Rome2Rio

How to get fromChicago to Princess Anneby plane, bus, train, bus (Greyhound), car or bus (Flixbus, Greyhound)

Find Transport to Princess Anne

See all options

There are 10 ways to get from Chicago to Princess Anne by plane, bus, train, bus (Greyhound), car, or bus (Flixbus, Greyhound)

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly Chicago Midway International Airport to Baltimore-Washington International Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Baltimore-Washington International Airport (BWI)plane plane MDW - BWI
    2. Take the bus from BWI-Thurgood Marshall Airport to Salisbury, MDbus bus
    6h 45m
    $228–670
  2. Fly Chicago Midway International Airport to Philadelphia International Airport, train, bus

    cheapest
    1. Fly from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL)plane plane MDW - PHL
    2. Take the train from 30th Street Station to Wilmingtontrain train
    3. Take the bus from Wilmington Bus Station to Princess Annebus bus
    8h 54m
    $126–613
  3. Train, bus via Rockville

    1. Take the train from Chicago Union Station to Rockville Amtraktrain train
    2. Take the train from Washington Union Station to BWI Thurgood Marshalltrain train
    3. Take the bus from BWI Amtrak Station to Salisbury, MDbus bus
    20h 58m
    $296–1,122
  4. Bus (Greyhound)

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Wilmington Bus Stationbus bus
    3. Take the bus from Wilmington Bus Station to Princess Annebus bus
    24h 15m
    $165–306
  5. Drive 805.8 mi

    1. Drive from Chicago to Princess Annecar car 805.8 mi
    14h 17m
    $148–213
  6. Fly Chicago O'Hare International Airport to Baltimore-Washington International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Baltimore-Washington International Airport (BWI)plane plane ORD - BWI
    2. Take the bus from BWI-Thurgood Marshall Airport to Salisbury, MDbus bus
    7h 11m
    $248–480
  7. Fly Chicago Midway International Airport to Ronald Reagan Washington National Airport, train, bus

    1. Fly from Chicago Midway International Airport (MDW) to Ronald Reagan Washington National Airport (DCA)plane plane MDW - DCA
    2. Take the train from Washington Union Station to Wilmingtontrain train
    3. Take the bus from Wilmington Bus Station to Princess Annebus bus
    9h 42m
    $236–1,217
  8. Fly Chicago O'Hare International Airport to Ronald Reagan Washington National Airport, train, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Ronald Reagan Washington National Airport (DCA)plane plane ORD - DCA
    2. Take the train from Washington Union Station to Wilmingtontrain train
    3. Take the bus from Wilmington Bus Station to Princess Annebus bus
    10h 4m
    $176–867
  9. Bus via Harrisburg

    1. Take the bus from Chicago Bus Station to Harrisburg Bus Stationbus bus
    2. Take the bus from Harrisburg Bus Station to Baltimore Downtown Bus Stationbus bus
    3. Take the bus from Baltimore, MD - Greyhound Bus Terminal Downtown to Salisbury, MDbus bus
    25h 57m
    $199–304
  10. Train, bus

    1. Take the train from Chicago Union Station to Wilmingtontrain train Cardinal
    2. Take the bus from Wilmington Bus Station to Princess Annebus bus Greyhound US0355
    29h 45m
    $294–632

Chicago to Princess Anne by bus (Greyhound)

Calendar7Weekly Buses
Duration24h 15mAverage Duration
Ticket$165Cheapest Price
See schedules

Questions & Answers

What companies run services between Chicago, IL, USA and Princess Anne, MD, USA?

You can take a bus from Chicago Bus Station to Princess Anne via Baltimore Downtown Bus Station and Wilmington Bus Station in around 24h 15m.

Airlines
Train operators
Bus operators

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.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers