Chicago in October – Travel Guide

Having grown up in the Chicago suburbs, I had countless opportunities to explore the city during this month and all it has to offer.

This experience has enabled me to create a detailed October guide:

• October Weather Overview
• What to Wear | Outfits | Packing List
• Crowds, Rates, Hotel Tips
• The Best Things to Do
• Events in October
• 5 Top Food Spots (at the end of this article 💡)

Chicago in October is one of the best times to visit the city, as you’ll experience crisp fall weather and comfortable temperatures. While the weather is generally unpredictable this month, you can still explore the city’s Halloween attractions (available indoors and outdoors).

However, there are a few things you need to know, especially about the weather and suitable outfits! More about that later.

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

Continue reading our Chicago October guide below for insight into the city, allowing you to make your trip amazing!

Weather Overview

Chicago in October is cool and crisp, with average high temperatures ranging from 56°F 13°C) to 68°F (20°C). With an average rainfall of 8-9 days during this month, you can expect the weather to be wet and drizzly.

Average Temperature

Chicago in October weather begins with an average high of 68°F at the beginning of the month and a 56°F average at the end. While the beginning of the month feels very fall-like, the temperature drop at the end of the month alerts Chicago natives to the incoming winter weather.

Average high temperatures in October:

• Early October: 68°F (20°C)
• Mid-October: 62°F (17°C)
• Late October: 56°F (13°C)

In the mornings, you’ll find chilly temperatures in the low 50s. I often wear extra layers and stay inside until mid-morning when the temperature is usually around the mid-50s.

Since October has many cloudy days, the mornings are a great time to cuddle up in bed with a new book. The temperatures are slightly higher mid-day, staying around the low 60s.

Typical temperature progression during a day in October:

• Morning (7 AM): 53°F
• Afternoon (3 PM): 62°F
• Evening (9 PM): 57°F

During October, the weather can be quite confusing. On some days, it feels like the ideal, sunny fall weather. On other days, it is gloomy, rainy (or snowy), and cloudy. Some days are a combination of sunny, rainy, cloudy, and snowy.

Because of the unpredictable weather, it’s not uncommon for Chicago residents to carry a compact umbrella throughout the month. This unpredictable weather is characteristic of Chicago and is what makes a visit to the city exciting. An unexpected rain allows you to explore the city’s indoor attractions.

There have been many occasions where I had to dart into a shop or café to escape the rain. Luckily, there’s always a restaurant or shop nearby in the city. Often, the rainfall is short, and you may even catch a rainbow peeking out from behind the skyscrapers when the weather clears.

Rainfall

The average rainfall remains fairly consistent throughout the month, slightly decreasing from 2.8″ to 2.6″. As mentioned, the weather is quite unpredictable in October. Chicagoans will carry an umbrella, windbreaker, or thicker jacket on these days.

What to Wear | Outfits | Packing Tips

As October offers chilly, sometimes wet weather, you wear jeans, water-resistant jackets, and layers, like sweaters, long Johns, and extra socks so that you can stay warm and dry during your visit. Additionally, pack water-resistant shoes like rain boots.

In early October, I typically wear a thicker sweater, jeans, and boots or sneakers (depending on the day’s activities). As the month continues, I (like many Chicagoans) slowly add more layers, such as light/water-resistant jackets, long-sleeved shirts, and long Johns.

💡 If the weather happens to be warmer and sunny, I will forego the jacket and may opt for a thinner sweater or sweatshirt instead.

Morning/Evening

When you visit Chicago during October, you’ll want to bring clothes for all seasons. You’ll need a thick sweater or jacket in the mornings and evenings to keep you warm. Consider always keeping a windbreaker on you, as the city can get quite gusty, especially near the lake or in open spaces.

As the mornings are generally in the 50s in October, it’s best to wear thermal layers, a sweater, and a light jacket to stay warm. Aim for a jacket that has a hood to protect your face and ears from the wind. SHOP NOW: Hooded Fall Jacket on Amazon

When I was younger and visiting Chicago for one of the first times, I did not realize the weather would be much different than in the suburbs.

ESSENTIAL: Windbreaker on Amazon

Since I did not bring a windbreaker, I had to purchase one before continuing my activities. Now, I always carry a windbreaker in my bag.

Daytime

During the daytime, the weather warms up slightly. At this point in the day, you may not need as many layers, especially toward the beginning of the month. If you plan to stay out for the entire day, consider bringing a water-resistant bag to stash extra layers as the temperature shifts.

