The cheapest and fastest trains from South Station, Boston, MA to Chicago Union Station, Chicago, IL
Cheapest price
$332
Average price
$524
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 $524 if you buy it on the day, but the cheapest tickets can be found for only $332.
Of the 4 trains that leave South Station, Boston, MA for Chicago Union Station, Chicago, IL on Mon, Dec 29, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Mon, Dec 29 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 Mon, Dec 29 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 Limited
449 Lake Shore Limited · 49 Lake Shore Limited
2155 Acela+
40 Floridian
95 Northeast Regional · 40 Floridian
449 Lake Shore Limited
449 Lake Shore Limited · 49 Lake Shore Limited
2155 Acela+
40 Floridian
95 Northeast Regional · 40 FloridianTravel 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 flight with prices starting from €40. For those with little time consider booking a flight which can get you there in 3h 18m. The ticket price range depends on the travel mode: a flight costs an average of €40, and a train costs an average of €105.
Distance: 849 miles (1367 km)
Compare train with
Most popular Train | Bus | Flight |
|---|---|---|
€293 Average price | €130 Average price | €128 Average price Cheapest |
22h 41m Average total duration 22h 11m Onboard + 30m Additional time* | 24h 12m Average total duration 23h 42m Onboard + 30m Additional time* | 6h 18m Average total duration Fastest 3h 18m Onboard + 3h 0m Additional time* |
![]() Most popular train company | ![]() Most popular bus company | ![]() Most popular airline |
Direct Options | Direct Options | Direct Options |
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, Sunday, December 28. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
449 Lake Shore Limited | 5:50 PM South Station, Boston, MA | 22h22 | 4:12 PM Chicago Union Station, Chicago, IL | 0 transfersDirect | |
449 Lake Shore Limited · 49 Lake Shore Limited | 5:50 PM South Station, Boston, MA | 22h22 | 4:12 PM 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.
Dec 29
Dec 30
Dec 31
Jan 01
Jan 02
Jan 03
Jan 04
Why should you book South Station to Chicago Union Station trains with Omio?
Amtrak operates all train services from South Station to Chicago Union Station. Omio is the only official third party seller for Amtrak tickets.
Why book with Omio vs Amtrak?
- 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 Amtrak with all available travel options, which are train, bus and flight to ensure you get the best deal for traveling from South Station to Chicago Union Station.
Why book with Omio over Trainline and Rail Europe?
- Official reseller: Amtrak tickets can only be bought on Omio or Amtrak's website as Omio is the only official third party seller for Amtrak tickets. Trainline, RailEurope, and Rail.Ninja do not sell Amtrak tickets as they are not official sellers.
- Multiple modes of transport: Omio allows you to compare travel options including train, bus and flight to find the ideal travel option from South Station to Chicago Union Station.
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 2 times per day, taking around 22h 11m. Cheap train tickets for this journey start at $132 (€105) but you can travel from only $50 (€40) by flight.
There are 1 trains per day. The earliest train runs at 10:10, the last at 22:45. 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 $132 (€105) |
Trains per day 2 |
Direct trains 1 |
Fastest train 22h 22m |
First train 10:10 |
Last train 22:45 |
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 $50 (€40). 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


