There are 10 ways to get from Wellfleet to Chicago by ferry, plane, car, train, bus (Greyhound), or bus
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
9h 8m$175–655Bus, train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport
cheapest- Take the bus from Wellfleet to Hyannisbus
- Take the bus from Hyannis to Bostonbus
- Take the train from South Station to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane PVD - ORD
10h 57m$102–428Drive, train
- Drive from Wellfleet to Kingstoncar
- Take the train from Kingston to South Stationtrain
- Take the train from Boston to Chicago Union Stationtrain
25h 50m$567–929Bus
- Take the bus from Wellfleet 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
26h 45m$214–322Drive 1,058 mi
- Drive from Wellfleet to Chicagocar 1,058 mi
18h 36m$175–253Ferry to Boston Logan Airport, fly to Chicago O'Hare International Airport
- 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
9h 24m$145–485Bus, bus to Manchester Airport, fly to Chicago Midway International Airport
- Take the bus from Wellfleet to Hyannisbus
- Take the bus from Hyannis to Bostonbus
- Take the bus from Boston to Boston Manchester Airportbus
- Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane MHT - MDW
9h 46m$117–516Bus, train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport
- Take the bus from Wellfleet to Hyannisbus
- Take the bus from Hyannis to Bostonbus
- Take the train from South Station to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane PVD - MDW
10h 24m$132–608Bus, bus to Bradley International Airport, fly to Chicago Midway International Airport
- Take the bus from Wellfleet to Hyannisbus
- Take the bus from Hyannis to Bostonbus
- Take the bus from Boston to Hartfordbus
- Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane BDL - MDW
11h 20m$140–629Ferry 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
11h 22m$250–939
Wellfleet to Chicago by bus
Comparing Your Travel Options
The cheapest way to get from Wellfleet to Chicago is to drive which costs $170 - $260 and takes 18h 36m.
The fastest way to get from Wellfleet to Chicago is to ferry and fly which takes 9h 8m and costs $170 - $700.
No, there is no direct bus from Wellfleet to Chicago station. However, there are services departing from Wellfleet and arriving at Chicago Bus Station via Hyannis Transportation Center, Boston and Cleveland Bus Station. The journey, including transfers, takes approximately 26h 45m.
The distance between Wellfleet and Chicago is 944 miles. The road distance is 1064.1 miles.
The best way to get from Wellfleet to Chicago without a car is to bus which takes 26h 45m and costs $210 - $330.
It takes approximately 9h 8m to get from Wellfleet to Chicago, including transfers.
Wellfleet to Chicago bus services, operated by Peter Pan Bus Lines, depart from Wellfleet station.
Wellfleet to Chicago bus services, operated by Peter Pan Bus Lines, arrive at Hyannis station.
Chicago is 1h behind Wellfleet. It is currently 1:22 AM in Wellfleet and 12:22 AM in Chicago.
Yes, the driving distance between Wellfleet to Chicago is 1064 miles. It takes approximately 18h 36m to drive from Wellfleet to Chicago.
What companies run services between Wellfleet, MA, USA and Chicago, IL, USA?
You can take a bus from Wellfleet to Chicago Bus Station via Hyannis Transportation Center, Boston, South Station, Boston, and Cleveland Bus Station in around 26h 45m.
- 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 Bradley International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 29m
- When
- Every day
- Estimated price
- $95–550
Flights from Bradley International Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 51m
- When
- Monday, Thursday, Friday, Sunday, and Saturday
- Estimated price
- $100–550
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 55m
- When
- Every day
- Estimated price
- $140–750
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
- Website
- aa.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 13m
- When
- Every day
- Estimated price
- $70–380
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 7m
- When
- Every day
- Estimated price
- $70–370
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 Boston Logan Airport to General Mitchell International Airport via Philadelphia
- Ave. Duration
- 5h 2m
- When
- Every day
- Estimated price
- $140–750
- Website
- united.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 3m
- When
- Every day
- Estimated price
- $70–380
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 9m
- When
- Every day
- Estimated price
- $70–370
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 5h 9m
- When
- Wednesday, Thursday, Sunday, Saturday, Monday, and Friday
- Estimated price
- $75–380
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
- 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 Theodore Francis Green State Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 6h 26m
- When
- Every day
- Estimated price
- $70–370
Flights from Bradley International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 5h 16m
- When
- Every day
- Estimated price
- $95–550
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
- Website
- jetblue.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 4m
- 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
Train from Kingston to South Station
- Ave. Duration
- 1h 1m
- Frequency
- Every 2 hours
- Estimated price
- $6–13
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $6–13
Train from South Station to TF Green Airport
- Ave. Duration
- 1h 30m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–16
Train from South Station to TF Green Airport
- Ave. Duration
- 1h 30m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–16
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
- Phone
- 1-800-343-9999
- Website
- Peter Pan
Bus from Wellfleet to Hyannis
- Ave. Duration
- 55 min
- Frequency
- Twice daily
- Estimated price
- $7–13
- Website
- Peter Pan
Bus from Wellfleet to Hyannis
- Ave. Duration
- 55 min
- Frequency
- Twice daily
- Estimated price
- $7–13
- Website
- Peter Pan
Bus from Hyannis to Boston
- Ave. Duration
- 1h 30m
- Frequency
- Every 3 hours
- Estimated price
- $14–25
- Website
- Peter Pan
Bus from Wellfleet to Hyannis
- Ave. Duration
- 55 min
- Frequency
- Twice daily
- Estimated price
- $7–13
- Website
- Peter Pan
Bus from Hyannis to Boston
- Ave. Duration
- 1h 30m
- Frequency
- Every 3 hours
- Estimated price
- $14–25
- Website
- Peter Pan
Bus from Wellfleet to Hyannis
- Ave. Duration
- 55 min
- Frequency
- Twice daily
- Estimated price
- $7–13
- Website
- Peter Pan
Bus from Hyannis to Boston
- Ave. Duration
- 1h 30m
- Frequency
- Every 3 hours
- Estimated price
- $14–25
- Website
- Peter Pan
Bus from Wellfleet to Hyannis
- Ave. Duration
- 55 min
- Frequency
- Twice daily
- Estimated price
- $7–13
- Website
- Peter Pan
Bus from Hyannis to Boston
- Ave. Duration
- 1h 30m
- Frequency
- Every 3 hours
- Estimated price
- $14–25
- Website
- Peter Pan
Bus from Boston to Hartford
- Ave. Duration
- 1h 50m
- Frequency
- Every 3 hours
- Estimated price
- $20–35
- 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
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
- $120–180
- 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
- +1 617-748-1428
- 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
- 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
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