- Must visit
Art Institute of Chicago
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
Cheapest price
$289
Average price
$398
Fastest journey
22 h 15 m
Average duration
23 h 11 m
Trains per day
8
Distance
1368 km
The best way to find a cheap train ticket from Boston, MA to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Boston, MA to Chicago, IL will cost around $398 if you buy it on the day, but the cheapest tickets can be found for only $289.
Of the 8 trains that leave Boston, MA for Chicago, IL on Mon, Aug 24, 2 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Mon, Aug 24 the direct trains cover the 1368 km distance in an average of 23 h 11 m but if you time it right, some trains will get you there in just 22 h 15 m .
On Mon, Aug 24 the slowest trains will take 1 d 2 h 40 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.
449 Lake Shore Limited
449 Lake Shore Limited
449 Lake Shore Limited · 49 Lake Shore Limited
449 Lake Shore Limited · 49 Lake Shore Limited
95 Northeast Regional · 40 Floridian
449 Lake Shore Limited · 49 Lake Shore Limited
449 Lake Shore Limited
449 Lake Shore Limited
449 Lake Shore Limited · 49 Lake Shore Limited
40 Floridian+
2155 NextGen AcelaOmio recommends booking the train as it is the most popular option from Boston, MA to Chicago, IL among Omio's users. If you are prioritising price take the flight with prices starting from $73. For those with little time consider booking a flight which can get you there in 3h 5m. In case you are seeking to minimise your carbon footprint the train is your best bet as it emits only 0.4 - 1.2kg. The ticket price range depends on the travel mode: a flight costs an average of $73, and a train costs an average of $89.
Distance: 850 miles (1368 km)
Most popular Train | Flight | Bus | Driving |
|---|---|---|---|
$251 Average price | $156 Average price Cheapest | $167 Average price | $307 Average price (fuel + tolls) |
22h 50m Average total duration 22h 20m Onboard + 30m Additional time* | 6h 5m Average total duration Fastest 3h 5m Onboard + 3h 0m Additional time* | 23h 54m Average total duration 23h 24m Onboard + 30m Additional time* | 14h 45m Average total duration (door-to-door) |
0.4 - 1.2kg CO2 emissions Lowest | 4.1 - 8.2kg CO2 emissions | 1.4 - 3.4kg CO2 emissions | - CO2 emissions |
![]() Most popular train company | ![]() Most popular airline | ![]() Most popular bus company | Your own car or car rental |
Direct Options | Direct Options | Direct Options | Direct Options |
Additional time: Average total travel duration to departure point, security checks and transfers.
This is compared to other travel options from Boston, MA to Chicago, IL:
A flight is $10 (€8) less than a bus for this route with tickets for a bus from Boston, MA to Chicago, IL costing on average $167 (€134).
A flight is $95 (€76) less than a train for this route with tickets for a train from Boston, MA to Chicago, IL costing on average $251 (€202).
Other travel options to Chicago, IL take longer:
Train takes on average 22h 20m.
Bus takes on average 23h 24m.
Tickets start at around $251 (€202) compared to roughly $307 (€247) in fuel and tolls — a saving of about $56 (€45). The journey takes 22h 20m versus 14h 45m by car, so you'll arrive a bit later, but you can work, read, or sleep along the way rather than spending the time behind the wheel. You'll also save the hassle of parking at the other end.
Direct services run with Amtrak.
Driving is worth it if you're on a tight schedule, travelling as a group, or want to stop somewhere en route.
