There are 10 ways to get from Chicago to Connecticut 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 Hartford  •  4 h 19 min

  1. Fly from Chicago Midway (MDW) to Hartford (BDL) MDW - BDL

$173 - $418

Cheapest option

Bus  •  20 h 19 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 / ...

$93 - $226

8 alternative options

Fly Chicago O'Hare to Hartford  •  4 h 39 min

  1. Fly from Chicago O'Hare (ORD) to Hartford (BDL) ORD - BDL

$163 - $359

Fly Chicago Midway to Newark, train  •  5 h 25 min

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

$119 - $403

Fly Chicago Midway to New York La Guardia, train  •  5 h 39 min

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

$157 - $656

Fly Chicago O'Hare to New York La Guardia, train  •  5 h 55 min

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

$122 - $537

Fly Chicago O'Hare to White Plains, line 971 bus  •  6 h 28 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 Main St and Athlantic St

$206 - $662

Bus, train  •  17 h 18 min

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

$109 - $134

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 Bridgeport Amtrak Vermonter / ...

$154 - $418

Drive  •  14 h 3 min

  1. Drive from Chicago to Bridgeport 846.8 miles

$80 - $120

Questions & Answers

No, there is no direct bus from Chicago to Connecticut. However, there are services departing from Chicago, Il and arriving at Bridgeport, Ct via New York, Ny. The journey, including transfers, takes approximately 20 h 19 min.

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

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The distance between Chicago and Connecticut is 771 miles. The road distance is 846.8 miles.

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The best way to get from Chicago to Connecticut without a car is to bus and train which takes 17 h 18 min and costs .

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It takes approximately 4 h 19 min to get from Chicago to Connecticut, including transfers.

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Chicago to Connecticut bus services, operated by Greyhound USA, depart from Chicago, Il station.

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

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The best way to get from Chicago to Connecticut is to fly which takes 4 h 19 min and costs . Alternatively, you can bus, which costs and takes 20 h 19 min, you could also train, which costs and takes 22 h 6 min.

Mode details

The quickest flight from Chicago Midway Airport to Hartford Airport is the direct flight which takes 1 h 55 min.

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Chicago to Connecticut bus services, operated by Greyhound USA, arrive at Bridgeport, Ct station.

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Map of how to get from Chicago to Connecticut.
Launch map view
  • Distance: 771.2 miles
  • Duration: 4 h 19 min

What companies run services between Chicago, IL, USA and Connecticut, USA?

Southwest Airlines and Delta fly from Chicago to Hartford every 4 hours. Alternatively, you can take a bus from Chicago to Bridgeport via New York, Ny in around 20 h 19 min.

Airlines
Southwest Airlines
Website
southwest.com
Flights from Chicago Midway to Hartford
Ave. Duration
1 h 57 min
When
Every day
Estimated price
$190 - $900
Flights from Chicago Midway to Hartford via Baltimore
Ave. Duration
4 h 6 min
When
Every day
Estimated price
$190 - $900
Flights from Chicago Midway to Newark
Ave. Duration
2 h
When
Every day
Estimated price
$120 - $750
Flights from Chicago Midway to New York La Guardia
Ave. Duration
2 h 2 min
When
Every day
Estimated price
$120 - $600
Delta
Website
delta.com
Flights from Chicago Midway to Hartford via Detroit
Ave. Duration
4 h 1 min
When
Every day
Estimated price
$200 - $750
Flights from Chicago O'Hare to Hartford via Detroit
Ave. Duration
4 h 2 min
When
Every day
Estimated price
$340 - $750
Flights from Chicago Midway to Newark via Detroit
Ave. Duration
4 h 16 min
When
Every day
Estimated price
$120 - $750
Flights from Chicago Midway to New York La Guardia via Detroit
Ave. Duration
3 h 56 min
When
Every day
Estimated price
$240 - $1,200
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2 h 8 min
When
Every day
Estimated price
$95 - $700
Flights from Chicago O'Hare to White Plains via Detroit
Ave. Duration
4 h 1 min
When
Every day
Estimated price
$280 - $1,100
Flights from Chicago O'Hare to White Plains via Atlanta
Ave. Duration
5 h 4 min
When
Every day
Estimated price
$280 - $1,100
American Airlines
Website
aa.com
Flights from Chicago O'Hare to Hartford
Ave. Duration
2 h 3 min
When
Every day
Estimated price
$320 - $700
Flights from Chicago O'Hare to Hartford via Philadelphia
Ave. Duration
3 h 56 min
When
Every day
Estimated price
$320 - $700
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2 h 9 min
When
Every day
Estimated price
$85 - $600
Flights from Chicago O'Hare to White Plains
Ave. Duration
2 h 10 min
When
Every day
Estimated price
$270 - $1,200
Flights from Chicago O'Hare to White Plains via Reagan Washington
Ave. Duration
4 h 46 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 Hartford
Ave. Duration
2 h 9 min
When
Every day
Estimated price
$320 - $750
Flights from Chicago O'Hare to Hartford via Washington Dulles
Ave. Duration
4 h 8 min
When
Every day
Estimated price
$320 - $750
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2 h 11 min
When
Every day
Estimated price
$110 - $700
Flights from Chicago O'Hare to White Plains
Ave. Duration
2 h 15 min
When
Every day
Estimated price
$400 - $1,200
Porter Airlines
Website
flyporter.com
Flights from Chicago Midway to Newark via Billy Bishop Toronto City
Ave. Duration
4 h 7 min
When
Monday, Thursday, Friday and Sunday
Estimated price
$230 - $1,100
Spirit Airlines
Website
spirit.com
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2 h 14 min
When
Every day
Estimated price
$85 - $600
Train operators
Metro-North Railroad (MNR)
Phone
+1 877-690-5116
Website
mta.info
Train from Grand Central to Stamford
Ave. Duration
1 h 10 min
Frequency
Every 20 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
Train from Grand Central to Bridgeport
Ave. Duration
1 h 33 min
Frequency
Every 30 minutes
Estimated price
$14 - $29
Schedules at
mta.info
Off-peak at station
$14 - $16
Off-peak onboard
$20 - $22
Onboard
$21 - $29
At station
$19 - $22
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 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
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 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
Train from New York Penn Station to Bridgeport Amtrak
Ave. Duration
1 h 13 min
Frequency
Every 4 hours
Estimated price
$25 - $50
Website
amtrak.com
Coach Seat
$25 - $40
Flexi Coach Seat
$40 - $65
Business Coach Seat
$35 - $50
Room
$140 - $200
Bus operators
CT Transit
Phone
+1 860-522-8101
Website
cttransit.com
Bus from Main St and S Broadway to Main St and Athlantic St
Ave. Duration
28 min
Frequency
Hourly
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

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
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

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

Connecticut is 1 h ahead of Chicago. It is currently 10:58 AM in Chicago and 11:58 AM in Connecticut.

Chicago to Connecticut train services, operated by Amtrak, arrive at Bridgeport Amtrak station.

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Yes, the driving distance between Chicago to Connecticut is 847 miles. It takes approximately 14 h 3 min to drive from Chicago to Connecticut.

Get driving directions

Delta and Southwest Airlines offer flights from Chicago Midway Airport to Hartford Airport.

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Book your Chicago to Connecticut train tickets online with Rome2rio.

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

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There are 100+ hotels available in Connecticut. Prices start at $69 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 .

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