There are 10 ways to get from Provincetown to Chicago by ferry, plane, train, bus (Greyhound), car, bus, 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.
Ferry to Boston Logan Airport, fly to Chicago Midway International Airport
best- Take the ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MAferry
- Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane BOS - MDW
7h 32m$177–652Ferry to Boston Logan Airport, fly to Chicago O'Hare International Airport
cheapest- Take the ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MAferry
- Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane BOS - ORD
7h 48m$147–482Ferry, train
- Take the ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MAferry Fast Ferry
- Take the train from Boston to Chicago Union Stationtrain Lake Shore Limited
26h 1m$623–992Bus via Brook Park
- Take the bus from Provincetown to Hyannisbus
- Take the bus from Hyannis Transportation Center to Boston South Busesbus
- Take the bus from Boston to Cleveland Bus Stationbus
- Take the bus from Cleveland Bus Station to Chicago Bus Stationbus
27h 10m$217–337Drive 1,071.8 mi
- Drive from Provincetown to Chicagocar 1,071.8 mi
18h 57m$184–265Ferry, bus to Manchester Airport, fly to Chicago Midway International Airport
- Take the ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MAferry
- Take the ferry from Seaport to Lovejoy Wharfferry
- Take the bus from Boston to Boston Manchester Airportbus
- Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane MHT - MDW
9h 38m$174–579Ferry, train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport
- Take the ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MAferry
- Take the ferry from Seaport to Lovejoy Wharfferry
- Take the train from Ruggles to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane PVD - MDW
9h 59m$189–670Ferry to Boston Logan Airport, fly to General Mitchell International Airport, train
- Take the ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MAferry
- Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane BOS - MKE
- Take the train from Milwaukee to Chicago Union Stationtrain
9h 46m$252–936Ferry, train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport
- Take the ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MAferry
- Take the ferry from Seaport to Lovejoy Wharfferry
- Take the train from Ruggles to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane PVD - ORD
10h 33m$159–490Bus
- Take the bus from Provincetown to Hyannisbus
- Take the bus from Hyannis Transportation Center to Boston South Busesbus
- Take the bus from Boston to New York Midtownbus
- Take the bus from New York Midtown to Chicago Bus Stationbus
30h 32m$227–347
Provincetown to Chicago by ferry, foot, bus, and train
Comparing Your Travel Options
The cheapest way to get from Provincetown to Chicago is to drive which costs $180 - $270 and takes 18h 57m.
The fastest way to get from Provincetown to Chicago is to ferry and fly which takes 7h 32m and costs $170 - $650.
No, there is no direct bus from Provincetown to Chicago station. However, there are services departing from Provincetown and arriving at Chicago Bus Station via Hyannis Transportation Center, Boston and Cleveland Bus Station. The journey, including transfers, takes approximately 27h 10m.
The distance between Provincetown and Chicago is 929 miles. The road distance is 1078.1 miles.
The best way to get from Provincetown to Chicago without a car is to ferry and train which takes 26h 1m and costs $600 - $1,000.
It takes approximately 7h 32m to get from Provincetown to Chicago, including transfers.
Provincetown to Chicago bus services, operated by Peter Pan Bus Lines, depart from Provincetown station.
Provincetown to Chicago bus services, operated by Peter Pan Bus Lines, arrive at Hyannis station.
Chicago is 1h behind Provincetown. It is currently 10:44 PM in Provincetown and 9:44 PM in Chicago.
Yes, the driving distance between Provincetown to Chicago is 1078 miles. It takes approximately 18h 57m to drive from Provincetown to Chicago.
What companies run services between Provincetown, MA, USA and Chicago, IL, USA?
You can take a bus from Provincetown to Chicago Bus Station via Hyannis Transportation Center, Boston, South Station, Boston, and Cleveland Bus Station in around 27h 10m.
- Website
- southwest.com
Flights from Boston Logan Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 45m
- When
- Every day
- Estimated price
- $100–550
Flights from Manchester Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 37m
- When
- Every day
- Estimated price
- $85–460
Flights from Manchester Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 5h 17m
- When
- Every day
- Estimated price
- $95–490
Flights from Manchester Airport to Chicago Midway International Airport via Nashville
- Ave. Duration
- 6h
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $120–600
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 35m
- When
- Every day
- Estimated price
- $100–550
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 59m
- When
- Every day
- Estimated price
- $100–550
Flights from Boston Logan Airport to General Mitchell International Airport via Baltimore
- Ave. Duration
- 4h 56m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $150–750
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 57m
- When
- Monday, Thursday, Friday, Sunday, and Saturday
- Estimated price
- $140–750
- Website
- aa.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 12m
- When
- Every day
- Estimated price
- $70–380
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 5h 2m
- When
- Every day
- Estimated price
- $140–750
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 8m
- When
- Every day
- Estimated price
- $70–370
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Philadelphia
- Ave. Duration
- 5h 23m
- When
- Every day
- Estimated price
- $70–380
- Website
- delta.com
Flights from Boston Logan Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 5h 18m
- When
- Every day
- Estimated price
- $100–550
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 1m
- When
- Every day
- Estimated price
- $70–380
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 5h 47m
- When
- Every day
- Estimated price