The table below shows live departures for Boston, MA to Chicago, IL trains for today, Sunday, August 23. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
449 Lake Shore Limited | 12:50 PM South Station, Boston, MA | 22h22 | 10:12 AM Chicago Union Station, Chicago, IL | 0 transfersDirect | |
449 Lake Shore Limited · 49 Lake Shore Limited | 12:50 PM South Station, Boston, MA | 22h22 | 10:12 AM Chicago Union Station, Chicago, IL | 1 transfer | |
449 Lake Shore Limited | 12:57 PM Back Bay station, Boston, MA | 22h15 | 10:12 AM Chicago Union Station, Chicago, IL | 0 transfersDirect | |
449 Lake Shore Limited · 49 Lake Shore Limited | 12:57 PM Back Bay station, Boston, MA | 22h15 | 10:12 AM Chicago Union Station, Chicago, IL | 1 transfer | |
2271 Acela+ 40 Floridian | 3:35 PM South Station, Boston, MA | 42h10 | 8:45 AM Chicago Union Station, Chicago, IL | 1 transfer | |
2271 Acela+ 40 Floridian | 3:40 PM Back Bay station, Boston, MA | 42h05 | 8:45 AM Chicago Union Station, Chicago, IL | 1 transfer | |
| Monday, August 24 | |||||
95 Northeast Regional · 40 Floridian | 6:10 AM South Station, Boston, MA | 27h35 | 8:45 AM Chicago Union Station, Chicago, IL | 1 transfer | |
95 Northeast Regional · 40 Floridian | 6:15 AM Back Bay station, Boston, MA | 27h30 | 8:45 AM Chicago Union Station, Chicago, IL | 1 transfer | |
40 Floridian+ 2155 NextGen Acela | 7:00 AM South Station, Boston, MA | 26h45 | 8:45 AM Chicago Union Station, Chicago, IL | 1 transfer | |
40 Floridian+ 2155 NextGen Acela | 7:05 AM Back Bay station, Boston, MA | 26h40 | 8:45 AM Chicago Union Station, Chicago, IL | 1 transfer | |
Find all the dates and times for this journey
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.
Trains from Boston, MA to Chicago, IL run on average 6 times per day, taking around 22h 20m. Cheap train tickets for this journey start at $89 (€72) but you can travel from only $73 (€59) by flight.
There are 1 trains per day. The earliest train runs at 06:10, the last at 21:30. The fastest train covers the 850 miles (1368 km) distance in 22h 15m.
Distance 850 miles (1368 km) |
Average train duration 22h 20m |
Cheapest ticket price $89 (€72) |
Trains per day 6 |
Direct trains 1 |
Fastest train 22h 15m |
First train 6:10 AM |
Last train 9:30 PM |
Cheapest Month Nov |
Cheapest Day Wed |
High Season Jul - Sep |
Low Season Jan - Mar |
Busiest Day Thu |
Least Busy Day Sun |
Best time to book 56 days |
Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.
Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.
Lively lakefront park with Cloud Gate, Crown Fountain, gardens, and major public art in central Chicago.
Famous shopping boulevard lined with architecture, hotels, riverfront views, and major city energy.
Scenic pedestrian-friendly riverwalk with boat docks, public art, bridges, and standout skyline perspectives.
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.
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 is thin-sliced roast beef piled onto a roll, often dipped in savory juices and topped with sweet peppers or spicy giardiniera.
Classic spot for juicy Italian beef sandwiches, especially dipped and topped with spicy giardiniera, with a casual local feel.
Legendary stand for Chicago-style hot dogs and char-grilled sausages, served fast in a no-frills local landmark.
World-famous fine dining destination offering a highly creative tasting menu and refined service in an elegant setting.
Moderate for a major US city: hotels can be pricey, but transit is affordable and dining ranges from cheap eats to upscale options.
Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and optional small change at cafes.
Traveling between Boston, MA and Chicago, IL is a scenic journey made convenient by Amtrak. This rail service offers comfortable accommodations and stunning views as you traverse the diverse landscapes of the Northeast to the Midwest. With multiple daily departures, passengers can enjoy an efficient travel experience while relaxing in spacious seating or dining on board. Whether you're heading for business or leisure, Amtrak connects these two cities seamlessly.
Traveling from Boston, MA to Chicago, IL takes approximately 22 hours and 15 minutes. There is 1 direct connection available each day. Passengers can depart from either Back Bay Station or South Station in Boston and arrive at Union Station in Chicago.
The first daily train journey departs from Boston at 4:50 PM and arrives in Chicago at 5:50 PM. This connection offers travelers a convenient option for starting their adventure between these two cities.
