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 58 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 16 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 White Plains, line 971 bus, train  •  6 h 56 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 O'Hare to New York JFK, train  •  6 h 46 min

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

$148 - $583

Fly Chicago Midway to Hartford, train  •  7 h

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

$203 - $481

Train to Milwaukee, fly to New York La Guardia, train  •  7 h 36 min

  1. Take the train from Chicago Union Station Amtrak to Milwaukee Intermodal Station Amtrak
  2. Fly from Milwaukee (MKE) to New York La Guardia (LGA) MKE - LGA
  3. Take the train from Grand Central to Fairfield

$148 - $602

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  •  20 h 46 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  •  21 h 53 min

  1. Take the train from Chicago Union Station Amtrak to New York Penn Station Lake Shore Limited
  2. Take the train from Grand Central to Fairfield New Haven

$144 - $410

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.

More details

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

More details

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

Get driving directions

It takes approximately 5 h 58 min to get from Chicago to Fairfield, including transfers.

More details

Map of how to get from Chicago to Fairfield.
Launch map view
  • Distance: 748.4 miles
  • Duration: 5 h 58 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 20 h 46 min. Alternatively, you can take a train from Chicago to Fairfield via New York Penn Station, W 32 St/7 Av, Madison Av/E 42 St, and Grand Central in around 21 h 53 min.

Airlines
Delta
Website
delta.com
Flights from Chicago Midway to New York La Guardia via Detroit
Ave. Duration
4 h
When
Every day
Estimated price
$240 - $1,200
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2 h 11 min
When
Every day
Estimated price
$95 - $700
Flights from Chicago Midway to Newark via Detroit
Ave. Duration
4 h
When
Saturday
Estimated price
$120 - $750
Flights from Chicago O'Hare to White Plains via Detroit
Ave. Duration
4 h 4 min
When
Monday to Saturday
Estimated price
$280 - $1,100
Flights from Chicago O'Hare to New York JFK
Ave. Duration
2 h 27 min
When
Every day
Estimated price
$100 - $650
Flights from Chicago O'Hare to New York JFK via Detroit
Ave. Duration
4 h 15 min
When
Every day
Estimated price
$100 - $650
Flights from Chicago Midway to Hartford via Detroit
Ave. Duration
3 h 48 min
When
Every day
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
Flights from Milwaukee to New York La Guardia via Detroit
Ave. Duration
3 h 45 min
When
Every day
Estimated price
$210 - $700
Southwest Airlines
Website
southwest.com
Flights from Chicago Midway to New York La Guardia
Ave. Duration
2 h 4 min
When
Every day
Estimated price
$120 - $600
Flights from Chicago Midway to Newark
Ave. Duration
2 h 1 min
When
Every day
Estimated price
$120 - $750
Flights from Chicago Midway to Hartford
Ave. Duration
2 h
When
Every day
Estimated price
$190 - $900
Flights from Chicago Midway to Hartford via Baltimore
Ave. Duration
4 h 5 min
When
Saturday and Sunday
Estimated price
$190 - $900
Flights from Milwaukee to New York La Guardia
Ave. Duration
2 h 2 min
When
Every day
Estimated price
$260 - $850
American Airlines
Website
aa.com
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2 h 10 min
When
Every day
Estimated price
$85 - $600
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 25 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$270 - $1,200
Flights from Chicago O'Hare to White Plains via Charlotte
Ave. Duration
4 h 51 min
When
Every day
Estimated price
$270 - $1,200
Flights from Chicago O'Hare to New York JFK
Ave. Duration
2 h 19 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 Toronto
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 37 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$110 - $650
United Airlines
Website
united.com
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2 h 13 min
When
Every day
Estimated price
$110 - $700
Flights from Chicago O'Hare to White Plains
Ave. Duration
2 h 16 min
When
Every day
Estimated price
$400 - $1,200
Flights from Milwaukee to New York La Guardia via Chicago O'Hare
Ave. Duration
3 h 58 min
When
Every day
Estimated price
$230 - $1,100
JetBlue Airways
Website
jetblue.com
Flights from Chicago O'Hare to New York JFK
Ave. Duration
2 h 15 min
When
Every day
Estimated price
$100 - $700
Spirit Airlines
Website
spirit.com
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2 h 13 min
When
Every day
Estimated price
$85 - $600
Porter Airlines
Website
flyporter.com
Flights from Chicago Midway to Newark via Billy Bishop Toronto City
Ave. Duration
4 h 5 min
When
Monday, Thursday, Friday and Sunday
Estimated price
$230 - $1,100
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
33 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 Acela Express
Rome2rio's guide to Amtrak Acela Express
Contact Details
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from New York Penn Station to Stamford Amtrak
Ave. Duration
45 min
Frequency
Hourly
Estimated price
$55 - $160
Website
amtrak.com
Business Seat
$55 - $150
First Class Seat
$120 - $160
Amtrak
Rome2rio's guide to Amtrak
Contact Details
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Hartford Amtrak to New Haven Union Station Amtrak
Ave. Duration
46 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 Amtrak to Milwaukee Intermodal Station Amtrak
Ave. Duration
1 h 29 min
Frequency
Every 4 hours
Estimated price
$28 - $60
Website
amtrak.com
Coach Seat
$28 - $45
Flexi Coach Seat
$50 - $75
Business Coach Seat
$40 - $60
Room
$150 - $210
Train from Chicago Union Station Amtrak 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
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
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
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
Hourly
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
Hourly
Estimated price
$13 - $29
Website
greyhound.com
Economy
$13 - $19
Flexible
$23 - $29

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