- Must visit
Art Institute of Chicago
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
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Journey information
Overview: Pittsfield, MA to Chicago, IL flight
USAUSA
Take a flight from Pittsfield, MA to Chicago, IL and enjoy the approximately 738 miles (1188 km) long journey. Find schedules and pricing options for a convenient and affordable trip.
The earliest flight runs at 00:52, the last at 22:34. August 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
Distance 738 miles (1188 km) |
First flight 12:52 AM |
Last flight 10:34 PM |
Cheapest Month Aug |
Cheapest Day Sat |
High Season Jul - Sep |
Low Season Apr - Jun |
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
Travel Information
Compare train and bus for Pittsfield, MA to Chicago, IL
Omio recommends booking the train as it is the most popular option from Pittsfield, MA to Chicago, IL among Omio's users.
Distance: 738 miles (1188 km)
Compare train with
Most popular Train | Bus | Driving |
|---|---|---|
$176 Average price (fuel + tolls) | ||
12h 58m Average total duration (door-to-door) | ||
Direct Options | Direct Options | Direct Options |
Compare prices and tickets Pittsfield, MA to Chicago, IL by train or bus
Compare train and bus 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 Pittsfield, MA to Chicago, IL flights with Omio?
Spirit Airlines operates all flights services from Pittsfield, MA to Chicago, IL.
Omio is an official ticket reseller for all your travel options from Pittsfield, MA to Chicago, IL.
Why book with Omio vs Spirit Airlines?
- 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 Spirit Airlines with all available travel options, which are train and bus to ensure you get the best deal for traveling from Pittsfield, MA to Chicago, IL.
Why book with Omio over Edreams or Kayak?
- Multiple modes of transport: Omio allows you to compare travel options including train and bus to find the ideal travel option from Pittsfield, MA to Chicago, IL.
Complete guide to Chicago, IL
Things to do in Chicago, IL
Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.
- Must visit
Field Museum
Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.
- Must visit
Museum of Science and Industry
Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.
- Must visit
Millennium Park
Lively lakefront park with Cloud Gate, Crown Fountain, gardens, and major public art in central Chicago.
- Must visit
Magnificent Mile
Famous shopping boulevard lined with architecture, hotels, riverfront views, and major city energy.
- Must visit
Chicago Riverwalk
Scenic pedestrian-friendly riverwalk with boat docks, public art, bridges, and standout skyline perspectives.
Deep-Dish Pizza
Deep-dish pizza is Chicago’s iconic pie with a tall buttery crust, layers of cheese and toppings, and chunky tomato sauce baked on top.
Chicago-Style Hot Dog
The Chicago-style hot dog is an all-beef frank on a poppy seed bun with mustard, relish, onion, tomato, pickle, peppers, and celery salt.
Italian Beef Sandwich
Italian beef is thin-sliced roast beef piled onto a roll, often dipped in savory juices and topped with sweet peppers or spicy giardiniera.
Johnnie's Beef
Classic spot for juicy Italian beef sandwiches, especially dipped and topped with spicy giardiniera, with a casual local feel.
Superdawg Drive-In
Legendary stand for Chicago-style hot dogs and char-grilled sausages, served fast in a no-frills local landmark.
Alinea
World-famous fine dining destination offering a highly creative tasting menu and refined service in an elegant setting.
US dollar ($)
Moderate for a major US city: hotels can be pricey, but transit is affordable and dining ranges from cheap eats to upscale options.
Average meal costs
- Budget
- $10-18 for fast food or casual takeout.
- Mid-range
- $20-40 per person for a restaurant meal.
- Fine dining
- $75+ per person for upscale restaurants.
- Coffee
- $3-6 for coffee or cappuccino.
Tipping culture
Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and optional small change at cafes.
FAQs: Pittsfield, MA to Chicago, IL Flight
Find answers to the most common questions about traveling from Pittsfield, MA to Chicago, IL 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 Chicago, IL, this guide helps you travel smarter and with confidence.
popular airports
Popular airports from Pittsfield, MA to Chicago, IL
Most Pittsfield, MA to Chicago, IL flights use the Bradley International Airport to O'Hare International Airport airport pair. Use this guide to compare Pittsfield, MA and Chicago, IL airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
Departure airports in Pittsfield
Arrival airports in Chicago
Which Chicago, IL airport do flights from Pittsfield, MA arrive at?
Flights from Pittsfield, MA to Chicago, IL arrive at O'Hare International Airport. O'Hare International Airport is 2 miles (4 km) from Chicago, IL city centre.
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 Pittsfield, MA to Chicago, IL
Here are some other resources that might have the information you need
Most popular flights to and from Chicago, IL and Pittsfield, MA
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