There are 8 ways to get from Waterville Valley to Chicago by car, plane, bus, train, or bus (Flixbus)
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Drive to Portland, fly to Chicago O'Hare International Airport
best- Drive from Waterville Valley to Portland (PWM)
- Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)PWM - ORD
6h 4m$98–447Bus, train
- Take the bus from Plymouth to Boston - South StationLittleton
- Take the train from Boston to Chicago Union StationLake Shore Limited
26h 32m$292–874Bus
- Take the bus from Lincoln to Boston - South Station
- Take the bus from Boston to New York Midtown
- Take the bus from New York Midtown to Chicago Bus Station
30h 33m$248–411Drive 972.6 mi
- Drive from Waterville Valley to Chicago972.6 mi
17h 58m$178–257Drive to Portland, fly to Chicago Midway International Airport
- Drive from Waterville Valley to Portland (PWM)
- Fly from Portland (PWM) to Chicago Midway International Airport (MDW)PWM - MDW
5h 31m$128–627Bus to Manchester Airport, fly to Chicago Midway International Airport
- Take the bus from Lincoln to Concord, NH
- Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)MHT - MDW
8h 14m$229–761Bus to Manchester Airport, fly to Chicago O'Hare International Airport
- Take the bus from Lincoln to Concord, NH
- Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)MHT - ORD
8h 41m$199–571Bus, bus to Boston Logan Airport, fly to Chicago Midway International Airport
- Take the bus from Lincoln to Concord, NH
- Take the bus from Concord, NH to Logan International Airport
- Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)BOS - MDW
9h 6m$210–605
Portland (PWM) to Chicago O'Hare International Airport (ORD) flights
Questions & Answers
The cheapest way to get from Waterville Valley to Chicago is to drive which costs $170 - $260 and takes 17h 58m.
The fastest way to get from Waterville Valley to Chicago is to drive and fly which takes 5h 31m and costs $120 - $650.
The distance between Waterville Valley and Chicago is 1006 miles. The road distance is 978.3 miles.
The best way to get from Waterville Valley to Chicago without a car is to bus and train which takes 26h 32m and costs $290 - $900.
It takes approximately 6h 4m to get from Waterville Valley to Chicago, including transfers.
Chicago is 1h behind Waterville Valley. It is currently 10:48 PM in Waterville Valley and 9:48 PM in Chicago.
Yes, the driving distance between Waterville Valley to Chicago is 978 miles. It takes approximately 17h 58m to drive from Waterville Valley to Chicago.
There are 1229+ hotels available in Chicago.
What companies run services between Waterville Valley, NH, USA and Chicago, IL, USA?
You can take a vehicle from Waterville Valley to Chicago Bus Station via Lincoln, Boston - South Station, Boston, and New York Midtown in around 30h 33m.
Transport is disrupted due to the Russia-Ukraine war. Read more
- Website
- southwest.com
Flights from Portland to Chicago Midway International Airport
- Ave. Duration
- 2h 35m
- When
- Monday, Thursday, and Friday
- Estimated price
- $110–600
Flights from Portland to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 5h 11m
- When
- Monday, Tuesday, Wednesday, Saturday, and Sunday
- Estimated price
- $130–650
Flights from Manchester Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 33m
- When
- Every day
- Estimated price
- $110–600
Flights from Manchester Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 50m
- When
- Tuesday, Thursday, and Sunday
- Estimated price
- $120–650
Flights from Boston Logan Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 46m
- When
- Every day
- Estimated price
- $85–450
- Website
- aa.com
Flights from Portland to Chicago O'Hare International Airport
- Ave. Duration
- 3h 13m
- When
- Every day
- Estimated price
- $80–420
Flights from Portland to Chicago O'Hare International Airport via New York La Guardia
- Ave. Duration
- 6h 12m
- When
- Monday, Tuesday, Wednesday, and Sunday
- Estimated price
- $90–440
Flights from Portland to Chicago O'Hare International Airport via Reagan Washington
- Ave. Duration
- 6h 15m
- When
- Monday, Tuesday, Wednesday, Thursday, Saturday, and Sunday
- Estimated price
- $95–460
Flights from Manchester Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 51m
- When
- Every day
- Estimated price
- $80–410
Flights from Manchester Airport to Chicago O'Hare International Airport via Philadelphia
- Ave. Duration
- 5h 22m
- When
- Monday, Tuesday, Wednesday, Friday, Saturday, and Sunday
- Estimated price
- $85–430
Flights from Manchester Airport to Chicago O'Hare International Airport via Reagan Washington
- Ave. Duration
- 5h 58m
- When
- Every day
- Estimated price
- $90–440
Flights from Manchester Airport to Chicago O'Hare International Airport via Charlotte
- Ave. Duration
- 6h 14m
- When
- Every day
- Estimated price
- $110–500
- Website
- united.com
Flights from Portland to Chicago O'Hare International Airport
- Ave. Duration
- 3h 4m
- When
- Every day
- Estimated price
- $80–420
Flights from Portland to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 5h 11m
- When
- Every day
- Estimated price
- $90–450
Flights from Manchester Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 5h 25m
- When
- Every day
- Estimated price
- $90–440
- Website
- delta.com
Flights from Portland to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 4h 48m
- When
- Thursday
- Estimated price
- $80–420
Flights from Portland to Chicago O'Hare International Airport via New York La Guardia
- Ave. Duration
- 6h 5m
- When
- Monday, Tuesday, Wednesday, Saturday, and Sunday
- Estimated price
- $90–440
Flights from Boston Logan Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 5h 21m
- When
- Monday, Tuesday, Wednesday, Saturday, and Sunday
- Estimated price
- $85–450
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Boston to Chicago Union Station
- Ave. Duration
- 22h 22m
- Frequency
- Once daily
- Estimated price
- $150–700
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 800 639 3317
- info@concordcoachlines.com
- Website
- concordcoachlines.com
Bus from Plymouth to Boston - South Station
- Ave. Duration
- 2h 45m
- Frequency
- Once daily
- Estimated price
- $24–35
- Website
- https://concordcoachlines.com
Bus from Lincoln to Boston - South Station
- Ave. Duration
- 3h 15m
- Frequency
- Once daily
- Estimated price
- $29–40
- Website
- https://concordcoachlines.com
Bus from Lincoln to Concord, NH
- Ave. Duration
- 1h 45m
- Frequency
- Once daily
- Estimated price
- $14–19
- Website
- https://concordcoachlines.com
Bus from Concord, NH to Logan International Airport
- Ave. Duration
- 1h 30m
- Frequency
- Hourly
- Estimated price
- $15–20
- Website
- https://concordcoachlines.com
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Boston to New York Midtown
- Ave. Duration
- 4h 20m
- Frequency
- Every 3 hours
- Estimated price
- $30–70
- Schedules at
- flixbus.com
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 20h 25m
- Frequency
- Twice daily
- Estimated price
- $95–190
- Schedules at
- flixbus.com
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