There are 6 ways to get from Wallkill to Chicago by train, plane, train (Amtrak), car, or bus
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 Laguardia Airport, fly to Chicago Midway International Airport
best- Take the train from Beacon to 125th Street - Harlemtrain
- Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane LGA - MDW
6h 37m$171–581Bus to Westchester County Airport, fly to Chicago O'Hare International Airport
cheapest- Take the bus from Newburgh to White Plains, Nybus
- Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane HPN - ORD
7h 38m$133–442Train (Amtrak)
- Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain Lake Shore Limited
18h 33m$213–430Drive 792.2 mi
- Drive from Wallkill to Chicagocar 792.2 mi
13h 6m$145–209Train to Laguardia Airport, fly to Chicago O'Hare International Airport
- Take the train from Beacon to 125th Street - Harlemtrain
- Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane LGA - ORD
6h 53m$141–371Train to Laguardia Airport, fly to General Mitchell International Airport, train
- Take the train from Beacon to 125th Street - Harlemtrain
- Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane LGA - MKE
- Take the train from Milwaukee to Chicago Union Stationtrain
9h 8m$303–786
Laguardia Airport (LGA) to Chicago Midway International Airport (MDW) flights
Questions & Answers
The cheapest way to get from Wallkill to Chicago is to drive which costs $140 - $210 and takes 13h 6m.
The fastest way to get from Wallkill to Chicago is to train and fly which takes 6h 37m and costs $170 - $600.
The distance between Wallkill and Chicago is 815 miles. The road distance is 796.8 miles.
The best way to get from Wallkill to Chicago without a car is to train which takes 18h 33m and costs $210 - $430.
It takes approximately 6h 37m to get from Wallkill to Chicago, including transfers.
Chicago is 1h behind Wallkill. It is currently 12:40 AM in Wallkill and 11:40 PM in Chicago.
Yes, the driving distance between Wallkill to Chicago is 797 miles. It takes approximately 13h 6m to drive from Wallkill to Chicago.
There are 920+ hotels available in Chicago.
What companies run services between Wallkill, NY, USA and Chicago, IL, USA?
Amtrak operates a train from Poughkeepsie Amtrak Station to Chicago Union Station once daily. Tickets cost $120–320 and the journey takes 18h 2m.
- Website
- aa.com
Flights from Laguardia Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 54m
- When
- Every day
- Estimated price
- $55–320
Flights from Westchester County Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 49m
- When
- Every day
- Estimated price
- $55–330
Flights from Westchester County Airport to Chicago O'Hare International Airport via Reagan Washington
- Ave. Duration
- 5h 49m
- When
- Every day
- Estimated price
- $60–340
Flights from Westchester County Airport to Chicago O'Hare International Airport via Charlotte
- Ave. Duration
- 5h 39m
- When
- Every day
- Estimated price
- $75–390
Flights from Laguardia Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 5h 2m
- When
- Every day
- Estimated price
- $150–850
- Website
- united.com
Flights from Laguardia Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 50m
- When
- Every day
- Estimated price
- $55–320
Flights from Laguardia Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 4h 47m
- When
- Every day
- Estimated price
- $150–850
- Website
- delta.com
Flights from Laguardia Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 5h 18m
- When
- Every day
- Estimated price
- $80–460
Flights from Laguardia Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 54m
- When
- Every day
- Estimated price
- $55–320
Flights from Westchester County Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 4h 57m
- When
- Every day
- Estimated price
- $55–330
Flights from Laguardia Airport to General Mitchell International Airport
- Ave. Duration
- 2h 41m
- When
- Every day
- Estimated price
- $140–850
Flights from Laguardia Airport to General Mitchell International Airport via Detroit
- Ave. Duration
- 4h 20m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $140–850
- Website
- southwest.com
Flights from Laguardia Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 36m
- When
- Every day
- Estimated price
- $80–460
Flights from Laguardia Airport to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 45m
- When
- Monday, Thursday, and Friday
- Estimated price
- $150–850
- Website
- spirit.com
Flights from Laguardia Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 42m
- When
- Every day
- Estimated price
- $50–240
- Phone
- +1 877.690.5114
- Website
- mta.info
Train from Beacon to 125th Street - Harlem
- Ave. Duration
- 1h 24m
- Frequency
- Hourly
- Estimated price
- $14–23
- Website
- https://www.mta.info/agency/metro-north-railroad
- Schedules at
- https://www.mta.info/schedules
- Off-Peak
- $14–17
- Peak
- $19–23
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Poughkeepsie Amtrak Station to Chicago Union Station
- Ave. Duration
- 18h 2m
- Frequency
- Once daily
- Estimated price
- $120–320
- Website
- https://www.amtrak.com/home.html
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $22–40
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 800-858-8555
- Website
- trailways.com
Bus from Newburgh to White Plains, Ny
- Ave. Duration
- 1h 10m
- Frequency
- Once daily
- Estimated price
- $15–35
- Website
- https://trailways.com
- Schedules at
- https://trailways.com/schedules/
- Saver
- $15–26
- Flexible
- $25–35
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
Travelling to the US: What do I need to know?
Read the travel guide
Why you should take the train in the US
Read the travel guide









