There are 6 ways to get from Chicago to Wellfleet by plane, bus, train, car, 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.
Fly Chicago O'Hare International Airport to Boston Logan Airport, bus
best- Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)ORD - BOS
- Take the bus from Logan International Airport to Hyannis Transportation Center
- Take the bus from Hyannis Transportation Center to Wellfleet
8h 58m$136–385Train, drive
cheapest- Take the train from Chicago Union Station to Boston
- Take the train from South Station to Kingston
- Drive from Kingston to Wellfleet
25h 28m$119–603Bus
- Take the bus from Chicago Bus Station to New York Midtown
- Take the bus from New York Midtown to Boston
- Take the bus from Boston South Station to Hyannis Transportation Center
- Take the bus from Hyannis Transportation Center to Wellfleet
30h 1m$147–411Drive 1,056.6 mi
- Drive from Chicago to Wellfleet1,056.6 mi
18h 22m$193–279Fly Chicago Midway International Airport to Boston Logan Airport, bus
- Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)MDW - BOS
- Take the bus from Logan International Airport to Hyannis Transportation Center
- Take the bus from Hyannis Transportation Center to Wellfleet
8h 37m$136–625Fly Chicago Midway International Airport to Provincetown Municipal Airport
- Fly from Chicago Midway International Airport (MDW) to Provincetown Municipal Airport (PVC)MDW - PVC
7h 9m$336–978
Chicago to Wellfleet by bus
Questions & Answers
The cheapest way to get from Chicago to Wellfleet is to drive which costs $190 - $280 and takes 18h 22m.
The fastest way to get from Chicago to Wellfleet is to fly which takes 7h 9m and costs $330 - $1,000.
No, there is no direct bus from Chicago station to Wellfleet. However, there are services departing from Chicago Bus Station and arriving at Wellfleet via New York Midtown, Boston South Station and Hyannis Transportation Center. The journey, including transfers, takes approximately 30h 1m.
The distance between Chicago and Wellfleet is 999 miles. The road distance is 1062.7 miles.
The best way to get from Chicago to Wellfleet without a car is to bus which takes 30h 1m and costs $140 - $420.
It takes approximately 8h 58m to get from Chicago to Wellfleet, including transfers.
Chicago to Wellfleet bus services, operated by Flixbus USA, depart from Chicago Bus Station.
The best way to get from Chicago to Wellfleet is to bus which takes 30h 1m and costs $140 - $420. Alternatively, you can fly, which costs $330 - $1,000 and takes 7h 9m.
Chicago to Wellfleet bus services, operated by Flixbus USA, arrive at New York Midtown station.
Wellfleet is 1h ahead of Chicago. It is currently 8:40 PM in Chicago and 9:40 PM in Wellfleet.
What companies run services between Chicago, IL, USA and Wellfleet, MA, USA?
You can take a bus from Chicago Bus Station to Wellfleet via New York Midtown, Boston, Boston South Station, and Hyannis Transportation Center in around 30h 1m. Alternatively, Southwest Airlines and Cape Air fly from Chicago Midway International Airport (MDW) to Provincetown Municipal Airport (PVC) 5 times a week.
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 30m
- When
- Every day
- Estimated price
- $80–420
Flights from Chicago O'Hare International Airport to Boston Logan Airport via Syracuse
- Ave. Duration
- 4h 39m
- When
- Monday, Tuesday, Wednesday, Friday, Saturday, and Sunday
- Estimated price
- $80–420
Flights from Chicago O'Hare International Airport to Boston Logan Airport via Buffalo
- Ave. Duration
- 5h 19m
- When
- Sunday
- Estimated price
- $80–420
- Website
- united.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 28m
- When
- Every day
- Estimated price
- $80–420
- Website
- southwest.com
Flights from Chicago Midway International Airport to Boston Logan Airport
- Ave. Duration
- 2h 15m
- When
- Every day
- Estimated price
- $100–550
- Website
- delta.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 30m
- When
- Every day
- Estimated price
- $80–420
- Website
- jetblue.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 29m
- When
- Every day
- Estimated price
- $80–420
Flights from Chicago Midway International Airport to Provincetown Municipal Airport via Boston Logan Airport
- Ave. Duration
- 3h 56m
- When
- Monday, Tuesday, Friday, Saturday, and Sunday
- Estimated price
- $150–750
- Website
- capeair.com
Flights from Chicago Midway International Airport to Provincetown Municipal Airport via Boston Logan Airport
- Ave. Duration
- 3h 56m
- When
- Monday, Tuesday, Friday, Saturday, and Sunday
- Estimated price
- $150–750
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to Boston
- Ave. Duration
- 22h 2m
- Frequency
- Once daily
- Estimated price
- $100–600
- Website
- https://www.amtrak.com/home.html
- Phone
- +1-617-222-3200
- Website
- mbta.com
Train from South Station to Kingston
- Ave. Duration
- 1h
- Frequency
- Every 3 hours
- Estimated price
- $4–13
- Website
- https://www.mbta.com
- Adult
- $4–13
- Phone
- +1 (508) 746-0378
- info@p-b.com
- Website
- p-b.com
Bus from Logan International Airport to Hyannis Transportation Center
- Ave. Duration
- 2h 15m
- Frequency
- Hourly
- Estimated price
- $28–40
- Website
- https://www.p-b.com
- One Way - Adult
- $28–40
- Phone
- 1-800-343-9999
- Website
- peterpanbus.com
Bus from Hyannis Transportation Center to Wellfleet
- Ave. Duration
- 1h
- Frequency
- 3 times a day
- Estimated price
- $5–30
- Website
- https://peterpanbus.com
- Adult
- $5–30
Bus from Boston South Station to Hyannis Transportation Center
- Ave. Duration
- 1h 35m
- Frequency
- Every 3 hours
- Estimated price
- $10–40
- Website
- https://peterpanbus.com
- Adult
- $10–40
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Chicago Bus Station to New York Midtown
- Ave. Duration
- 20h 10m
- Frequency
- Once daily
- Estimated price
- $100–270
- Schedules at
- flixbus.com
Bus from New York Midtown to Boston
- Ave. Duration
- 4h 20m
- Frequency
- Hourly
- Estimated price
- $30–75
- Schedules at
- flixbus.com
Want to know more about travelling around United States
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More Questions & Answers
Yes, the driving distance between Chicago to Wellfleet is 1063 miles. It takes approximately 18h 22m to drive from Chicago to Wellfleet.
There are 521+ hotels available in Wellfleet.















