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Journey information
Overview: Chicago, IL to Pittsfield, MA flight
USAUSA
Flights from Chicago, IL to Pittsfield, MA depart on average 30 times per day, taking around 3h 59m. Cheap flight tickets for this journey start at $455 but you can travel from only $195 by bus.
There are 4 flights per day. The earliest flight runs at 05:00, the last at 21:38. The fastest flight covers the 738 miles (1188 km) distance in 2h 6m. October is the cheapest month to fly.
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Bus from $195
Distance 738 miles (1188 km) |
Average flight duration 3h 59m |
Cheapest ticket price $455 |
Flights per day 30 |
Direct flights 4 |
Fastest flight 2h 6m |
First flight 5:00 AM |
Last flight 9:38 PM |
Cheapest Month Oct |
Cheapest Day Sun |
High Season Jan - Mar |
Low Season Apr - Jun |
Best time to book 77 days |
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Bus from $195
Travel Information
Compare train, bus, and flight for Chicago, IL to Pittsfield, MA
Omio recommends booking the flight as it is the most popular option from Chicago, IL to Pittsfield, MA among Omio's users. If you are prioritising price, take the bus, with an average ticket price of $202 For those with little time, consider booking a flight, which has an average total journey time of 5h 59m. Average ticket prices depend on the travel mode: a bus costs an average of $202, while a flight costs an average of $882.
Distance: 738 miles (1188 km)
Compare flight with
Most popular Flight | Train | Bus | Driving |
|---|---|---|---|
$882 Average price | $303 Average price | $202 Average price Cheapest | $175 Average price (fuel + tolls) |
5h 59m Average total duration Fastest 3h 59m Onboard + 2h 0m Additional time* | 18h 13m Average total duration 17h 43m Onboard + 30m Additional time* | 31h 25m Average total duration 30h 55m Onboard + 30m Additional time* | 12h 59m Average total duration (door-to-door) |
 Most popular airline |  Most popular train company |  Most popular bus company | Your own car or car rental |
Direct Options | Direct Options | Direct Options | Direct Options |
The cheapest way to travel from Chicago, IL to Pittsfield, MA is a bus with an average price of $202.
This is compared to other travel options from Chicago, IL to Pittsfield, MA:
A bus is $101 less than a train for this route with tickets for a train from Chicago, IL to Pittsfield, MA costing on average $303.
A bus is $681 less than a flight for this route with tickets for a flight from Chicago, IL to Pittsfield, MA costing on average $882.
The fastest way to travel from Chicago, IL to Pittsfield, MA is by flight with an average journey time of 3h 59m.
Other travel options to Pittsfield, MA take longer:
Train takes on average 17h 43m.
Bus takes on average 30h 55m.
It's helpful to compare your options as there are 3 ways to travel between Chicago, IL and Pittsfield, MA including taking a train, bus, and flight.
We recommend using the train as it is the most popular way to get from Chicago, IL to Pittsfield, MA among Omio's users.
Compare prices and tickets Chicago, IL to Pittsfield, MA by train, bus, or flight
Compare train, bus, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
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Why should you book Chicago, IL to Pittsfield, MA flights with Omio?
American Airlines as well as Republic Airlines or United offer flights services from Chicago, IL to Pittsfield, MA.
Omio is an official ticket reseller for all your travel options from Chicago, IL to Pittsfield, MA.
Why book with Omio vs American Airlines?
- Compare with other providers: On Omio, you can not only buy tickets for American Airlines, but also compare tickets for the likes of Republic Airlines or United to find the best option for your trip from Chicago, IL to Pittsfield, MA.
- Designed for International Travelers: Omio is in your language including 24/7 customer service and offers multiple payment options, including PayPal, credit cards, and bank transfer, in your preferred currency.
- Compare all your options: Omio allows you to compare American Airlines with all available travel options, which are train, bus and flight to ensure you get the best deal for traveling from Chicago, IL to Pittsfield, MA.
Why book with Omio over Trip, Edreams or Skyscanner?
- Compare with other providers: On Omio, you can also compare tickets for the likes of Republic Airlines or United to find the best option for your trip from Chicago, IL to Pittsfield, MA.
- Multiple modes of transport: Omio allows you to compare travel options including train, bus and flight to find the ideal travel option from Chicago, IL to Pittsfield, MA.
