There are 10 ways to get from Wellfleet to Chicago by bus, plane, car, 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.
Bus, bus to Boston Logan Airport, fly to Chicago O'Hare International Airport
best- Take the bus from Wellfleet to Hyannis Transportation Centerbus
- Take the bus from Hyannis Transportation Center to Logan International Airportbus
- Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane BOS - ORD
8h 33m$155–455Bus, train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport
cheapest- Take the bus from Wellfleet to Hyannis Transportation Centerbus
- Take the bus from Hyannis Transportation Center to Boston South Stationbus
- 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 55m$68–331Drive, train
- Drive from Wellfleet to Kingstoncar
- Take the train from Kingston to South Stationtrain
- Take the train from Boston to Chicago Union Stationtrain
25h 49m$116–631Bus
- Take the bus from Wellfleet to Hyannis Transportation Centerbus
- 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 9m$152–285Drive 1,058 mi
- Drive from Wellfleet to Chicagocar 1,058 mi
18h 35m$194–279Bus, bus to Boston Logan Airport, fly to Chicago Midway International Airport
- Take the bus from Wellfleet to Hyannis Transportation Centerbus
- Take the bus from Hyannis Transportation Center to Logan International Airportbus
- Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane BOS - MDW
8h 17m$120–535Bus, bus to Boston Logan Airport, fly to General Mitchell International Airport, train
- Take the bus from Wellfleet to Hyannis Transportation Centerbus
- Take the bus from Hyannis Transportation Center to Logan International Airportbus
- Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane BOS - MKE
- Take the train from Milwaukee to Chicago Union Stationtrain
10h 18m$207–1,040Bus, bus to Manchester Airport, fly to Chicago Midway International Airport
- Take the bus from Wellfleet to Hyannis Transportation Centerbus
- Take the bus from Hyannis Transportation Center to Boston South Stationbus
- Take the bus from Boston to Boston Manchester Airportbus
- Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane MHT - MDW
10h 1m$130–644Bus, train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport
- Take the bus from Wellfleet to Hyannis Transportation Centerbus
- Take the bus from Hyannis Transportation Center to Boston South Stationbus
- 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 33m$88–441Fly Provincetown Municipal Airport to Chicago Midway International Airport
- Fly from Provincetown Municipal Airport (PVC) to Chicago Midway International Airport (MDW)plane PVC - MDW
12h 32m$93–471
Wellfleet to Chicago by bus
Questions & Answers
The cheapest way to get from Wellfleet to Chicago is to bus and train and fly which costs $65 - $340 and takes 10h 55m.
The fastest way to get from Wellfleet to Chicago is to bus and fly which takes 8h 17m and costs $120 - $550.
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 New York Midtown. The journey, including transfers, takes approximately 30h 9m.
The distance between Wellfleet and Chicago is 999 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 30h 9m and costs $150 - $290.
It takes approximately 8h 33m to get from Wellfleet to Chicago, including transfers.
Wellfleet to Chicago bus services, operated by Peter Pan Bus Lines, depart from Wellfleet station.
The best way to get from Wellfleet to Chicago is to bus which takes 30h 9m and costs $150 - $290. Alternatively, you can fly, which costs $90 - $480 and takes 12h 32m.
Wellfleet to Chicago bus services, operated by Peter Pan Bus Lines, arrive at Hyannis Transportation Center station.
Chicago is 1h behind Wellfleet. It is currently 11:26 PM in Wellfleet and 10:26 PM in 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, Bus Terminal South Station, Boston, and New York Midtown in around 30h 9m. Alternatively, Cape Air, Southwest Airlines, and JetBlue Airways fly from Provincetown Municipal Airport (PVC) to Chicago Midway International Airport (MDW) twice daily.
