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There are 10 ways to get from Chicago to Westport by plane, train, 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

Fly Chicago Midway to New York La Guardia, train

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

Cheapest

Bus

  1. Take the bus from Chicago to New York, NY - 3 Allen St
  2. Take the bus from 230 W 36th St. NYC to New Haven, CT

Fly Chicago O'Hare to New York La Guardia, train

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

Fly Chicago O'Hare to Newark, train

  1. Fly from Chicago O'Hare (ORD) to Newark (EWR)
  2. Take the train from Newark Airport Railroad Station to New York Penn Station
  3. Take the train from Ny Moynihan Train Hall At Penn Station to Stamford Amtrak Station
  4. Take the train from Stamford to Westport

Fly Chicago O'Hare to New York JFK, train

  1. Fly from Chicago O'Hare (ORD) to New York JFK (JFK)
  2. Take the train from Ny Moynihan Train Hall At Penn Station to Stamford Amtrak Station

Fly Chicago O'Hare to White Plains, line 971 bus, train

  1. Fly from Chicago O'Hare (ORD) to White Plains (HPN)
  2. Take the line 971 bus from Westchester Ave and S Kensico Ave to Stamford Transportation Ctr Bay A and N State St
  3. Take the train from Stamford to Westport

Fly Chicago Midway to Hartford, train

  1. Fly from Chicago Midway (MDW) to Hartford (BDL)
  2. Take the train from Hartford Amtrak Station to New Haven
  3. Take the train from New Haven to Westport

Train

  1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Station
  2. Take the train from Croton-Harmon to Harlem-125th St.
  3. Take the train from Harlem-125th St. to Westport

Bus, train

  1. Take the bus from Chicago Amtrak to Baltimore Downtown
  2. Take the bus from Baltimore Downtown Bus Terminal, Baltimore, MD to Port Authority Bus Terminal, New York, NY
  3. Take the train from Grand Central to Westport

Drive

  1. Drive from Chicago to Westport

Questions & Answers

The cheapest way to get from Chicago to Westport is to drive which costs $80 - $120 and takes 13h 52m.

More details

The quickest way to get from Chicago to Westport is to fly and train which costs $120 - $500 and takes 7h 39m.

More details

The distance between Chicago and Westport is 744 miles. The road distance is 836.1 miles.

Get driving directions

The best way to get from Chicago to Westport without a car is to bus which takes 18h 28m and costs $70 - $140.

More details

It takes approximately 7h 14m to get from Chicago to Westport, including transfers.

More details

The best way to get from Chicago to Westport is to bus which takes 18h 28m and costs $70 - $140. Alternatively, you can train, which costs and takes 23h 6m.

Mode details

The quickest flight from Chicago Midway Airport to New York La Guardia Airport is the direct flight which takes 2h 5m.

Search flights

Westport is 1h ahead of Chicago. It is currently 6:41 AM in Chicago and 7:41 AM in Westport.

Yes, the driving distance between Chicago to Westport is 836 miles. It takes approximately 13h 52m to drive from Chicago to Westport.

Get driving directions

Southwest Airlines offers flights from Chicago Midway Airport to New York La Guardia Airport.

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Map of how to get from Chicago to Westport.
Launch map view
  • Distance: 743.5 miles
  • Duration: 7h 14m

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

You can take a bus from Chicago to Westport via New York, NY - 3 Allen St, Canal St, 34 St-Herald Sq, 230 W 36th St. NYC, New Haven, CT, New Haven, Bridgeport, and Bridgeport Transportation Center in around 18h 28m. Alternatively, you can take a train from Chicago to Westport via Croton-Harmon, Harlem-125th St., Westport, and Saugatuck Rr in around 23h 6m.

