There are 7 ways to get from Winslow to Chicago by train, plane, train (Amtrak), taxi, bus, car, or shuttle
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Train to Flagstaff, fly to Chicago O'Hare International Airport
best- Take the train from Winslow Station to Flagstafftrain
- Fly from Flagstaff (FLG) to Chicago O'Hare International Airport (ORD)plane FLG - ORD
9h 42m$135–520Train (Amtrak)
- Take the train from Winslow Station to Chicago Union Stationtrain Southwest Chief
31h 39m$500–1,100Taxi, bus
- Take the taxi from Winslow to Holbrooktaxi
- Take the bus from Holbrook to St Louis Bus Stationbus
- Take the bus from St Louis Bus Station to Chicago Bus Stationbus
37h 42m$307–534Drive 1,541.8 mi
- Drive from Winslow to Chicagocar 1,541.8 mi
27h$282–407Train, shuttle to Phoenix, fly to Chicago Midway International Airport
- Take the train from Winslow Station to Flagstafftrain
- Take a shuttle bus from Flagstaff Amtrak to Sky Harbor International Airport
- Fly from Phoenix (PHX) to Chicago Midway International Airport (MDW)plane PHX - MDW
9h 2m$323–455Train, shuttle to Phoenix, fly to Chicago O'Hare International Airport
- Take the train from Winslow Station to Flagstafftrain
- Take a shuttle bus from Flagstaff Amtrak to Sky Harbor International Airport
- Fly from Phoenix (PHX) to Chicago O'Hare International Airport (ORD)plane PHX - ORD
9h 20m$403–595Train to Flagstaff, fly to Chicago Midway International Airport
- Take the train from Winslow Station to Flagstafftrain
- Fly from Flagstaff (FLG) to Chicago Midway International Airport (MDW)plane FLG - MDW
8h$155–610
Winslow to Chicago by train (Amtrak)
Questions & Answers
The cheapest way to get from Winslow to Chicago is to train and fly which costs $130 - $550 and takes 9h 42m.
The fastest way to get from Winslow to Chicago is to train and fly which takes 8h and costs $150 - $650.
Yes, there is a direct train departing from Winslow Station station and arriving at Chicago Union Station station. Services depart once daily, and operate every day. The journey takes approximately 31h 39m.
The distance between Winslow and Chicago is 1453 miles. The road distance is 1550.8 miles.
The best way to get from Winslow to Chicago without a car is to train which takes 31h 39m and costs $500 - $1,100.
It takes approximately 9h 42m to get from Winslow to Chicago, including transfers.
Winslow to Chicago train services, operated by Amtrak, depart from Winslow Station.
Chicago is 2h ahead of Winslow. It is currently 1:22 AM in Winslow and 3:22 AM in Chicago.
Winslow to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Winslow to Chicago is 1551 miles. It takes approximately 27h to drive from Winslow to Chicago.
What companies run services between Winslow, AZ, USA and Chicago, IL, USA?
Amtrak operates a train from Winslow Station to Chicago Union Station once daily. Tickets cost $500–1,100 and the journey takes 31h 39m.
- Website
- southwest.com
Flights from Phoenix to Chicago Midway International Airport
- Ave. Duration
- 3h 16m
- When
- Every day
- Estimated price
- $110–490
Flights from Phoenix to Chicago Midway International Airport via Kansas City
- Ave. Duration
- 4h 52m
- When
- Sunday, Tuesday, and Wednesday
- Estimated price
- $110–490
Flights from Phoenix to Chicago Midway International Airport via St. Louis
- Ave. Duration
- 5h 10m
- When
- Monday, Thursday, and Friday
- Estimated price
- $110–500
Flights from Flagstaff to Chicago Midway International Airport via Phoenix
- Ave. Duration
- 6h 11m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $120–550
Flights from Flagstaff to Chicago Midway International Airport via Phoenix, St. Louis
- Ave. Duration
- 9h 20m
- When
- Monday
- Estimated price
- $130–550
- Website
- aa.com
Flights from Flagstaff to Chicago O'Hare International Airport via Dallas/Ft.Worth
- Ave. Duration
- 6h 41m
- When
- Every day
- Estimated price
- $110–480
Flights from Flagstaff to Chicago O'Hare International Airport via Phoenix
- Ave. Duration
- 8h 6m
- When
- Every day
- Estimated price
- $100–460
Flights from Phoenix to Chicago O'Hare International Airport
- Ave. Duration
- 3h 48m
- When
- Every day
- Estimated price
- $95–420
- Website
- united.com
Flights from Phoenix to Chicago O'Hare International Airport
- Ave. Duration
- 3h 39m
- When
- Every day
- Estimated price
- $95–420
Flights from Phoenix to Chicago O'Hare International Airport via Denver
- Ave. Duration
- 5h 27m
- When
- Monday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $95–430
- Website
- flyfrontier.com
Flights from Phoenix to Chicago O'Hare International Airport
- Ave. Duration
- 3h 29m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $200–240
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Winslow Station to Flagstaff
- Ave. Duration
- 1h 6m
- Frequency
- Once daily
- Estimated price
- $18–40
- Website
- Amtrak
Train from Winslow Station to Chicago Union Station
- Ave. Duration
- 31h 39m
- Frequency
- Once daily
- Estimated price
- $500–1,100
- Website
- Amtrak
Train from Winslow Station to Flagstaff
- Ave. Duration
- 1h 6m
- Frequency
- Once daily
- Estimated price
- $18–40
- Website
- Amtrak
Train from Winslow Station to Flagstaff
- Ave. Duration
- 1h 6m
- Frequency
- Once daily
- Estimated price
- $18–40
- Website
- Amtrak
Train from Winslow Station to Flagstaff
- Ave. Duration
- 1h 6m
- Frequency
- Once daily
- Estimated price
- $18–40
- Website
- Amtrak
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Holbrook to St Louis Bus Station
- Ave. Duration
- 30h 5m
- Frequency
- 4 times a day
- Estimated price
- $190–370
- Website
- Greyhound
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from St Louis Bus Station to Chicago Bus Station
- Ave. Duration
- 6h 5m
- Frequency
- 4 times a day
- Estimated price
- $50–85
- Schedules at
- Flixbus USA
- Phone
- +1-480-710-3441
- [email protected]
- Website
- Airport Shuttle of Phoenix
Shuttle from Flagstaff Amtrak to Sky Harbor International Airport
- Ave. Duration
- 2h 30m
- Frequency
- On demand
- Estimated price
- $182
- Website
- Airport Shuttle of Phoenix
Shuttle from Flagstaff Amtrak to Sky Harbor International Airport
- Ave. Duration
- 2h 30m
- Frequency
- On demand
- Estimated price
- $182
- Website
- Airport Shuttle of Phoenix
- Ave. Duration
- 32 min
- Estimated price
- $65–80
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