There are 9 ways to get from Chicago to Maine by plane, car, bus or train

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 O'Hare to Portland  •  4 h 27 min

  1. Fly from Chicago O'Hare (ORD) to Portland (PWM) ORD - PWM

$163 - $368

Cheapest option

Bus  •  25 h 9 min

  1. Take the bus from Chicago, Il to New York, Ny
  2. Take the bus from New York, Ny to Boston, Ma
  3. Take the bus from Boston, Ma to Portland, Me

$118 - $305

7 alternative options

Fly Chicago O'Hare to Bangor  •  5 h 20 min

  1. Fly from Chicago O'Hare (ORD) to Bangor (BGR) ORD - BGR

$234 - $487

Fly Chicago Midway to Manchester, drive  •  4 h 55 min

  1. Fly from Chicago Midway (MDW) to Manchester (MHT) MDW - MHT
  2. Drive from Manchester to Sanford

$118 - $433

Fly Chicago O'Hare to Manchester, drive  •  5 h 31 min

  1. Fly from Chicago O'Hare (ORD) to Manchester (MHT) ORD - MHT
  2. Drive from Manchester to Sanford

$168 - $434

Fly Chicago Midway to Boston, bus  •  6 h 33 min

  1. Fly from Chicago Midway (MDW) to Boston (BOS) MDW - BOS
  2. Take the bus from Boston, Ma to Wells

$148 - $480

Fly Chicago O'Hare to Boston, bus  •  6 h 50 min

  1. Fly from Chicago O'Hare (ORD) to Boston (BOS) ORD - BOS
  2. Take the bus from Boston, Ma to Wells

$133 - $361

Train, bus  •  24 h 40 min

  1. Take the train from Chicago Union Station Amtrak to Boston South Station Amtrak Lake Shore Limited
  2. Take the bus from Boston, MA - South Station to Portland, ME Boston-Portland-Bates College / ...

$157 - $432

Drive  •  18 h 13 min

  1. Drive from Chicago to Portland 1100 miles

$100 - $160

Questions & Answers

The cheapest way to get from Chicago to Maine is to drive which costs $100 - $160 and takes 18 h 13 min.

More details

The quickest way to get from Chicago to Maine is to fly which takes 4 h 27 min and costs $160 - $370.

More details

The distance between Chicago and Maine is 1561 km. The road distance is 1760 km.

Get driving directions

It takes approximately 4 h 27 min to get from Chicago to Maine, including transfers.

More details

No, there is no direct bus from Chicago to Maine. However, there are services departing from Chicago, Il and arriving at Congress St + Hampshire St via New York, Ny, Boston, Ma and Congress St + Valley St. The journey, including transfers, takes approximately 25 h 9 min.

More details

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

American Airlines, United Airlines and two other airlines fly from Chicago to South Portland Gardens hourly. Alternatively, you can take a bus from Chicago to Portland via New York, Ny, Boston, Ma, Portland, Me, and Congress St + Valley St in around 25 h 9 min.

