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 Midway International Airport
best- Take the bus from Wellfleet to Hyannis Transportation Center
- Take the bus from Hyannis Transportation Center to Logan International Airport
- Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)BOS - MDW
8h 12m$120–515Bus, train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport
cheapest- Take the bus from Wellfleet to Hyannis Transportation Center
- Take the bus from Hyannis Transportation Center to Boston South Station
- Take the train from Boston to Providence
- Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)PVD - ORD
10h 13m$79–977Drive, train
- Drive from Wellfleet to Kingston
- Take the train from Kingston to South Station
- Take the train from Boston to Chicago Union Station
25h 49m$156–731Bus
- Take the bus from Wellfleet to Hyannis Transportation Center
- Take the bus from Hyannis Transportation Center to Boston South Buses
- Take the bus from Boston to New York Midtown
- Take the bus from New York Midtown to Chicago Bus Station
30h 16m$157–365Drive 1,058 mi
- Drive from Wellfleet to Chicago1,058 mi
18h 24m$194–279Bus, bus to Boston Logan Airport, fly to Chicago O'Hare International Airport
- Take the bus from Wellfleet to Hyannis Transportation Center
- Take the bus from Hyannis Transportation Center to Logan International Airport
- Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)BOS - ORD
8h 33m$135–385Bus, bus to Boston Logan Airport, fly to General Mitchell International Airport, train
- Take the bus from Wellfleet to Hyannis Transportation Center
- Take the bus from Hyannis Transportation Center to Logan International Airport
- Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)BOS - MKE
- Take the train from Milwaukee to Chicago Union Station
10h 18m$317–795Bus, train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport
- Take the bus from Wellfleet to Hyannis Transportation Center
- Take the bus from Hyannis Transportation Center to Boston South Station
- Take the train from Boston to Providence
- Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)PVD - MDW
9h 41m$99–1,067Bus, bus to Manchester Airport, fly to Chicago Midway International Airport
- Take the bus from Wellfleet to Hyannis Transportation Center
- Take the bus from Hyannis Transportation Center to Boston South Station
- Take the bus from Boston to Boston Manchester Airport
- Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)MHT - MDW
9h 51m$130–654Bus, bus to Manchester Airport, fly to Chicago O'Hare International Airport
- Take the bus from Wellfleet to Hyannis Transportation Center
- Take the bus from Hyannis Transportation Center to Boston South Station
- Take the bus from Boston to Boston Manchester Airport
- Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)MHT - ORD
10h 18m$110–514
Wellfleet to Chicago by bus
Questions & Answers
The cheapest way to get from Wellfleet to Chicago is to bus which costs $150 - $370 and takes 30h 16m.
The fastest way to get from Wellfleet to Chicago is to bus and fly which takes 8h 12m 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 16m.
The distance between Wellfleet and Chicago is 985 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 16m and costs $150 - $370.
It takes approximately 8h 12m 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 Transportation Center station.
Chicago is 1h behind Wellfleet. It is currently 10:23 AM in Wellfleet and 9:23 AM in Chicago.
Yes, the driving distance between Wellfleet to Chicago is 1064 miles. It takes approximately 18h 24m 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, Bus Terminal South Station, Boston, and New York Midtown in around 30h 16m.
- Website
- aa.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 12m
- When
- Every day
- Estimated price
- $65–330
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 5h 16m
- When
- Every day
- Estimated price
- $160–850
Flights from Boston Logan Airport to General Mitchell International Airport via Philadelphia
- Ave. Duration
- 5h 26m
- When
- Monday, Tuesday, Wednesday, Friday, Saturday, and Sunday
- Estimated price
- $170–850
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
- 6h 4m
- When
- Every day
- Estimated price
- $85–430
Flights from Manchester Airport to Chicago O'Hare International Airport via Reagan Washington
- Ave. Duration
- 5h 47m
- When
- Every day
- Estimated price
- $90–440
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 5m
- When
- Every day
- Estimated price
- $55–300
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Philadelphia
- Ave. Duration
- 5h 5m
- When
- Every day
- Estimated price
- $60–300
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Reagan Washington
- Ave. Duration
- 5h 53m
- When
- Every day
- Estimated price
- $60–310
- Website
- southwest.com
Flights from Boston Logan Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 46m
- When
- Every day
- Estimated price
- $85–440
Flights from Boston Logan Airport to General Mitchell International Airport via Baltimore
- Ave. Duration
- 4h 41m
- When
- Monday, Tuesday, Friday, Saturday, and Sunday
- Estimated price
- $170–850
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 35m
- When
- Every day
- Estimated price
- $75–390
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 5h 16m
- When
- Monday, Tuesday, Wednesday, Friday, Saturday, and Sunday
- Estimated price
- $80–410
Flights from Manchester Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 30m
- When
- Every day
- Estimated price
- $100–550
Flights from Manchester Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 5h 17m
- When
- Every day
- Estimated price
- $110–600
- Website
- delta.com
Flights from Boston Logan Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 5h 22m
- When
- Every day
- Estimated price
- $85–440
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 3m
- When
- Every day
- Estimated price
- $65–330
Flights from Boston Logan Airport to General Mitchell International Airport
- Ave. Duration
- 2h 52m
- When
- Every day
- Estimated price
- $150–800
Flights from Boston Logan Airport to General Mitchell International Airport via Detroit
- Ave. Duration
- 4h 48m
- When
- Every day
- Estimated price
- $160–800
Flights from Boston Logan Airport to General Mitchell International Airport via New York La Guardia
- Ave. Duration
- 5h 24m
- When
- Monday, Tuesday, Friday, Saturday, and Sunday
- Estimated price
- $160–850
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 4h 54m
- When
- Monday, Tuesday, Friday, and Sunday
- Estimated price
- $55–300
- Website
- united.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 3m
- When
- Every day
- Estimated price
- $65–330
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 5h 41m
- When
- Every day
- Estimated price
- $160–850
Flights from Manchester Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 5h 23m
- When
- Every day
- Estimated price
- $90–440
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 56m
- When
- Every day
- Estimated price
- $55–300
- Website
- jetblue.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 15m
- When
- Every day
- Estimated price
- $65–330
Flights from Boston Logan Airport to General Mitchell International Airport
- Ave. Duration
- 2h 30m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $150–800
- 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 Boston to Providence
- Ave. Duration
- 1h 10m
- Frequency
- Hourly
- Estimated price
- $5–14
- Website
- https://www.mbta.com
- Adult
- $5–14
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
- $140–700
- Website
- https://www.amtrak.com/home.html
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $22–45
- Website
- https://www.amtrak.com/home.html
Rome2Rio's guide to Amtrak Northeast Regional
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Boston to Providence
- Ave. Duration
- 39 min
- Frequency
- Every 3 hours
- Estimated price
- $6–210
- Website
- https://www.amtrak.com/home.html
- Schedules at
- https://www.amtrak.com/northeast-regional-train
- Coach
- $6–210
- Business Class
- $45–240
Rome2Rio's guide to Amtrak Acela
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Boston to Providence
- Ave. Duration
- 34 min
- Frequency
- Every 4 hours
- Estimated price
- $10–600
- Schedules at
- https://www.amtrak.com/acela-train
- Website
- https://www.amtrak.com/home.html
- Business Class
- $10–450
- First Class
- $110–600
- 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 25m
- Frequency
- Hourly
- Estimated price
- $30–70
- Schedules at
- flixbus.com
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 20h 25m
- Frequency
- Once daily
- Estimated price
- $95–230
- 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
- $13–29
- Website
- https://www.greyhound.com/
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