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

Bus to Hartford, fly to Chicago Midway  •  5 h 48 min

  1. Take the bus from W Main St and Leavenworth St to Asylum St and Opp Union Pl
  2. Fly from Hartford (BDL) to Chicago Midway (MDW) BDL - MDW

$175 - $422

Cheapest option

Bus Greyhound USA  •  21 h 55 min

  1. Take the bus from Waterbury, CT - Travel Center to New York, NY - Port Authority Bus Terminal
  2. Take the bus from New York, Ny to Chicago Amtrak, Il 4425

$92 - $234

8 alternative options

Bus to Hartford, fly to Chicago O'Hare  •  6 h 11 min

  1. Take the bus from W Main St and Leavenworth St to Asylum St and Opp Union Pl
  2. Fly from Hartford (BDL) to Chicago O'Hare (ORD) BDL - ORD

$165 - $362

Train, train to New York La Guardia, fly to Chicago Midway  •  7 h 16 min

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

$121 - $534

Train, train to Newark, fly to Chicago Midway  •  7 h 19 min

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

$128 - $421

Train, bus to White Plains, fly to Chicago O'Hare  •  8 h 15 min

  1. Take the train from Waterbury to Bridgeport
  2. Take the bus from Bridgeport, Ct to White Plains, Ny
  3. Fly from White Plains (HPN) to Chicago O'Hare (ORD) HPN - ORD

$226 - $702

Bus D&J Bus  •  17 h 25 min

  1. Take the bus from Waterbury, CT to New York
  2. Take the bus from New York to Chicago, IL Djb149 / ...

$110 - $134

Bus, train  •  21 h 42 min

  1. Take the bus from S Elm St and Opp St Mary's Hospital to Pearl St and Trumbull St 925 / ...
  2. Take the train from Springfield Amtrak to Chicago Union Station Amtrak Lake Shore Limited

$131 - $384

Train  •  23 h 22 min

  1. Take the train from Waterbury to Bridgeport
  2. Take the train from Bridgeport Amtrak to New York Penn Station
  3. Take the train from New York Penn Station to Chicago Union Station Amtrak

$201 - $581

Drive  •  14 h 11 min

  1. Drive from Waterbury to Chicago 866 miles

$85 - $130

Questions & Answers

The cheapest way to get from Waterbury to Chicago is to drive which costs $85 - $130 and takes 14 h 11 min.

More details

The quickest way to get from Waterbury to Chicago is to bus and fly which costs $170 - $430 and takes 5 h 48 min.

More details

The distance between Waterbury and Chicago is 756 miles. The road distance is 866 miles.

Get driving directions

It takes approximately 5 h 48 min to get from Waterbury to Chicago, including transfers.

More details

No, there is no direct bus from Waterbury to Chicago. However, there are services departing from Waterbury, CT - Travel Center and arriving at Chicago Amtrak, Il via New York, Ny. The journey, including transfers, takes approximately 21 h 55 min.

More details

No, there is no direct train from Waterbury to Chicago station. However, there are services departing from Waterbury and arriving at Chicago Union Station Amtrak via Bridgeport Amtrak and New York Penn Station. The journey, including transfers, takes approximately 23 h 22 min.

More details

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

You can take a bus from Waterbury to Chicago via New York, W 4 St, East Broadway, New York, Chicago, IL, and Cermak-Chinatown in around 17 h 25 min. Alternatively, you can take a train from Waterbury to Chicago via Bridgeport, Bridgeport Amtrak, and New York Penn Station in around 23 h 22 min.

Airlines
Southwest Airlines
Website
southwest.com
Flights from Hartford to Chicago Midway
Ave. Duration
2 h 21 min
When
Every day
Estimated price
$190 - $900
Flights from Hartford to Chicago Midway via Baltimore
Ave. Duration
4 h 22 min
When
Every day
Estimated price
$190 - $900
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
American Airlines
Website
aa.com
Flights from Hartford to Chicago O'Hare
Ave. Duration
2 h 42 min
When
Every day
Estimated price
$320 - $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
United Airlines
Website
united.com
Flights from Hartford to Chicago O'Hare
Ave. Duration
2 h 34 min
When
Every day
Estimated price
$320 - $750
Flights from Hartford to Chicago O'Hare via Washington Dulles
Ave. Duration
4 h
When
Saturday
Estimated price
$320 - $750
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 Hartford to Chicago Midway via Detroit
Ave. Duration
4 h 27 min
When
Saturday
Estimated price
$200 - $750
Flights from Hartford to Chicago O'Hare via Detroit
Ave. Duration
4 h 29 min
When
Every day
Estimated price
$340 - $750
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 1 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
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 Waterbury to Bridgeport
Ave. Duration
55 min
Frequency
Every 4 hours
Estimated price
$10 - $22
Schedules at
mta.info
Off-peak at station
$10 - $12
Off-peak onboard
$16 - $18
Onboard
$15 - $22
At station
$11 - $16
Train from Bridgeport to Grand Central
Ave. Duration
1 h 35 min
Frequency
Every 30 minutes
Estimated price
$8 - $19
Schedules at
mta.info
Off-peak at station
$8 - $10
Off-peak onboard
$9 - $10
Onboard
$13 - $19
At station
$14 - $17
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 Springfield Amtrak to Chicago Union Station Amtrak
Ave. Duration
18 h 52 min
Frequency
Once daily
Estimated price
$120 - $360
Website
amtrak.com
Coach Seat
$120 - $190
Flexi Coach Seat
$220 - $320
Business Coach Seat
$250 - $360
Room
$490 - $700
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
Amtrak Northeast Regional
Rome2rio's guide to Amtrak Northeast Regional
Contact Details
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Bridgeport Amtrak to New York Penn Station
Ave. Duration
1 h 22 min
Frequency
Every 3 hours
Estimated price
$70 - $190
Website
amtrak.com
Coach Seat
$70 - $110
Business Seat
$100 - $190
Bus operators
CT Transit
Phone
+1 860-522-8101
Website
cttransit.com
Bus from W Main St and Leavenworth St to Asylum St and Opp Union Pl
Ave. Duration
1 h 4 min
Frequency
Hourly
Estimated price
$1 - $4
Schedules at
cttransit.com
Book at
buypasses.storesecured.com
Bus from S Elm St and Opp St Mary's Hospital to Pearl St and Trumbull St
Ave. Duration
1 h 4 min
Frequency
Hourly
Estimated price
$1 - $4
Schedules at
cttransit.com
Book at
buypasses.storesecured.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 Bridgeport, Ct to White Plains, Ny
Ave. Duration
1 h
Frequency
Hourly
Estimated price
$10 - $23
Website
greyhound.com
Economy
$10 - $15
Flexible
$18 - $23
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
Peter Pan Bus Lines
Phone
1-800-343-9999
Website
peterpanbus.com
Bus from Waterbury, CT to New York
Ave. Duration
2 h 5 min
Frequency
Every 4 hours
Estimated price
$15 - $29
Schedules at
peterpanbus.com
Book at
webstore.peterpanbus.com
Bus from Waterbury, CT - Travel Center to New York, NY - Port Authority Bus Terminal
Ave. Duration
2 h 30 min
Frequency
5 times a day
Estimated price
$12 - $25
Schedules at
peterpanbus.com
Book at
webstore.peterpanbus.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

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