The cheapest and fastest trains from South Station, Boston, MA to Chicago Union Station, Chicago, IL
Cheapest price
$252
Average price
$291
Fastest journey
22 h 22 m
Average duration
1 d 26 m
Trains per day
2
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 $291 if you buy it on the day, but the cheapest tickets can be found for only $252.
Of the 2 trains that leave South Station, Boston, MA for Chicago Union Station, Chicago, IL on Sun, Mar 29, 2 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Sun, Mar 29 the direct trains cover the 1367 km distance in an average of 1 d 26 m but if you time it right, some trains will get you there in just 22 h 22 m .
On Sun, Mar 29 the slowest trains will take 1 d 2 h 30 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.
12:15PM26h30South Station, Boston, MA02:45PMChicago Union Station, Chicago, IL$2521One-way0 transfers
05:50PM22h22South Station, Boston, MA04:12PMChicago Union Station, Chicago, IL$3311One-way0 transfers
05:50PM22h22South Station, Boston, MA04:12PMChicago Union Station, Chicago, IL$3311One-way0 transfers
12:15PM26h30South Station, Boston, MA02:45PMChicago Union Station, Chicago, IL$2521One-way0 transfers
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 flight with prices starting from $52. 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 flight costs an average of $52, and a train costs an average of $90.
Distance: 849 miles (1367 km)
Compare train with
Most popular Train | Flight | Bus |
|---|---|---|
$320 Average price | $147 Average price Cheapest | $190 Average price |
22h 43m Average total duration 22h 13m Onboard + 30m Additional time* | 5h 59m Average total duration Fastest 2h 59m Onboard + 3h 0m Additional time* | 24h 12m Average total duration 23h 42m Onboard + 30m Additional time* |
![]() Most popular train company | ![]() Most popular airline | ![]() Most popular bus company |
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, Saturday, March 28. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
449 Lake Shore Limited | 4:50 PM South Station, Boston, MA | 22h22 | 3:12 PM Chicago Union Station, Chicago, IL | 0 transfersDirect | |
449 Lake Shore Limited · 49 Lake Shore Limited | 4:50 PM South Station, Boston, MA | 22h22 | 3:12 PM Chicago Union Station, Chicago, IL | 1 transfer | |
| Sunday, March 29 | |||||
![]() | 12:15 PM South Station, Boston, MA | 26h30 | 2:45 PM Chicago Union Station, Chicago, IL | 0 transfersDirect | |
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.
Mar 28
Mar 29
Mar 30
Mar 31
Apr 01
Apr 02
Apr 03
Apr 04
Apr 05
Apr 06
Apr 07
Apr 08
Apr 09
Apr 10
Apr 11
Apr 12
Apr 13
Apr 14
Apr 15
Apr 16
Apr 17
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 13m. Cheap train tickets for this journey start at $90 (€73) but you can travel from only $52 (€42) by flight.
There are 1 trains per day. The earliest train runs at 11:10, 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 13m |
Cheapest ticket price $90 (€73) |
Trains per day 2 |
Direct trains 1 |
Fastest train 22h 22m |
First train 11:10 |
Last train 23:45 |
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 $52 (€42). 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