- Website
- aa.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 12m
- When
- Every day
- Estimated price
- $55–320
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 5h 12m
- When
- Every day
- Estimated price
- $160–850
Flights from Boston Logan Airport to General Mitchell International Airport via Philadelphia
- Ave. Duration
- 5h 14m
- When
- Monday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $160–900
Flights from Boston Logan Airport to General Mitchell International Airport via Reagan Washington
- Ave. Duration
- 5h 16m
- When
- Every day
- Estimated price
- $170–900
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 5m
- When
- Every day
- Estimated price
- $45–240
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Philadelphia
- Ave. Duration
- 5h 51m
- When
- Every day
- Estimated price
- $45–250
- Website
- southwest.com
Flights from Boston Logan Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 50m
- When
- Every day
- Estimated price
- $85–460
Flights from Boston Logan Airport to General Mitchell International Airport via Baltimore
- Ave. Duration
- 4h 57m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $170–900
Flights from Manchester Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 40m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $100–550
Flights from Manchester Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 5h 8m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $110–600
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 40m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $65–350
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 35m
- When
- Monday and Sunday
- Estimated price
- $70–370
Flights from Provincetown Municipal Airport to Chicago Midway International Airport via Boston Logan Airport
- Ave. Duration
- 8h 50m
- When
- Every day
- Estimated price
- $85–460
Flights from Provincetown Municipal Airport to Chicago Midway International Airport via Boston Logan Airport, Pittsburgh
- Ave. Duration
- 11h 22m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $90–470
- Website
- delta.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 8m
- When
- Every day
- Estimated price
- $55–320
Flights from Boston Logan Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 5h 23m
- When
- Every day
- Estimated price
- $85–460
Flights from Boston Logan Airport to General Mitchell International Airport
- Ave. Duration
- 3h 4m
- When
- Every day
- Estimated price
- $150–850
Flights from Boston Logan Airport to General Mitchell International Airport via Detroit
- Ave. Duration
- 4h 56m
- When
- Every day
- Estimated price
- $150–850
Flights from Boston Logan Airport to General Mitchell International Airport via New York La Guardia
- Ave. Duration
- 5h 14m
- When
- Every day
- Estimated price
- $160–850
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 5h 16m
- When
- Every day
- Estimated price
- $45–240
- Website
- united.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 3m
- When
- Every day
- Estimated price
- $55–320
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 5h 23m
- When
- Every day
- Estimated price
- $160–850
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h
- When
- Every day
- Estimated price
- $45–240
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 5h 55m
- When
- Every day
- Estimated price
- $45–260
- Website
- jetblue.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 5m
- When
- Every day
- Estimated price
- $55–320
Flights from Boston Logan Airport to General Mitchell International Airport
- Ave. Duration
- 2h 30m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $150–850
- Phone
- +1-617-222-3200
- Website
- mbta.com
Train from Kingston to South Station
- Ave. Duration
- 1h 1m
- Frequency
- Every 3 hours
- Estimated price
- $4–13
- Website
- https://www.mbta.com
- Adult
- $4–13
Train from South Station to TF Green Airport
- Ave. Duration
- 1h 25m
- Frequency
- Every 4 hours
- Estimated price
- $6–16
- Website
- https://www.mbta.com
- Adult
- $6–16
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
- $100–600
- Website
- https://www.amtrak.com/home.html
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $22–40
- Website
- https://www.amtrak.com/home.html
- Phone
- 1-800-343-9999
- Website
- peterpanbus.com
Bus from Wellfleet to Hyannis Transportation Center
- Ave. Duration
- 55 min
- Frequency
- 3 times a day
- Estimated price
- $5–30
- Website
- https://peterpanbus.com
- Adult
- $5–30
Bus from Hyannis Transportation Center to Boston South Station
- Ave. Duration
- 1h 40m
- Frequency
- Every 4 hours
- Estimated price
- $10–40
- Website
- https://peterpanbus.com
- Adult
- $10–40
- Phone
- +1 (508) 746-0378
- info@p-b.com
- Website
- p-b.com
Bus from Hyannis Transportation Center to Logan International Airport
- Ave. Duration
- 2h 15m
- Frequency
- Hourly
- Estimated price
- $28–40
- Website
- https://www.p-b.com
- One Way - Adult
- $28–40
Bus from Hyannis Transportation Center to Boston South Buses
- Ave. Duration
- 1h 50m
- Frequency
- Hourly
- Estimated price
- $27–35
- Website
- https://www.p-b.com
- One Way - Adult
- $27–35
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Boston to New York Midtown
- Ave. Duration
- 4h 20m
- Frequency
- Hourly
- Estimated price
- $30–60
- Schedules at
- flixbus.com
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 20h 25m
- Frequency
- Once daily
- Estimated price
- $90–160
- Schedules at
- flixbus.com
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Boston to Boston Manchester Airport
- Ave. Duration
- 1h 5m
- Frequency
- Twice daily
- Estimated price
- $13–19
- Website
- https://www.greyhound.com/
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More Questions & Answers
Yes, the driving distance between Wellfleet to Chicago is 1064 miles. It takes approximately 18h 35m to drive from Wellfleet to Chicago.
There are 1279+ hotels available in Chicago.
