Airlines: United, American Airlines, Republic Airlines from Chicago, IL to Pittsfield, MAFind the best flights between Chicago, IL to Pittsfield, MA with Omio's travel partners United, American Airlines, Republic Airlines from $195. We can find you the best deals, schedules and tickets when comparing and booking the best trip.
United
About
United Airlines, established in 1926, is a major U.S. airline headquartered in Chicago, Illinois. Operating an extensive domestic and international network, United serves more destinations than any other airline, connecting travelers across six continents. The airline's eight hubs include Chicago–O'Hare, Denver, Houston–Intercontinental, Los Angeles, Newark, San Francisco, Washington–Dulles, and Guam. As a founding member of the Star Alliance, United offers a comprehensive range of services, including regional flights through United Express, catering to both leisure and business travelers. The airline is committed to sustainability, investing in sustainable aviation fuel and innovative technologies to reduce its environmental impact.
Luggage & cancellation policy
Average United Duration
2h 6m
Cheapest United Price
$455
United frequency
18 a day
Luggage included
Carry-on baggage allowance is 7kg total (2 pieces max. ) for both Choice and Flex fares on United Airlines and Virgin Australia flights.
Additional luggage
Excess baggage fees apply for additional checked luggage beyond the standard allowance.
Luggage storage
Both airlines provide checked baggage services for storing luggage during flights.
Cancellation Policy
Cancellation fees apply per person, per booking, with specific fees for different fare types.
Refund
Not applicable to flights; however, full refunds are available if flights are canceled by the airline.
Pregnant on board
Pregnant passengers are permitted to travel, with specific guidelines and medical certificates required after a certain gestational period.
Unaccompagned minor
Unaccompanied minors are permitted to travel, with specific age restrictions and services provided.
Amenities on board the airplane
Wifi
Food sold onboard
Meals and snacks are included on international flights operated by United Airlines and Virgin Australia.
Seat reservation
Seat selection may incur additional fees, depending on the fare type and airline.
Toilets
USB plugs
Accessibility
United Airlines and Virgin Australia offer services to and within Australia, providing accessible travel options for passengers with mobility needs.
Bikes
Both airlines permit bicycles onboard, with specific guidelines and fees.
Pets
United Airlines and Virgin Australia allow pets onboard, subject to specific policies and fees.
American Airlines
About
American Airlines is one of the largest airlines in the world, connecting travelers to hundreds of destinations across the United States, Latin America, Europe, Asia, and beyond. Operating from major hubs such as Dallas/Fort Worth, Miami, and Charlotte, American offers a wide range of travel options. Passengers can choose from Economy with affordable fares, Premium Economy with extra space, or Business and First Class featuring flat-bed seats, premium dining, and lounge access. With a modern fleet and membership in the oneworld alliance, American Airlines combines global reach with comfort and reliability.
Luggage & cancellation policy
Average American Airlines Duration
3h 13m
Cheapest American Airlines Price
$556
American Airlines frequency
9 a day
Luggage included
1 carry-on bag (22 x 14 x 9 inches) and 1 personal item (18 x 14 x 8 inches) included in most fares
Additional luggage
Checked bags fees vary by route. First checked bag typically $30, second $40 on domestic flights
Cancellation Policy
Basic Economy tickets cannot be changed or refunded. Other fares allow changes with fee, refunds subject to fare rules.
Pregnant on board
Passengers can fly up to 36 weeks for single pregnancies, 32 weeks for multiple pregnancies. Medical certificate required within 7 days of departure if within 4 weeks of due date.
Unaccompagned minor
Children ages 5-14 can travel alone using American Airlines Unaccompanied Minor Service. Service fee is $150 each way.
Amenities on board the airplane
Wifi
Food sold onboard
USB plugs
Accessibility
American Airlines provides wheelchair assistance and special services for passengers with disabilities. Assistance must be requested at least 48 hours before departure.
Pets
Small dogs and cats allowed in cabin for $125 fee. Must be in approved carrier under seat. Service animals allowed.
