There are 11 ways to get from Chicago to Healdsburg by plane, bus, train, bus (Greyhound, Amtrak), car, subway, or ferry
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 San Francisco International Airport, bus, train
best- Fly from Chicago O'Hare International Airport (ORD) to San Francisco International Airport (SFO)plane ORD - SFO
- Take the bus from San Francisco Airport to Larkspur - dropoffbus
- Take the train from SMART Larkspur to SMART Windsortrain
11h 21m$110–435Bus
- Take the bus from Chicago Bus Station to Denver Union Stationbus
- Take the bus from Denver Union Station to Sparks Transit Centerbus
- Take the bus from Sparks Transit Center to Vallejo Transit Centerbus
- Take the bus from Vallejo to Healdsburg Amtrak Bus Stopbus
2d 3hTrain, bus (Amtrak)
- Take the train from Chicago Union Station to Martineztrain California Zephyr
- Take the bus from Martinez to Healdsburg Amtrak Bus Stopbus Amtrak Thruway Connecting Service
2d 7hDrive 2,141.4 mi
- Drive from Chicago to Healdsburgcar 2,141.4 mi
33h 26m$391–565Fly Chicago Midway International Airport to San Francisco International Airport, bus, train
- Fly from Chicago Midway International Airport (MDW) to San Francisco International Airport (SFO)plane MDW - SFO
- Take the bus from San Francisco Airport to Larkspur - dropoffbus
- Take the train from SMART Larkspur to SMART Windsortrain
11h 39m$144–595Fly Chicago O'Hare International Airport to Sacramento International Airport, train, bus
- Fly from Chicago O'Hare International Airport (ORD) to Sacramento International Airport (SMF)plane ORD - SMF
- Take the train from Sacramento to Martineztrain
- Take the bus from Martinez to Healdsburg Amtrak Bus Stopbus
12h 24mFly Chicago Midway International Airport to Sacramento International Airport, train, bus
- Fly from Chicago Midway International Airport (MDW) to Sacramento International Airport (SMF)plane MDW - SMF
- Take the train from Sacramento to Martineztrain
- Take the bus from Martinez to Healdsburg Amtrak Bus Stopbus
12h 14mFly Chicago Midway International Airport to Oakland International Airport, bus, train
- Fly from Chicago Midway International Airport (MDW) to Oakland International Airport (OAK)plane MDW - OAK
- Take the bus from Oakland International Airport to San Rafaelbus
- Take the train from SMART San Rafael to SMART Windsortrain
11h 36m$246–1,070Fly Chicago Midway International Airport to Norman Y. Mineta San José International Airport, BART, ferry, train
- Fly from Chicago Midway International Airport (MDW) to Norman Y. Mineta San José International Airport (SJC)plane MDW - SJC
- Take the subway from Milpitas to Embarcaderosubway
- Take the ferry from San Francisco Ferry Terminal-Gate C to Larkspur Ferry Terminalferry
- Take the train from SMART Larkspur to SMART Windsortrain
13h 35m$290–1,342Fly Chicago O'Hare International Airport to Norman Y. Mineta San José International Airport, BART, ferry, train
- Fly from Chicago O'Hare International Airport (ORD) to Norman Y. Mineta San José International Airport (SJC)plane ORD - SJC
- Take the subway from Milpitas to Embarcaderosubway
- Take the ferry from San Francisco Ferry Terminal-Gate C to Larkspur Ferry Terminalferry
- Take the train from SMART Larkspur to SMART Windsortrain
13h 54m$210–892Fly Chicago O'Hare International Airport to Reno/Tahoe International Airport, bus
- Fly from Chicago O'Hare International Airport (ORD) to Reno/Tahoe International Airport (RNO)plane ORD - RNO
- Take the bus from Reno Amtrak to Vallejo Transit Centerbus
- Take the bus from Vallejo to Healdsburg Amtrak Bus Stopbus
15h 38m
Chicago O'Hare International Airport (ORD) to San Francisco International Airport (SFO) flights
Questions & Answers
The cheapest way to get from Chicago to Healdsburg is to fly and bus and train which costs $110 - $440 and takes 11h 21m.
The fastest way to get from Chicago to Healdsburg is to fly and bus and train which takes 11h 21m and costs $110 - $440.