A water-resistant bag is also great when visiting museums, as they keep the temperature low. You’ll want to remove any wet layers to avoid getting overly chilly while browsing the exhibits.

More Essential Clothing Items

Waterproof Jacket

A light to medium-weight jacket is perfect for early October. As the month progresses and temperatures drop, a medium-weight jacket that is waterproof will provide the necessary warmth and comfort to stay dry.

Hoodies

Comfortable and Warm
Hoodies are great for casual outings and add an extra layer of warmth. They can be worn over t-shirts and under jackets, making them versatile for different weather conditions. In early October, a hoodie might be too warm for a sunny afternoon, but it is perfect for cooler mornings and evenings, or for later in the month when temperatures drop.

Lightweight Sweaters

Breathable and Versatile
Pack a few lightweight sweaters made of cashmere or wool blends. These materials are warm yet breathable, making them ideal for layering without causing you to overheat. A sweater can be paired with a t-shirt underneath and a jacket over it if needed.

Denim Jeans

Durable and Comfortable
A good pair of denim jeans is perfect for exploring the city. They are durable, comfortable, and provide enough warmth for cooler days. Choose a darker wash to easily dress them up for evening outings.

Walking Shoes

Comfort is Key
Chicago involves a lot of walking, so comfortable shoes are a must. Opt for well-cushioned walking shoes or sneakers that provide good support. Avoid bringing new shoes that need breaking in to prevent blisters and discomfort.

Basic Packing List

• Waterproof jacket (easiest way to stay dry in the rain)
• Windbreaker (to help you stay warm on windy days)
• Waterproof boots/shoes (to help avoid soggy feet while in the city)
• Multiple pairs of socks
• Hoodies or medium to thick sweaters/jackets (for cooler morning temps + layering)
• Thermal layers (usually only needed for mid to late October)
• Jeans/pants
• Long-sleeve t-shirts
• Sweater dresses (for special occasions, get-togethers, dinners)
• Hat/gloves (for mid to late October)
• Comfortable walking shoes!
• Halloween costume (if you plan on partaking in themed events)

Crowds and Rates

While visiting Chicago in October, you might notice some crowds because of the many activities available. You’ll see more crowds out towards the beginning and middle of this month. At the end of the month, the crowds will start to lessen as the temperatures continue to decrease.

💡 You may have to wait in some lines, though the crowds are overall manageable.

Both outdoor and indoor activities are popular, depending on whether it’s snowing, raining, or sunny. You may notice larger crowds at specific events, like the Chicago Marathon. Since wintery November is around the corner, many Chicagoans will participate in as many October events as possible.

If I’m heading to a Halloween-themed event, I like to visit the event during slower times, like mid-afternoon or early evening. Most people will attend the events around noon or later in the evening, so 2-4 pm is usually quieter for these activities.

I learned this method for avoiding crowds during fall time by accident when I went to purchase timed tickets for a Halloween event, and they were completely sold out at my desired time. Luckily, they had plenty of tickets available between 2-4 pm on most days.

Rates and Hotel Tips

Rates in October for hotels and airfare are moderate. The price of accommodations and travel decreases toward the end of the month as the weather gets colder.

There is a noticeable rate for hotels and airfare on the weekend the Chicago Marathon falls on. The marathon typically occurs on the second Sunday of the month. For the best rates, avoid traveling to Chicago this weekend.

Find our hotel tips for October below, with some of the best locations so you can walk to the most intriguing places:

Fairmont Chicago Millennium Park

The staff is super friendly, our beds were very comfortable, everything was 100% clean and its location is perfect for a visit:  It is only 1 block away from Millennium Park and Navy Pier. You can walk easily to so many hot spots.  It’s also quite close to Lake Michigan beach (20 minutes walk).

Trump International Hotel & Tower

This hotel offers spectacular views from every room! The view of Lake Michigan, the Chicago River, or the city skyline is iconic. It’s simply the best location when visiting during October.

It is very comfortable from here to join a hop-on/off bus tour, walk along the river or to the Navy Pier, and walk to various restaurants and many other area attractions.

The rooms are luxurious, and spacious, with everything you need.

Home2 Suites By Hilton | Budget Tip

This is our favorite budget hotel in Chicago in the month of October! The location is excellent: It is located in Chicago’s River North district, a short walk from the Magnificent Mile’s (Mag Mile), shops, and restaurants. The Navy Pier, downtown, and the Chicago Loop are less than 15 minutes away.

