There are 8 ways to get from Upper Darby to Chicago by plane, train (Amtrak), bus (Flixbus), car, train, 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.
Fly Philadelphia International Airport to Chicago Midway International Airport
best- Fly from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW)plane PHL - MDW
4h$145–378Fly Philadelphia International Airport to Chicago O'Hare International Airport
cheapest- Fly from Philadelphia International Airport (PHL) to Chicago O'Hare International Airport (ORD)plane PHL - ORD
4h 29m$125–228Train via Washington (Amtrak)
- Take the train from 30th Street Station to Washington Union Stationtrain Northeast Regional / ...
- Take the train from Rockville Amtrak to Chicago Union Stationtrain Floridian
21h 34m$225–1,096Bus (Flixbus)
- Take the bus from Philadelphia Bus Station to Chicago Bus Stationbus FlixBus N2642
21h 51m$133–213Drive 751 mi
- Drive from Upper Darby to Chicagocar 751 mi
12h 32m$138–198Train to Baltimore-Washington International Airport, fly to Chicago Midway International Airport
- 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
5h 56m$149–958Bus via Baltimore (Greyhound)
- Take the bus from Wilmington Bus Station to Baltimore Downtown Bus Stationbus Greyhound US0305 / ...
- Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus Greyhound US0164
23h 58m$125–214Train (Amtrak)
- Take the train from 30th Street Station to Chicago Union Stationtrain Cardinal
28h 26m$273–603
Upper Darby to Chicago by train and subway (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Upper Darby to Chicago is to bus via Baltimore which costs $120 - $220 and takes 23h 58m.
The fastest way to get from Upper Darby to Chicago is to fly which takes 4h and costs $140 - $380.
No, there is no direct bus from Upper Darby to Chicago station. However, there are services departing from Wycombe Loop 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 Upper Darby to Chicago station. However, there are services departing from Gladstone 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 21h 34m.
The distance between Upper Darby and Chicago is 687 miles. The road distance is 755.4 miles.
The best way to get from Upper Darby to Chicago without a car is to train via Washington which takes 21h 34m and costs $220 - $1,100.
It takes approximately 4h to get from Upper Darby to Chicago, including transfers.
Upper Darby to Chicago bus services, operated by Flixbus USA, depart from Philadelphia Bus Station.
Upper Darby to Chicago train services, operated by Amtrak, depart from 30th Street Station.
The best way to get from Upper Darby to Chicago is to fly which takes 4h and costs $140 - $380. Alternatively, you can train via Washington, which costs $220 - $1,100 and takes 21h 34m, you could also bus, which costs $130 - $220 and takes 21h 51m.
What companies run services between Upper Darby, PA, USA and Chicago, IL, USA?
Southwest Airlines and Delta fly from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a train from Gladstone to Chicago Union Station via 30th Street Station, Washington Union Station, Union Station, Red Line Center Platform, Rockville, Red Line Center Platform, and Rockville Amtrak in around 21h 34m.
- Website
- southwest.com
Flights from Philadelphia International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 6m
- When
- Every day
- Estimated price
- $90–550
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 1m
- When
- Every day
- Estimated price
- $75–420
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport via Pittsburgh
- Ave. Duration
- 3h 35m
- When
- Tuesday and Wednesday
- Estimated price
- $75–420
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport via Columbus
- Ave. Duration
- 3h 36m
- When
- Tuesday, Wednesday, Monday, Thursday, Friday, and Sunday
- Estimated price
- $75–420
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 3h 42m
- When
- Tuesday and Wednesday
- Estimated price
- $75–430
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
- $35–80
- Website
- Amtrak
Train from Rockville Amtrak to Chicago Union Station
- Ave. Duration
- 17h 24m
- Frequency
- Once daily
- Estimated price
- $190–440
- Website
- Amtrak
Train from 30th Street Station to BWI Thurgood Marshall
- Ave. Duration
- 1h 25m
- Frequency
- Hourly
- Estimated price
- $27–60
- Website
- Amtrak
Train from 30th Street Station to Chicago Union Station
- Ave. Duration
- 27h 10m
- Frequency
- 3 times a week
- Estimated price
- $270–600
- Website
- Amtrak
- 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
- $130–210
- Schedules at
- Flixbus USA
Want to know more about travelling around United States
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Booking & Getting There
Upper Darby to Chicago bus services, operated by Flixbus USA, arrive at Chicago Bus Station.
Chicago is 1h behind Upper Darby. It is currently 1:07 AM in Upper Darby and 12:07 AM in Chicago.
Upper Darby to Chicago train services, operated by Amtrak, arrive at Washington Union Station.
Yes, the driving distance between Upper Darby to Chicago is 755 miles. It takes approximately 12h 32m to drive from Upper Darby to Chicago.
There are 1285+ hotels available in Chicago.