The cheapest and fastest trains from South Station, Boston, MA to Chicago Union Station, Chicago, IL
Cheapest price
$335
Average price
$561
Fastest journey
22 h 22 m
Average duration
1 d 42 m
Trains per day
4
Distance
1367 km
The best way to find a cheap train ticket from South Station, Boston, MA to Chicago Union Station, Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from South Station, Boston, MA to Chicago Union Station, Chicago, IL will cost around $561 if you buy it on the day, but the cheapest tickets can be found for only $335.
Of the 4 trains that leave South Station, Boston, MA for Chicago Union Station, Chicago, IL on Wed, May 13, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Wed, May 13 the direct trains cover the 1367 km distance in an average of 1 d 42 m but if you time it right, some trains will get you there in just 22 h 22 m .
On Wed, May 13 the slowest trains will take 1 d 3 h 35 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 Limited12:50 PM22h22South Station, Boston, MA10:12 AMChicago Union Station, Chicago, IL$3351One-way0 transfers
449 Lake Shore Limited · 49 Lake Shore Limited12:50 PM22h22South Station, Boston, MA10:12 AMChicago Union Station, Chicago, IL$3821One-way1 transfer
95 Northeast Regional · 40 Floridian6:10 AM27h35South Station, Boston, MA8:45 AMChicago Union Station, Chicago, IL$6511One-way1 transfer
40 Floridian+
2155 NextGen Acela7:15 AM26h30South Station, Boston, MA8:45 AMChicago Union Station, Chicago, IL$8751One-way1 transfer
449 Lake Shore Limited · 49 Lake Shore Limited12:50 PM22h22South Station, Boston, MA10:12 AMChicago Union Station, Chicago, IL$3821One-way1 transfer
449 Lake Shore Limited12:50 PM22h22South Station, Boston, MA10:12 AMChicago Union Station, Chicago, IL$3351One-way0 transfers
40 Floridian+
2155 NextGen Acela7:15 AM26h30South Station, Boston, MA8:45 AMChicago Union Station, Chicago, IL$8751One-way1 transfer
95 Northeast Regional · 40 Floridian6:10 AM27h35South Station, Boston, MA8:45 AMChicago Union Station, Chicago, IL$6511One-way1 transfer
Travel Information
Compare train, bus, and flight for South Station, Boston, MA to Chicago Union Station, Chicago, IL
Omio recommends booking the train as it is the most popular option from South Station, Boston, MA to Chicago Union Station, Chicago, IL among Omio's users. If you are prioritising price take the bus with prices starting from $77. For those with little time consider booking a flight which can get you there in 2h 59m. The ticket price range depends on the travel mode: a bus costs an average of $77, and a train costs an average of $159.
Distance: 849 miles (1367 km)
Compare train with
Most popular Train | Flight | Bus | Driving |
|---|---|---|---|
$435 Average price | $197 Average price | $176 Average price Cheapest | $299 Average price (fuel + tolls) |
22h 41m Average total duration 22h 11m Onboard + 30m Additional time* | 5h 59m Average total duration Fastest 2h 59m Onboard + 3h 0m Additional time* | 23h 46m Average total duration 23h 16m Onboard + 30m Additional time* | 14h 34m Average total duration (door-to-door) |
![]() 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 |
This is compared to other travel options from South Station, Boston, MA to Chicago Union Station, Chicago, IL:
A bus is $21 (€17) less than a flight for this route with tickets for a flight from South Station, Boston, MA to Chicago Union Station, Chicago, IL costing on average $197 (€158).
A bus is $259 (€207) less than a train for this route with tickets for a train from South Station, Boston, MA to Chicago Union Station, Chicago, IL costing on average $435 (€348).
Other travel options to Chicago Union Station, Chicago, IL take longer:
Train takes on average 22h 11m.
Bus takes on average 23h 16m.
Tickets start at around $435 (€348) compared to roughly $299 (€240) in fuel and tolls — a saving of about $-135.19 (€-108.21). The journey takes 22h 11m versus 14h 34m 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.
Driving is worth it if you're on a tight schedule, travelling as a group, or want to stop somewhere en route.
