There are 6 ways to get from Regina to Chicago by plane, bus, car, or train
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly to Chicago O'Hare International Airport
best- Fly from Regina (YQR) to Chicago O'Hare International Airport (ORD)plane YQR - ORD
6h 4m$349–1,075Fly to Chicago Midway International Airport
cheapest- Fly from Regina (YQR) to Chicago Midway International Airport (MDW)plane YQR - MDW
6h 57m$160–680Bus, drive, train
- Take the bus from Regina to Lethbridgebus
- Drive from Lethbridge to Port of Sweet Grasscar
- Take the bus from Port of Sweet Grass to Shelby Transit Centerbus
- Take the train from Shelby Amtrak Station to Chicago Union Stationtrain
40h 27m$514–1,067Drive 1,147.6 mi
- Drive from Regina to Chicagocar 1,147.6 mi
19h 55m$263–380Fly to South Bend, train
- Fly from Regina (YQR) to South Bend (SBN)plane YQR - SBN
- Take the train from South Bend Airport to Van Buren St.train
11h 15m$261–1,068Fly to General Mitchell International Airport, train
- Fly from Regina (YQR) to General Mitchell International Airport (MKE)plane YQR - MKE
- Take the train from Milwaukee to Chicago Union Stationtrain
9h 28m$254–1,040
Regina (YQR) to Chicago O'Hare International Airport (ORD) flights
Questions & Answers
The cheapest way to get from Regina to Chicago is to drive which costs $260 - $380 and takes 19h 55m.
The fastest way to get from Regina to Chicago is to fly which takes 6h 4m and costs $340 - $1,100.
The distance between Regina and Chicago is 1011 miles. The road distance is 1154.3 miles.
It takes approximately 6h 4m to get from Regina to Chicago, including transfers.
Chicago is 1h ahead of Regina. It is currently 7:02 PM in Regina and 8:02 PM in Chicago.
Yes, the driving distance between Regina to Chicago is 1154 miles. It takes approximately 19h 55m to drive from Regina to Chicago.
There are 1080+ hotels available in Chicago.
What companies run services between Regina, SK, Canada and Chicago, IL, USA?
WestJet, Delta, and two other airlines fly from Regina (YQR) to Chicago O'Hare International Airport (ORD) 5 times a day.
- Website
- westjet.com
Flights from Regina to Chicago O'Hare International Airport via Minneapolis
- Ave. Duration
- 5h 19m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $340–1,100
Flights from Regina to Chicago O'Hare International Airport via Calgary
- Ave. Duration
- 7h 5m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $340–1,100
Flights from Regina to Chicago Midway International Airport via Minneapolis
- Ave. Duration
- 6h 16m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $230–1,300
Flights from Regina to South Bend via Minneapolis
- Ave. Duration
- 9h 48m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $360–2,000
Flights from Regina to South Bend via Denver, Minneapolis
- Ave. Duration
- 10h 48m
- When
- Every day
- Estimated price
- $260–1,100
Flights from Regina to General Mitchell International Airport via Minneapolis
- Ave. Duration
- 6h 32m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $330–1,900
Flights from Regina to General Mitchell International Airport via Calgary, Minneapolis
- Ave. Duration
- 9h 29m
- When
- Monday, Thursday, Friday, and Saturday
- Estimated price
- $240–2,000
Flights from Regina to General Mitchell International Airport via Toronto, Detroit
- Ave. Duration
- 9h 2m
- When
- Every day
- Estimated price
- $400–2,000
- Website
- delta.com
Flights from Regina to Chicago O'Hare International Airport via Minneapolis
- Ave. Duration
- 5h 19m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $340–1,100
Flights from Regina to Chicago O'Hare International Airport via Calgary
- Ave. Duration
- 7h 5m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $340–1,100
Flights from Regina to Chicago Midway International Airport via Minneapolis
- Ave. Duration
- 6h 16m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $230–1,300
Flights from Regina to South Bend via Minneapolis
- Ave. Duration
- 9h 48m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $360–2,000
Flights from Regina to South Bend via Toronto, Detroit
- Ave. Duration
- 12h 50m
- When
- Every day
- Estimated price
- $410–2,100
Flights from Regina to South Bend via Denver, Minneapolis
- Ave. Duration
- 10h 48m
- When
- Every day
- Estimated price
- $260–1,100
Flights from Regina to General Mitchell International Airport via Minneapolis
- Ave. Duration
- 6h 32m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $330–1,900
Flights from Regina to General Mitchell International Airport via Calgary, Minneapolis
- Ave. Duration
- 8h 42m
- When
- Monday, Thursday, Friday, and Saturday
- Estimated price
- $240–1,100
Flights from Regina to General Mitchell International Airport via Toronto, Detroit
- Ave. Duration
- 9h 2m
- When
- Every day
- Estimated price
- $400–2,000
- Website
- united.com
Flights from Regina to Chicago O'Hare International Airport via Toronto
- Ave. Duration
- 6h 33m
- When
- Every day
- Estimated price
- $130–600
Flights from Regina to Chicago O'Hare International Airport via Denver
- Ave. Duration
- 6h 20m
- When
- Every day
- Estimated price
- $130–600
Flights from Regina to Chicago O'Hare International Airport via Calgary
- Ave. Duration
- 6h 5m
- When
- Every day
- Estimated price
- $140–650
Flights from Regina to South Bend via Denver, Chicago O'Hare International Airport
- Ave. Duration
- 8h 17m
- When
- Every day
- Estimated price
- $240–1,100
Flights from Regina to General Mitchell International Airport via Denver
- Ave. Duration
- 6h 23m
- When
- Every day
- Estimated price
- $220–1,000
- Website
- aircanada.com
Flights from Regina to Chicago O'Hare International Airport via Toronto
- Ave. Duration
- 6h 33m
- When
- Every day
- Estimated price
- $130–600
Flights from Regina to Chicago O'Hare International Airport via Calgary
- Ave. Duration
- 6h 5m
- When
- Every day
- Estimated price
- $140–650
- Website
- southwest.com
Flights from Regina to Chicago Midway International Airport via Denver
- Ave. Duration
- 6h 20m
- When
- Tuesday and Wednesday
- Estimated price
- $150–700
Flights from Regina to Chicago Midway International Airport via Phoenix
- Ave. Duration
- 8h 55m
- When
- Sunday
- Estimated price
- $230–950
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Shelby Amtrak Station to Chicago Union Station
- Ave. Duration
- 28h 17m
- Frequency
- Twice daily
- Estimated price
- $440–950
- Website
- Amtrak
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $25–55
- Website
- Amtrak
- Phone
- +1 219-926-5744
- Website
- mysouthshoreline.com
Train from South Bend Airport to Van Buren St.
- Ave. Duration
- 2h 1m
- Frequency
- Every 2 hours
- Estimated price
- $13–15
- Schedules at
- mysouthshoreline.com
- Adults 14-64
- $13–15
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Regina to Lethbridge
- Ave. Duration
- 8h 5m
- Frequency
- 5 times a week
- Estimated price
- $55–95
- Schedules at
- Flixbus USA
- Phone
- +1 406-470-0727
- [email protected]
- Website
- northern.rural-transit.com
Bus from Port of Sweet Grass to Shelby Transit Center
- Ave. Duration
- 45 min
- Frequency
- Once daily
- Schedules at
- northern.rural-transit.com
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