- Must visit
Art Institute Of Chicago
One of the premier art museums in the US, known for Impressionist masterpieces, modern works, and the iconic bronze lions at its entrance.
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Travel Information
Compare bus and flight for Greenfield, MA to Chicago, IL
Omio recommends booking the flight as it is the most popular option from Greenfield, MA to Chicago, IL among Omio's users. If you are prioritising price take the bus with prices starting from $185. For those with little time consider booking a flight which can get you there in 3h 14m. The ticket price range depends on the travel mode: a bus costs an average of $185, and a flight costs an average of $267.
Distance: 770 miles (1240 km)
Compare bus with
| Bus | Most popular Flight | Driving |
|---|---|---|
$185 Average price Cheapest | $267 Average price | $179 Average price (fuel + tolls) |
27h 0m Average total duration 26h 30m Onboard + 30m Additional time* | 6h 14m Average total duration Fastest 3h 14m Onboard + 3h 0m Additional time* | 13h 52m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options |
The cheapest way to travel from Greenfield, MA to Chicago, IL is a bus with an average price of $185 (€152).
This is compared to other travel options from Greenfield, MA to Chicago, IL:
A bus is $81 (€66) less than a flight for this route with tickets for a flight from Greenfield, MA to Chicago, IL costing on average $267 (€218).
The fastest way to travel from Greenfield, MA to Chicago, IL is by flight with an average journey time of 3h 14m.
Other travel options to Chicago, IL take longer:
Train takes on average 22h 26m.
Bus takes on average 26h 30m.
It's helpful to compare your options as there are 2 ways to travel between Greenfield, MA and Chicago, IL including taking a bus and flight.
We recommend using the train as it is the most popular way to get from Greenfield, MA to Chicago, IL among Omio's users.
Take the bus. On this route, it's both cheaper and quicker than driving.
You'll arrive about {timeSavings} sooner ({durationInMinutes} by bus vs {drivingDurationInMinutes} by car) and save roughly {savingsAmount} compared to fuel and tolls ({cheapestPrice} vs {drivingPriceInCents}). You also skip the drive itself — no traffic stress, no parking, and you can use the time to work, nap, or catch up on a series with the onboard Wi-Fi.
Direct coaches are operated by {directProviders}.
Driving is still worth considering if you're travelling with bulky luggage, need flexibility on departure times, or plan to stop along the way.
Greenfield, MA to Chicago, IL Bus Timetables
| Operator | Departure Time | Arrival Time | Duration | Departure days | Cheapest price |
|---|---|---|---|---|---|
Operator Greyhound | Departure Time 12:30PM | Arrival Time 03:00PM | Duration 26h30 | Departure days Fri | Cheapest price $185 |
Compare prices and tickets Greenfield, MA to Chicago, IL by bus or flight
Compare 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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Journey information
Overview: Bus from Greenfield, MA to Chicago, IL
USAUSA
Buses from Greenfield, MA to Chicago, IL run on average 4 times per day, taking around 26h 30m. Cheap bus tickets for this journey start at $185 (€152) if you book in advance.
The earliest bus runs at 06:55, the last at 23:15. The fastest bus covers the 770 miles (1240 km) distance in 26h 30m.
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 770 miles (1240 km) |
Average bus duration 26h 30m |
Cheapest ticket price $185 (€152) |
Buses per day 4 |
Fastest bus 26h 30m |
First bus 6:55 AM |
Last bus 11:15 PM |
Cheapest Month Apr |
Cheapest Day Fri |
High Season Jan - Mar |
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
Complete guide to Chicago
Things to do in Chicago
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
- Must visit
Field Museum
Major natural history museum famous for Sue the T. rex, ancient cultures, and extensive science collections that appeal to both adults and children.
- Must visit
Museum Of Science And Industry
Large hands-on science museum in Hyde Park featuring a submarine, space exhibits, engineering displays, and immersive family-friendly experiences.
- Must visit
Millennium Park
The city’s signature public space, home to Cloud Gate, gardens, events, and major skyline views that define modern Chicago.
- Must visit
The Magnificent Mile
Famous stretch of Michigan Avenue lined with historic buildings, shops, hotels, and frequent first-time visitor photo stops.
- Must visit
Chicago Riverwalk
Highly popular waterfront promenade with architecture views, bridges, and one of the best urban walks in the city.
Deep-Dish Pizza
Chicago’s iconic thick-crust pizza baked in a deep pan, layered with cheese, toppings, and chunky tomato sauce. It is one of the city’s most famous comfort foods.
Chicago-Style Hot Dog
An all-beef hot dog on a poppy seed bun topped with mustard, onions, neon relish, tomato, pickle spear, sport peppers, and celery salt. It is a classic local street food.
Italian Beef Sandwich
Thinly sliced roast beef piled onto an Italian roll, often dipped in seasoned jus and topped with sweet peppers or giardiniera. It is a defining Chicago sandwich.
Gene & Georgetti
A historic old-school steakhouse serving steaks, chops, and classic Italian-American dishes in a traditional setting.
Alinea
Chicago’s internationally acclaimed fine-dining restaurant known for highly inventive tasting menus and exceptional service.
Lou Malnati's Pizzeria
A long-established Chicago favorite known for buttery deep-dish pizza and a casual, family-friendly atmosphere.
United States Dollar
Moderate for a major U.S. city: casual food is manageable, but hotels, attractions, and downtown dining can be pricey.
Average meal costs
- Budget
- USD 10-18 for fast food or casual takeout.
