in Chicago. Opt for chunky knits or lightweight layers, depending on the temperature. They’re great for mixing and matching with jeans or skirts.

Lightweight Rain Poncho

Even though it’s more sunny than rainy in September, sometimes it can rain unexpectedly. It’s a good idea to pack a lightweight rain poncho. These ponchos are super easy to carry because they can fold up really small and fit into your pocket or a little bag.

They hardly take up any space in your luggage, so you won’t even notice you’re carrying one until you need it. After checking the weather forecast, you can decide whether to bring it with you for the day.

This makes it worth bringing one along, just in case it rains. You can keep having fun on your day out, without having to lug around a heavy raincoat.

Sneakers/Boots

As you’ll be walking a lot, pack comfortable sneakers and/or boots. Flat or low-heeled styles are a good choice for long city walks. You don’t need heavy winter boots.

Packing 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/Jeans
• Dresses/skirts
• Long-sleeved shirts, light sweaters (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.

Booking.com

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.

Events

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 Top Food Spots | Restaurants

1. Charly’s Burgers

• BURGERS
• Location: HERMOSA
• Price: $
• PERFECT FOR:
  • SERIOUS TAKE-OUT OPERATION
  • QUICK EATS

Charly’s Burgers, a spot in Hermosa, is perfect for when you’re craving a really good burger. These burgers are made with a mix of beef and bacon, giving them a juicy and smoky flavor. They’re topped with just the right amount of cheese, onions, garlic aioli, and pickles, all on a soft bun that stays together as you eat.

Why you should go: It’s the ideal burger spot for any time, not just when you’re feeling the effects of the night before. The combination of flavors and the quality of the ingredients make these burgers stand out.

Tip: Try to go at off-peak hours to avoid a long wait. And don’t forget to ask about their special sauces to add an extra zing to your burger!

2. Johnnie’s Beef

• Hot dogs
• Location: Suburbs
• Price: $

Johnnie’s Beef is an old-school stand in Elmwood Park known for its Italian beef and ice. It’s a place that feels like stepping back in time, where the Italian beef sandwiches are a local legend.

Why you should go: It’s a must-visit for anyone wanting to experience a true Chicago Italian beef. The long lines are a testament to its popularity, but the wait is worth it for that juicy beef, dipped with hot peppers, and a refreshing lemon Italian ice to cool down after.

Tip: Plan your visit to avoid the busiest times, usually around lunch and dinner. And if it’s your first time, trying the beef dipped with hot peppers is a must for the full experience.

3. Birrieria Zaragoza

• Mexican
• Location: Archer Heights
• Price: $

Birrieria Zaragoza, a family-owned Mexican spot in Archer Heights, is known for its incredible goat meat dishes. They serve their food with thick handmade tortillas and fresh salsas, perfect for making tacos.

Why you should go: Their unique approach to birria, where the goat meat isn’t combined with consommé until it’s served, sets them apart. It’s a flavor experience that’s hard to find elsewhere, making it the best place for tacos in the city.

Tip: Don’t skip on the extras like the hot sauce, lime, and onions to customize your tacos to your taste. And try the bright-pink agua fresca for a refreshing drink alongside your meal.

4. Kasama

• Restaurants
• Filipino
• Location: East Village
• Price: $$

Kasama is a modern Filipino-American restaurant in East Village, offering both a casual daytime menu and a Michelin-starred tasting menu at night. It’s run by a husband-and-wife team known for their culinary expertise.

Why you should go: Whether you’re there for the breakfast sandwich in the morning or the 13-course tasting menu at night, Kasama provides an unforgettable dining experience. It’s a journey through Filipino-inspired dishes that are as innovative as they are delicious.

Tip: If dining indoors isn’t a must for you, consider ordering online for pickup. It’s a great way to enjoy Kasama’s offerings without the wait, especially on weekends.

5. The Publican

• Restaurants
• American
• Location: West Loop
• Price: $$

The Publican is a European-style beer hall in West Loop, specializing in pork and seafood. It’s known for its lively atmosphere and communal dining setup, inviting guests to share in the enjoyment of food and beer.

Why you should go: For a taste of everything from fresh oysters to charcuterie and seasonal plates, The Publican is a standout. Their commitment to sourcing ingredients from local farms adds to the freshness and quality of each dish.

Tip: The brunch at The Publican is among the best in the city, featuring items like maple-braised bacon. Don’t miss out on this weekend treat, and make sure to try the spicy pork rinds and bread from Publican Quality Bread.