There are 11 ways to get from Stamford to Chicago by train, plane, bus or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2rio's travel planner.

Recommended option

Train to New York La Guardia, fly to Chicago Midway  •  5 h 20 min

  1. Take the train from Stamford Amtrak to New York Penn Station
  2. Fly from New York La Guardia (LGA) to Chicago Midway (MDW) LGA - MDW

$160 - $647

Cheapest option

Bus  •  20 h 50 min

  1. Take the bus from Stamford, Ct to New York, Ny 3469 / ...
  2. Take the bus from New York, Ny to Chicago Amtrak, Il 4425

$91 - $233

9 alternative options

Train to New York La Guardia, fly to Chicago O'Hare  •  5 h 33 min

  1. Take the train from Stamford Amtrak to New York Penn Station
  2. Fly from New York La Guardia (LGA) to Chicago O'Hare (ORD) LGA - ORD

$125 - $528

Train to Newark, fly to Chicago Midway  •  5 h 40 min

  1. Take the train from Stamford to Grand Central
  2. Fly from Newark (EWR) to Chicago Midway (MDW) EWR - MDW

$120 - $402

Train to Newark, fly to Chicago O'Hare  •  6 h 3 min

  1. Take the train from Stamford to Grand Central
  2. Fly from Newark (EWR) to Chicago O'Hare (ORD) EWR - ORD

$115 - $423

Train to New York JFK, fly to Chicago O'Hare  •  5 h 52 min

  1. Take the train from Stamford Amtrak to New York Penn Station
  2. Fly from New York JFK (JFK) to Chicago O'Hare (ORD) JFK - ORD

$142 - $555

Line 971 bus to White Plains, fly to Chicago O'Hare  •  6 h 16 min

  1. Take the line 971 bus from Stamford Transportation Ctr Bay A and N State St to Martine Ave and Court St
  2. Fly from White Plains (HPN) to Chicago O'Hare (ORD) HPN - ORD

$207 - $662

Train to Philadelphia, fly to Chicago Midway  •  6 h 29 min

  1. Take the train from Stamford Amtrak to Philadelphia 30th Street Station
  2. Fly from Philadelphia (PHL) to Chicago Midway (MDW) PHL - MDW

$230 - $679

Train, bus  •  16 h 42 min

  1. Take the train from Stamford to Grand Central New Haven / ...
  2. Take the bus from New York to Chicago, IL Djb149 / ...

$106 - $127

Train  •  20 h 57 min

  1. Take the train from Stamford Amtrak to New York Penn Station Acela Express / ...
  2. Take the train from New York Penn Station to Chicago Union Station Lake Shore Limited

$178 - $521

Drive  •  13 h 37 min

  1. Drive from Stamford to Chicago 824.3 miles

$80 - $120

Questions & Answers

No, there is no direct bus from Stamford to Chicago. However, there are services departing from Stamford, Ct and arriving at Chicago Amtrak, Il via New York, Ny. The journey, including transfers, takes approximately 20 h 50 min.

More details

No, there is no direct train from Stamford to Chicago station. However, there are services departing from Stamford Amtrak and arriving at Chicago Union Station via New York Penn Station. The journey, including transfers, takes approximately 20 h 57 min.

More details

The distance between Stamford and Chicago is 735 miles. The road distance is 824.3 miles.

Get driving directions

The best way to get from Stamford to Chicago without a car is to train and bus which takes 16 h 42 min and costs .

More details

It takes approximately 5 h 20 min to get from Stamford to Chicago, including transfers.

More details

Stamford to Chicago bus services, operated by Greyhound USA, depart from Stamford, Ct station.

More details

Stamford to Chicago train services, operated by Amtrak Acela Express, depart from Stamford Amtrak station.

More details

The best way to get from Stamford to Chicago is to bus which takes 20 h 50 min and costs . Alternatively, you can train, which costs and takes 20 h 57 min.

Mode details

The quickest flight from New York La Guardia Airport to Chicago Midway Airport is the direct flight which takes 2 h 20 min.

Search flights

Stamford to Chicago bus services, operated by Greyhound USA, arrive at Chicago Amtrak, Il station.

More details

Map of how to get from Stamford to Chicago.
Launch map view
  • Distance: 735.1 miles
  • Duration: 5 h 20 min

What companies run services between Stamford, CT, USA and Chicago, IL, USA?

You can take a bus from Stamford to Chicago via New York, Ny in around 20 h 50 min. Alternatively, you can take a train from Stamford to Chicago via New York Penn Station in around 20 h 57 min.