Live departures
South Station, Boston, MA to Chicago Union Station, Chicago, IL train times
The table below shows live departures for South Station, Boston, MA to Chicago Union Station, Chicago, IL trains for today, Tuesday, May 12. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 4:50 PM South Station, Boston, MA | 22h22 | 3:12 PM Chicago Union Station, Chicago, IL | 0 transfersDirect | |
![]() | 5:50 PM South Station, Boston, MA | 22h22 | 4:12 PM Chicago Union Station, Chicago, IL | 0 transfersDirect | |
| Wednesday, May 13 | |||||
95 Northeast Regional · 40 Floridian | 6:10 AM South Station, Boston, MA | 27h35 | 8:45 AM Chicago Union Station, Chicago, IL | 1 transfer | |
2155 NextGen Acela+ 40 Floridian | 7:15 AM South Station, Boston, MA | 26h30 | 8:45 AM Chicago Union Station, Chicago, IL | 1 transfer | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets South Station, Boston, MA to Chicago Union Station, Chicago, IL 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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Journey information
Overview: Train from South Station, Boston, MA to Chicago Union Station, Chicago, IL
Trains from South Station, Boston, MA to Chicago Union Station, Chicago, IL run on average 3 times per day, taking around 22h 11m. Cheap train tickets for this journey start at $159 (€127) but you can travel from only $71 (€57) by flight.
There are 1 trains per day. The earliest train runs at 10:10, the last at 23:45. The fastest train covers the 849 miles (1367 km) distance in 22h 22m.
Distance 849 miles (1367 km) |
Average train duration 22h 11m |
Cheapest ticket price $159 (€127) |
Trains per day 3 |
Direct trains 1 |
Fastest train 22h 22m |
First train 10:10 AM |
Last train 11:45 PM |
Cheapest Month Aug |
Cheapest Day Wed |
High Season Apr - Jun |
Low Season Oct - Dec |
Busiest Day Fri |
Least Busy Day Sun |
Train companies: Amtrak from South Station, Boston, MA to Chicago Union Station, Chicago, IL trainsAmtrak trains will get you between South Station, Boston, MA and Chicago Union Station, Chicago, IL from $71 (€57). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
FAQs: Trains from South Station, Boston, MA to Chicago Union Station, Chicago, IL
Find answers to the most common questions about traveling from South Station, Boston, MA to Chicago Union Station, 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 Union Station, Chicago, IL, this guide helps you travel smarter and with confidence.

popular train stations
Popular train stations from South Station, Boston, MA to Chicago Union Station, Chicago, IL
- 5:00 AM - 11:00 PM Monday - Sunday
- Free
- The car park is open 24/7. Access via Atlantic Avenue.
- Legal Sea Foods
- Tavern in the Square
- Outside the main entrance.
- Elevators, restrooms.
- $0.50
- InterContinental Boston
- The Langham, Boston
- Boston Harbor Hotel
- Located in the main hall
- Avis
- Budget
- Enterprise
- Located in the main hall
- Free
- Hall 1: main entrance, platforms 1-5 for Amtrak services
- Hall 2: platforms 6-13 for MBTA Commuter Rail services
- Bus terminal located on the upper level.
- Subway: Red Line
- Bus: Several lines available
- Commuter Rail: Multiple lines
- 5:00 AM - 12:00 AM Monday - Sunday
- Free
- The car park is open 7 days a week from 5:00 a.m. to 12:00 a.m. Departures can be made outside of opening hours. Access via Canal Street.
- The Chicago Firehouse Restaurant
- Lou Mitchell's
- Outside the main entrance.
- Elevators, ramps, restrooms.
- $1
- The Kimpton Gray Hotel
- JW Marriott Chicago
- W Chicago - City Center
- Located in the main hall
- Located in the main hall
- Avis
- Budget
- Enterprise
- Located in the main hall
- Free
- Hall 1: main entrance, Amtrak services
- Hall 2: Metra services
- Hall 3: food court and retail shops
- Bus: Several lines available
- CTA: Blue Line, Pink Line