No, there is no direct bus from Chicago station to Healdsburg. However, there are services departing from Chicago Bus Station and arriving at Healdsburg Amtrak Bus Stop via Denver Union Station, Sparks Transit Center and Vallejo. The journey, including transfers, takes approximately 2 days 3h.
The distance between Chicago and Healdsburg is 1957 miles. The road distance is 2153.9 miles.
The best way to get from Chicago to Healdsburg without a car is to bus which takes 2 days 3h and costs .
It takes approximately 11h 21m to get from Chicago to Healdsburg, including transfers.
Chicago to Healdsburg bus services, operated by Greyhound USA, depart from Chicago Bus Station.
Chicago to Healdsburg bus services, operated by Greyhound USA, arrive at Denver Union Station.
Healdsburg is 2h behind Chicago. It is currently 3:10 PM in Chicago and 1:10 PM in Healdsburg.
Yes, the driving distance between Chicago to Healdsburg is 2154 miles. It takes approximately 33h 26m to drive from Chicago to Healdsburg.
What companies run services between Chicago, IL, USA and Healdsburg, CA, USA?
You can take a bus from Chicago Bus Station to Healdsburg Amtrak Bus Stop via Denver Union Station, Sparks Transit Center, and Vallejo in around 2d 3h.
- Website
- southwest.com
Flights from Chicago Midway International Airport to San Francisco International Airport
- Ave. Duration
- 5h
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $120–550
Flights from Chicago Midway International Airport to San Francisco International Airport via Las Vegas
- Ave. Duration
- 8h 3m
- When
- Every day
- Estimated price
- $130–600
Flights from Chicago Midway International Airport to San Francisco International Airport via Denver
- Ave. Duration
- 7h 53m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $120–550
Flights from Chicago O'Hare International Airport to Sacramento International Airport via Denver
- Ave. Duration
- 6h 35m
- When
- Monday, Thursday, and Friday
- Estimated price
- $190–850
Flights from Chicago O'Hare International Airport to Sacramento International Airport via Las Vegas
- Ave. Duration
- 7h 57m
- When
- Every day
- Estimated price
- $200–900
Flights from Chicago Midway International Airport to Sacramento International Airport
- Ave. Duration
- 4h 45m
- When
- Every day
- Estimated price
- $270–1,200
Flights from Chicago Midway International Airport to Sacramento International Airport via Denver
- Ave. Duration
- 7h 15m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $270–1,300
Flights from Chicago Midway International Airport to Sacramento International Airport via Las Vegas
- Ave. Duration
- 7h 8m
- When
- Every day
- Estimated price
- $280–1,300
Flights from Chicago Midway International Airport to Sacramento International Airport via Boise
- Ave. Duration
- 7h 15m
- When
- Monday, Thursday, and Friday
- Estimated price
- $280–1,300
Flights from Chicago Midway International Airport to Sacramento International Airport via Kansas City
- Ave. Duration
- 7h 45m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $270–1,300
Flights from Chicago Midway International Airport to Sacramento International Airport via Salt Lake City
- Ave. Duration
- 9h 15m
- When
- Monday, Tuesday, Wednesday, and Sunday
- Estimated price
- $270–1,200
Flights from Chicago Midway International Airport to Oakland International Airport
- Ave. Duration
- 4h 55m
- When
- Every day
- Estimated price
- $220–1,000
Flights from Chicago Midway International Airport to Oakland International Airport via Las Vegas
- Ave. Duration
- 6h 56m
- When
- Every day
- Estimated price
- $230–1,000
Flights from Chicago Midway International Airport to Oakland International Airport via Long Beach
- Ave. Duration
- 7h 50m
- When
- Monday
- Estimated price
- $240–1,100
Flights from Chicago Midway International Airport to Oakland International Airport via Denver
- Ave. Duration
- 8h 15m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $220–1,000
Flights from Chicago Midway International Airport to Norman Y. Mineta San José International Airport
- Ave. Duration