Republic Airlines
About
Republic Airways is a major regional airline in the United States, operating as a subsidiary of Republic Airways Holdings. It provides scheduled passenger service for American Airlines (as American Eagle), Delta Air Lines (as Delta Connection), and United Airlines (as United Express) using a fleet of Embraer 170 and 175 regional jets. Headquartered in Indianapolis, Indiana, Republic Airways operates over 900 daily flights to more than 80 cities across the U.S. and Canada. The company is known for its large fleet of Embraer E-Jets and its state-of-the-art training facilities. In April 2025, Republic Airways Holdings announced its acquisition of Mesa Air Group, which is expected to create the second-largest regional carrier in the U.S.
Luggage & cancellation policy
Average Republic Airlines Duration
2h 13m
Cheapest Republic Airlines Price
$455
Republic Airlines frequency
3 a day
Luggage included
One carry-on bag (24 x 16 x 10) and one personal item
Additional luggage
Checked bags for a fee
Cancellation Policy
Tickets are non-refundable but may be cancelled for future flight credit minus applicable fees
Pregnant on board
Passengers can fly up to the end of their 36th week for single pregnancies and the end of their 32nd week for multiple pregnancies
Unaccompagned minor
Unaccompanied minor service is available for children ages 5-14. Must be booked directly with Republic Airlines
Amenities on board the airplane
USB plugs
Accessibility
Republic Airlines offers assistance for passengers with reduced mobility, including wheelchair services and priority boarding. Passengers are advised to request these services in advance to ensure availability and proper arrangements.
Complete guide to Pittsfield, MA
Things to do in Pittsfield, MA
Discover the best of Pittsfield, MA — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Pittsfield, MA trip today.
- Recommended
The Mount
Historic house museum in nearby Lenox presenting author Edith Wharton’s home, gardens, and design-focused exhibitions.
- Recommended
Ventfort Hall Mansion and Gilded Age Museum
Gilded Age museum inside Ventfort Hall with exhibits on regional history, domestic life, and the Berkshires’ summer estates.
- Recommended
Upstreet Cultural District
Downtown Pittsfield district with shops, public art, theaters, and event spaces, ideal for walking and experiencing local life.
- Recommended
Burbank Park on Onota Lake
Large city park with ponds, trails, athletic fields, and mountain views, popular for walks, picnics, and seasonal events.
- Recommended
Berry Pond and Balance Rock
Wooded reservation with hiking trails and a summit observation tower offering broad views over Pittsfield and the Berkshires.
FAQs: Chicago, IL to Pittsfield, MA Flight
Find answers to the most common questions about traveling from Chicago, IL to Pittsfield, MA by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Pittsfield, MA, this guide helps you travel smarter and with confidence.
Cheap plane tickets from Chicago, IL to Pittsfield, MA can start from as little as $455 when you book in advance. The average flight ticket price for Chicago, IL to Pittsfield, MA is $882 ; however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
The average journey time by plane from Chicago, IL to Pittsfield, MA is 2h 6m to travel the 738 miles (1188 km) long route. Journey times can vary on weekends and holidays, so use our Journey Planner to search for a specific date.
The earliest flight from Chicago, IL to Pittsfield, MA leaves at 5:00 AM. Plan your trip with the Journey Planner from Omio.
The latest flight from Chicago, IL to Pittsfield, MA leaves at 9:38 PM.
Yes, there are 4 direct flights a day from Chicago, IL to Pittsfield, MA with Republic Airlines, United. Schedules can vary on holidays or weekends with fewer direct flights.
When taking a flight from Chicago, IL to Pittsfield, MA, you can count on American Airlines, Republic Airlines, United for the best way to get you to Pittsfield, MA. You can also check all possible airlines who offer a service between Chicago, IL and Pittsfield, MA and compare the amenities they offer before buying a plane ticket.
Flights from Chicago, IL to Pittsfield, MA generally leave from O'Hare International Airport and arrive in Bradley International Airport.O'Hare International Airport is 1 miles (3 km) away from Chicago, IL city centre and Bradley International Airport is 2 miles (4 km) from Pittsfield, MA city centre.
The cheapest month for a flight from Chicago, IL to Pittsfield, MA is October.
It's helpful to compare your options as there are 3 ways to travel between Chicago, IL and Pittsfield, MA including taking a train, bus, and flight.
Since neither Chicago, IL nor Pittsfield, MA are in the Schengen Area, passport requirements depend on the specific immigration rules of United States and United States. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
There is a time difference of 1 h between Chicago, IL and Pittsfield, MA all year round.