The cheapest ticket price for the train connection from Boston to Chicago is $102 (92€). The average ticket price tends to be around $198 (178.2€), making it a more economical option if you book in advance or look out for special deals.
Welcome to the Willis Tower, formerly known as the Sears Tower, which was completed in 1973 and held the title of the tallest building in the world for nearly 25 years. This iconic skyscraper is significant not only for its height but also for its innovative design that has influenced modern architecture worldwide. One of its unique features is The Skydeck on the 103rd floor, where you can step out onto a glass ledge and experience breathtaking views of Chicago from over a thousand feet above ground.
Next up is Millennium Park, inaugurated in 2004 as part of an urban revitalization project aimed at enhancing public spaces within downtown Chicago. Its significance lies in how it brings together art, music, and nature while serving as a cultural hub that attracts millions each year. Be sure to check out Cloud Gate—affectionately known as "The Bean"—a stunning stainless steel sculpture that reflects both visitors and city life around it.
Finally, we arrive at Navy Pier—a historic landmark opened in 1916 originally designed as a shipping facility but now transformed into one of Chicago's top tourist destinations. Its significance comes from being home to various attractions like theaters, restaurants, shops, and even fireworks displays during summer nights along Lake Michigan’s shoreline. Unique features include rides such as The Centennial Wheel offering panoramic views over Lake Michigan or taking leisurely boat cruises right from this vibrant pier!
Find answers to the most common questions about traveling from Boston, MA to Chicago, IL by train. 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 train, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

Most Boston, MA to Chicago, IL trains use the South Station to Union Station station pair. Use this guide to compare Boston, MA and Chicago, IL train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
South Station has practical services for this route, including Wifi, Lockers, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Lost and Found Office, Ticket Office, Bike Parking, Bike Rental, Car Rental, Information Desk, and Luggage Carts.
Food options include: Legal Sea Foods, Tavern in the Square
Free. ATMs are available in the train station.
Ticket office support is available at South Station. Information desks are located in the main hall.
Luggage storage is available at South Station. Lost and found is available at the station.
Available at South Station: Parking, Taxis, WC.
Available at South Station: Bike Parking, Bike Rental, Car Rental.
Accessibility facilities are available at South Station: Elevators, restrooms.
Nearby hotels include InterContinental Boston, The Langham, Boston, Boston Harbor Hotel.
Back Bay Station is 1 km from Boston city centre. Public transport options include:
Back Bay Station has practical services for this route, including Wifi, Lockers, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Lost and Found Office, Ticket Office, Bike Parking, Bike Rental, Car Rental, Information Desk, and Luggage Carts.
Food options include: Sorellina, Atlantic Fish Company
Free. ATMs are available in the train station.
Ticket office support is available at Back Bay Station. Information desks are located in the main hall.
Luggage storage is available at Back Bay Station. Lost and found is available at the station.
Available at Back Bay Station: Parking, Taxis, WC.
Available at Back Bay Station: Bike Parking, Bike Rental, Car Rental.
Accessibility facilities are available at Back Bay Station: Elevators, ramps, restrooms.
Nearby hotels include Copley Square Hotel, The Westin Copley Place, Fairmont Copley Plaza.
Union Station is 3 km from Chicago city centre. Public transport options include:
Union Station has practical services for this route, including Wifi, Lockers, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Lounge, Lost and Found Office, Ticket Office, Bike Parking, Car Rental, Information Desk, and Luggage Carts.
Food options include: The Chicago Firehouse Restaurant, Lou Mitchell's
Free. ATMs are available in the train station.
Ticket office support is available at Union Station. Information desks are located in the main hall.
Luggage storage is available at Union Station. Lost and found is available at the station.
Available at Union Station: Parking, Taxis, WC.
Available at Union Station: Bike Parking, Car Rental.
Accessibility facilities are available at Union Station: Elevators, ramps, restrooms.
Nearby hotels include The Kimpton Gray Hotel, JW Marriott Chicago, W Chicago - City Center.
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