Airlines
Southwest Airlines
Website
southwest.com
Flights from Chicago Midway to New York La Guardia
Ave. Duration
2h 5m
When
Every day
Estimated price
$100 - $360
Flights from Chicago Midway to New York La Guardia via St. Louis
Ave. Duration
4h 25m
When
Monday, Thursday and Friday
Estimated price
$100 - $360
Flights from Chicago Midway to Hartford
Ave. Duration
1h 57m
When
Every day
Estimated price
$120 - $400
Flights from Chicago Midway to Hartford via Baltimore
Ave. Duration
3h 55m
When
Monday, Thursday, Friday and Saturday
Estimated price
$130 - $410
Flights from Chicago Midway to Hartford via Nashville
Ave. Duration
4h 31m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$140 - $460
American Airlines
Website
aa.com
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2h 8m
When
Every day
Estimated price
$100 - $480
Flights from Chicago O'Hare to Newark
Ave. Duration
2h 2m
When
Every day
Estimated price
$120 - $490
Flights from Chicago O'Hare to New York JFK
Ave. Duration
2h 11m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$120 - $490
Flights from Chicago O'Hare to New York JFK via Reagan Washington
Ave. Duration
3h 55m
When
Every day
Estimated price
$120 - $490
Flights from Chicago O'Hare to New York JFK via Columbus
Ave. Duration
4h 53m
When
Tuesday, Thursday and Saturday
Estimated price
$120 - $490
Flights from Chicago O'Hare to New York JFK via Charlotte
Ave. Duration
5h 8m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$120 - $490
Flights from Chicago O'Hare to White Plains
Ave. Duration
2h 13m
When
Every day
Estimated price
$310 - $550
Flights from Chicago O'Hare to White Plains via Reagan Washington
Ave. Duration
4h 56m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$310 - $550
Flights from Chicago O'Hare to White Plains via Charlotte
Ave. Duration
4h 55m
When
Every day
Estimated price
$310 - $550
Delta
Website
delta.com
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2h 17m
When
Every day
Estimated price
$250 - $310
Flights from Chicago O'Hare to Newark via Detroit
Ave. Duration
3h 58m
When
Monday, Thursday, Friday and Sunday
Estimated price
$230 - $290
Flights from Chicago O'Hare to New York JFK
Ave. Duration
2h 19m
When
Every day
Estimated price
$240 - $310
Flights from Chicago O'Hare to New York JFK via Detroit
Ave. Duration
4h 43m
When
Every day
Estimated price
$240 - $310
Flights from Chicago O'Hare to New York JFK via Atlanta
Ave. Duration
5h 4m
When
Every day
Estimated price
$260 - $380
Flights from Chicago O'Hare to New York JFK via Minneapolis
Ave. Duration
5h 13m
When
Every day
Estimated price
$260 - $380
Flights from Chicago O'Hare to New York JFK via Boston
Ave. Duration
5h 16m
When
Every day
Estimated price
$250 - $340
Flights from Chicago O'Hare to White Plains via Atlanta
Ave. Duration
5h 14m
When
Every day
Estimated price
$420 - $600
United Airlines
Website
united.com
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2h 13m
When
Every day
Estimated price
$140 - $600
Flights from Chicago O'Hare to Newark
Ave. Duration
2h 17m
When
Every day
Estimated price
$120 - $490
Flights from Chicago O'Hare to Newark via Grand Rapids
Ave. Duration
4h 2m
When
Monday to Saturday
Estimated price
$120 - $490
Flights from Chicago O'Hare to Newark via Washington Dulles
Ave. Duration
4h 4m
When
Every day
Estimated price
$120 - $490
Flights from Chicago O'Hare to White Plains
Ave. Duration
2h 15m
When
Every day
Estimated price
$310 - $350
JetBlue Airways
Website
jetblue.com
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2h 7m
When
Every day
Estimated price
$100 - $480
Flights from Chicago O'Hare to Newark
Ave. Duration
2h 2m
When
Every day
Estimated price
$120 - $490
Flights from Chicago O'Hare to New York JFK
Ave. Duration
2h 15m
When
Every day
Estimated price
$130 - $550
Train operators
MTA Bus Company
Website
mta.info
Train from Grand Central to Westport
Ave. Duration
1h 13m
Frequency
Hourly
Schedules at
mta.info
Train from Stamford to Westport
Ave. Duration
22 min
Frequency
Hourly
Schedules at
mta.info
Train from New Haven to Westport
Ave. Duration
47 min
Frequency
Hourly
Schedules at
mta.info
Train from Croton-Harmon to Harlem-125th St.
Ave. Duration
1h 1m
Frequency
Every 30 minutes
Schedules at
mta.info
Train from Harlem-125th St. to Westport
Ave. Duration
1h 3m
Frequency
Hourly
Schedules at
mta.info
NJ Transit
Phone
+1 973-491-7000
Website
njtransit.com
Train from Newark Airport Railroad Station to New York Penn Station
Ave. Duration
28 min
Frequency
Every 20 minutes
Estimated price
$13 - $17
Schedules at
njtransit.com
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
+1 215-856-7924
Website
amtrak.com
Train from Ny Moynihan Train Hall At Penn Station to Stamford Amtrak Station
Ave. Duration
45 min
Frequency
Every 3 hours
Estimated price
$70 - $100
Schedules at
amtrak.com
Business Seat - Adult
$70 - $100
Business Seat - Seniors and Active Military
$70 - $100
Business Seat - Child
$70 - $100
First Class - Adult
$120 - $170
First Class - Senior Citizens and Active Military
$120 - $170
First Class - Child
$110 - $160
Amtrak Northeast Regional

Amtrak’s Northeast Regional train service serves the US’ busy northeast corridor from Virginia to Massachusetts; major stops include Boston, Providence, New York City, Philadelphia, Washington DC and Baltimore. Amenities include Wi-Fi, a quiet car, cafe and business-class seating, and travelling with a small dog or cat is permitted. Book at least 14 days in advance for a cheaper Saver Fare.