Another thing we loved when we stayed there: You can prepare your own food in the room.

Fall Color Viewing

October is a great time for checking out the fall colors here. These are the best spots:

Lincoln Park:

• Located near Lake Michigan, this park is perfect for seeing fall foliage.
• Offers various spots like Nature Boardwalk, Lincoln Park Conservatory, and Alfred Caldwell Lily Pool to enjoy the autumn colors.

Millennium Park and Lurie Garden:

• This is downtown Chicago’s place to be for fall colors.
• You’ll find beautiful leaves near the famous Cloud Gate (The Bean) and in the hidden Lurie Garden.

Jackson Park:

• Known for its historical significance, it’s situated near Hyde Park.
• Don’t miss the Garden of the Phoenix, a serene Japanese garden, for some fall color spotting.

Lakefront Trail:

• Runs 18 miles along Lake Michigan.
• Perfect for walking or biking while taking in the fall foliage of different neighborhoods.

Humboldt Park:

• Located in the Humboldt Park neighborhood, this park is quite expansive.
• Features scenic lagoons, gardens, and ball fields, offering plenty of spots to enjoy autumn colors.

Columbus Park:

• Found in the Austin neighborhood and is a National Historic Landmark.
• The foliage around the lagoon and waterfall turns vibrant in the fall, offering an enchanted setting.

Washington Park:

• Home to the Dusable Black History Museum.
• Walk around the lagoon, visit the Harvest Garden, and see the beautiful Fountain of Time sculpture surrounded by autumn leaves.

Chicago Botanic Garden:

• It is located in suburban Glencoe and is not just a city-bound beauty.
• Offers 27 gardens and nine islands filled with autumn colors, plus seasonal events like Night of 1,000 Pumpkins.

Morton Arboretum:

• A living museum featuring over 4,000 types of trees.
• Offers cool fall events like the Scarecrow Trail and Cider and Ale Festival.

The 606:

• This elevated path offers a unique viewpoint of the city’s fall colors.
• The trail is landscaped and lets you see neighborhood parks and boulevards from above.

Things To Do

Many events occur in October, making it a great time to visit for people of all ages. The most notable event that occurs during this month is the Chicago Marathon. Even if you’re not a runner, watching the athletes make their way over the finish line is exciting.

Other worthwhile events include various fall film festivals, Arts in the Dark, local Halloween-themed events (like the Haunted Halsted Halloween Parade), and the Chicago River Tiki Cruise.

I love checking out Chicago in October since it’s not too hot to spend the day exploring the streets of Chicago. With the many Halloween and fall-themed events available, I plan to spend at least one full weekend in the city. Since these events are popular, I always book my tickets as far in advance as possible.

Below, you’ll find the most exciting things to do and see while in Chicago during this month.

Architecture River Cruise

Chicago River architecture tours are a must-do activity.

The Architecture River Cruise is still popular in October, even on chillier days. Bring a jacket and book your ticket early to ensure you get to experience this Chicago must-do activity.

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 October. This 200-foot Ferris wheel offers spectacular panoramic views of the Chicago skyline, Lake Michigan, and Navy Pier. Each car is temperature-controlled!

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

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 October, 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.

Skip the Line Tickets!

Art Institute Tour

If you’ve never experienced the Art Institute in Chicago, we highly recommend visiting this location in October. 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

Walking by Lake Michigan in October lets you view the beautiful fall foliage. Focus on walking in Lincoln Park and nearby Millennium Park for some of the best views of the changing leaves.

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 October. 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 October. 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 October 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 October on a chilly and rainy day. 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!

Events

It might seem like as the temperatures cool off, there would be fewer activities in Chicago. No matter the weather, there are always events that can be attended. Chicagoans like to stay busy throughout the whole year. October is no exception and provides a large number of things to do.

If you’re a movie buff, head to the Chicago International Film Festival. You’ll be able to experience and see the year’s newest international films. They can be viewed in various ways, from drive-in movie theaters and streamed to your devices. The films are separated based on categories like comedies and documentaries. This is an event that should not be missed.

For those who love running or enjoy watching others run, the Bank of America Chicago Marathon is also during October. People travel from all around to participate in this running event.

If you’re not planning on participating – either as a runner or as a participant – make sure you take public transportation or walk. Multiple streets downtown are closed off for this event.

💡 Parking and driving downtown are already crazy enough when events are not going on. Avoid driving during this event; grab a taxi or Uber instead.

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.