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  • Greyhound USA
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  • Amtrak
  • Acela Express
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There are 11 ways to get from Chicago to Fairfield 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 option

Fly Chicago Midway to New York La Guardia, train  •  5 h 53 min

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

$115 - $522

Cheapest option

Fly Chicago O'Hare to New York La Guardia, train  •  6 h 10 min

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

$80 - $403

9 alternative options

Fly Chicago Midway to Newark, train  •  5 h 44 min

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

$122 - $409

Fly Chicago O'Hare to New York JFK, train  •  6 h 17 min

  1. Fly from Chicago O'Hare (ORD) to New York JFK (JFK) ORD - JFK
  2. Take the train from Grand Central to Fairfield

$98 - $431

Fly Chicago O'Hare to White Plains, line 971 bus, train  •  6 h 43 min

  1. Fly from Chicago O'Hare (ORD) to White Plains (HPN) ORD - HPN
  2. Take the line 971 bus from Main St and S Broadway to S State St and Stamford Station
  3. Take the train from Stamford to Fairfield

$213 - $679

Fly Chicago Midway to Hartford, train  •  6 h 58 min

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

$203 - $481

Bus to Milwaukee, fly to New York La Guardia, train  •  8 h

  1. Take the bus from Chicago, IL - O'Hare International Airport to Milwaukee, WI - Airport
  2. Fly from Milwaukee (MKE) to New York La Guardia (LGA) MKE - LGA
  3. Take the train from Grand Central to Fairfield

$140 - $568

Bus, train  •  17 h 6 min

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

$108 - $133

Bus  •  21 h 11 min

  1. Take the bus from Chicago, Il to New York, Ny 1604
  2. Take the bus from New York, Ny to Bridgeport, Ct 3464 / ...

$96 - $239

Train  •  22 h 6 min

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

$191 - $545

Drive  •  13 h 57 min

  1. Drive from Chicago to Fairfield 841.4 miles

$80 - $120

Questions & Answers

The cheapest way to get from Chicago to Fairfield is to drive which costs $80 - $120 and takes 13 h 57 min.

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The quickest way to get from Chicago to Fairfield is to fly and train which costs $120 - $410 and takes 5 h 44 min.

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No, there is no direct train from Chicago station to Fairfield. However, there are services departing from Chicago Union Station and arriving at Fairfield via New York Penn Station and Stamford. The journey, including transfers, takes approximately 22 h 6 min.

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The distance between Chicago and Fairfield is 748 miles. The road distance is 841.4 miles.

Get driving directions

The best way to get from Chicago to Fairfield without a car is to bus and train which takes 17 h 6 min and costs $100 - $140.

More details

It takes approximately 5 h 53 min to get from Chicago to Fairfield, including transfers.

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

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The best way to get from Chicago to Fairfield is to bus which takes 21 h 11 min and costs $95 - $240. Alternatively, you can train, which costs $190 - $550 and takes 22 h 6 min.

Mode details

The quickest flight from Chicago Midway Airport to New York La Guardia Airport is the direct flight which takes 1 h 55 min.

Search flights

Fairfield is 1 h ahead of Chicago. It is currently 1:22 PM in Chicago and 2:22 PM in Fairfield.

Map of how to get from Chicago to Fairfield.
Launch map view
  • Distance: 748.4 miles
  • Duration: 5 h 53 min

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

You can take a bus from Chicago to Fairfield via New York, Ny, Bridgeport, Ct, and Bridgeport in around 21 h 11 min. Alternatively, you can take a train from Chicago to Fairfield via New York Penn Station, Stamford Amtrak, and Stamford in around 22 h 6 min.

