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 19 min

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

$113 - $515

Cheapest option

Train to New York La Guardia, fly to Chicago O'Hare  •  5 h 35 min

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

$78 - $396

9 alternative options

Train to Newark, fly to Chicago Midway  •  5 h 22 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  •  5 h 34 min

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

$115 - $423

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 New York JFK, fly to Chicago O'Hare  •  5 h 47 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

$141 - $557

Train to Philadelphia, fly to Chicago Midway  •  6 h 27 min

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

$230 - $679

Train, bus  •  16 h 24 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

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

Train  •  20 h 53 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 Amtrak Lake Shore Limited

$178 - $521

Drive  •  13 h 37 min

  1. Drive from Stamford to Chicago 824.3 miles

$80 - $120

Questions & Answers

The cheapest way to get from Stamford to Chicago is to drive which costs $80 - $120 and takes 13 h 37 min.

More details

The quickest way to get from Stamford to Chicago is to train and fly which costs $110 - $550 and takes 5 h 19 min.

More details

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

Get driving directions

It takes approximately 5 h 19 min to get from Stamford to Chicago, including transfers.

More details

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 Amtrak via New York Penn Station. The journey, including transfers, takes approximately 20 h 53 min.

More details

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 53 min.

Airlines
Southwest Airlines
Website
southwest.com
Flights from New York La Guardia to Chicago Midway
Ave. Duration
2 h 27 min
When
Every day
Estimated price
$120 - $600
Flights from Newark to Chicago Midway
Ave. Duration
2 h 23 min
When
Every day
Estimated price
$120 - $750
Flights from Philadelphia to Chicago Midway
Ave. Duration
2 h 13 min
When
Every day
Estimated price
$170 - $900
Flights from Philadelphia to Chicago Midway via Nashville
Ave. Duration
4 h 45 min
When
Monday to Friday
Estimated price
$170 - $900
American Airlines
Website
aa.com
Flights from New York La Guardia to Chicago O'Hare
Ave. Duration
2 h 51 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 White Plains to Chicago O'Hare
Ave. Duration
2 h 36 min
When
Every day
Estimated price
$270 - $1,200
Flights from White Plains to Chicago O'Hare via Charlotte
Ave. Duration
5 h 30 min
When
Every day
Estimated price
$270 - $1,200
Flights from White Plains to Chicago O'Hare via Reagan Washington
Ave. Duration
5 h 19 min
When
Every day
Estimated price
$270 - $1,200
Flights from New York JFK to Chicago O'Hare
Ave. Duration
3 h 9 min
When
Every day
Estimated price
$110 - $650
Flights from New York JFK to Chicago O'Hare via Pittsburgh
Ave. Duration
4 h 34 min
When
Monday to Friday
Estimated price
$110 - $650
Flights from New York JFK to Chicago O'Hare via Raleigh/Durham
Ave. Duration
4 h 59 min
When
Every day
Estimated price
$110 - $650
Flights from New York JFK to Chicago O'Hare via Toronto
Ave. Duration
5 h
When
Every day
Estimated price
$110 - $650
Flights from New York JFK to Chicago O'Hare via Charlotte
Ave. Duration
5 h 21 min
When
Every day
Estimated price
$110 - $650
Flights from New York JFK to Chicago O'Hare via Cleveland
Ave. Duration
5 h 22 min
When
Saturday
Estimated price
$110 - $650
United Airlines
Website
united.com
Flights from New York La Guardia to Chicago O'Hare
Ave. Duration
2 h 35 min
When
Every day
Estimated price
$110 - $700
Flights from Newark to Chicago O'Hare
Ave. Duration
2 h 30 min
When
Every day
Estimated price
$110 - $650
Flights from Newark to Chicago O'Hare via Cleveland
Ave. Duration
4 h 2 min
When
Saturday
Estimated price
$110 - $650
Flights from Newark to Chicago O'Hare via Washington Dulles
Ave. Duration
4 h 10 min
When
Every day
Estimated price
$110 - $650
Flights from Newark to Chicago O'Hare via Columbus
Ave. Duration
4 h 10 min
When
Saturday
Estimated price
$110 - $650
Flights from White Plains to Chicago O'Hare
Ave. Duration
2 h 36 min
When
Every day
Estimated price
$400 - $1,200
Delta
Website
delta.com
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 15 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$120 - $750
Flights from White Plains to Chicago O'Hare via Detroit
Ave. Duration
5 h 2 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 56 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$280 - $1,100
Flights from New York JFK to Chicago O'Hare
Ave. Duration
2 h 55 min
When
Every day
Estimated price
$100 - $650
Flights from Philadelphia to Chicago Midway via Detroit
Ave. Duration
4 h 2 min
When
Every day
Estimated price
$130 - $750
JetBlue Airways
Website
jetblue.com
Flights from New York JFK to Chicago O'Hare
Ave. Duration
2 h 45 min
When
Every day
Estimated price
$100 - $700
Flights from New York JFK to Chicago O'Hare via Boston
Ave. Duration
5 h 20 min
When
Every day
Estimated price
$100 - $700
Spirit Airlines
Website
spirit.com
Flights from New York La Guardia to Chicago O'Hare
Ave. Duration
2 h 31 min
When
Every day
Estimated price
$85 - $600
Porter Airlines
Website
flyporter.com
Flights from Newark to Chicago Midway via Toronto Island
Ave. Duration
4 h 17 min
When
Monday
Estimated price
$230 - $1,100
Train operators
Metro-North Railroad (MNR)
Website
mta.info
Train from Stamford to Grand Central
Ave. Duration
52 min
Frequency
Every 30 minutes
Estimated price
$10 - $22
Schedules at
mta.info
Off-peak at station
$10 - $12
Off-peak onboard
$16 - $18
Onboard
$15 - $22
At station
$12 - $16
Amtrak Acela Express
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
48 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 Amtrak
Ave. Duration
2 h 11 min
Frequency
Hourly
Estimated price
$90 - $240
Website
amtrak.com
Business Seat
$90 - $200
First Class Seat
$170 - $240
Amtrak
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 Amtrak
Ave. Duration
19 h 5 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
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

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