The best events to attend in Pittsfield, MA include:
- Pittsfield Fourth of July Celebration, a festive event featuring fireworks, parades, and community activities to celebrate Independence Day
- Pittsfield Arts Festival, an annual celebration of local artists with exhibitions, performances, and workshops
- Berkshire International Film Festival, a showcase of independent films from around the world with screenings and discussions.
The best holidays to experience in Pittsfield, MA include:
- Independence Day, vibrant fireworks and festive parades celebrating American heritage
- Labor Day, pleasant weather perfect for outdoor activities and local events
- Thanksgiving, a cozy atmosphere with family gatherings and community festivities.
The best season to visit Pittsfield, MA is Spring or Fall. The best weather to explore Pittsfield, MA is during June-August or September-October.
We recommend using the flight as it is the most popular way to get from Chicago, IL to Pittsfield, MA among Omio's users.
For domestic flights we recommend to arrive 1.5 to 2 hours before departure. Please check the website of your departure airport if in doubt. Some airports may offer booking time slots for security checks or offer additional information on when to get there based on time of day.
Most airlines permit carry-on bags that fit within specific dimensions (e.g., 22 x 14 x 9 inches or 56 x 36 x 23 cm), including handles and wheels. Bags must fit in the overhead bin or under the seat in front of you.
Many airlines impose weight limits, commonly ranging between 7 kg (15 lbs) and 12 kg (26 lbs). Typically, passengers are allowed one carry-on bag and one personal item (for example a purse, laptop bag, or backpack). Personal items must fit under the seat in front of you. Budget Airlines (like Ryanair or Wizz Air) have stricter size and weight limits, often requiring fees for larger carry-ons. Full-Service Airlines have more lenient policies, sometimes including more spacious dimensions or higher weight limits depending on your ticket class.
The list of items prohibited on an airplane varies by country and airline, but in general, the following items are not allowed in carry-on or checked baggage: Weapons and self-defence items, sharp objects, flammable materials, explosives, toxic substances, or liquids over 100ml (except for medications and baby essentials). In checked baggage, firearms (without authorization), explosives, large lithium batteries, and hazardous chemicals are prohibited. Electronic cigarettes must be in carry-on bags, while alcohol and dry ice have restrictions. Always check with your airline for specific regulations.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Pittsfield, MA, travelers should be mindful of typical urban safety concerns such as petty theft and vehicle break-ins, especially in busy areas or parking lots. It is advisable to stay alert in crowded places and avoid poorly lit streets at night. While there are no widespread reports of specific scams targeting visitors, travelers should be cautious of common scams like overcharging by taxis or unfamiliar vendors. Using reputable transportation services and securing personal belongings can help ensure a safe visit.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.
popular airports
Popular airports from Chicago, IL to Pittsfield, MA
Most Chicago, IL to Pittsfield, MA flights use the O'Hare International Airport to Bradley International Airport airport pair. Use this guide to compare Chicago, IL and Pittsfield, MA airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
Departure airports in Chicago
Arrival airports in Pittsfield
Which Chicago, IL airport do flights to Pittsfield, MA leave from?
Flights from Chicago, IL to Pittsfield, MA depart from O'Hare International Airport. The airport is 2 miles (4 km) from Chicago, IL city centre at 10000 W O'Hare Ave, Chicago, IL 60666, USA.
O'Hare International Airport (ORD)10000 W O'Hare Ave, Chicago, IL 60666, USA
City-centre transport
Getting to O'Hare International Airport from Chicago city centre
O'Hare International Airport is 3 km from Chicago city centre. Public transport options include:
SubwayBlue Line · 1h 7m · $6 · every ~23 min
O'Hare International Airport airport facilities and services
O'Hare International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food and drink
Food options include: Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Wi-Fi and ATMs
Free Wi-Fi available throughout the airport. ATMs are located throughout all terminals.
Luggage and lost property
Lost and found is available at the station.
Parking, taxis and toilets
Available at O'Hare International Airport: Parking, Taxis, WC.
Bike and car services
Available at O'Hare International Airport: Car Rental.
Accessibility
Accessibility facilities are available at O'Hare International Airport: Elevators, ramps, toilets.
Shops, hotels and contact
Nearby hotels include Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby..
More options for your journey from Chicago, IL to Pittsfield, MA
Here are some other resources that might have the information you need
Most popular flights to and from Pittsfield, MA and Chicago, IL
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