There are 10 ways to get from Cape Cod to Chicago by bus, plane, bus (Flixbus), train, car, or bus (Greyhound)
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Bus to Boston Logan Airport, fly to Chicago Midway International Airport
best- 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
7h 26m$113–488Bus, train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport
cheapest- 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 15m$93–414Bus
- 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
25h 54m$167–288Bus, train
- Take the bus from Hyannis Transportation Center to Boston South Busesbus Hyannis - South Shore to Logan Airport
- Take the train from Boston to Chicago Union Stationtrain Lake Shore Limited
26h 11m$300–638Drive 1,031 mi
- Drive from Cape Cod to Chicagocar 1,031 mi
17h 57m$189–272Bus to Boston Logan Airport, fly to Chicago O'Hare International Airport
- 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
7h 44m$213–598Bus, bus to Manchester Airport, fly to Chicago Midway International Airport
- 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
9h 10m$127–654Bus to Boston Logan Airport, fly to General Mitchell International Airport, train
- 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
9h 46m$196–857Bus, train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport
- 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
9h 48m$108–484Bus via Brook Park
- 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 19m$185–358
Cape Cod to Chicago by bus
Questions & Answers
The cheapest way to get from Cape Cod to Chicago is to bus which costs $160 - $290 and takes 25h 54m.
The fastest way to get from Cape Cod to Chicago is to bus and fly which takes 7h 26m and costs $110 - $490.
No, there is no direct bus from Cape Cod to Chicago station. However, there are services departing from Town Hall Lawton Bus Shelter and arriving at Chicago Bus Station via Hyannis Transportation Center, Boston and New York Midtown. The journey, including transfers, takes approximately 25h 54m.
The distance between Cape Cod and Chicago is 956 miles. The road distance is 1037.1 miles.
The best way to get from Cape Cod to Chicago without a car is to bus which takes 25h 54m and costs $160 - $290.
It takes approximately 7h 26m to get from Cape Cod to Chicago, including transfers.
Cape Cod to Chicago bus services, operated by Plymouth & Brockton, depart from Hyannis Transportation Center station.
Cape Cod to Chicago bus services, operated by Plymouth & Brockton, arrive at Boston South Buses station.
Yes, the driving distance between Cape Cod to Chicago is 1037 miles. It takes approximately 17h 57m to drive from Cape Cod to Chicago.
There are 2010+ hotels available in Chicago.
What companies run services between Cape Cod, MA, USA and Chicago, IL, USA?
You can take a bus from Town Hall Lawton Bus Shelter to Chicago Bus Station via Hyannis Transportation Center, Boston, Bus Terminal South Station, Boston, and New York Midtown in around 25h 54m.
- Website
- southwest.com
Flights from Boston Logan Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 43m
- When
- Every day
- Estimated price
- $80–440
Flights from Manchester Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 30m
- When
- Every day
- Estimated price
- $100–600
Flights from Manchester Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 5h 15m
- When
- Every day
- Estimated price
- $120–600
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 33m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $150–750
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 32m
- When
- Every day
- Estimated price
- $80–430
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 43m
- When
- Monday, Thursday, Friday, and Saturday
- Estimated price
- $85–450
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Reagan Washington
- Ave. Duration
- 5h 7m
- When
- Every day
- Estimated price
- $90–450
- Website
- aa.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 6m
- When
- Every day
- Estimated price
- $70–370
Flights from Boston Logan Airport to General Mitchell International Airport via Reagan Washington
- Ave. Duration
- 4h 42m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $160–800
Flights from Boston Logan Airport to General Mitchell International Airport via Philadelphia
- Ave. Duration
- 5h 4m
- When
- Every day
- Estimated price
- $150–800
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 3m
- When
- Every day
- Estimated price
- $65–360
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Philadelphia
- Ave. Duration
- 5h 25m
- When
- Every day
- Estimated price
- $70–370
- Website
- united.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 56m
- 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
- 4h 58m
- When
- Every day
- Estimated price
- $150–750
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 1m
- When
- Every day
- Estimated price
- $65–360
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 5h 5m
- When
- Tuesday, Wednesday, and Saturday
- Estimated price
- $75–380
- Website
- delta.com
Flights from Boston Logan Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 4h 37m
- When
- Every day
- Estimated price
- $80–440
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 58m
- When
- Every day
- Estimated price
- $70–370
Flights from Boston Logan Airport to General Mitchell International Airport
- Ave. Duration
- 2h 43m
- When
- Every day
- Estimated price
- $140–750
Flights from Boston Logan Airport to General Mitchell International Airport via Detroit
- Ave. Duration
- 4h 23m
- When
- Every day
- Estimated price
- $140–750
Flights from Boston Logan Airport to General Mitchell International Airport via New York La Guardia
- Ave. Duration
- 5h 2m
- 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
- 5h 8m
- When
- Every day
- Estimated price
- $65–360
- Website
- jetblue.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 5m
- When
- Every day
- Estimated price
- $70–370
Flights from Boston Logan Airport to General Mitchell International Airport
- Ave. Duration
- 2h 36m
- When
- Every day
- Estimated price
- $140–750
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
- $270–600
- Website
- https://www.amtrak.com/home.html
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $23–50
- Website
- https://www.amtrak.com/home.html
- Phone
- +1-617-222-3200
- Website
- mbta.com
Train from South Station to TF Green Airport
- Ave. Duration
- 1h 30m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- https://www.mbta.com
- Adult
- $9–16
- 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
- https://www.flixbus.com
Bus from Boston to New York Midtown
- Ave. Duration
- 4h 20m
- Frequency
- Hourly
- Estimated price
- $27–50
- Schedules at
- flixbus.com
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 16h 55m
- Frequency
- Twice daily
- Estimated price
- $110–200
- Schedules at
- flixbus.com
- Phone
- 1-800-343-9999
- Website
- peterpanbus.com
Bus from Hyannis Transportation Center to Boston South Station
- Ave. Duration
- 1h 40m
- Frequency
- Every 4 hours
- Estimated price
- $14–30
- Website
- https://peterpanbus.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
- $8–16
- Website
- https://www.greyhound.com/
Bus from Boston to Cleveland Bus Station
- Ave. Duration
- 13h 50m
- Frequency
- Once daily
- Estimated price
- $100–210
- Website
- https://www.greyhound.com/
Bus from Cleveland Bus Station to Chicago Bus Station
- Ave. Duration
- 7h 40m
- Frequency
- Twice daily
- Estimated price
- $55–110
- Website
- https://www.greyhound.com/
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