- Mid-range
- USD 20-40 per person at a mid-range restaurant.
- Fine dining
- USD 75+ per person before drinks and tax.
- Coffee
- USD 4-7 for a regular café coffee.
Tipping culture
Tip 18-20% in restaurants; 20%+ for great service. Tip bartenders USD 1-2 per drink, taxis about 10-15%, and hotel staff a few dollars.
FAQs: Bus from Greenfield, MA to Chicago, IL
Find answers to the most common questions about traveling from Greenfield, MA to Chicago, IL by bus. 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 bus, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.
Cheap bus tickets from Greenfield, MA to Chicago, IL can start from as little as $185 (€152) when you book in advance. The average bus ticket price for Greenfield, MA to Chicago, IL is $185 (€152) ; 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 bus from Greenfield, MA to Chicago, IL is 26h 30m to travel the 770 miles (1240 km) long journey. Journey times can vary on weekends and holidays, so use our Journey Planner to search for a specific date.
The earliest bus from Greenfield, MA to Chicago, IL leaves at 6:55 AM. Plan your trip with the Journey Planner from Omio.
The latest bus from Greenfield, MA to Chicago, IL leaves at 11:15 PM.
A trip to Chicago, IL from Greenfield, MA is worth doing but not as a day trip with a journey time of 26h 30m each way. Check with Omio app the best way to travel.
The cheapest month for a bus from Greenfield, MA to Chicago, IL is April.
It's helpful to compare your options as there are 2 ways to travel between Greenfield, MA and Chicago, IL including taking a bus and flight.
No, the bus from Greenfield, MA to Chicago, IL has no accessibility options.
No, there are no bathrooms on board the bus from Greenfield, MA to Chicago, IL.
Some of the most interesting sights to explore in Chicago, IL are:
- Millennium Park, a public park known for its modern art installations and the iconic Cloud Gate sculpture
- Art Institute of Chicago, a renowned museum housing an extensive collection of art from around the world
- Navy Pier, a popular entertainment destination featuring rides, restaurants, and lakefront views
- Willis Tower Skydeck, an observation deck offering panoramic views of the city from one of the tallest buildings in the Western Hemisphere
- Field Museum, a natural history museum with vast exhibits including the famous T. rex skeleton, Sue.
The best things to do in Chicago, IL include:
- Museum of Science and Industry, an interactive museum featuring exhibits on science, technology, and industry
- Explore the vibrant neighborhoods of Chicago, such as Wicker Park and Lincoln Park, known for their unique shops and eateries
- Take a river cruise to see the city's iconic architecture from a different perspective
- Attend a live performance at the historic Chicago Theatre
- Enjoy a day at Lincoln Park Zoo, one of the oldest zoos in the U.S., offering free admission.
No, bikes are not allowed on board the bus from Greenfield, MA to Chicago, IL.
Tickets are often cheaper when booked early. Traveling during off-peak hours or on weekdays can help you save money. Sort results by price to quickly identify the most affordable options. Check for promotions or discounts available on our website and app.
No, there is no food available to purchase on board the bus from Greenfield, MA to Chicago, IL.
No, luggage for the bus from Greenfield, MA to Chicago, IL needs to be booked in addition.
No, there are no additional luggage options for the bus from Greenfield, MA to Chicago, IL.
Unfortunately, pets are not allowed on the bus from Greenfield, MA to Chicago, IL.
No, there are no USB plugs on board the bus from Greenfield, MA to Chicago, IL.
No, there is no WiFi on board the bus from Greenfield, MA to Chicago, IL.
Since neither Greenfield, MA nor Chicago, IL 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.
We recommend using the train as it is the most popular way to get from Greenfield, MA to Chicago, IL among Omio's users.
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 Chicago, IL, travelers should be cautious of pickpocketing and purse snatching, especially in crowded areas like public transit and popular tourist spots. Common scams include fake charity solicitations and distraction thefts. It is advisable to stay alert in neighborhoods outside downtown after dark and use authorized transportation services to avoid unlicensed taxi scams. Keeping valuables secure and being aware of surroundings helps mitigate these risks.
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 bus stations
Popular bus stations from Greenfield, MA to Chicago, IL
Most Greenfield, MA to Chicago, IL buses use the Greenfield, Olive St (Greyhound Bus Station) to Chicago, Greyhound Bus Station station pair, with some services arriving at Chicago, Union Station (Amtrak). Use this guide to compare Greenfield, MA and Chicago, IL bus stations on this route, check city-centre transport, alongside checking practicalities like bus station facilities and services.
Departure bus stations in Greenfield
Arrival bus stations in Chicago
Greenfield, Olive St (Greyhound Bus Station)
City-centre transport
Getting to Greenfield, Olive St (Greyhound Bus Station) from Greenfield city centre
Bus20, 21, 23, 24 · 2m · every ~4 min
Chicago, Greyhound Bus Station
City-centre transport
Getting to Chicago, Greyhound Bus Station from Chicago city centre
Bus7 · 8m · $4 · every ~6 min
Chicago, Union Station (Amtrak)
City-centre transport
Getting to Chicago, Union Station (Amtrak) from Chicago city centre
Bus28, 151 · 7m · $4 · every ~13 min
Most popular bus connections from Greenfield, MA
More options for your journey from Greenfield, MA to Chicago, IL
Here are some other resources that might have the information you need
Most popular buses to and from Chicago, IL and Greenfield, MA
Most popular bus connections to Chicago, IL
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