Airlines
Southwest Airlines
Website
southwest.com
Flights from New York La Guardia to Chicago Midway
Ave. Duration
2 h 30 min
When
Every day
Estimated price
$120 - $600
Flights from Newark to Chicago Midway
Ave. Duration
2 h 22 min
When
Every day
Estimated price
$120 - $750
Flights from Philadelphia to Chicago Midway
Ave. Duration
2 h 12 min
When
Every day
Estimated price
$170 - $900
United Airlines
Website
united.com
Flights from New York La Guardia to Chicago O'Hare
Ave. Duration
2 h 33 min
When
Every day
Estimated price
$110 - $700
Flights from Newark to Chicago O'Hare
Ave. Duration
2 h 31 min
When
Every day
Estimated price
$110 - $650
Flights from Newark to Chicago O'Hare via Pittsburgh
Ave. Duration
3 h 57 min
When
Every day
Estimated price
$110 - $650
Flights from Newark to Chicago O'Hare via Cleveland
Ave. Duration
4 h 2 min
When
Monday, Tuesday, Thursday, Friday and Sunday
Estimated price
$110 - $650
Flights from Newark to Chicago O'Hare via Grand Rapids
Ave. Duration
4 h 6 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$110 - $650
Flights from Newark to Chicago O'Hare via Reagan Washington
Ave. Duration
4 h 6 min
When
Every day
Estimated price
$110 - $650
Flights from Newark to Chicago O'Hare via Columbus
Ave. Duration
4 h 7 min
When
Every day
Estimated price
$110 - $650
Flights from White Plains to Chicago O'Hare
Ave. Duration
2 h 29 min
When
Every day
Estimated price
$400 - $1,200
Delta
Website
delta.com
Flights from New York La Guardia to Chicago Midway via Detroit
Ave. Duration
4 h 18 min
When
Every day
Estimated price
$240 - $1,200
Flights from New York La Guardia to Chicago O'Hare
Ave. Duration
2 h 40 min
When
Every day
Estimated price
$95 - $700
Flights from Newark to Chicago Midway via Detroit
Ave. Duration
4 h 11 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$120 - $750
Flights from New York JFK to Chicago O'Hare
Ave. Duration
2 h 46 min
When
Every day
Estimated price
$100 - $650
Flights from New York JFK to Chicago O'Hare via Detroit
Ave. Duration
4 h 43 min
When
Every day
Estimated price
$100 - $650
Flights from White Plains to Chicago O'Hare via Detroit
Ave. Duration
4 h 40 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$280 - $1,100
Flights from White Plains to Chicago O'Hare via Atlanta
Ave. Duration
5 h 28 min
When
Every day
Estimated price
$280 - $1,100
American Airlines
Website
aa.com
Flights from New York La Guardia to Chicago O'Hare
Ave. Duration
2 h 44 min
When
Every day
Estimated price
$85 - $600
Flights from Newark to Chicago O'Hare
Ave. Duration
2 h 42 min
When
Every day
Estimated price
$110 - $700
Flights from New York JFK to Chicago O'Hare
Ave. Duration
2 h 58 min
When
Every day
Estimated price
$110 - $650
Flights from New York JFK to Chicago O'Hare via Pittsburgh
Ave. Duration
4 h 30 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$110 - $650
Flights from New York JFK to Chicago O'Hare via Covington
Ave. Duration
4 h 34 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$110 - $650
Flights from New York JFK to Chicago O'Hare via Cleveland
Ave. Duration
4 h 45 min
When
Monday to Friday
Estimated price
$110 - $650
Flights from New York JFK to Chicago O'Hare via Toronto
Ave. Duration
5 h 2 min
When
Every day
Estimated price
$110 - $650
Flights from New York JFK to Chicago O'Hare via Boston
Ave. Duration
5 h 10 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$110 - $650
Flights from New York JFK to Chicago O'Hare via Charlotte
Ave. Duration
5 h 17 min
When
Every day
Estimated price
$110 - $650
Flights from White Plains to Chicago O'Hare
Ave. Duration
2 h 39 min
When
Every day
Estimated price
$270 - $1,200
Flights from White Plains to Chicago O'Hare via Reagan Washington
Ave. Duration
5 h 9 min
When
Every day
Estimated price
$270 - $1,200
Spirit Airlines
Website
spirit.com
Flights from New York La Guardia to Chicago O'Hare
Ave. Duration
2 h 32 min
When
Every day
Estimated price
$85 - $600
Porter Airlines
Website
flyporter.com
Flights from Newark to Chicago Midway via Billy Bishop Toronto City
Ave. Duration
4 h 23 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$230 - $1,100
JetBlue Airways
Website
jetblue.com
Flights from New York JFK to Chicago O'Hare
Ave. Duration
2 h 44 min
When
Every day
Estimated price
$100 - $700
Train operators
Amtrak Acela Express

Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.