- 4h 50m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $270–1,300
Flights from Chicago Midway International Airport to Norman Y. Mineta San José International Airport via Las Vegas
- Ave. Duration
- 7h 3m
- When
- Every day
- Estimated price
- $280–1,300
Flights from Chicago Midway International Airport to Norman Y. Mineta San José International Airport via Ontario/San Bernardino
- Ave. Duration
- 7h 20m
- When
- Monday, Tuesday, Wednesday, and Sunday
- Estimated price
- $290–1,300
Flights from Chicago Midway International Airport to Norman Y. Mineta San José International Airport via Long Beach
- Ave. Duration
- 7h 20m
- When
- Monday, Thursday, and Friday
- Estimated price
- $300–1,300
Flights from Chicago Midway International Airport to Norman Y. Mineta San José International Airport via Reno/Tahoe International Airport
- Ave. Duration
- 7h 50m
- When
- Monday, Thursday, and Friday
- Estimated price
- $270–1,300
Flights from Chicago Midway International Airport to Norman Y. Mineta San José International Airport via Denver
- Ave. Duration
- 8h 15m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $270–1,300
Flights from Chicago O'Hare International Airport to Norman Y. Mineta San José International Airport via Las Vegas
- Ave. Duration
- 6h 50m
- When
- Monday, Thursday, Friday, and Saturday
- Estimated price
- $190–900
Flights from Chicago O'Hare International Airport to Reno/Tahoe International Airport via Denver
- Ave. Duration
- 6h 25m
- When
- Monday, Thursday, and Friday
- Estimated price
- $130–650
Flights from Chicago O'Hare International Airport to Reno/Tahoe International Airport via Las Vegas
- Ave. Duration
- 7h 52m
- When
- Monday, Tuesday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $140–650
- Website
- united.com
Flights from Chicago O'Hare International Airport to San Francisco International Airport
- Ave. Duration
- 4h 56m
- When
- Every day
- Estimated price
- $85–390
Flights from Chicago O'Hare International Airport to San Francisco International Airport via Denver
- Ave. Duration
- 6h 43m
- When
- Every day
- Estimated price
- $85–390
Flights from Chicago O'Hare International Airport to Sacramento International Airport
- Ave. Duration
- 4h 46m
- When
- Every day
- Estimated price
- $190–850
Flights from Chicago O'Hare International Airport to Sacramento International Airport via San Francisco International Airport
- Ave. Duration
- 7h 13m
- When
- Every day
- Estimated price
- $200–900
Flights from Chicago O'Hare International Airport to Sacramento International Airport via Denver
- Ave. Duration
- 6h 53m
- When
- Every day
- Estimated price
- $190–850
Flights from Chicago O'Hare International Airport to Norman Y. Mineta San José International Airport
- Ave. Duration
- 4h 53m
- When
- Monday, Thursday, and Friday
- Estimated price
- $190–850
Flights from Chicago O'Hare International Airport to Norman Y. Mineta San José International Airport via Denver
- Ave. Duration
- 6h 45m
- When
- Every day
- Estimated price
- $190–850
Flights from Chicago O'Hare International Airport to Reno/Tahoe International Airport
- Ave. Duration
- 4h 21m
- When
- Every day
- Estimated price
- $130–650
Flights from Chicago O'Hare International Airport to Reno/Tahoe International Airport via Denver
- Ave. Duration
- 6h 37m
- When
- Every day
- Estimated price
- $130–650
- Website
- aa.com
Flights from Chicago O'Hare International Airport to San Francisco International Airport
- Ave. Duration
- 4h 43m
- When
- Every day
- Estimated price
- $85–390
Flights from Chicago O'Hare International Airport to Sacramento International Airport
- Ave. Duration
- 4h 39m
- When
- Every day
- Estimated price
- $190–850
Flights from Chicago O'Hare International Airport to Norman Y. Mineta San José International Airport
- Ave. Duration
- 4h 55m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $190–850
Flights from Chicago O'Hare International Airport to Norman Y. Mineta San José International Airport via Los Angeles
- Ave. Duration
- 7h 5m
- When
- Thursday and Friday
- Estimated price
- $210–950