Airlines
Southwest Airlines
Website
southwest.com
Flights from Chicago Midway to New York La Guardia
Ave. Duration
2 h
When
Every day
Estimated price
$120 - $600
Flights from Chicago Midway to Newark
Ave. Duration
2 h
When
Every day
Estimated price
$120 - $750
Flights from Chicago Midway to Hartford
Ave. Duration
1 h 55 min
When
Every day
Estimated price
$190 - $900
Flights from Chicago Midway to Hartford via Baltimore
Ave. Duration
3 h 45 min
When
Tuesday, Wednesday, Friday, Saturday and Sunday
Estimated price
$190 - $900
Flights from Milwaukee to New York La Guardia
Ave. Duration
2 h 3 min
When
Every day
Estimated price
$260 - $850
Delta
Website
delta.com
Flights from Chicago Midway to New York La Guardia via Detroit
Ave. Duration
3 h 52 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$240 - $1,200
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2 h 10 min
When
Every day
Estimated price
$95 - $700
Flights from Chicago O'Hare to New York JFK
Ave. Duration
2 h 20 min
When
Every day
Estimated price
$100 - $650
Flights from Chicago O'Hare to New York JFK via Detroit
Ave. Duration
4 h 17 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$100 - $650
Flights from Chicago O'Hare to White Plains via Detroit
Ave. Duration
4 h 3 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$280 - $1,100
Flights from Chicago O'Hare to White Plains via Atlanta
Ave. Duration
4 h 59 min
When
Every day
Estimated price
$280 - $1,100
Flights from Chicago Midway to Hartford via Detroit
Ave. Duration
3 h 46 min
When
Saturday
Estimated price
$200 - $750
Flights from Milwaukee to New York La Guardia
Ave. Duration
2 h 14 min
When
Every day
Estimated price
$210 - $700
American Airlines
Website
aa.com
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2 h 6 min
When
Every day
Estimated price
$85 - $600
Flights from Chicago O'Hare to New York JFK
Ave. Duration
2 h 4 min
When
Every day
Estimated price
$110 - $650
Flights from Chicago O'Hare to New York JFK via Cleveland
Ave. Duration
4 h
When
Saturday
Estimated price
$110 - $650
Flights from Chicago O'Hare to New York JFK via Columbus
Ave. Duration
4 h 14 min
When
Every day
Estimated price
$110 - $650
Flights from Chicago O'Hare to New York JFK via Reagan Washington
Ave. Duration
4 h 27 min
When
Every day
Estimated price
$110 - $650
Flights from Chicago O'Hare to New York JFK via Indianapolis
Ave. Duration
4 h 34 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$110 - $650
Flights from Chicago O'Hare to New York JFK via Boston
Ave. Duration
4 h 35 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$110 - $650
Flights from Chicago O'Hare to White Plains
Ave. Duration
2 h 7 min
When
Every day
Estimated price
$270 - $1,200
Flights from Chicago O'Hare to White Plains via Reagan Washington
Ave. Duration
4 h 45 min
When
Every day
Estimated price
$270 - $1,200
Flights from Chicago O'Hare to White Plains via Charlotte
Ave. Duration
5 h 2 min
When
Every day
Estimated price
$270 - $1,200
United Airlines
Website
united.com
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2 h 6 min
When
Every day
Estimated price
$110 - $700
Flights from Chicago O'Hare to White Plains
Ave. Duration
2 h 9 min
When
Every day
Estimated price
$400 - $1,200
Flights from Milwaukee to New York La Guardia via Chicago O'Hare
Ave. Duration
4 h
When
Every day
Estimated price
$230 - $1,100
Spirit Airlines
Website
spirit.com
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2 h 10 min
When
Every day
Estimated price
$85 - $600
JetBlue Airways
Website
jetblue.com
Flights from Chicago O'Hare to New York JFK
Ave. Duration
2 h 5 min
When
Every day
Estimated price
$100 - $700
Train operators
Metro-North Railroad (MNR)
Phone
+1 877-690-5116
Website
mta.info
Train from Grand Central to Fairfield
Ave. Duration
1 h 22 min
Frequency
Every 30 minutes
Estimated price
$13 - $28
Schedules at
mta.info
Off-peak at station
$13 - $15
Off-peak onboard
$20 - $21
Onboard
$20 - $28
At station
$17 - $21
Train from Stamford to Fairfield
Ave. Duration
35 min
Frequency
Every 30 minutes
Estimated price
$7 - $17
Schedules at
mta.info
Off-peak at station
$8 - $10
Off-peak onboard
$14 - $15
Onboard
$12 - $17
At station
$7 - $12
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 Hartford Amtrak to New Haven Union Station
Ave. Duration
49 min
Frequency
Every 3 hours
Estimated price
$22 - $45
Website
amtrak.com
Coach Seat
$22 - $35
Flexi Coach Seat
$40 - $60
Business Coach Seat
$30 - $45
Room
$130 - $190
Train from Chicago Union Station to New York Penn Station
Ave. Duration
19 h 53 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
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 New York Penn Station to Stamford Amtrak
Ave. Duration
43 min
Frequency
Hourly
Estimated price
$55 - $160
Website
amtrak.com
Business Seat
$55 - $150
First Class Seat
$120 - $160
Bus operators
CT Transit
Phone
+1 860-522-8101
Website
cttransit.com
Bus from Main St and S Broadway to S State St and Stamford Station
Ave. Duration
24 min
Frequency
Every 30 minutes
Estimated price
$1 - $4
Schedules at
cttransit.com
Book at
buypasses.storesecured.com
Coach USA
D&J Bus
Bus from Chicago, IL to New York
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 Chicago to New York, NY
Ave. Duration
13 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 Chicago, Il to New York, Ny
Ave. Duration
17 h 40 min
Frequency
Once daily
Estimated price
$80 - $200
Website
greyhound.com
Economy
$80 - $130
Flexible
$150 - $200
Bus from New York, Ny to Bridgeport, Ct
Ave. Duration
2 h 4 min
Frequency
3 times a day
Estimated price
$13 - $29
Website
greyhound.com
Economy
$13 - $19
Flexible
$23 - $29

Want to know more about travelling around United States

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More Questions & Answers

Chicago to Fairfield train services, operated by Amtrak Acela Express, arrive at Stamford Amtrak station.

More details

Yes, the driving distance between Chicago to Fairfield is 841 miles. It takes approximately 13 h 57 min to drive from Chicago to Fairfield.

Get driving directions

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

Search flights

There are 42+ hotels available in Fairfield. Prices start at $89 USD per night.

More details

The best way to get from Chicago to Chicago Midway Airport is to subway which takes 23 min and costs $2 - $4.

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