Airlines
Southwest Airlines
Website
southwest.com
Flights from Chicago Midway to Manchester
Ave. Duration
2 h 5 min
When
Every day
Estimated price
$120 - $900
Flights from Chicago Midway to Manchester via Baltimore
Ave. Duration
4 h 21 min
When
Every day
Estimated price
$120 - $900
Flights from Chicago Midway to Boston
Ave. Duration
2 h 14 min
When
Every day
Estimated price
$130 - $550
American Airlines
Website
aa.com
Flights from Chicago O'Hare to Portland
Ave. Duration
2 h 21 min
When
Every day
Estimated price
$320 - $1,100
Flights from Chicago O'Hare to Portland via Reagan Washington
Ave. Duration
4 h 11 min
When
Every day
Estimated price
$320 - $1,100
Flights from Chicago O'Hare to Bangor
Ave. Duration
2 h 30 min
When
Saturday
Estimated price
$410 - $1,000
Flights from Chicago O'Hare to Bangor via New York La Guardia
Ave. Duration
4 h 36 min
When
Every day
Estimated price
$410 - $1,000
Flights from Chicago O'Hare to Bangor via Philadelphia
Ave. Duration
4 h 59 min
When
Every day
Estimated price
$410 - $1,000
Flights from Chicago O'Hare to Bangor via Reagan Washington
Ave. Duration
5 h 25 min
When
Saturday
Estimated price
$410 - $1,000
Flights from Chicago O'Hare to Manchester via Philadelphia
Ave. Duration
4 h 45 min
When
Every day
Estimated price
$340 - $750
Flights from Chicago O'Hare to Manchester via Charlotte
Ave. Duration
5 h 4 min
When
Every day
Estimated price
$340 - $750
Flights from Chicago O'Hare to Manchester via Reagan Washington
Ave. Duration
5 h 19 min
When
Saturday
Estimated price
$340 - $750
Flights from Chicago O'Hare to Boston
Ave. Duration
2 h 17 min
When
Every day
Estimated price
$120 - $490
United Airlines
Website
united.com
Flights from Chicago O'Hare to Portland
Ave. Duration
2 h 29 min
When
Every day
Estimated price
$270 - $1,100
Flights from Chicago O'Hare to Portland via Washington Dulles
Ave. Duration
4 h 30 min
When
Every day
Estimated price
$270 - $1,100
Flights from Chicago O'Hare to Portland via Newark
Ave. Duration
4 h 26 min
When
Monday, Wednesday, Thursday, Friday, Saturday and Sunday
Estimated price
$270 - $1,100
Flights from Chicago O'Hare to Bangor
Ave. Duration
2 h 32 min
When
Every day
Estimated price
$240 - $1,100
Flights from Chicago O'Hare to Bangor via Newark
Ave. Duration
5 h 28 min
When
Every day
Estimated price
$250 - $1,200
Flights from Chicago O'Hare to Manchester
Ave. Duration
2 h 23 min
When
Every day
Estimated price
$320 - $800
Flights from Chicago O'Hare to Boston
Ave. Duration
2 h 20 min
When
Every day
Estimated price
$130 - $650
Delta
Website
delta.com
Flights from Chicago O'Hare to Portland via Detroit
Ave. Duration
4 h 42 min
When
Saturday and Sunday
Estimated price
$230 - $1,100
Flights from Chicago O'Hare to Portland via New York La Guardia
Ave. Duration
4 h 46 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$230 - $1,100
Flights from Chicago O'Hare to Bangor via New York La Guardia
Ave. Duration
5 h
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$480 - $1,100
Flights from Chicago O'Hare to Bangor via New York JFK
Ave. Duration
4 h 43 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$480 - $1,100
Flights from Chicago Midway to Manchester via Detroit
Ave. Duration
3 h 56 min
When
Monday to Friday
Estimated price
$180 - $850
Flights from Chicago O'Hare to Manchester via Detroit
Ave. Duration
4 h 31 min
When
Every day
Estimated price
$390 - $900
Flights from Chicago O'Hare to Manchester via New York La Guardia
Ave. Duration
4 h 34 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$390 - $900
Flights from Chicago Midway to Boston via Detroit
Ave. Duration
4 h
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$140 - $850
JetBlue Airways
Website
jetblue.com
Flights from Chicago O'Hare to Boston
Ave. Duration
2 h 22 min
When
Every day
Estimated price
$140 - $600
Porter Airlines
Website
flyporter.com
Flights from Chicago Midway to Boston via Toronto Island
Ave. Duration
4 h 10 min
When
Wednesday, Thursday, Friday and Sunday
Estimated price
$220 - $1,100
Spirit Airlines
Website
spirit.com
Flights from Chicago O'Hare to Boston
Ave. Duration
2 h 27 min
When
Every day
Estimated price
$110 - $450
Train operators
Amtrak
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Chicago Union Station Amtrak to Boston South Station Amtrak
Ave. Duration
21 h 31 min
Frequency
Once daily
Estimated price
$130 - $390
Website
amtrak.com
Coach Seat
$130 - $200
Flexi Coach Seat
$240 - $340
Business Coach Seat
$280 - $390
Room
$500 - $750
Bus operators
Greyhound USA
Phone
+1 214-849-8100/1-800-231-2222
Email
ifsr@greyhound.com
Website
greyhound.com
Bus from Boston, Ma to Wells
Ave. Duration
1 h 45 min
Frequency
Hourly
Estimated price
$14 - $35
Website
greyhound.com
Economy
$14 - $21
Flexible
$24 - $35
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 Boston, Ma
Ave. Duration
4 h 20 min
Frequency
Every 30 minutes
Estimated price
$25 - $65
Website
greyhound.com
Economy
$25 - $40
Flexible
$45 - $65
Bus from Boston, Ma to Portland, Me
Ave. Duration
2 h 20 min
Frequency
Hourly
Estimated price
$16 - $40
Website
greyhound.com
Economy
$16 - $25
Flexible
$29 - $40
Concord Coach Lines
Website
concordcoachlines.com
Bus from Boston, MA - South Station to Portland, ME
Ave. Duration
1 h 55 min
Frequency
Every 3 hours
Estimated price
$20 - $40
Schedules at
concordcoachlines.com
Book at
webstore.concordcoachlines.com
Bus from Boston, MA - South Station to Portland, ME
Ave. Duration
1 h 55 min
Frequency
5 times a day
Estimated price
$20 - $28
Schedules at
concordcoachlines.com
Book at
webstore.concordcoachlines.com
Peter Pan Bus Lines
Phone
1-800-343-9999
Website
peterpanbus.com
Bus from New York City, NY - Port Authority Bus Terminal to Boston, MA - South Station
Ave. Duration
4 h 15 min
Frequency
Hourly
Estimated price
$21 - $40
Schedules at
peterpanbus.com
Book at
webstore.peterpanbus.com

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