There are 10 ways to get from Winslow to Chicago by train, plane, bus (Flixbus), train (Amtrak), car, bus, 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.
Train to Philadelphia International Airport, fly to Chicago Midway International Airport
best- Take the train from Hammonton to 30th Street Stationtrain
- Fly from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW)plane PHL - MDW
5h 40m$171–416Train, bus to Lehigh Valley International Airport, fly to Chicago O'Hare International Airport
cheapest- Take the train from Hammonton to 30th Street Stationtrain
- Take the bus from Philadelphia 30th St Station to Allentown Transportation Centerbus
- Fly from Lehigh Valley International Airport (ABE) to Chicago O'Hare International Airport (ORD)plane ABE - ORD
8h 37m$100–389Bus (Flixbus)
- Take the bus from Philadelphia Bus Station to Chicago Bus Stationbus FlixBus N2642
21h 51m$169–261Train via Washington
- Take the train from Hammonton to 30th Street Stationtrain
- Take the train from 30th Street Station to Washington Union Stationtrain
- Take the train from Rockville Amtrak to Chicago Union Stationtrain
22h 30m$459–1,340Drive 787 mi
- Drive from Winslow to Chicagocar 787 mi
13h$144–208Train to Philadelphia International Airport, fly to Chicago O'Hare International Airport
- Take the train from Hammonton to 30th Street Stationtrain
- Fly from Philadelphia International Airport (PHL) to Chicago O'Hare International Airport (ORD)plane PHL - ORD
6h 5m$141–266Train, train to Baltimore-Washington International Airport, fly to Chicago Midway International Airport
- Take the train from Hammonton to 30th Street Stationtrain
- Take the train from 30th Street Station to BWI Thurgood Marshalltrain
- Fly from Baltimore-Washington International Airport (BWI) to Chicago Midway International Airport (MDW)plane BWI - MDW
6h 48m$163–992Train, train to Laguardia Airport, fly to Chicago Midway International Airport
- Take the train from Hammonton to 30th Street Stationtrain
- Take the train from 30th Street Station to Ny Moynihan Train Hall At Penn Stationtrain
- Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane LGA - MDW
8h 13m$247–1,309Bus via Baltimore (Greyhound)
- Take the bus from Philadelphia Bus Station to Baltimore Greyhound Garagebus Greyhound US0305
- Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus Greyhound US0164
26h 58m$174–270Train
- Take the train from Hammonton to 30th Street Stationtrain Atlc
- Take the train from 30th Street Station to Chicago Union Stationtrain Cardinal
29h 22m$567–937
Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW) flights
Comparing Your Travel Options
The cheapest way to get from Winslow to Chicago is to drive which costs $140 - $210 and takes 13h.
The fastest way to get from Winslow to Chicago is to train and fly which takes 5h 40m and costs $170 - $420.
No, there is no direct bus from Winslow to Chicago station. However, there are services departing from Avandale Park & Ride and arriving at Chicago Bus Station via Philadelphia Bus Station. The journey, including transfers, takes approximately 21h 51m.
No, there is no direct train from Winslow to Chicago station. However, there are services departing from Hammonton and arriving at Chicago Union Station via 30th Street Station, Union Station, Red Line Center Platform and Rockville Amtrak. The journey, including transfers, takes approximately 22h 30m.
The distance between Winslow and Chicago is 733 miles. The road distance is 791.6 miles.
The best way to get from Winslow to Chicago without a car is to bus which takes 21h 51m and costs $160 - $270.
It takes approximately 5h 40m to get from Winslow to Chicago, including transfers.
Winslow to Chicago bus services, operated by Flixbus USA, depart from Philadelphia Bus Station.
Winslow to Chicago train services, operated by NJ Transit, depart from Hammonton station.
The best way to get from Winslow to Chicago is to bus which takes 21h 51m and costs $160 - $270. Alternatively, you can train via Washington, which costs $450 - $1,400 and takes 22h 30m.
What companies run services between Winslow, NJ, USA and Chicago, IL, USA?
Flixbus USA operates a bus from Philadelphia Bus Station to Chicago Bus Station 3 times a week. Tickets cost $140–220 and the journey takes 20h. Alternatively, you can take a vehicle from Winslow to Chicago Union Station via Hammonton, 30th Street Station, Washington Union Station, Union Station, Red Line Center Platform, Rockville, Red Line Center Platform, and Rockville Amtrak in around 22h 30m.