Rome2rio's guide to Amtrak Northeast Regional
Contact Details
Phone
+1 215-856-7924
Website
amtrak.com
Train from Ny Moynihan Train Hall At Penn Station to Stamford Amtrak Station
Ave. Duration
51 min
Frequency
Every 3 hours
Estimated price
$13 - $75
Schedules at
amtrak.com
Child 2-12 with paid adult
$13 - $40
Reserved Coach Seat
$25 - $75
Business Class Seat
$40 - $100
Train from Hartford Amtrak Station to New Haven
Ave. Duration
51 min
Frequency
Once daily
Estimated price
$13 - $75
Schedules at
amtrak.com
Child 2-12 with paid adult
$13 - $40
Reserved Coach Seat
$25 - $75
Business Class Seat
$40 - $100
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
+1 215-856-7924
Website
amtrak.com
Train from Ny Moynihan Train Hall At Penn Station to Stamford Amtrak Station
Ave. Duration
43 min
Frequency
Once daily
Estimated price
$23 - $35
Schedules at
amtrak.com
Coach Seat
$23 - $35
Premium
$180 - $250
Flexi Coach Seat
$30 - $50
Business Seat
$29 - $45
Train from Hartford Amtrak Station to New Haven
Ave. Duration
49 min
Frequency
Every 4 hours
Estimated price
$23 - $35
Schedules at
amtrak.com
Coach Seat
$23 - $35
Premium
$180 - $250
Flexi Coach Seat
$30 - $50
Business Seat
$29 - $45
Train from Chicago Union Station to Croton-Harmon Amtrak Station
Ave. Duration
19h 23m
Frequency
Twice daily
Estimated price
$95 - $140
Schedules at
amtrak.com
Coach Seat
$95 - $140
Premium
$310 - $440
Flexi Coach Seat
$190 - $280
Business Seat
$200 - $290
Bus operators
CT Transit
Phone
+1 860-522-9181
Website
cttransit.com
Bus from Westchester Ave and S Kensico Ave to Stamford Transportation Ctr Bay A and N State St
Ave. Duration
22 min
Frequency
Hourly
Estimated price
$1 - $4
Schedules at
cttransit.com
Book at
buypasses.storesecured.com
Two-Hour Pass - Senior (65+) / Disabled
$1
Two-Hour Pass - Youth (Age 5-18)
$2
Two-Hour Pass
$2
Two-Hour Pass Express - Senior (65+) / Disabled
$1 - $2
Two-Hour Pass express
$3 - $4
Two-Hour Pass Express - Youth (Age 5-18)
$4
Wanda Coach
Phone
646-630-7186
Email
help@wandacoach.com
Website
wandacoach.com
Bus from Chicago to New York, NY - 3 Allen St
Ave. Duration
13h
Frequency
3 times a week
Estimated price
$50 - $100
Book at
GoTo Bus
Boltbus
Phone
+1 1-877-265-8287
Website
boltbus.com
Bus from 230 W 36th St. NYC to New Haven, CT
Ave. Duration
1h 31m
Frequency
3 times a week
Estimated price
$9 - $13
Website
boltbus.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 Chicago Amtrak to Baltimore Downtown
Ave. Duration
18h 55m
Frequency
Once daily
Estimated price
$80 - $120
Website
greyhound.com
Economy
$80 - $120
Flexible
$120 - $180
Bus from Baltimore Downtown to New York
Ave. Duration
3h 40m
Frequency
Every 4 hours
Estimated price
$25 - $40
Website
greyhound.com
Economy
$25 - $40
Flexible
$45 - $70
Peter Pan Bus Lines
Phone
1-800-343-9999
Website
peterpanbus.com
Bus from Baltimore Downtown Bus Terminal, Baltimore, MD to Port Authority Bus Terminal, New York, NY
Ave. Duration
3h 20m
Frequency
Every 4 hours
Estimated price
$35 - $50
Website
peterpanbus.com

Want to know more about travelling around United States

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More Questions & Answers

There are 47+ hotels available in Westport. Prices start at $100 USD per night.

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The best way to get from Chicago to Chicago Midway Airport is to subway which takes 23 min and costs $1 - $5.

More details