Flights from Chicago O'Hare International Airport to Reno/Tahoe International Airport via Phoenix
- Ave. Duration
- 7h 21m
- When
- Every day
- Estimated price
- $160–700
- Website
- delta.com
Flights from Chicago O'Hare International Airport to Sacramento International Airport via Salt Lake City
- Ave. Duration
- 6h 39m
- When
- Every day
- Estimated price
- $190–850
Flights from Chicago O'Hare International Airport to Sacramento International Airport via Minneapolis
- Ave. Duration
- 6h 59m
- When
- Monday, Thursday, and Friday
- Estimated price
- $190–900
Flights from Chicago Midway International Airport to Sacramento International Airport via Minneapolis
- Ave. Duration
- 9h 7m
- When
- Every day
- Estimated price
- $280–1,300
Flights from Chicago O'Hare International Airport to Reno/Tahoe International Airport via Minneapolis
- Ave. Duration
- 6h 22m
- When
- Monday, Thursday, and Friday
- Estimated price
- $140–650
Flights from Chicago O'Hare International Airport to Reno/Tahoe International Airport via Salt Lake City
- Ave. Duration
- 6h 48m
- When
- Every day
- Estimated price
- $130–650
- Phone
- +1 707-794-3330
- Website
- sonomamarintrain.org
Train from SMART Larkspur to SMART Windsor
- Ave. Duration
- 1h 20m
- Frequency
- Twice daily
- Estimated price
- $1–8
- Schedules at
- sonomamarintrain.org
Train from SMART San Rafael to SMART Windsor
- Ave. Duration
- 1h 13m
- Frequency
- Twice daily
- Estimated price
- $1–8
- Schedules at
- sonomamarintrain.org
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to Martinez
- Ave. Duration
- 2d 4h
- Frequency
- Once daily
- Estimated price
- $230–1,900
- Website
- https://www.amtrak.com/home.html
Train from Sacramento to Martinez
- Ave. Duration
- 1h
- Frequency
- Hourly
- Estimated price
- $17–21
- Website
- https://www.amtrak.com/home.html
- Phone
- +1-510-464-6000
- Website
- bart.gov
Subway from Milpitas to Embarcadero
- Ave. Duration
- 59 min
- Frequency
- Every 30 minutes
- Estimated price
- $7–10
- Website
- https://www.bart.gov
- Phone
- +1 415-461-4222
- Website
- marinairporter.com
Bus from San Francisco Airport to Larkspur - dropoff
- Ave. Duration
- 1h 6m
- Frequency
- Hourly
- Estimated price
- $20–30
- Website
- https://marinairporter.com/
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Chicago Bus Station to Denver Union Station
- Ave. Duration
- 21h 9m
- Frequency
- Once daily
- Estimated price
- $75–210
- Website
- https://www.greyhound.com/
Bus from Denver Union Station to Sparks Transit Center
- Ave. Duration
- 20h 45m
- Frequency
- Once daily
- Estimated price
- $85–210
- Website
- https://www.greyhound.com/
Bus from Sparks Transit Center to Vallejo Transit Center
- Ave. Duration
- 4h 50m
- Frequency
- Once daily
- Estimated price
- $40–75
- Website
- https://www.greyhound.com/
Bus from Reno Amtrak to Vallejo Transit Center
- Ave. Duration
- 4h 30m
- Frequency
- Once daily
- Estimated price
- $40–75
- Website
- https://www.greyhound.com/
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Bus from Vallejo to Healdsburg Amtrak Bus Stop
- Ave. Duration
- 2h 10m
- Frequency
- Once daily
- Website
- https://www.amtrak.com/home.html
Bus from Martinez to Healdsburg Amtrak Bus Stop
- Ave. Duration
- 2h 35m
- Frequency
- Once daily
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 707-837-8700
- Website
- groometransportation.com
Bus from Oakland International Airport to San Rafael
- Ave. Duration
- 45 min
- Frequency
- Every 3 hours
- Estimated price
- $21–55
- Website
- https://groometransportation.com/sonoma-county/
- First Passenger
- $21–55
- Phone
- +1 415-455-2000
- contact@goldengate.org
- Website
- goldengate.org
Ferry from San Francisco Ferry Terminal-Gate C to Larkspur Ferry Terminal
- Ave. Duration
- 35 min
- Frequency
- Hourly
- Estimated price
- $6–14
- Website
- https://www.goldengate.org
- Schedules at
- https://www.goldengate.org/ferry/schedules-maps/
- Adult
- $14
- Youth 5-18, Seniors 65+, disabled
- $6–7
Want to know more about travelling around United States
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