- Website
- southwest.com
Flights from Philadelphia International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 5m
- When
- Every day
- Estimated price
- $90–500
Flights from Philadelphia International Airport to Chicago Midway International Airport via Baltimore-Washington International Airport
- Ave. Duration
- 4h 32m
- When
- Monday, Thursday, and Friday
- Estimated price
- $95–550
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h
- When
- Every day
- Estimated price
- $80–450
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport via Pittsburgh
- Ave. Duration
- 3h 25m
- When
- Saturday
- Estimated price
- $80–450
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport via Columbus
- Ave. Duration
- 3h 25m
- When
- Tuesday and Wednesday
- Estimated price
- $80–450
Flights from Laguardia Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 24m
- When
- Every day
- Estimated price
- $100–550
- Website
- united.com
Flights from Philadelphia International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 31m
- When
- Every day
- Estimated price
- $70–400
Flights from Lehigh Valley International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 26m
- When
- Every day
- Estimated price
- $50–300
- Website
- aa.com
Flights from Philadelphia International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 38m
- When
- Every day
- Estimated price
- $70–400
Flights from Lehigh Valley International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 36m
- When
- Every day
- Estimated price
- $50–300
Flights from Lehigh Valley International Airport to Chicago O'Hare International Airport via Charlotte
- Ave. Duration
- 5h 17m
- When
- Every day
- Estimated price
- $70–360
- Website
- delta.com
Flights from Philadelphia International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 4h 10m
- When
- Every day
- Estimated price
- $90–550
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 3h 57m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $80–460
- Website
- flyfrontier.com
Flights from Philadelphia International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 30m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $120–220
- Phone
- +1 973-275-5555
- Website
- New Jersey Transit
Train from Hammonton to 30th Street Station
- Ave. Duration
- 1h 5m
- Frequency
- Every 2 hours
- Estimated price
- $3–20
- Website
- New Jersey Transit
- Website
- NJ Transit: World Cup 2026
- Adult
- $3–20
Train from Hammonton to 30th Street Station
- Ave. Duration
- 1h 5m
- Frequency
- Every 2 hours
- Estimated price
- $3–20
- Website
- New Jersey Transit
- Website
- NJ Transit: World Cup 2026
- Adult
- $3–20
Train from Hammonton to 30th Street Station
- Ave. Duration
- 1h 5m
- Frequency
- Every 2 hours
- Estimated price
- $3–20
- Website
- New Jersey Transit
- Website
- NJ Transit: World Cup 2026
- Adult
- $3–20
Train from Hammonton to 30th Street Station
- Ave. Duration
- 1h 5m
- Frequency
- Every 2 hours
- Estimated price
- $3–20
- Website
- New Jersey Transit
- Website
- NJ Transit: World Cup 2026
- Adult
- $3–20
Train from Hammonton to 30th Street Station
- Ave. Duration
- 1h 5m
- Frequency
- Every 2 hours
- Estimated price
- $3–20
- Website
- New Jersey Transit
- Website
- NJ Transit: World Cup 2026
- Adult
- $3–20
Train from Hammonton to 30th Street Station
- Ave. Duration
- 1h 5m
- Frequency
- Every 2 hours
- Estimated price
- $3–20
- Website
- New Jersey Transit
- Website
- NJ Transit: World Cup 2026
- Adult
- $3–20
Train from Hammonton to 30th Street Station
- Ave. Duration
- 1h 5m
- Frequency
- Every 2 hours
- Estimated price
- $3–20
- Website
- New Jersey Transit
- Website
- NJ Transit: World Cup 2026
- Adult
- $3–20
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from 30th Street Station to Washington Union Station
- Ave. Duration
- 1h 58m
- Frequency
- Hourly
- Estimated price
- $70–120
- Website
- Amtrak
Train from Rockville Amtrak to Chicago Union Station
- Ave. Duration
- 17h 24m
- Frequency
- Once daily
- Estimated price
- $410–650
- Website
- Amtrak
Train from 30th Street Station to BWI Thurgood Marshall
- Ave. Duration
- 1h 25m
- Frequency
- Hourly
- Estimated price
- $55–90
- Website
- Amtrak
Train from 30th Street Station to Ny Moynihan Train Hall At Penn Station
- Ave. Duration
- 1h 24m
- Frequency
- Every 30 minutes
- Estimated price
- $50–80
- Website
- Amtrak
Train from 30th Street Station to Chicago Union Station
- Ave. Duration
- 27h 10m
- Frequency
- 3 times a week
- Estimated price
- $550–900
- Website
- Amtrak
Rome2Rio's guide to Amtrak Acela
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from 30th Street Station to Washington Union Station
- Ave. Duration
- 1h 49m
- Frequency
- Hourly
- Estimated price
- $30–650
- Schedules at
- Amtrak Acela
- Website
- Amtrak
- Business Class
- $30–470
- First Class
- $150–650
Train from 30th Street Station to BWI Thurgood Marshall
- Ave. Duration
- 1h 22m
- Frequency
- 5 times a day
- Estimated price
- $24–650
- Schedules at
- Amtrak Acela
- Website
- Amtrak
- Business Class
- $24–460
- First Class
- $140–650
Train from 30th Street Station to Ny Moynihan Train Hall At Penn Station
- Ave. Duration
- 1h 17m
- Frequency
- Hourly
- Estimated price
- $20–600
- Schedules at
- Amtrak Acela
- Website
- Amtrak
- Business Class
- $20–460
- First Class
- $130–600
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Philadelphia Bus Station to Chicago Bus Station
- Ave. Duration
- 20h
- Frequency
- 3 times a week
- Estimated price
- $140–220
- Schedules at
- Flixbus USA
- Phone
- 570.821.3800
- customerservice@martzbus.com
- Website
- Martz Bus
Bus from Philadelphia 30th St Station to Allentown Transportation Center
- Ave. Duration
- 1h 10m
- Frequency
- Once daily
- Estimated price
- $30–45
- Website
- Martz Bus
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- Greyhound
Bus from Philadelphia Bus Station to Baltimore Greyhound Garage
- Ave. Duration
- 5h
- Frequency
- Once daily
- Estimated price
- $30–45
- Website
- Greyhound
Bus from Baltimore Downtown Bus Station to Chicago Bus Station
- Ave. Duration
- 18h 40m
- Frequency
- Twice daily
- Estimated price
- $130–200
- Website
- Greyhound
Want to know more about travelling around United States
Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.
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Booking & Getting There
Winslow to Chicago bus services, operated by Flixbus USA, arrive at Chicago Bus Station.
Chicago is 1h behind Winslow. It is currently 12:22 AM in Winslow and 11:22 PM in Chicago.
Winslow to Chicago train services, operated by NJ Transit, arrive at 30th Street Station.
Yes, the driving distance between Winslow to Chicago is 792 miles. It takes approximately 13h to drive from Winslow to Chicago.
There are 1308+ hotels available in Chicago.