Rome2rio's guide to Amtrak Acela Express
Contact Details
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Stamford Amtrak to New York Penn Station
Ave. Duration
47 min
Frequency
Hourly
Estimated price
$55 - $160
Website
amtrak.com
Business Seat
$55 - $150
First Class Seat
$120 - $160
Train from Stamford Amtrak to Philadelphia 30th Street Station
Ave. Duration
2 h 7 min
Frequency
Hourly
Estimated price
$90 - $240
Website
amtrak.com
Business Seat
$90 - $200
First Class Seat
$170 - $240
Metro-North Railroad (MNR)
Phone
+1 877-690-5116
Website
mta.info
Train from Stamford to Grand Central
Ave. Duration
1 h 10 min
Frequency
Every 15 minutes
Estimated price
$10 - $22
Schedules at
mta.info
Off-peak at station
$10 - $12
Off-peak onboard
$17 - $18
Onboard
$15 - $22
At station
$12 - $16
Amtrak

Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.

Rome2rio's guide to Amtrak
Contact Details
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from New York Penn Station to Chicago Union Station
Ave. Duration
19 h 10 min
Frequency
Once daily
Estimated price
$120 - $370
Website
amtrak.com
Coach Seat
$120 - $190
Flexi Coach Seat
$220 - $330
Business Coach Seat
$260 - $370
Room
$500 - $700
Bus operators
CT Transit
Phone
+1 860-522-8101
Website
cttransit.com
Bus from Stamford Transportation Ctr Bay A and N State St to Martine Ave and Court St
Ave. Duration
24 min
Frequency
Every 30 minutes
Estimated price
$1 - $4
Schedules at
cttransit.com
Book at
buypasses.storesecured.com
D&J Bus
Bus from New York to Chicago, IL
Ave. Duration
14 h
Frequency
Once daily
Estimated price
$90
Schedules at
gotobus.com
Book at
gotobus.com
Wanda Coach
Phone
6466307186
Email
help@wandacoach.com
Website
wandacoach.com
Bus from New York, NY to Chicago
Ave. Duration
15 h
Frequency
3 times a week
Estimated price
$100
Schedules at
wandacoach.com
Greyhound USA

Greyhound is a leading bus company based in Dallas, Texas, serving over 3800 destinations across North America, Mexico and Canada. Greyhound carries around 18 million passengers a year who travel 5.4 billion miles (8.6 billion km) a year on their fleet of around 1700 vehicles. For travel flexibility, you can board or get off a Greyhound bus at official Greyhound stations, partner stations and curbside stops. There are around 230 Greyhound stations across the US where you can both catch your bus and buy tickets, that are also available on the official website and via the mobile app.

Rome2rio's guide to Greyhound USA
Contact Details
Phone
+1 214-849-8100/1-800-231-2222
Email
ifsr@greyhound.com
Website
greyhound.com
Bus from Stamford, Ct to New York, Ny
Ave. Duration
1 h 25 min
Frequency
Hourly
Estimated price
$11 - $24
Website
greyhound.com
Economy
$11 - $16
Flexible
$18 - $24
Bus from New York, Ny to Chicago Amtrak, Il
Ave. Duration
18 h 25 min
Frequency
Every 3 hours
Estimated price
$80 - $210
Website
greyhound.com
Economy
$80 - $140
Flexible
$150 - $210

Want to know more about travelling around United States

Rome2rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

More Questions & Answers

Chicago is 1 h behind Stamford. It is currently 8:53 PM in Stamford and 7:53 PM in Chicago.

Stamford to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.

More details

Yes, the driving distance between Stamford to Chicago is 824 miles. It takes approximately 13 h 37 min to drive from Stamford to Chicago.

Get driving directions

Delta and Southwest Airlines offer flights from New York La Guardia Airport to Chicago Midway Airport.

Search flights

Book your Stamford to Chicago train tickets online with Rome2rio.

Search and book

Book your Stamford to Chicago bus tickets online with Greyhound and Greyhound.

Search and book

There are 580+ hotels available in Chicago. Prices start at $103 USD per night.

More details