- $100–550
Flights from Boston Logan Airport to General Mitchell International Airport
- Ave. Duration
- 2h 52m
- When
- Every day
- Estimated price
- $130–750
Flights from Boston Logan Airport to General Mitchell International Airport via New York La Guardia
- Ave. Duration
- 5h 8m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $140–750
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 6h 26m
- When
- Every day
- Estimated price
- $70–370
- Website
- united.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 2m
- When
- Every day
- Estimated price
- $70–380
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 5h 4m
- When
- Every day
- Estimated price
- $140–750
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 9m
- When
- Every day
- Estimated price
- $70–370
- Website
- jetblue.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 6m
- When
- Every day
- Estimated price
- $70–380
Flights from Boston Logan Airport to General Mitchell International Airport
- Ave. Duration
- 2h 36m
- When
- Every day
- Estimated price
- $130–750
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Boston to Chicago Union Station
- Ave. Duration
- 22h 22m
- Frequency
- Once daily
- Estimated price
- $550–900
- Website
- Amtrak
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $45–75
- Website
- Amtrak
Train from Ruggles to TF Green Airport
- Ave. Duration
- 1h 17m
- Frequency
- Every 4 hours
- Estimated price
- $9–15
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–15
Train from Ruggles to TF Green Airport
- Ave. Duration
- 1h 17m
- Frequency
- Every 4 hours
- Estimated price
- $9–15
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–15
- Phone
- 1-800-343-9999
- Website
- Peter Pan
Bus from Provincetown to Hyannis
- Ave. Duration
- 1h 20m
- Frequency
- Twice daily
- Estimated price
- $9–17
- Website
- Peter Pan
Bus from Provincetown to Hyannis
- Ave. Duration
- 1h 20m
- Frequency
- Twice daily
- Estimated price
- $9–17
- Website
- Peter Pan
- Phone
- +1 (508) 746-0378
- [email protected]
- Website
- Plymouth & Brockton
Bus from Hyannis Transportation Center to Boston South Buses
- Ave. Duration
- 1h 50m
- Frequency
- Hourly
- Estimated price
- $27–35
- Website
- Plymouth & Brockton
- One Way - Adult
- $27–35
Bus from Hyannis Transportation Center to Boston South Buses
- Ave. Duration
- 1h 50m
- Frequency
- Hourly
- Estimated price
- $27–35
- Website
- Plymouth & Brockton
- One Way - Adult
- $27–35
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Boston to Cleveland Bus Station
- Ave. Duration
- 13h 50m
- Frequency
- Once daily
- Estimated price
- $120–190
- Website
- Greyhound
Bus from Cleveland Bus Station to Chicago Bus Station
- Ave. Duration
- 7h 25m
- Frequency
- Twice daily
- Estimated price
- $60–95
- Website
- Greyhound
Bus from Boston to Boston Manchester Airport
- Ave. Duration
- 1h 5m
- Frequency
- Twice daily
- Estimated price
- $9–14
- Website
- Greyhound
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Boston to New York Midtown
- Ave. Duration
- 4h 20m
- Frequency
- Hourly
- Estimated price
- $30–55
- Schedules at
- Flixbus USA
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 20h 25m
- Frequency
- Twice daily
- Estimated price
- $160–240
- Schedules at
- Flixbus USA
- Phone
- +1 617-748-1428
- Website
- Provincetown Fast Ferry
Ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MA
- Ave. Duration
- 1h 35m
- Frequency
- 3 times a day
- Estimated price
- $87
- Website
- Provincetown Fast Ferry
Ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MA
- Ave. Duration
- 1h 35m
- Frequency
- 3 times a day
- Estimated price
- $87
- Website
- Provincetown Fast Ferry
Ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MA
- Ave. Duration
- 1h 35m
- Frequency
- 3 times a day
- Estimated price
- $87
- Website
- Provincetown Fast Ferry
Ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MA
- Ave. Duration
- 1h 35m
- Frequency
- 3 times a day
- Estimated price
- $87
- Website
- Provincetown Fast Ferry
Ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MA
- Ave. Duration
- 1h 35m
- Frequency
- 3 times a day
- Estimated price
- $87
- Website
- Provincetown Fast Ferry
Ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MA
- Ave. Duration
- 1h 35m
- Frequency
- 3 times a day
- Estimated price
- $87
- Website
- Provincetown Fast Ferry
Ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MA
- Ave. Duration
- 1h 35m
- Frequency
- 3 times a day
- Estimated price
- $87
- Website
- Provincetown Fast Ferry
- Phone
- +1 866-307-2469
- Website
- City Experiences
Ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MA
- Ave. Duration
- 1h 30m
- Frequency
- Once daily
- Estimated price
- $72
- Website
- City Experiences
Ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MA
- Ave. Duration
- 1h 30m
- Frequency
- Once daily
- Estimated price
- $72
- Website
- City Experiences
Ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MA
- Ave. Duration
- 1h 30m
- Frequency
- Once daily
- Estimated price
- $72
- Website
- City Experiences
Ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MA
- Ave. Duration
- 1h 30m
- Frequency
- Once daily
- Estimated price
- $72
- Website
- City Experiences
Ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MA
- Ave. Duration
- 1h 30m
- Frequency
- Once daily
- Estimated price
- $72
- Website
- City Experiences
Ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MA
- Ave. Duration
- 1h 30m
- Frequency
- Once daily
- Estimated price
- $72
- Website
- City Experiences
Ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MA
- Ave. Duration
- 1h 30m
- Frequency
- Once daily
- Estimated price
- $72
- Website
- City Experiences
Ferry from Seaport to Lovejoy Wharf
- Ave. Duration
- 30 min
- Frequency
- Hourly
- Estimated price
- $3–10
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $3–10
Ferry from Seaport to Lovejoy Wharf
- Ave. Duration
- 30 min
- Frequency
- Hourly
- Estimated price
- $3–10
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $3–10
Ferry from Seaport to Lovejoy Wharf
- Ave. Duration
- 30 min
- Frequency
- Hourly
- Estimated price
- $3–10
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $3–10
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